Chem.Soc.Rev.,2012,41,7938–Defect-related luminescent materials

Efficient Photocyclization of Dithienylethene Dimer,Trimer, and Tetramer:Quantum Yield and Reaction DynamicsTeruaki Kaieda,†Seiya Kobatake,†Hiroshi Miyasaka,*,‡Masataka Murakami,‡Nobuyuki Iwai,§Yasushi Nagata,§Akira Itaya,§and Masahiro Irie*,†Contribution from the Department of Chemistry and Biochemistry,Graduate School ofEngineering,Kyushu Uni V ersity,and CREST,Japan Science and Technology Corporation,Higashi-ku,Fukuoka812-8581,Japan,Department of Chemistry,Graduate School of Engineering Science,Osaka Uni V ersity,Toyonaka,Osaka560-8531,Japan,and Department of Polymer Science and Engineering,Kyoto Institute of Technology,Matsugasaki,Sakyo,Kyoto606-8585,JapanReceived June27,2001.Revised Manuscript Received October22,2001Abstract:Multi-dithienylethene arrays,in which two,three,or four1,2-bis(2,4-dimethylthiophen-3-yl)-perfluorocyclopentenes are ethynylene-bridged,were synthesized.Upon irradiation with ultraviolet light the hexane solutions of the arrays turned violet-blue and the color disappeared by irradiation with visible light.The quantum yields of photocyclization reactions successively increased from0.21to0.40by increasing the number of the dithienylethene moieties in the arrays from one to four.Picosecond laser photolysis as well as the fluorescence depolarization experiment confirmed that efficient excited energy migration in the arrays from the photochemically inactive parallel conformer to the photoactive antiparallel conformer resulted in the high quantum yields.IntroductionConsiderable attention has been paid to photochromic dyes which show reversible photoisomerizations upon irradiation with light of appropriate wavelengths because of their potential applicability to optoelectronic devices.1In general,photoge-nerated colored isomers of photochromic dyes are thermally unstable and return to the initial colorless isomers in the dark. Recently,several thermally irreversible photochromic com-pounds,such as furylfulgides,2diarylethenes,3and phenoxy-naphthacenequinones,4have been developed.The photogener-ated colored isomers are stable and never return back to the initial colorless isomers in the dark.Among the compounds, diarylethenes with heterocyclic aryl rings are the most promising for the optoelectronic devices,5-8such as optical memory,photooptical switching,display,and photodriven actuators, because of their fatigue-resistant property.6,7For practical applications it is required to further improve the performance of the photochromic diarylethenes,such as efficient photore-activity(high cyclization quantum yields),high absorption coefficients of the colored isomers,rapid response,and reactivity in the solid state.In the present study,we have prepared sensitive multi-dithienylethene arrays with high cyclization quantum yields.The open-ring isomers of dithienylethenes in solution have two conformations,antiparallel and parallel,in almost equal amounts,as shown in Scheme1.9,10The interconversion rate between the two conformations is much slower than the lifetime of photoexcited states.9Therefore,both conformers are photo-excited independently.Among the two conformers,only the antiparallel conformer has a chance to be converted to the closed-ring isomer.11Therefore,the maximum cyclization quantum yield cannot exceed0.5.12There are two strategies to increase the cyclization quantum yield in solution.One is to increase the ratio of the antiparallel conformers in the ground state.When a sodium sulfonate derivative of bis(2-methyl-1-benzothiophen-3-yl)perfluorocy-clopentene was included in the -cyclodextrin cavity,the molecule was force to adopt an antiparallel conformation.The†Kyushu University.‡Osaka University.§Kyoto Institute of Technology.(1)(a)Du¨rr,H.;Bouas-Laurent,H.Photochromism,Molecules and Systems;Elsevier:Amsterdam,1990.(b)McArdle,C.B.Applied Photochromic Polymer Systems;Blankie:Glasgow,1992.(c)Crano,J.C.;Guglielmetti, anic Photochromic and Thermochromic Compounds;Plenum Press:New York,1999.(2)(a)Heller,H.G.;Oliver,S.J.Chem.Soc.,Perkin Trans.11981,197.(b)Darcy,P.J.;Heller,H.G.;Strydom,P.J.;Whittall,J.J.Chem.Soc.,Perkin Trans.11981,202.(3)(a)Irie,M.;Mohri,.Chem.1988,53,803.(b)Hanazawa,M.;Sumiya,R.;Horikawa,Y.;Irie,M.J.Chem.Soc.,mun.1992, 206.(4)Buchholtz,F.;Zelichenok,A.;Krongauz,V.Macromolecules1993,26,906(5)Irie,M.Photoreacti V e Materials for Ultrahigh-Density Optical Memory;Elsevier:Amsterdam,1994.(6)Irie,M.;Uchida,K.Bull.Chem.Soc.Jpn.1998,71,985.(7)Irie,M.Chem.Re V.2000,100,1685.(8)Irie,M.;Kobatake,S.;Horichi,M.Science2001,291,1769.(9)Uchida,K.;Nakayama,Y.;Irie,M.Bull.Chem.Soc.Jpn.1990,63,1311.(10)Irie,M.;Miyatake,O.;Uchida,K.;Eriguchi,T.J.Am.Chem.Soc.1994,116,9894.(11)Nakamura,S.;Irie,.Chem.1988,53,6136.(12)Irie,M.;Sakemura,K.;Okinaka,M.;Uchida,.Chem.199560,8305.Published on Web02/09/200210.1021/ja0115722CCC:$22.00©2002American Chemical Society J.AM.CHEM.SOC.9VOL.124,NO.9,20022015cyclization quantum yield was found to increase from 0.32to 0.49.13Zerbi et al.14also ascribed the high cyclization quantum yield of a polymer having dithienylethenes in the main chain to the enforced antiparallel conformation of the dithienylethene moieties in the ground state.The other strategy is to increase the ratio of antiparallel conformers in the photoexcited state.When photoexcited energy can be transferred from the photo-chemically inactive parallel conformation unit to the photoactive antiparallel one,the quantum yield is expected to increase.Such energy transfer is probable in dithienylethene dimer,trimer,or tetramer,in which the dithienylethene moieties are ethynylene-bridged.15-18Recently,Branda et al .19reported limited photo-chromic reactivity of dithienylethene dimers,in which two dithienylethene moieties are connected by a single bond.When N dithienylperfluorocyclopentene moieties are con-nected with conjugated bonds,the system has 2N conformations by a combination of parallel and antiparallel conformations.Among the 2N conformations,only one conformation,in which all dithienylethene moieties are in the parallel conformation,cannot cyclize to the closed-ring isomer by photoirradiation,while (2N -1)other conformations can undergo the photocy-clization reaction by transferring the photoexcited energy to the antiparallel conformation unit.Figure 1lists all conformations of the monomer,dimer,trimer,and tetramer systems.From the list it is inferred that the ratio of photoactive systems increases from 0.5to 0.94by increasing the number of dithienylethene moieties in the arrays from one to four,resulting in high quantum yields.In this work,the dimer,trimer,and tetramer in Scheme 2were synthesized and the quantum yields and the mechanism of the cyclization reactions were studied by irradia-tion with continuous as well as picosecond laser pulse light.Results and DiscussionPhotochromism of Dimer in Hexane.Figure 2shows the absorption spectral change of the dimer in hexane by photoir-radiation.Upon irradiation with 320nm light,the colorless solution of the open-ring form dimer with the absorptionmaximum at 320nm ( ,2.3×104M -1cm -1)turned violet,in which characteristic absorption maxima were observed at 365and 584nm.The violet color indicates formation of the closed-ring isomer.6Upon visible (λ>540nm)light irradiation,the violet color disappeared indicating return to the initial open-ring isomer.The coloration/decoloration cycle could be repeated more than 10times and a clear isosbestic point was observed at 338nm even after 10cycles.The photoirradiated sample was analyzed with high perfor-mance liquid chromatography (HPLC,silica gel column,Wa-kosil 5SIL,eluent hexane/ethyl acetate (96:4)).When monitored at the isosbestic point of 338nm,two peaks were observed.When the monitoring wavelength was shifted to 584nm,at which wavelength only the closed-ring form absorbs,only one peak was observed in the HPLC chart.This indicates that only one closed-ring isomer was produced by UV irradiation.Even after prolonged irradiation any other photoproduct was not(13)(a)Takeshita,M.;Choi,C.N.;Irie,mun.1997,2265.(b)Takeshita,M.;Kato,N.;Kawauchi,S.;Imase,T.;Watanabe,J.;Irie,.Chem.1998,63,9306.(14)Stellacci,F.;Bertarelli,C.;Toscano,F.;Gallazzi,M.C.;Zolti,G.;Zerbi,G.Ad V .Mater.1999,11,292.(15)Hsiao,J.-S.;Krueger,B.P.;Wagner,R.W.;Johnson,T.E.;Delaney,J.K.;Mauzerall,D.C.;Fleming,G.R.;Lindsey,J.S.;Bocian,D.F.;Donohoe,R.J.J.Am.Chem.Soc.1996,118,11181.(16)Yang,S.I.;Lammi,R.K.;Seth,J.;Riggs,J.A.;Arai,T.;Kim,D.;Bocian,D.F.;Holten,D.;Lindsey,J.S.J.Phys.Chem.B 1998,102,9426.(17)Li,J.;Ambroise A.;Yang,S.R.;Diers,J.R.;Seth,J.;Wack,C.R.;Bocian,D.F.;Holten,D.;Lindsey,J.S.J.Am.Chem.Soc.1999,121,8927.(18)Lammi,R.K.;Ambroise A.;Balasubramanian,T.;Wagner,R.W.;Bocian,D.F.;Holten,D.;Lindsey,J.S.J.Am.Chem.Soc.2000,122,7579.