Reevaluating electron-phonon coupling strengths Indium as a test case for ab initio and man

Liang Guo Stephen L.Hodson Timothy S.FisherXianfan Xu1e-mail:xxu@ School of Mechanical Engineering and Birck Nanotechnology Center,Purdue University,West Lafayette,IN47907Heat Transfer AcrossMetal-Dielectric Interfaces During Ultrafast-Laser Heating Heat transfer across metal-dielectric interfaces involves transport of electrons and pho-nons accomplished either by coupling between phonons in metal and dielectric or by cou-pling between electrons in metal and phonons in dielectric.In this work,we investigate heat transfer across metal-dielectric interfaces during ultrafast-laser heating of thin metalfilms coated on dielectric substrates.By employing ultrafast-laser heating that cre-ates strong thermal nonequilibrium between electrons and phonons in metal,it is possible to isolate the effect of the direct electron–phonon coupling across the interface and thus facilitate its study.Transient thermo-reflectance measurements using femtosecond laser pulses are performed on Au–Si samples while the simulation results based on a two-temperature model are compared with the measured data.A contact resistance between electrons in Au and phonons in Si represents the coupling strength of the direct electron–phonon interactions at the interface.Our results reveal that this contact resist-ance can be sufficiently small to indicate strong direct coupling between electrons in metal and phonons in dielectric.[DOI:10.1115/1.4005255]Keywords:interface thermal resistance,ultrafast laser,thermo-reflectance,two-temper-ature model,electron–phonon coupling1IntroductionInterface heat transfer is one of the major concerns in the design of microscale and nanoscale devices.In metal,electrons,and pho-nons are both energy carriers while in dielectric phonons are the main energy carrier.Therefore,for metal-dielectric composite structures,heat can transfer across the interface by coupling between phonons in metal and dielectric or by coupling between electrons in metal and phonons in dielectric through electron-interface scattering.Phonon–phonon coupling has been simulated mainly by the acoustic mismatch model and the diffuse mismatch model[1].As for electron–phonon coupling,there are different viewpoints.Some studies have assumed that electron–phonon coupling across a metal-dielectric interface is negligible and heat transfer occurs as electron–phonon coupling within metal and then phonon–phonon coupling across the interface[2].Electron–phonon coupling between metal(Cr,Ti,Al,Ni,and Pt)and SiO2 has exhibited negligible apparent thermal resistance using a parallel-strip technique[3].On the other hand,comparison between simulations and transient thermal reflectance(TTR) measurements for Au-dielectric interfaces reveals that energy could be lost to the substrate by electron-interface scattering dur-ing ultrafast-laser heating,and this effect depends on electron temperature and substrate thermal properties[4–6].In this study,we employ TTR techniques to investigate inter-face heat transfer for thin goldfilms of varying thicknesses on sili-con substrates.(Here,we consider silicon as a dielectric since heat is carried by phonons in silicon.)Similar work has been reported [5].In our model,we consider two temperatures in metal and also the temperature in the dielectric substrate.This allows us to inves-tigate the effect of both the coupling between electrons in metal and phonons in the dielectric substrate,and the coupling between phonons in metal and phonons in the dielectric substrate,and allows us to isolate the effect of the electron–phonon coupling across the interface that can be determined from the TTR mea-surement.Experimentally,we employ pulse stretching to mini-mize the effect of nonequilibrium among the electrons.As a result,the experimental data can be well-explained using the com-putational model.The thermal resistance between electrons in Au and phonons in Si,which quantifies the direct electron–phonon coupling strength,is calculated from the measured data.The results reveal that in the thermal nonequilibrium state,this electron–phonon coupling at the interface is strong enough to dominate the overall interface heat transfer.2TTR MeasurementAu–Si samples of varying Au thicknesses were prepared by thermal evaporation at a pressure of the order of10À7Torr.The thicknesses of the goldfilms are39,46,60,77,and250nm,meas-ured using an atomic force microscope.The pump-and-probe technique is used in a collinear scheme to measure the thermo-reflectance signal.The laser pulses are generated by a Spectra Physics Ti:Sapphire amplified femtosecond system with a central wavelength of800nm and a repetition rate of5kHz.The wave-length of the pump beam is then converted to400nm with a sec-ond harmonic crystal.The pump pulse has a pulse width(full width at half maximum-FWHM)of390fs measured by the sum-frequency cross-correlation method and is focused onto the sam-ple with a spot radius of20.3l m.The probe beam has a central