(19)Peters,A.;Branda,N.R.Ad V .Mater.Opt.Electron.2000,10,245.Scheme 1.Photochromism ofDithienyletheneFigure 1.Conformations of monomer,dimer,trimer,and tetramermolecules.Figure 2.Absorption spectral change of the dimer in hexane upon irradiation with 320nm light:(s )before photoirradiation and (---)after UV-light irradiation for 11min.The fluorescence spectrum of the (O -O)dimer in hexane was also shown (---).Scheme 2.Structure of Monomer,Dimer,Trimer,andTetramerA R T I C L E SKaieda et al.2016J.AM.CHEM.SOC.9VOL.124,NO.9,2002detected.The absence of the isomer having two closed-ring forms in the photoirradiated dimer agrees to the result observed in the dimers reported by Branda et al .19The colored isomer was collected and the structure was analyzed by 1H NMR spectroscopy.The methyl protons of the colored dimer showed seven signals,as shown in Figure 3a.In the NMR spectrum there existed a characteristic signal at 2.00ppm assigned to the methyl protons of the closed-ring form and a characteristic signal at 2.04ppm assigned to the methyl protons of the open-ring form.20The ratio of the two signals was 1:1,which means that the colored isomer is an (O -C)dimer having an open-ring form (O)and a closed-ring form (C).The isomer in which both dithienylethenes are in the closed-ring form (C -C)was not detected.To search for the reason the isomer having two closed-ring forms (C -C)was not produced,fluorescence spectra of the initial open-ring form (O -O)dimer and the photogenerated (O -C)dimer were measured in hexane.When excited at 320nm,the (O -O)dimer gave fluorescence at 440nm,while the (O -C)dimer did not give fluorescence.As can be seen from Figure 2,there is an overlap of the fluorescence of the (O -O)dimer and the absorption of the (O -C)dimer.The overlap suggests that the intramolecular energy transfer is possible from the excited open-ring unit to the closed-ring unit.In other words,when the (O -C)dimer is excited with UV light,the excited energy of the open-ring form unit is efficiently transferred to the closed-ring form unit in the same molecule,as shown inScheme 3.Therefore,the cyclization reaction of the remaining open-ring form unit cannot take place.The efficient intramo-lecular energy transfer process will be discussed in detail in later sections,using the fluorescence depolarization experiment and picosecond laser photolysis.Photochromism of Trimer in Hexane.Figure 4shows the absorption spectral change of the trimer by UV irradiation in hexane.Upon irradiation with 320nm light,the colorless solution of all open-ring form (O -O -O)trimer with the absorption maximum at 325nm ( ,4.6×104M -1cm -1)turned blue,in which characteristic absorption maxima were observed at 365and 620nm.Upon visible (λ>540nm)light irradiation,the blue color disappeared.The HPLC chromatogram (monitoring wavelength 342nm)of the solution after UV irradiation is shown in Figure 5.Four peaks were observed.When the monitoring wavelength was changed to 600nm where the open-ring form unit has no absorption,three peaks except the second peak were observed,indicating that there existed three kinds of closed-ring form isomers.The four peaks were isolated and their structures were determined by UV -vis absorption spectral measurement and 1H NMR spectroscopy.The first peak trimer had the absorption maximum at 635nm ( ,2.4×104M -1cm -1).The third and fourth peak trimers had the maxima at 584nm.These colored isomers converted(20)In the NMR spectrum of the monomer,the methyl signals of the open-ring isomer were observed at 2.04and 2.29ppm,while they shifted to 2.00and 2.14ppm in the closed-ringisomer.Figure 3.1H NMR methyl signals of the (O -C)dimer (a)and the (O -C -O)trimer(b).Figure 4.Absorption spectral change of the trimer in hexane upon irradiation with 320nm light:(s )before photoirradiation and (---)after UV-light irradiation for 11min.Figure 5.HPLC chromatogram of the trimer irradiated with 320nm for 11min in hexane.A UV detector was used for monitoring at 342nm.The column was silica gel (Wakosil 5SIL)and the eluent was hexane/ethyl acetate (98:2).Scheme 3.Intramolecular Energy Transfer in the ExcitedStatePhotocyclization of Dithienylethene Di-,Tri-,and Tetramers A R T I C L E SJ.AM.CHEM.SOC.9VOL.124,NO.9,20022017to the open-ring form trimer by irradiation with visible light (λ>540nm).The absorption maxima suggest that the first peak trimer has the closed-ring form in the middle,while the third and fourth peak trimers have the closed-ring form unit(s)at the end,because the absorption maximum of 584nm was the same as the maximum of the (O -C)dimer.The structures were further examined by 1H NMR measurement.The methyl protons of the second peak trimer were observed at 2.04,2.11,and 2.29ppm,which are assigned to an all open-ring form (O -O -O)trimer.The methyl protons of the first peak trimer showed five signals,as shown in Figure 3b.In the NMR spectrum there was no characteristic signal at 2.00ppm,which is assigned to the methyl protons of the terminal closed-ring form.This result indicates that the product does not contain the terminal closed-ring form.Thus,the first peak is the (O -C -O)trimer having one closed-ring form unit at the middle.The methyl protons of the third peak trimer showed six peaks.In the NMR spectrum there existed a characteristic signal at 2.00ppm assigned to the terminal closed-ring form and a characteristic signal at 2.04ppm assigned to the terminal open-ring form.The ratio of the two signals was 1:1,which means the colored isomer is the (O -O -C)trimer having one closed-ring form at the one end.The absorption coefficient of the fourth peak trimer (584nm; ,2.9×104M -1cm -1)was twice as large as that of the third peak trimer (584nm; ,1.4×104M -1cm -1),which is the same as that of the (O -C)dimer.This indicates that the peak is due to the (C -O -C)trimer having two closed-ring form units at both ends.The fourth peak is not due to the (O -C -C)trimer,because the absorption maxima was observed at 584nm (assigned to the terminal closed-ring form),not at 635nm (assigned to the middle closed-ring form),and the characteristic signal at 2.04ppm assigned to the terminal open-ring form was not observed.Any isomer in which neighboring two dithienylethene units are converted to the closed-ring forms was not detected.The time-course of formation of the three isomers (O -C -O,O -O -C,C -O -C)was measured by HPLC,as shown in Figure 6.Upon UV-light irradiation,the amount of all open-ring form (O -O -O)trimer decreased.At the same time the amount of two trimers,O -C -O and C -O -O,having closed-ring form units increased.After 11min of photoirradiation,the ratio of (C -O -C),(O -C -O),and (O -O -C)isomers was 3:54:39.The amount of (C -O -C)trimer having two closed-ring form units at both ends increased gradually.The rate for formation of the (O -C -O)trimer having one closed-ring formunit in the middle was faster than that of the (O -O -C)trimer having one closed-ring form unit at the end.Photochromism of Tetramer in Hexane.The absorption spectral change of the tetramer in hexane is shown in Figure 7.Upon irradiation with 320nm light,the colorless solution of the open-ring form tetramer with the absorption maximum at 325nm ( ,6.9×104M -1cm -1)turned greenish-blue,in which characteristic absorption maxima were observed at 354and 625nm.Upon visible (λ>540nm)light irradiation,the greenish-blue color disappeared.Figure 8shows the HPLC chromatogram (monitoring wave-length 346nm)of the solution after UV irradiation.Five peaks were observed.When the monitoring wavelength was changed to 600nm,where the open-ring form has no absorption,four peaks except the third peak were observed.These four peaks were ascribed to the closed-ring form isomers.The first peak tetramer had the absorption maximum at 635nm,while the maximum shifted to 620nm in the second peak tetramer.The fourth and fifth peaks had the absorption maximum at 584nm.These colored compounds converted to the open-ring form isomer by irradiation with visible light (λ>540nm).These colored and colorless isomers were isolated and their structures were determined by 1H NMR and absorption spectroscopy.The methyl protons of the third peak tetramer were observed at 2.04,2.11,and 2.29ppm,which are identical to those of the open-ring form isomer.The methyl protons of the first peak tetramer showed six signals,in which there was no characteristic signal at 2.00ppm.This indicates that the first peak is due to the tetramer having no closed-ring form unit at the end and having one inner closed-ring form unit.The methyl protonsofFigure 6.The change in the content of the isomers of the trimer upon irradiation with 320nm:the (O -O -O)trimer (O ),the (O -C -O)trimer (0),the (O -O -C)trimer ()),and the (C -O -C)trimer (×).Figure 7.Absorption spectral change of the tetramer in hexane upon irradiation with 320nm light:(s )before photoirradiation and (---)after UV-light irradiation for 8min.Figure 8.HPLC chromatogram of the tetramer irradiated with 320nm in hexane.A UV detector was used for monitoring at 346nm.The column was silica gel (Wakosil 5SIL)and the eluent was hexane/ethyl acetate (96:4).A R T I C L E S Kaieda et al.2018J.AM.CHEM.SOC.9VOL.124,NO.9,2002the second peak tetramer showed six peaks.In the spectrum there existed characteristic signals at 2.00and 2.04ppm assigned to the terminal closed-ring and open-ring forms,respectively.The peak intensity of a characteristic signal at 2.17ppm,which is assigned to the methyl protons at the quantarnary carbons in the closed-ring form units,indicates that two closed-ring form units are included in the molecule.This means that the colored isomer is the (O -C -O -C)tetramer having one terminal closed-ring form unit and one inner closed-ring form unit.This peak is not due to the (O -O -C -C)tetramer,because the signal at 2.33ppm was 3times larger than the signal at 2.29ppm.The fourth and fifth peaks had the same absorption maximum at 584nm.The absorption coefficient of the fifth peak ( ,2.8×104M -1cm -1)was twice as large as that of the fourth peak ( ,1.4×104M -1cm -1)at 584nm,indicating that the fourth peak is due to the (O -O -O -C)tetramer having one closed-ring form at the end.The fifth peak is the (C -O -O -C)tetramer having two closed-ring form units at both ends.Even in the tetramer any isomer,in which both neighboring dithienylethene units are converted to the closed-ring form,was not detected.The time-course of formation of the four isomers,(O -C -O -O),(O -O -O -C),(O -C -O -C),and (C -O -O -C),was measured by HPLC,as shown in Figure 9.Upon UV irradiation,the amount of all open-ring tetramer immediately decreased and at the same time the amount of two closed-ring isomers,(O -C -O -O)and (O -O -O -C),increased.The amount of the (C -O -O -C)tetramer having two closed-ring form units at both ends and the (O -C -O -C)tetramer having both inner and terminal closed-ring form units increased gradually.The rate of formation of the (O -C -O -O)tetramer having an inner closed-ring form unit was faster than that of the (O -O -O -C)tetramer having a terminal closed-ring form unit.Quantum Yields of Dimer,Trimer,and Tetramer.The cyclization quantum yields of dimer,trimer,and tetramer were measured at room temperature.The quantum yield measurement was carried out as follows.The dimer and the trimer were dissolved in hexane and the solutions were irradiated with ultraviolet light (λ)340nm).Cyclohexane was used as the solvent for the tetramer because of its low solubility in hexane.A 500W xenon lamp was used as the light source and the irradiation wavelength (λ)340nm)was isolated by passing the light through a monochromator.In the case of the monomer and the dimer the rate of cyclization reaction was followed by measuring the absorption increase at 534nm ( ,5.0×103M -1cm -1)21and 584nm ( ,1.4×104M -1cm -1),respectively.Inthe case of the trimer and the tetramer the irradiated hexane or cyclohexane solutions were passed through HPLC and the ratio change of each product upon irradiation was analyzed by setting the monitoring wavelength to the quasi-isosbestic point.The absorption increase at 584and 635nm was also followed to confirm the accuracy of the quantum yield determination.The light intensity was monitored by a photometer,which was cali-brated by the photoreaction of furylfulgide in hexane solution.The quantum yield measurement was carried out three times for each multi-dithienylethene arrays and the average values were adopted as the quantum yields.The error of the relative quantum yields among the oligomers was less than (5%,while the error of absolute values was on the order of (10%.The quantum yield of the open-ring form (O -O)dimer to the (O -C)dimer was determined to be 0.31.The yields of the trimer from the all open-ring form (O -O -O)isomer to the (O -C -O)isomer having one closed-ring form unit at the middle and the (O -O -C)isomer having one closed-ring form unit at the end were 0.20and 0.16,respectively.The total cyclization yield of the trimer was 0.36.The cyclization quantum yields of the tetramer from the all open-ring form (O -O -O -O)isomer to the (O -C -O -O)isomer having one inner closed-ring form unit and the (O -O -O -C)isomer having one terminal closed-ring form unit were determined to be 0.30and 0.10,respectively.The total cyclization quantum yield was 0.40.The photocyclization quantum yields increased by increasing the number of dithienylethene moieties in the arrays.The increase in the quantum yields is attributed to the intramolecular energy migration from the photochemically inactive parallel conforma-tion unit to the photoactive one,as described in the introductory section.Fluorescence Depolarization.To confirm the intramolecular energy migration in the arrays,depolarization of fluorescence was measured in a 2-methyltetrahydrofuran rigid glass at 77K.An excitation wavelength of 320nm was selected.Dithie-nylethenes undergo photochromic reactions even in the solid state at low temperature.22Fluorescence spectra of the dimer,the trimer and the tetramer gave a similar emission at 440nm,while the emission of the monomer was observed at 420nm.The fluorescence polarization values (p )(I ||-I ⊥)/(I ||+I ⊥))were determined to be 0.51(monomer),0.23(dimer),0.17(trimer),and 0.14(tetramer),respectively.For the monomer,the polarization of the fluorescence directly correlates with the direction of the polarized excitation light.In the case of the multi-dithienylethene arrays,depolarization took place.The p values decreased by increasing the number of the dithienylethene moieties in the arrays.This result clearly indicates that the excited energy migrates in the arrays.23Reaction Dynamics.To reveal the dynamics of the excited energy migration,a laser photolysis experiment was carried out with use of a picosecond laser pulse.Figure 10a shows the time-resolved transient absorption spectra of the dimer in a hexane solution excited with a picosecond 355nm laser pulse.A broad absorption spectrum with maxima around 490and 750nm appeared within the time resolution of the apparatus,followed(21)Uchida,K.;Irie,M.Chem.Lett.1995,969.(22)(a)Kobatake,S.;Yamada,T.;Uchida,K.;Kato,N.;Irie,M.J.Am.Chem.Soc.1999,121,2380.(b)Irie,M.;Lifka,T.;Kobatake,S.;Kato,N.J.Am.Chem.Soc.2000,122,4871.(23)(a)David,C.;Baeyens-Volant,D.;Geuskens,G.Eur.Polym.J.1976,12,71.(b)David,C.;Putman-de Lavareille,N.;Geuskens,G.Eur.Polym.J.1977,13,15.Figure 9.The change in the content of the isomers of the tetramer upon irradiation with 320nm:the (O -O -O -O)tetramer (O ),the (O -O -C -O)tetramer (0),the (O -O -O -C)tetramer ()),the (O -C -O -C)tetramer (×),and the (C -O -O -C)tetramer (4).Photocyclization of Dithienylethene Di-,Tri-,and Tetramers A R T I C L E SJ.AM.CHEM.SOC.9VOL.124,NO.9,20022019by the growth of sharp absorption maximum at 465nm in the time region of a few hundred picoseconds and the apparent decrease in absorption intensity in the wavelength region >650nm.No spectral change was observed in subnanoseconds to nanoseconds time region.Figure 10b shows the time profile of the transient absorption band at 780nm.The solid line in Figure 10b shows the results calculated on the basis of the double-exponential function as eq 1,where τ1and τ2are 35and 100ps,and A 1,A 2,and A 3are 46,46,and 8%,respectively.The pulse widths of the excitation and the monitoring pulses were convoluted in the curve.Since the broad spectrum appeared within the time resolution of the apparatus and the time constant of the fluorescence decay was obtained to be ca.100ps,24it is concluded that the broad absorption observed immediately after the excitation is due to the S 1state.To explore the spectral evolution in the early stage after the excitation,the difference spectrum between that at 100ps and that at 0ps was plotted in Figure 10c.Both of the spectra used for the calculation were normalized at 750nm.A sharp absorption peak at 465nm and a broad absorption band at 580nm were obtained as the difference.Since the former sharp absorption at 465nm did not decrease in the time window examined here (6ns),this band is ascribed to a long-living species such as a triplet state.On the other hand,the absorption band at 580nm is ascribed to the (O -C)dimer.On the basis of the above results,the spectral evolution around 580nm is attributable to the formation of the closed-ring form.To quantitatively elucidate the formation process of the closed-ring form,the time profiles of various wavelength points were analyzed.However,all the time profiles except for the wavelength region around 465nm showed only the decay behaviors,indicating that the broad absorption due to the S 1state has rather large extinction coefficients in the entire wavelength region >650nm.The absorption signals in the longer wavelength region are mainly due to the S 1state.Accordingly,we subtracted the contribution of this S 1spectrum (the spectrum at 0ps)from each of the spectra observed at various delay times after the excitation by adjusting the intensity of the spectrum at 750nm to those at various delay times.The transient spectra thus obtained are shown Figure 11a.The absorption spectra with maxima at 465and 580nm increase with an increase in the delay time after the excitation.The time profile of the transient absorbance at 580nm due to the closed-ring form (O -C)is exhibited in Figure 11b.The solid line in this figure shows the result calculated on the basis of the double-exponential rise function (eq 2).The initial instaneous rise was eliminated for the calculation,where τf and τs are (35(5)and (100(10)ps,respectively.The relative preexponential factors,A f and A s ,are 47and 53%.These time constants were in agreement with those for the decay of the S 1state monitored at 780nm (Figure 10b).Similar biphasic rise behavior was also observed for the transient absorbance at 465nm.To precisely elucidate the production pathways of the closed-ring form,the difference spectra between those at several delay times were plotted.Figure 12exhibits the difference spectra between those at 500ps and 120ps and between those at 120ps and 20ps.As is clearly shown in these spectra,the latter spectrum actually shows the formation of the closed-ring form(24)Single photon counting with a subnanosecond light pulse was used for thefluorescence measurement.Since the time resolution is not so sufficient to precisely determine the biphasic decay behaviors,single-exponential decay was assumed for the fluorescencedecay.Figure 10.(a)Time-resolved transient absorption spectra of the open-ring form (O -O)dimer in hexane,excited with a picosecond 355nm laser pulse.(b)Time profile of transient absorbance at 780nm.This solid line is the result calculated on the basis of the double-exponential function (see text).(c)Difference spectrum between that at 100ps and that at 0ps for the time-resolved transient absorption spectra of the open-ring form (O -O)dimer in hexane,excited with a picosecond 355nm laser pulse.A 780(t ))A 1exp(-t /τ1)+A 2exp(-t /τ2)+A 3(1)A (t ))A -{A f exp(-t /τf )+A s exp(-t /τs )}(2)A R T I C L E S Kaieda et al.2020J.AM.CHEM.SOC.9VOL.124,NO.9,2002。