wavelength of800nm and a pulse width of205fs measured by autocorrelation and is focused with a spot radius of16.9l m.This pump pulse width is intentionally stretched from the original pulse width of50fs to minimize the influence of thermal nonequili-brium among electrons since the electron thermalization time in Au can be of the order of100fs[7].This thermalization time is pump wavelength and pumpfluence dependent,and can be of the order of10fs if higher laserfluence is used[8,9].Our experiments did show the importance of pulse stretching.Figure1shows the TTR measurement results for the sample of thickness77nm with different pumpfluences before and after stretching the pulse.The plots show the normalized relative reflectance change(ÀD R/R)1Corresponding author.Contributed by the Heat Transfer Division of ASME for publication in the J OURNAL OF H EAT T RANSFER.Manuscript received May18,2011;final manuscript received September30,2011;published online February13,2012.Assoc.Editor: Robert D.Tzou.with the delay time between the pump and the probe pulses to show the contrast in cooling rates.With a shorter pulse (Fig.1(a )),a steep initial drop is seen in the signal,which is attributed to the behavior of nonequilibrium among electrons.Since the TTM to be used for simulation assumes a well-defined tempera-ture for electrons,i.e.,the electrons in gold have reached thermal equilibrium (not necessarily a uniform temperature),the model cannot predict the fast initial drop in the signals in Fig.1(a ).As will be shown later,the signals obtained by stretching the pulse can be predicted well using the TTM.3Two-Temperature Model for Thermal Reflectance MeasurementsUltrafast-laser heating induces thermal nonequilibrium between electrons and phonons in metal,which can be described by the TTM [10–13].We note that the heterogeneous interface consid-ered here involves three primary temperature variables (two in the metal and one in the dielectric).The “two-temperature”model is applied to the metal side.For investigating electron–phonon and phonon–phonon coupling at the interface,two thermal resistances are defined:R es (its reciprocal)indicates the coupling strength between electrons in metal and phonons in dielectric,while R ps indicates the coupling strength between phonons in metal and phonons in dielectric.(Large thermal resistance corresponds to weak coupling.)The resulting governing equations,initial,and interface conditions areC e @T e @t ¼k e @2T e@x2ÀG ðT e ÀT p ÞþS (1a )C p @T p @t ¼k p @2T p @x 2þG ðT e ÀT p Þ(1b )C s @T s @t ¼k s @2T s@x(1c )T e ðt ¼0Þ¼T p ðt ¼0Þ¼T s ðt ¼0Þ¼T 0(2)Àk e@T e @xx ¼L ¼T e ÀT s R es x ¼L(3a )Àk p @T px ¼L ¼T p ÀT s ps x ¼L(3b )Àk s@T sx ¼L ¼T e ÀT s es x ¼L þT p ÀT s ps x ¼L(3c )The subscripts e ,p ,and s denote electrons in metal,phonons in metal,and phonons in the dielectric substrate,respectively.C is the volumetric heat capacity,k is the thermal conductivity,G is the electron–phonon coupling factor governing the rate of energy transfer from electrons to phonons in metal,and L is the thickness of the metal layer.At the front surface of the metal layer insula-tion boundary condition is used due to the much larger heat flux caused by laser heating relative to the heat loss to air.At the rear surface of the substrate,since the thickness of the substrate used is large enough (1l m)so that there is no temperature rise during the time period of consideration,the insulation boundary condition is also applied.Thermal properties of phonons in both metal and dielectric are taken as temperature-independent due to the weak temperature dependence.The thermal conductivity of phonons in metal is much smaller than that of the electrons and is taken in this work as 0.001times the bulk thermal conductivity of gold (311W/(mK)).The volumetric heat capacity of the metal phonon is taken as that of the bulk gold.C e is taken as proportional to T e [14]with the proportion coefficient being 70J/(m 3K 2)[15],and k e is calculated by the model and the data used in Ref.[13]which is valid from the room temperature to the Fermi temperature (6.39Â104K in Au,[14]).G can be obtained using the model derived in Ref.[16].In this work,the value of G at the room tem-perature is taken as 4.6Â1016W/(m 3K)[17],and its dependence on electron and phonon temperatures follows [16].The laser heat-ing source term S is represented by the model used in [13]asS ¼0:94ð1ÀR ÞJ t p ðd þd b Þ1Àexp ÀL d þd bexp Àx d þd b À2:77t t p2"#(4)which assumes all the absorbed laser energy is deposited in the metal layer.J is the fluence of the pump laser,R is the surface re-flectance to the pump,t p is the pulse width (FWHM),d is the opti-cal penetration depth,and d b is the electron ballistic length (around 100nm in Au,[18]).R es and R ps are treated as free pa-rameters for fitting the experimental data.The wavelength of the probe laser in the experiment is centered at 800nm.For this wavelength,the incident photon energy is below the interband transition threshold in Au,which is around 2.47eV [18],and the Drude model can be used to relate the tem-peratures of electrons and phonons to the dielectric function and then the index of refraction,which is expressed as [19]e ¼e 1Àx 2px ðx þi x s Þ(5)x is the frequency of the probe laser and x p is the plasma fre-quency (1.37Â1016rad/s in Au evaluated using the data in Ref.