盐酸左旋咪唑稀土化合物的制备及其对三元乙丙橡胶胶料性能的影响吴启浩，岑　兰*，黄　坤（广东工业大学材料与能源学院，广东广州　510006）摘要：采用稀土氧化钇与盐酸左旋咪唑制备盐酸左旋咪唑稀土化合物（LHLC），考察LHLC对三元乙丙橡胶（EPDM）/炭黑胶料的硫化特性和物理性能的影响。

红外光谱分析结果表明，盐酸左旋咪唑与稀土元素发生了配位反应。

试验结果表明：LHLC对胶料的硫化促进效率与促进剂M相当；LHLC用量增大，胶料的表观交联密度和M H增大，t90缩短；促进剂TRA/促进剂BZ/LHLC硫黄硫化体系有利于提高胶料的物理性能，随着LHLC用量的增大，硫化胶的拉伸强度、撕裂强度、硬度、100%定伸应力都有所增大，拉断伸长率呈下降趋势；LHLC对硫化胶的喷霜和耐热氧老化性能影响不大；LHLC 用量超过0.8份后，胶料的阿克隆磨耗量减小，随着LHLC用量的增大，硫化胶的耐磨性能变好。

关键词：稀土；盐酸左旋咪唑；硫化促进剂；三元乙丙橡胶中图分类号：TQ333.4；TQ330.38＋5 文献标志码：A 文章编号：1000-890X（2017）06-0340-04盐酸左旋咪唑（Levamisole Hydrochloride，简称LH）是一种普通医疗用药，分子结构中含有—N=C—S—基团，类似于橡胶硫化促进剂的基团，倘若能够用作硫化促进剂，在硫化过程中不会释放出亚硝胺，属于安全胺的范畴；本课题组前期研究表明，LH能够促进SBR的硫化，但直接使用时促进效果不理想。

另一方面，稀土元素具有独特的4f电子层结构及较大的原子转矩和较强的自旋耦合等特性，因此具有独特的物理化学性质，稀土元素倾向于与硬碱原子生成配合物，如稀土元素能够与橡胶硫化促进剂配合，提高其硫化促进性能[1-2]。

三元乙丙橡胶（EPDM）主链饱和而侧链含有少量的不饱和键，采用硫黄体系硫化时，其硫化反应活性较低，且硫黄和极性促进剂在胶料中的分散性不好，胶料容易喷霜。

Vol.412020年12月No.122766~2773CHEMICAL JOURNAL OF CHINESE UNIVERSITIES高等学校化学学报胺基膦钌卡宾化合物的合成及催化烯烃复分解反应王晋宇，柳春丽，陈延辉（天津科技大学化工与材料学院,天津卤水化工与资源生态化利用重点实验室,天津300457）摘要合成并表征了一类含新型胺基膦配体的Grubbs 二代型钌卡宾烯烃复分解催化剂[RuCl 2(H 2IMes)·(R 1HNPR 22)(=CHPh)],采用核磁共振波谱和单晶X 射线衍射确定了催化剂的结构.在室温条件下,以N,N -二烯丙基-对甲苯磺酰胺的关环复分解反应(RCM)为模型,考察了不同胺基膦配体对钌卡宾催化反应速率的影响.结果表明,G 2⁃1表现出最佳的催化活性.通过底物研究发现,G 2⁃1催化剂(摩尔分数,1%)对双端烯及多端烯的RCM 反应具有较好的活性和官能团适应性,产物收率均>95%;G 2⁃1催化剂同样适用于同(异)端烯底物的交叉复分解反应(CM),其催化苯乙烯与3-苯氧基丙烯的CM 反应时产物收率高达92%.关键词胺基膦配体；钌卡宾配合物；关环复分解；交叉复分解中图分类号O621.2文献标志码A烯烃复分解反应是指烯烃的碳碳双键在金属化合物的作用下被切断并重组为新分子结构的一类反应，是一种简单、快速、绿色且高效构建复杂分子的有效手段［1~10］.目前，含有钼、钨和钌金属的催化剂已被广泛用于生物医药和有机合成等领域［11~13］.与钼和钨催化剂相比，钌基催化剂对官能团兼容性好，对水和氧不敏感，因而备受关注［14］.1996年，具有代表性和开创性的钌催化剂—二（三环己基膦）亚苄基二氯化钌被发现，该催化剂对空气稳定、催化活性高，为钌催化剂的发展奠定了基础，被称为Grubbs 一代催化剂（G 1，结构见图1）［15］.G 1催化剂存在寿命短的缺点，在催化一些难以关环底物的反应时收率较低.1999年，Grubbs 等［16］利用空间位阻较大的N -杂环卡宾（NHC ）取代G 1中的一个三环己基膦，开发出Grubbs 二代催化剂（G 2，结构见图1）.与G 1催化剂相比，G 2催化剂的活性提升了2个数量级，显著降低了反应中催化剂的使用量，为工业化的大规模应用提供了可能性［17~19］.随后，G 2催化剂的一个膦配体被双吡啶取代，发展成为Grubbs 三代催化剂（G 3，结构见图1）［20］.G 3催化剂能够快速引发反应，且具有良好的官能团适应性.另外，G 3催化剂还可通过开环交叉聚合反应（ROMP ）制备分子量可控和低分散的聚合物［21~24］.纵观G 1~G 3钌基催化剂的发展历程，辅助配体的使用与调变起着关键作用，这为钌催化剂的进一步优化和发展指明了方向.基于卡宾钌G 2催化剂，已有大量研究集中于卡宾配体和膦配体的修饰和调变，以求提高催化剂的性能.2018年，Grubbs 等［25］首次将膦胺配体引入G 2钌基催化剂体系，开发出Fig.1Grubbs ruthenium olefin metathesis catalystsdoi ：10.7503/cjcu20200420收稿日期：2020-07-02.网络出版日期：2020-10-07.基金项目：国家自然科学基金(批准号:21371131)资助.联系人简介：陈延辉,男,博士,教授,主要从事金属有机均相催化应用研究.E -mail:************.cnNo.12王晋宇等：胺基膦钌卡宾化合物的合成及催化烯烃复分解反应具有膦胺配体的Grubbs 二代钌烯烃复分解催化剂（Scheme 1），并系统地研究了膦胺配体对其催化性能的影响.研究发现，P —N 键插入膦配体骨架能有效加速G 2催化剂的引发，提高初始反应速率.这种速率的提高可能与膦胺配体（相对于三环己基膦配体）更易于从钌金属中心解离有关［26，27］.这一过程促使G 2催化剂转变为一个14电子的活性钌中间体，进而引发烯烃复分解反应.由此可见，在G 2催化剂体系中，辅助膦配体的解离速率直接决定反应的初始速率和催化剂活性.理论上，通过调变G 2催化剂膦配体中取代基的电子效应和空间效应，即可有效降低膦配体和钌中心的结合力，促使配体从金属中心解离.胺基膦是一种重要的有机膦配体，具有独特的P —N 双齿配位特性，已经被广泛应用于各种金属有机化合物的合成和应用研究中.双烷基取代膦胺配体已经被应用于G 2钌基催化剂体系，迄今胺基膦在钌基烯烃复分解催化剂领域的应用尚未见报道.与双烷基取代的膦胺配体相比，胺基膦具有更低的磷上电子云密度，可使配体更易于从钌金属中心解离，利于提高催化剂的活性.本文从Grubbs 第三代催化剂出发，设计合成了一系列含胺基膦配位的钌卡宾化合物G 2-1~G 2-6（Scheme 1），通过调变取代基效应研究了催化剂的烯烃复分解反应特性.目标化合物的结构经核磁共振波谱和单晶X 射线衍射表征.利用模型反应，比较了合成的系列催化剂的性能，发现G 2⁃1表现出最佳的催化活性，并且优于同等反应条件下的商用催化剂G 2和G 3.另外，从底物取代基的电子效应、杂原子效应和空间效应等几个方面，系统评价了G 2⁃1催化剂对关环复分解反应（RCM ）和交叉复分解反应（CM ）的催化性能.1实验部分1.1试剂与仪器环己胺、正丙胺、异丙胺、叔丁胺、二苯基氯化膦、二异丙基氯化膦和二环己基氯化膦均为分析纯，购于百灵威科技有限公司；正己烷、甲苯和四氢呋喃均为分析纯，购于天津江天化工有限公司.所用溶剂均在氮气气氛下经Na 或CaH 2干燥.参照文献［28］方法合成胺基膦配体，并采用核磁共振波谱进行表征.德利斯手套箱（成都德利斯实业有限公司）；Agilent 7890A 型气相色谱仪（GC ，美国Agilent 公司，HP -5色谱柱）；AV Ⅲ400MB 型核磁共振波谱仪（NMR ，德国Bruker 公司），TMS 为内标，1H NMR 频率为400MHz ，31P NMR 频率为162MHz ；Brucker SMART APEX Ⅱ型单晶X 射线衍射仪（XRD ，德国Bruker 公司），采用单色化的Mo Kα辐射源（λ=0.071073nm ），在低温（113.15K ）下收集衍射数据.1.2实验过程胺基膦钌卡宾化合物的合成路线如Scheme 2所示.Scheme 1Structures of aminophosphine rutheniumcomplexesScheme 2Synthesis of aminophosphine ruthenium complexes2767Vol.41高等学校化学学报在氮气气氛下，将2.90g （4.00mmol ）钌卡宾配合物G 3加入到含有15mL 甲苯的圆底烧瓶中，再缓慢滴加1.11g （4.00mmol ）N -叔丁基-1，1-二环己基膦胺的甲苯溶液（5mL ），搅拌10min ；反应结束后，抽干溶剂甲苯，固体用正己烷洗涤，经过滤、干燥，得到化合物G 2⁃1（2.75g ，3.28mmol ），收率为81%.参照化合物G 2⁃1的合成方法制备钌卡宾化合物G 2⁃2~G 2⁃6，收率在72%~77%之间.化合物G 2⁃1~G 2⁃6的1H NMR 和31P NMR 数据见表1.图2示出了化合物G 2⁃3晶体的分子结构，其晶体数据及结构参数列于表2和表3.由图2可见，化合物G 2⁃3的胺基膦配体通过磷原子和钌中心配位，而氮原子不参与配位，钌中心呈现一个五配位的三角方锥构型.钌原子分别与2个氯、2个卡宾碳和1个磷原子配位.其中,2个钌氯键的键长分别为0.24079(12)和0.23923(13)nm,相差不大.但金属钌中心和两个卡宾碳原子的键长相差较大,分别为0.2085(5)和0.1833(5)nm,充分显示出钌碳单键和双键的配位特性.钌膦键的键长为0.24220(13)nm,在正常的范围之内。

j. am. chem. soc.的文章类型-回复首先，需要明确的是，j. am. chem. soc. 是《美国化学学会杂志》（Journal of the American Chemical Society）的简称。

作为一个高影响力的学术期刊，它涉及的文章类型非常广泛，覆盖了化学领域的各个方向。

下面以中括号内的内容为主题，我们来一步一步回答和解析这个问题。

[文章类型]：以这个主题为基础，我们可以选择一种比较通用的文章类型进行分析，例如综述文章（review article）。

综述文章通常对某个领域的最新进展和研究成果进行总结和评述，把相关文献进行归类整理，可以为该领域的学者提供一个全面的概览及从中获得灵感和启发。

在综述文章中，我们可以对该主题进行全面的研究回顾、对比、综合和分析，以期帮助读者了解并深入探讨该主题。

下面是一份可能的文章大纲：Ⅰ. 引言A. 引入主题：介绍[文章类型] 这个主题的研究背景和意义B. 论述目的：说明本文的目的和构成Ⅱ. 研究历史与进展A. 回顾过去：通过文献回顾，介绍过去在[文章类型] 方面的研究和发展情况B. 当前挑战：讨论目前研究领域的挑战和问题Ⅲ. [文章类型]方法与技术A. 介绍常用的[文章类型] 实验方法和技术B. 分析这些方法和技术的优缺点Ⅳ. [文章类型]应用与前景A. 阐述[文章类型] 在不同领域的应用案例B. 展望[文章类型] 的未来发展方向和可能的研究热点Ⅴ. 结论A. 总结本文的主要内容和观点B. 强调[文章类型] 的重要性和潜在的贡献在这份大纲的基础上，我们可以逐步展开文章内容，提取相关文献进行综述，并且可以加入自己的观点和分析。