[14]).x s is the electron collisional frequency,the inverse of the electron relaxation time.The temperature dependence ofelectricalFig.1TTR measurement results for the Au–Si sample of Authickness 77nm with different fluences.(a )Results before pulse stretching;(b )results after pulse stretching.resistivity indicates that x s is approximately proportional to pho-non temperature at high temperature [14]and from the Fermi liq-uid theory,its variation with electron temperature is quadratic (T e 2)[20].Therefore,x s is related to T e and T p approximately asx s ¼A ee T 2e þB ep T p(6)A ee is estimated from the low-temperature measurement [21]andB ep is usually estimated from the thermal or electrical resistivity near the room temperature [14].In this work,A ee is taken as the lit-erature value 1.2Â107s À1K À2[6]while e 1and B ep are evaluated by fitting the room-temperature value of the complex dielectric con-stant at 800nm wavelength provided in Ref.[22],which are found to be 9.7and 3.6Â1011s À1K À1,respectively.The complex index of refraction n 0þin 00is the square root of the dielectric ing Eqs.(5)and (6),n 0and n 00are evaluated as 0.16and 4.90,respectively,which agree with the empirical values [23].The re-flectance is then calculated from n 0and n 00by the method of transfer matrix [24],which considers multiple reflections in thin films.4Results and DiscussionThe results of TTR measurements with a pump fluence of 147J/m 2are plotted in Fig.2.The fast decrease of the reflectance indicates that energy transfer between electrons and phonons in metal,followed by a relatively slow decrease after several ps which indicates electrons and phonons have reached thermal equi-librium.The initial cooling rates are smaller for samples with thicknesses less than the electron ballistic length since the electron temperature is almost uniform across the thin film,and coupling with phonons within the metal film and the dielectric substrate is the only cooling mechanism.For a thicker sample of thickness 250nm,the initial decrease is much faster due to thermal diffu-sion in the gold film caused by a gradient of the electron tempera-ture in the film.We investigate the effect of R es and R ps using the thermo-reflectance signal.Two values of R ps ,1Â10À10m 2K/W and 1Â10À7m 2K/W,are used,each with a parameterized range of values for R es .Figure 3shows the calculated results for the sample with a 39nm-thick gold film.Little difference can be seen between Figs.3(a )and 3(b )while different cooling rates are obtained with varying R es in either plot,indicating that the cooling rate is not sensitive to the coupling strength between phonons in metal and dielectric.Note that an interface resistance of 1Â10À10m 2K/W is lower than any reported value,indicating a very high coupling strength between the phonons in metal and dielectric.Conversely,the results vary greatly with the coupling strength between electrons in metal and phonons in dielectric at the interface.This is because the lattice (phonon)temperature rise in metal is much smaller than the elec-tron temperature that the interface coupling between phonons in metal and dielectric does not influence the surface temperature,which directly determines the measured reflectance.On the other hand,the temperature rise of electrons is much higher,and conse-quently,the cooling rate is sensitive to R es .The relatively high sensitivity of R es to that of R ps demonstrates that the former can be isolated for the study of the coupling between electrons in metal and phonons in dielectric.We now use the measured TTR data to estimate R es ,the thermal resistance between electrons in metal and phonons in dielectric.R es is adjusted by the least square method to fit the simulation results with the measured data,and the results are shown in Fig.4.We note that it is impossible to fit the measured results using insu-lation interface condition (i.e.,no coupling or extremely large thermal resistance between electrons in metal and phonons in the dielectric substrate),which will significantly underestimate the cooling rate.For thin samples,we find that the value of R es is of the order of 10À10to 10À9m 2K/W.This value is below the ther-mal resistances of representative solid–solid interfaces measured in thermal equilibrium [25].This indicates that the direct coupling between electrons in metal and phonons in dielectric is strong.It is also noted that the resistance values increases with the thickness of the gold film,indicating a decrease in the coupling strength between electrons in metal and the dielectric substrate.This could be due to the lower electron temperature obtained in thicker films,and a decrease of the coupling strength with a decrease in the electron temperature [5].For the sample of thickness 250nm,R es has little effect on the simulation result since the interface is too far from the absorbing surface to influence the surface tempera-ture,and therefore it is not presented here.The agreement between the fitted results and the measured data is generally good.The small discrepancy between the measured and the fitted results can result from inaccuracy in computingtheFig.2TTR measurement results on Au–Si samples of varying AuthicknessesFig.3Simulation results with varying R es for the Au–Si sample of Au thickness 39nm.