总体而言，一篇关于[文章类型] 主题的综述文章应该具备以下特点：全面回顾、系统综合、观点独特、观点支持。

通过这样的文章，我们可以向读者传达对该主题的全面理解和深入见解，并为进一步研究和创新性思考提供思路和基础知识。

需要注意的是，以上仅仅是对一种可能的文章类型进行解析和概述，并不能代表所有的j. am. chem. soc. 文章类型。

Cite this:Chem.Soc.Rev.,2013,42,794Three dimensional macroporous architectures and aerogels built of carbon nanotubes and/or graphene:synthesis and applicationsStefania Nardecchia,Daniel Carriazo,M.Luisa Ferrer,Marı´a C.Gutie ´rrez and Francisco del Monte*Carbon nanotubes and graphene are some of the most intensively explored carbon allotropes in materials science.This interest mainly resides in their unique properties with electrical conductivities as high as 104S cm À1,thermal conductivities as high as 5000W m À1K and superior mechanical properties with elastic moduli on the order of 1TPa for both of them.The possibility to translate the individual properties of these monodimensional (e.g.carbon nanotubes)and bidimensional (e.g.graphene)building units into two-dimensional free-standing thick and thin films has paved the way for using these allotropes in a number of applications (including photocatalysis,electrochemistry,electronics and optoelectronics,among others)as well as for the preparation of biological and chemical sensors.More recently and while recognizing the tremendous interest of these two-dimensional structures,researchers are noticing that the performance of certain devices can experience a significant enhancement by the use of three-dimensional architectures and/or aerogels because of the increase of active material per projected area.This is obviously the case as long as the nanometre-sized building units remain accessible so that the concept of hierarchical three-dimensional organization is critical to guarantee the mass transport and,as consequence,performance enhancement.Thus,this review aims to describe the different synthetic processes used for preparation of these three-dimensional architectures and/or aerogels containing either any or both allotropes,and the different fields of application in which the particular structure of these materials provided a significant enhancement in theefficacy as compared to their two-dimensional analogues or even opened the path to novel applications.The unprecedented compilation of information from both CNT-and graphene-based three-dimensional architectures and/or aerogels in a single revision is also of interest because it allows a straightforward comparison between the particular features provided by each allotrope.Nanoparticles (NPs)and nanocomposites benefiting from the synergy between inorganic and organic compounds are indeed playing a major role in the development of advanced functional materials for a number of emerging applications (e.g.,catalysis,storage and controlled release systems,smart fillers,and bio-technologies).1Within this context,assembling NPs into struc-turally macroscopic structures is of special relevance for the realistic development of any of the above-cited applications because the resulting materials would offer a desirable combi-nation of high internal reactive surface area and straightforward molecular transport through broad ‘‘highways’’leading to such a surface.2These morphologies are also obtained in monolithsexhibiting hierarchical structures that combine micro-,meso-,and macropores—so that the micro and mesoporosity provide high surface areas while the macroporosity guaranties accessi-bility to this surface.Besides morphology,it is obvious that the chemical nature of the monolith also plays a role and will ultimately determine the particular application of these materi-als.For instance,the use of monolithic aerogels based on silica as columns in high-pressure liquid chromatography (HPLC)is quite extended 3–5whereas the electrically conductive framework of monolithic carbon aerogels has determined their preferred application as electrodes in electrochemical devices (supercapa-citors,fuel cells,batteries,etc.).6–8Interestingly,sol–gel chemis-try is one of the most common synthetic processes used for preparation of both silica and carbon hierarchical monoliths.Thus,Tanaka and coworkers first described the preparation of silica columns for HPLC in 19969using a sol–gel process basedInstituto de Ciencia de Materiales de Madrid (ICMM),Consejo Superior deInvestigaciones Cientı´ficas (CSIC),Cantoblanco 28049,Madrid,Spain.E-mail:delmonte@icmm.csic.es;Fax:+34913720623;Tel:+34913349033Received 24th August 2012DOI:10.1039/c2cs35353a/csrChem Soc RevP u b l i s h e d o n 16 N o v e m b e r 2012. D o w n l o a d e d b y U n i v e r s i t y o f S c i e n c e a n d T e c h n o l o g y o f C h i n a o n 01/10/2013 09:10:35.on the hydrolysis and polycondensation of tetramethoxysilane (TMOS)in the presence of polyethylene oxide (PEO)as a tem-plate.10,11Meanwhile and inspired by the seminal work on silica aerogels by Kistler in 1931,12Pekala et al.13first reported on the use of sol–gel chemistry for the achievement of highly cross-linked organic gels that,after supercritical drying and subsequent thermal treatment in an inert atmosphere,resulted in carbon monoliths.The main features that determined the popularization of the sol–gel process are the capability to produce materials in a variety of forms that includes thin films and three-dimensional (3D)architectures,the textural and chemical characteristics of which can be easily tuned for the achievement of co-continuous structures with well defined hierarchical structures for bare silica-or carbon-based materials as well as hybrids and composites.14–18While recognizing the tremendous relevance of silica,hybrid-silica and carbon mono-liths,the focus of this review will not be on these particular materials because there are already excellent reviews and books that cover most of the recent advances in this area.19–25Less revised has been however the preparation and application of composite-based monolithic aerogels and,in particular,of those containing carbon nanotubes (CNTs)and/or Ts and graphene are both allotropes of Ts exhibit a cylindrical hollow nanostructure with the walls formed by one-atom-thick sheets of carbon that are rolled at specific and discrete angles,which ultimately determine whether the individual nanotube shell is a metal or a Ts are categorized as single-,double-or multi-walled CNTs (SWCNTs,DWCNTs or MWCNTs,respectively)depending on the number of the rolled walls.Mean-while,graphene is a planar monolayer of carbon atoms arranged into a two-dimensional (2D)honeycomb lattice with a C–C bond length of 0.142nm.These two well-known allotropes of carbon have attracted much attention from the scientific community because they exhibit unique properties (electrical conductivities as high as 104S cm À1,thermal conductivities as high as 5000W m À1K and superior mechanical properties with elastic moduli on the order of 1TPa,for both of them)26–31that,eventually,can be translated into any architecture built up with any of them.In this review,we will summarize the use of CNTs and graphene oxide (GO)as,respectively,monodimensional (1D)and 2D building units in the synthesis of 3D macroporous architectures and aerogels.We will also describe the great potential of the resulting hydrogels and aerogels in the field of actuators,supercapacitors and polymer composites.T-based 3D architectures and aerogelsSince their discovery in 1991,32CNTs have been the subject of numerous research works given their unique properties,for example,extremely high electrical conductivities,very high thermal conductiv-ities,and outstanding mechanical properties.However,the proces-sing of CNT-based materials into engineered 3D macroporous structures is still in its infancy and most of the arrays prepared to date with controlled areas and nanotube lengths are 2D-type;e.g.well vertically aligned CNT architectures,33,34self-assembled CNTStefania Nardecchia,Francisco del Monte,M.Luisa Ferrer,Daniel Carriazo and Marı´a C.Gutie ´rrez Stefania Nardecchia graduated in Industrial Chemistry in 2005at the University of Roma ,obtained her PhD from the University of Madrid in 2012.In 2008she joined the Group of Bioinspired Materials at the Institute of Materials Science of Madrid (ICMM-CSIC)where she is currently working.Her research interests focused on materials for drug release and biomaterials for bone and neural tissue regeneration.Daniel Carriazo obtained his PhD from the University of Salamanca in 2008on the synthesis of layered double hydroxides and porous oxides for catalytic applications.In 2009he joined the Group of Bioinspired Materials at the Institute of Materials Science of Madrid (ICMM-CSIC)where he is currently working.During 2011he spent eight monthsworking in the group headed by Prof.Niederberger at the ETH-Zu¨rich on the synthesis of nano-materials by non-aqueous routes.His present scientific interest is focused on the synthesis of carbonaceous materials with hierarchical porosity for energy storage and environmental applications.Marı´a Luisa Ferrer is a tenured scientist at the Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC).After an MSc degree in Polymer Science (1992),she completed her PhD in chemistry at the University Autonoma of Madrid (1995).She was a postdoctoral fellow over the next three years ,first at the University of Patras (Greece)and ,after that ,at UCLA (USA).After that ,she got a teaching appointment at the UMH (Spain).She joined the ICMM-CSIC in 2000to work on the preparation of hierarchical materials with applications in both energy and biomaterials.Marı´a C.Gutie ´rrez obtained her PhD in Organic Chemistry at the University of Granada in 2001.From 2001to 2003,she worked as a postdoctoral fellow with Prof.Furstoss in Biocatalysis and Fine Chemistry at the Universite´de la Me ´diterrane ´e (France),and participated in European projects from IV and V Framework Programmes.In 2004,she joined the Group of Bioinspired Materials at the ICMM-CSIC in Spain and became a tenured scientist in 2009.Her research interest is the development of New Routes for Preparation of Hierarchical and Multifunctional Materials for Applications in Biotechnology and Biomedicine.Francisco del Monte is a Scientist at the Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC)in Spain.He received a BSc degree in organic chemistry in 1991,an MSc degree in polymer science in 1992,and a PhD in chemistry in 1996.He then spent two years as a post-doctoral fellow at the University of Los Angeles ,California.Since 2004,he leads the Group of Bioinspired Materials at the ICMM-CSIC.His current scientific interest is the use of biomimetic chemistry and deep eutectic solvents for the preparation of hierarchically organized materials.Review ArticleChem Soc RevP u b l i s h e d o n 16 N o v e m b e r 2012. D o w n l o a d e d b y U n i v e r s i t y o f S c i e n c e a n d T e c h n o l o g y o f C h i n a o n 01/10/2013 09:10:35.sheets 35or textiles containing nanotube-fiber capacitors woven in orthogonal directions,36among others.37Eventually,3D sieve architectures have also been constructed,38although the length of the third dimension of the regular patterned cavities is typically limited to that of some few CNTs,39,40except for those composites where the CNT fraction is minor.41The valuable contribution of these works to different applications has been highlighted in recent reviews 42–48and,for this reason,will not be the subject of this review either.Chemical vapor deposition (CVD)techniques have been recently used to prepare 3D structures composed of freestanding films of vertically aligned carbon nanotubes.49Considering the valuable contribution of these 3D structures to different applications,50it is our belief that ‘‘true’’3D architectures—in which the third dimen-sion is within the range of the other two—produced by chemical routes could exhibit interesting properties (e.g.in terms of both electrical conductivity and mechanical properties)for industrial applications.This belief is actually corroborated by the increased number of works dealing with CNT-based 3D architectures pub-lished within the last two years;i.e.ca.65%of the works revised herein correspond to the 2011–2012period.The main reason behind this tremendous activity is that,as a general trend for any catalytic application,the performance of any device based on CNTs can experience a significant enhancement by the use of 3D architectures rather than 2D ones because of the obvious increase of active material in the former case.Hydrogels,organogels,and aerogels based on silica or carbon and consisting of micro-,meso-and even macroporous networks forming a hierarchical structure that guaranties molecular transport throughout the entire 3D architecture to gain access to the internal reactive surface are illustrative examples of 3D macroscopic assemblies corroborating this issue.19–25Thus,the aim of this review with regard to CNTs will be to summarize those self-assembling processes described to date that have been capable of building ‘‘true’’3D hierarchical macro-structures and have explored those applications where silica and carbon monoliths have already proved efficient (e.g.membranes and columns for water treatment and chromatographic separa-tions,electrodes for supercapacitors,fuel cells and batteries,and catalytic substrates,among others).1.1Organogels and aerogels from CNT suspensionsThe organic functionalization of either SWCNTs or MWCNTs with an organogelator can result in the formation of freestanding CNT organogels.For instance,SWCNTs functionalized by ferrocene-grafted poly(p -phenyleneethynylene)can gelate common organic solvents such as chloroform to form robust 3D nanotube networks that cannot be re-dispersed in any organic solvent.51Thermally annealed CNT aerogels were mechanically stable and stiff(Fig.1),highly porous (99%),and exhibited excellent electrical conductivity (ca.1–2S cm À1)and large specific surface area (590–680m 2g À1).52Moreover,Fmoc-protected-amino-acid-based (Fmoc-Phe-OH,where Fmoc stands for N -fluorenyl-9-methoxycarbonyl and Phe for Phenyl-alanine)hydrogels have also been used to incorporate and disperse SWCNT within the gel phase at physiological pH and temperature.53The resulting hydrogels exhibited an intriguing 1D alignment of SWCNTs on the surface of the gel nanofibers that enhanced theelastic properties as well as the thermal stability,and provided a notorious electrical conductivity of 3.1S cm À1to the resulting hydrogels.Meanwhile,the presence of functional groups on MWCNTs that remained available after gelation allowed the conjugation of the properties of gels and nanostructured car-bon materials.54The benefits of using organogelators were therefore multiple considering that,besides inducing gelation and conferring additional properties to the resulting gels,functionalization helps for CNT dispersion at the