(a )R ps 51310210m 2K/W;(b )R ps 5131027m 2K/W.absorption or the temperature.Figure 1(b)shows the normalized TTR measurement results on the sample of thickness 77nm with three laser fluences.It is seen that small variations in the shape of the TTR signals can be caused by different laser fluences and thus the maximum temperature reached in the film.Absorption in metal,multiple reflections between the metal surface and the Au–Si inter-face,and possible deviations of the properties of thin films from those of bulk can all contribute to uncertainties in the temperature simulation;therefore affecting the calculated reflectance.With the values of R es shown in Fig.4,the calculation shows that the highest electron temperature,which is at the surface of 39nm–thick gold film,is about 6700K.The highest temperature of electrons is roughly inversely proportional to the thickness of the films for the four thinner films.The highest temperature of elec-trons is much less than the Fermi temperature and thus ensures the validity of the linear dependence of C e on T e [14].The highest temperature for the lattice in metal is about 780K,also in the 39nm-thick gold film.This large temperature difference between electrons and lattice indicates that the interface heat transfer is dominated by the coupling between electrons in metal and the phonons in the dielectric substrate.As shown in Fig.4,the meas-ured R es is very low,of the order of 10À10to 10À9m 2K/W.Even if R ps ,which is not determined in this study,is also that low (note that 10À10to 10À9m 2K/W is lower than any reported values),because of the large difference in temperatures between electrons and the phonons in metal,the interface heat transfer rate (Eqs.(3a )–(3c ))due to the coupling between electrons in metal and the substrate is much larger than that due to the coupling between phonons in metal and the substrate.5ConclusionsIn conclusion,TTR measurements using femtosecond laser pulses are performed on Au–Si samples and the results are analyzed using the TTM model.It is shown that due to the strong nonequilibrium between electrons and phonons during ultrafast-laser heating,it is possible to isolate the effect of the direct electron–phonon coupling across the interface,allowing investiga-tion of its ing stretched femtosecond pulses is shown to be able to minimize the nonequilibrium effect among electrons,and is thus more suitable for this study.The TTR measurement data can be well-represented using the TTM parison between the TTR data and the TTM results indicates that the direct coupling due to electron-interface scattering dominates the interface heat transfer during ultrafast-laser heating of thin films.AcknowledgmentThis paper is based upon work supported by the Defense Advanced Research Projects Agency and SPAWAR Systems Cen-ter,Pacific under Contract No.N66001-09-C-2013.The authors also thank C.Liebig,Y.Wang,and W.Wu for helpful discussions.NomenclatureA ee ¼coefficient in Eq.(6),s À1K À2B ep ¼coefficient in Eq.(6),s À1K À1C ¼volumetric heat capacity,J/(m 3K)G ¼electron–phonon coupling factor,W/(m 3K)i ¼unit of the imaginary number J ¼fluence of the pump,J/m 2k ¼thermal conductivity,W/(mK)L ¼metal film thickness,mn 0¼real part of the complex index of refractionn 00¼imaginary part of the complex index of refraction R ¼interface thermal resistance,m 2K/W;reflectance S ¼laser source term,W/m3Fig.4Comparison between the measurement and the simulation results for Au–Si samples of different Au thicknesses.The open circle represents the meas-ured data and the solid line represents the simulation results.(a )39nm fitted by R es 55310210m 2K/W;(b )46nm fitted by R es 56310210m 2K/W;(c )60nm fitted by R es 51.231029m 2K/W;and (d )77nm fitted by R es 51.831029m 2K/W.T¼temperature,Kt¼time,st p¼pulse width of the pump(FWHM),sx¼spatial coordinate,me¼complex dielectric constante1¼constant in the Drude modeld¼radiation penetration depth,md b¼electron ballistic depth,mx¼angular frequency of the probe,rad/sx p¼plasma frequency,rad/sx s¼electron collisional frequency,rad/sSubscripts0¼initial statee¼electron in metales¼electron in metal and phonon in dielectricp¼phonon in metalps¼phonon in metal and phonon in dielectrics¼phonon in 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专利名称：二甲基噻吩骨架三齿膦配体、其合成方法、其铜配合物及其铜配合物的合成方法和应用
专利类型：发明专利
发明人：柳利,魏琼
申请号：CN201910552283.3
申请日：20190625
公开号：CN110272453A
公开日：
20190924
专利内容由知识产权出版社提供
摘要：本发明属于铜配合物技术领域，具体涉及一种基于二甲基噻吩骨架的三齿膦配体、其合成方法、其铜配合物及其铜配合物的合成方法和应用。

本发明所提供的基于二甲基噻吩骨架的三齿膦配体的单核四配位卤化亚铜配合物可发强烈的黄绿光，热分解温度高，热稳定高，适合作为OLED发光材料。

申请人：湖北大学
地址：430062 湖北省武汉市武昌区友谊大道368号
国籍：CN
代理机构：北京轻创知识产权代理有限公司
代理人：冯瑛琪
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图片简介:本技术涉及一种具有改良溶出速度的组合物，其包含达芦那韦和酸性聚合物形成的盐。

本技术达芦那韦:酸性聚合物盐组合物具有更快的溶出速度和较好的稳定性，该组合物可应用于病毒感染类疾病的治疗，例如获得性免疫缺陷综合征(HIV)、病毒性肝炎、冠状病毒感染。

技术要求1.一种具有改良溶出速度的组合物，其特征在于，包含达芦那韦和酸性聚合物形成的盐。

2.根据权利要求1所述的具有改良溶出速度的组合物，其特征在于，所述达芦那韦在分子水平上分散于所述酸性聚合物中。

3.根据权利要求1所述的具有改良溶出速度的组合物，其特征在于，所述达芦那韦:酸性聚合物盐是无定型分散体，且在至少2个月的加速稳定性试验(40℃，75％相对湿度)中保持无定型态。

4.根据权利要求1所述的具有改良溶出速度的组合物，其特征在于，在溶出试验中，所述达芦那韦:酸性聚合物盐组合物2.5分钟的释放度是对照组合物的至少2倍，所述达芦那韦:酸性聚合物盐组合物达到80％释放度所需的时间比对照组合物缩短至少1倍。

5.根据权利要求4所述的具有改良溶出速度的组合物，其特征在于，所述对照组合物是以下达芦那韦溶剂化物中的一种：达芦那韦乙醇溶剂化物、达芦那韦水合物、达芦那韦甲醇溶剂化物、达芦那韦丙酮溶剂化物、达芦那韦二氯甲烷溶剂化物、达芦那韦乙酸乙酯溶剂化物、达芦那韦1-乙氧基-2-丙醇溶剂化物、达芦那韦苯甲醚溶剂化物、达芦那韦四氢呋喃溶剂化物、达芦那韦异丙醇溶剂化物、达芦那韦甲磺酸溶剂化物。

6.根据权利要求1所述的具有改良溶出速度的组合物，其特征在于，所述达芦那韦:酸性聚合物盐组合物为口服剂型。

7.根据权利要求1所述的具有改良溶出速度的组合物，其特征在于，所述达芦那韦:酸性聚合物盐组合物包含达芦那韦:酸性聚合物的重量比为20:1至1:20，或，所述达芦那韦:酸性聚合物盐组合物包含达芦那韦:酸性聚合物的重量比为10:1至1:10。