solution stage and hence,to the achievement of a homogeneous distribution of CNT throughout the resulting gel.Within the context of monomers and polymers,Zhang et al.demonstrated that embedding either MWCNTs or acid-treated MWCNTs into a poly(3,4-ethylenedioxythiophene)–poly(styrene-sulfonate)(PEDOT–PSS)aerogel matrix can significantly enhance the specific surface areas (280–400m 2g À1)of the resulting compo-site aerogels while maintaining good thermal stability and electrical conductivities (1.2–6.9Â10À2S cm À1).55Poly (3-(trimethoxysilyl)propylmethacrylate)(PTMSPMA)can also be used to disperse and functionalize MWCNTs.In this case,strong and permanent chemical bonding between percolated MWCNTs in the resulting free-standing monolithic aerogel was obtained upon the hydrolysis and condensation of PTMSPMA.The entangled MWCNTs generated mesoporous structures on the honeycomb walls,creating aerogels with a surface area of 580m 2g À1(nearly 2-fold the surface area of pristine MWCNTs),remarkable elastic properties and good electrical conductivity (e.g.up to 0.67S cm À1).All these features determined the exceptional pressure and chemical vapor sensing capabilities of these aerogels.56Surfactants have also been used for dispersion of CNT and subsequent formation of aerogels.For instance,Ostojic solubilized SWCNTs in 1%w/v sodium dodecyl sulphate (SDS)aqueous solution.Streptavidin phosphate and DNA complexes were there-after used for SDS replacement and so induce SWCNT gelation.Ethanol and ethanol–water solvent exchange and subsequent critical-point-drying resulted in the formation of SWCNT aerogels exhibiting a previously unobserved peak at 1.3eV in the photo-luminescence spectrum that corresponds to a phonon-assisted recombination of photoexcited charges.57In another interesting example,Yodh and coworkers suspended different concentrations of as-received CNTs (e.g.weight fractions ranging from 5to 13mg mL À1)in water with sodium dodecylbenzene sulfonate.58The suspensions were left overnight to set into elastic gels thatwereFig.1Picture of SWCNT aerogels weighing 17.4mg (density:9.8mg mL À1)before (a),during (b)and after (c)application of a 20g weight.Monoliths were obtained from SWCNTs functionalized with ferrocene-graftedpoly(p -phenyleneethynylene).(Reproduced with permission from ref.52.Copyright (2011)Elsevier Publishing Group).Chem Soc RevReview ArticleP u b l i s h e d o n 16 N o v e m b e r 2012. D o w n l o a d e d b y U n i v e r s i t y o f S c i e n c e a n d T e c h n o l o g y o f C h i n a o n 01/10/2013 09:10:35.subsequently soaked at 901C in aqueous solutions of polyvinyl alcohol (PVA)for structural reinforcement.Reinforced and non-reinforced gels were thereafter submitted to either freeze-or critical-point-drying processes for the achievement of the aero-gel structure.PVA-reinforced aerogels exhibited outstanding mechanical properties (for instance,they were able to hold 8000times their weight,Fig.2)whereas much better conductiv-ities were found for non-reinforced ones (e.g.0.6S cm À1for non-reinforced versus ca.10À5S cm À1for reinforced ones).More recently,Islam and coworkers,using a similar approach in which they substituted PVA by polydimethylsiloxane (PDMS),produced transparent (ca.93%of transmittance for a 3m m-thick aerogel)and stretchable conductors,the electrical conductivity of which (ranging 0.7–1.1S cm À1)remained basically the same under high bending strain.59Transparent SWCNT aerogels can also be obtained using silica as binder (Fig.3a).In this case,SWCNTs were dispersed in water using SDS or sodium deoxy-cholate and then reacted with a silica precursor like TMOS either by a chemical vapor-into-liquid sol–gel process—in which the low boiling point of TMOS allows vapours diffusion through the SWCNT aqueous suspension—or by a regular liquid-phase sol–gel process—in which small aliquots of TMOS are added into the SWCNT aqueous suspension.60After CO 2supercritical drying,the resulting solution-free and surfactant-free SWCNT-silica aerogels provided access to new photophysical properties of SWCNT and hence,converted this solid-state nanomaterial into not only an ideal system for making fundamental optical measurements,but also a novel and suitable platform for the development of applications in sensing,photonics,and opto-electronics in the near future (Fig.3b–d).Within the context of dispersing CNTs in aqueous solutions that also contain a certain molecular precursor in charge of building up the 3D architecture where the CNT will be finally immobilized,the sol–gel polymerization of resorcinol andformaldehyde offers interesting perspectives.For instance,Baumann and coworkers have recently performed a quite extensive and stimulating work on SWCNTs and DWCNTs 3D architectures synthesized by resorcinol–formaldehyde polycondensation.By intro-ducing low concentrations of the sol–gel precursors to a suspension of highly purified SWCNTs,the polymerization was primarily induced on the walls of the CNT bundles and,more importantly,at the junctions between adjacent bundles to form an organic binder.The resulting assembly was dried and subsequently pyrolyzed to convert the organic binder into carbon.61TheaerogelsFig.2(a)Picture of SWCNT aerogels (density:7.5mg mL À1)non-reinforced (left,black coloured)and reinforced (right,gray coloured)with 1wt%PVA.(b)Three PVA-reinforced aerogel monoliths (total mass =13.0mg)supporting 100g (ca.8000times their weight).(c)SEM micrograph revealing themacroporus architecture of PVA-reinforced aerogel (0.5wt%PVA,10mg mL À1CNT content).(d)TEM micrograph of non-reinforced CNT aerogel.(Reproduced with permission from ref.58.Copyright (2007)Wiley-VCH).Fig.3(a)Picture of aerogels without (blank)and with SWCNTs.(b)PL spectrum of aerogels exposed to CO 2,THF,and ether vapors.The PL spectrum of non-exposed (e.g.in vacuum)is also included for comparison.(c)Shift in PL emission wavelength relative to the signal collected under vacuum as a function of SWCNT diameter after exposure of SWNT-aerogels to air (green square),CO 2(red dots),THF (blue triangle),and ether (yellow star).(d)Emission wavelength shifts for SWCNTs with different diameter after alternating exposure to ether and vacuum:(9,5)light blue squares;(7,6)red dots;(7,5)green triangle;and (8,3)blue triangle.(Adapted with permission from ref.60.Copyright (2011)American Chemical Society).Review Article Chem Soc RevP u b l i s h e d o n 16 N o v e m b e r 2012. D o w n l o a d e d b y U n i v e r s i t y o f S c i e n c e a n d T e c h n o l o g y o f C h i n a o n 01/10/2013 09:10:35.could be also prepared with varying SWCNT loading (0–55wt%).62At nanotube loadings of 55wt%,shrinkage of the aerogel monoliths during carbonization and drying was almost completely eliminated and the electrical conductivities improved by an order of magnitude as compared to those of foams without SWCNTs.Particularly interesting in terms of conductivity (up to 8S cm À1)and surface area (above 500m 2g À1)were those composites based on DWCNTs.63Interestingly,the porous network of these architectures can be surface decorated with oxide coatings (Fig.4).64In this case,sol–gel deposition of SiO 2,SnO 2or TiO 2produced a conformal overlayer on the primary ligament structure of the SWCNT-based support,thus preserving open porosity within the monolithic part.The result-ing aerogels (SWCNT-CA)exhibited good electrical conductivity (up to 1S cm À1)and an enhancement in the mechanical properties relative to the uncoated SWCNT-CA support that should prove advantageous for a number of applications,such as battery electrodes,sensing devices,and catalysts.Morerecently,Gutie´rrez et al.have studied the polycondensation of not only resorcinol and formaldehyde 65but also furfuryl alco-hol 66in deep eutectic solvents (DES)because of their capability to homogeneously disperse high amounts of CNTs.In the furfuryl alcohol case,the presence of DES induced the formation of monolithic carbons with a bimodal porosity that comprises from micro-up to macropores.The morphology of the resulting carbons (C FA ,without CNTs)consisted of a bicontinuous porous network built of highly cross-linked clusters that aggregated and assembled into a stiff,interconnected structure (Fig.5).This sortof morphology is typical of carbons obtained via spinodal decomposition processes where the formation of a rich-polymer phase by polycondensation is accompanied by the segregation of the non-condensed matter (creating first a poor-polymer phase that,ultimately,becomes a depleted-polymer phase),the elimina-tion of which (either before carbonization by washing or during carbonization by thermal decomposition)results in the formation of the above-mentioned bicontinuous porous structure.67In this particular case,furfuryl alcohol condensated on the walls of the MWCNTs so that the resulting bicontinuous porous network resembled a skeleton network composed of interconnected MWCNTs ‘‘glued’’by the carbon resulting from the furfuryl alcohol condensation and pyrolysis (C FACNT ).The presence of a carbon shell that coated every MWCNT and formed strong junctions between them was reflected in both the electrical conductivity (up to 4.8S cm À1,as measured by the four-probe method)and the elastic character (Young’s modulus,11MPa)of the monoliths having the largest MWCNT content.The combi-nation of high electrical conductivity,hierarchical structure and pseudo elastic properties contributed to retain 75%of theinitialFig.4SEM images of (a and b)as-synthesized and (c and d)annealed at 3201C TiO 2/SWCNT-CA composites at low and high magnifications.TEM images of annealed (e and f)TiO 2–SWCNT-CA composites at low and high magnifications.Inset in (f)is the electron diffraction pattern of the annealed TiO 2/SWCNT-CA.(Reproduced with permission from ref.64.Copyright (2011)American ChemicalSociety).Fig.5SEM micrographs of C FA (a,b and c),C FACNT1(d)and C FACNT5(f,h and i).TEM micrographs of colloidal carbon corresponding to C FA and C FACNT1(c),and fibrillar carbon corresponding to C FACNT1and C FACNT5(e and g).(Reproduced with permission from ref.66.Copyright (2011)Wiley-VCH).Chem Soc Rev Review ArticleP u b l i s h e d o n 16 N o v e m b e r 2012. D o w n l o a d e d b y U n i v e r s i t y o f S c i e n c e a n d T e c h n o l o g y o f C h i n a o n 01/10/2013 09:10:35.capacitance at current densities of up to 765mA cm À2(29A g À1)when two of these monoliths (each monolith was 1.2cm in diameter and 1.1mm in height,and weighed 17mg)were assembled into a supercapacitor cell.It is also worth noting those works using polymers that can play an ‘‘all-in-one’’role as both dispersing agents helping to the achievement of homogeneous aqueous suspensions of CNT and structural binders holding the 3D architecture formed after any sort of processing (e.g.freeze-drying,electrospun,etc.).For instance,Tasis and coworkers used PVA as a dispersing-aid agent of KMnO 4-treated MWCNTs in water.The application of flash freezing to the MWCNT/PVA aqueous suspension (e.g.in liquid nitrogen)and subsequent freeze-drying resulted in MWCNT aerogels that exhibited interesting thermal and cata-lytic properties as well as absorption capacity of polynuclear aromatic substances.68This ‘‘all-in-one’’approach can be further extended upon the use of different polymers.For instance,del Monte and coworkers used chitosan for disper-sing HNO 3-treated MWCNTs (up to 8wt%)in water.69MWCNT aerogels were obtained upon the application of the ISISA (ice segregation induced self-assembly)process that basically con-sists of a unidirectional freezing of the sample (e.g.by dipping it into a nitrogen liquid bath at a constant rate)followed by freeze-drying.70In this case,unidirectional freezing allowed the achievement of macroporous structures with well-aligned micro-channels in the freezing direction and a well-patterned morphol-ogy between channels (mellar and microhoneycomb,respectively)(Fig.6).These ultralightweight aerogels (specific gravity ranging from 4.9Â10À2to 9.4Â10À2along with the MWCNT content)exhibited remarkable electrical conductivities of up to 2.5S cm À1for those aerogels composed of 89wt%MWCNTs and 11wt%CHI.Interestingly,the aerogel structure could be reinforced upon exposure to glutaraldehyde vapors without detri-mental effects on either the morphology or the electrical con-ductivity.71These features allowed the use of these aerogels as high-perfomance 3D electrodes in both direct methanol and microbial fuel cells (DMFCs and MFCs,respectively).69,72Particularly interesting was the microchanneled structure in this latter case,allowing the possibility to work in the ‘‘flow-through’’mode so that bacteria could colonize the entire internal structure of cylindrical aerogels of ca.4mm in diameter and 12mm in height (Fig.7)that,otherwise (e.g.in static conditions),was not possible.73The validity of these aerogels to work as high-perfo-mance 3D electrodes under ‘‘flow-through’’conditions was not only demonstrated in MFCs,but also for electrodeposition of a layer of calcium–phosphate salts homogenously distributed throughout the entire internal surface of the aerogels.Interest-ingly,the crystal habit of the deposited mineral was easily controlled by the electrodeposition conditions (Fig.8).74It is worth noting that,as in the previous case,homogeneous coatings were not attained upon chemical mineralization carried out under non-flow conditions.71More recently,the same group has explored the capability of different polysaccharides (e.g.chondroi-tin sulphate)and protein-like polymers (e.g.gelatin)for the preparation of analogue MWCNT aerogels.75The authors have also explored the potential application of these MWCNT aerogels as scaffolds for tissue engineering purposes.71,74–761.2.CNT-surface modified aerogelsCNT functionalization of the internal surface of preformed aerogels has recently gained increased interest because it offers a tremendous versatility considering the existing palette of 3D architectures that may be suitable for this purpose.For instance,Petrov and coworkers reported on the ice-mediated deposition of individual CNTs onto the inner surface of a pre-formed macroporous polymer cryogel.77Fig.6SEM micrographs of MWCNT scaffolds:(a)cross-section view,(b)longitudinal view according to plane 1and (c)longitudinal view according to plane 2.Bars are 200m m in every case.(Reproduced with permission from ref.74.Copyright (2012)Wiley-VCH).Fig.7SEM images (a–c)of biofilm at different magnifications taken from the inner part of the 3D scaffold.(Adapted with permission from ref.72.Copyright (2011)Royal Society of Chemistry).Review ArticleChem Soc RevP u b l i s h e d o n 16 N o v e m b e r 2012. D o w n l o a d e d b y U n i v e r s i t y o f S c i e n c e a n d T e c h n o l o g y o f C h i n a o n 01/10/2013 09:10:35.。

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Title: Understanding Chemical Physics Letters Journal and Its CategorizationIntroduction:In the realm of scientific research, academic journals play a pivotal role in disseminating knowledge and driving progress in various disciplines. Researchers and scholars often strive to publish their work in reputable journals, respected within their respective fields. Chemical Physics Letters is a prominent journal catering to the interdisciplinary niche of chemical physics. This article aims to provide a comprehensive explanation of Chemical Physics Letters, its significance, and its categorization within the scientific community.1. Chemical Physics Letters: An OverviewChemical Physics Letters (CPL) is an esteemed scientific journal that publishes groundbreaking research in the field of chemical physics. Founded in 1970, CPL has been instrumental in promotinginterdisciplinary research encompassing both chemistry and physics. It serves as a platform for scientists to share their discoveries, theories, and experimental data, facilitating collaboration and advancement in the field.2. Scope and Content:CPL focuses on a wide range of topics, including molecular dynamics, spectroscopy, quantum chemistry, computational chemistry, chemical kinetics, and surface science. The journal welcomes contributions that highlight the interface between chemistry and physics, encouraging scientists to explore novel approaches towards understanding chemical phenomena using physical principles.3. Editorial Process and Peer Review:Chemical Physics Letters adopts a rigorous peer-review process to ensure that publications meet high scientific standards. After submission, manuscripts undergo a thorough evaluation by subject matter experts, who scrutinize the quality, significance, and originality of the research. This critical appraisal helps maintain the journal's credibility by identifying flaws, suggesting revisions, and selecting the most cutting-edge research for publication.4. Impact Factor and Reputation:The impact factor (IF) is a widely used metric to assess the influence and relevance of academic journals. It quantifies the average number of citations received by articles published in a particular journal over a specific period. Chemical Physics Letters consistently achieves an excellent impact factor, implying that the research published within its pages garners substantial attention from the scientific community. A high IF reflects the journal's reputation and the significance of the research it showcases.5. Categorization and Ranking:To facilitate better navigation for researchers, academic journals are categorized, often referred to as journal indexing. Chemical Physics Letters falls into the Chemical Physics category, marking its specialization as a journal bridging the gap between chemistry and physics. Within this category, CPL has established itself as one of the leading publications, displaying a consistently impressive impact factor and attracting high-quality research submissions.6. Practical Implications:The categorization and reputation of Chemical Physics Letters holdpractical implications for researchers in the field of chemical physics. By submitting their research to CPL, scientists have the opportunity to gain exposure, reach a wide audience, and receive constructive feedback from experts in the field. Additionally, publications within Chemical Physics Letters can enhance researchers' academic credentials, contributing to career development and the potential for future collaborations.Conclusion:Chemical Physics Letters' consistent publication of cutting-edge research, interdisciplinary focus, and high impact factor make it a sought-after platform for researchers in the field of chemical physics. By bridging the gap between chemistry and physics, CPL facilitates the advancement of knowledge and fosters collaboration. Its categorization within the Chemical Physics index confirms its prominence and relevance within the scientific community. As research continues to push boundaries, Chemical Physics Letters is likely to maintain its pivotal role as a platform for groundbreaking discoveries and innovative ideas in the field.。

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刊名简称刊名全称ISSN PLOS PATHOG PLoS Pathogens1553-7366 REV MED VIROL REVIEWS IN MEDICAL VIROLOGY1052-9276 ADV VIRUS RES ADVANCES IN VIRUS RESEARCH0065-3527 AIDS AIDS0269-9370 ANTIVIR THER ANTIVIRAL THERAPY1359-6535 J VIROL JOURNAL OF VIROLOGY0022-538X RETROVIROLOGY Retrovirology 1742-4690 ANTIVIR RES ANTIVIRAL RESEARCH0166-3542 INFLUENZA OTHER RESP Influenza and Other Respiratory Viruses1750-2640 INT J MED MICROBIOL INTERNATIONAL JOURNAL OF MEDICAL MICROBIOLOGY1438-4221 J CLIN VIROL JOURNAL OF CLINICAL VIROLOGY1386-6532 J GEN VIROL JOURNAL OF GENERAL VIROLOGY0022-1317 J MED VIROL JOURNAL OF MEDICAL VIROLOGY0146-6615 J VIRAL HEPATITIS JOURNAL OF VIRAL HEPATITIS1352-0504 MICROBES INFECT MICROBES AND INFECTION1286-4579 VIROLOGY VIROLOGY0042-6822 ACTA VIROL ACTA VIROLOGICA0001-723X AIDS RES HUM RETROV AIDS RESEARCH AND HUMAN RETROVIRUSES0889-2229 ARCH VIROL ARCHIVES OF VIROLOGY0304-8608 CURR HIV RES CURRENT HIV RESEARCH1570-162X FOOD ENVIRON VIROL Food and Environmental Virology1867-0334 FUTURE 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