8.根据权利要求1所述的具有改良溶出速度的组合物，其特征在于，单剂量中包含酸性聚合物的重量范围为1mg至10g、20mg至1g、20mg至400mg中的一种；单剂量中包含达芦那韦的重量范围为1mg至800mg、20mg至600mg、1mg至200mg、1mg至100mg、1mg至30mg中的一种。

偕胺肟基化合物的合成及表征
本文将对偕胺肟基化合物的合成及表征进行介绍。

偕胺肟基化合物是指具有活性偶氮结构的有机化合物，它们以N-N异构体形式
存在，常备受到医药科学、农药以及苯氧类衍生物的研究和应用。

由于其具有稳定性好，围绕C=N这一共价键合成活性元素组合是一类重要的化学反应，在有机合成中发挥着重要作用。

偕胺肟基化合物的合成有两种方法，一种是通过氢化反应，另一种是通过格氏
外电子环扩散（Grignard reaction）。

在氢化反应中，胺肟会经历还原和氢化机理，它们可以与受氢作用后的羰基相互反应，形成氯化物通过水解还原到直键异构体。

在Grignard reaction中，Grignard试剂可以与胺肟的直接碱水合物发生反应，生成活性偶氮结构，从而获得偕胺肟类化合物。

偕胺肟基化合物表征主要有正核磁共振（NMR）、质谱（mass spectrometry）、X射线衍射（XRD）和电子探针（EPT）等等，其中NMR是用来鉴定一种化合物的杂
化性质，而mass spectrometry可以识别出分子中的元素和分子，从而辨识化合物的结构，同样XRD可以用来判断分子同位异构体的存在，而电子探针可判断不同位置原子间的位置关系。

综上所述，偕胺肟基化合物的合成及表征在医药科学、农药以及苯氧类衍生物
的研究中发挥着重要作用，获得偕胺肟类化合物可以通过氢化反应或格氏外电子环扩散来实现，而用于偕胺肟类化合物表征的主要方法是NMR、mass spectrometry、XRD和EPT。

从微藻中提取β-烟酰胺单核苷酸的方法及微藻提取物下载提示：该文档是本店铺精心编制而成的，希望大家下载后，能够帮助大家解决实际问题。

文档下载后可定制修改，请根据实际需要进行调整和使用，谢谢！本店铺为大家提供各种类型的实用资料，如教育随笔、日记赏析、句子摘抄、古诗大全、经典美文、话题作文、工作总结、词语解析、文案摘录、其他资料等等，想了解不同资料格式和写法，敬请关注！Download tips: This document is carefully compiled by this editor. I hope that after you download it, it can help you solve practical problems. The document can be customized and modified after downloading, please adjust and use it according to actual needs, thank you! In addition, this shop provides you with various types of practical materials, such as educational essays, diary appreciation, sentence excerpts, ancient poems, classic articles, topic composition, work summary, word parsing, copy excerpts, other materials and so on, want to know different data formats and writing methods, please pay attention!从微藻中提取β烟酰胺单核苷酸的方法及微藻提取物1. 引言在当今社会，人们对健康和美容的关注度越来越高。

专利名称：双极性反式类胡萝卜素盐及其应用专利类型：发明专利
发明人：约翰·L·盖纳,雷蒙德·C·格拉别克
申请号：CN03804566.4
申请日：20030225
公开号：CN1671643A
公开日：
20050921
专利内容由知识产权出版社提供
摘要：本发明涉及双极性反式类胡萝卜素盐化合物、该类化合物的增溶方法、合成方法以及使用方法。

这类化合物可用于改善氧在包括人类在内的哺乳动物的血红细胞和机体组织之间的扩散能力。

申请人：扩散药品有限公司
地址：美国弗吉尼亚州
国籍：US
代理机构：北京三友知识产权代理有限公司
代理人：丁香兰
更多信息请下载全文后查看。

徐艺凤，徐承娥，熊海涛. 聚鲁米诺修饰复合电极电化学发光分析法测定豆类样品中钼（Ⅵ）含量[J]. 食品工业科技，2024，45（5）：205−211. doi: 10.13386/j.issn1002-0306.2023030272XU Yifeng, XU Cheng’e, XIONG Haitao. Electrochemiluminescence Determination of Mo(Ⅵ) Content in Beans Based on Polyluminol Composite Modified Electrode[J]. Science and Technology of Food Industry, 2024, 45(5): 205−211. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023030272· 分析检测 ·聚鲁米诺修饰复合电极电化学发光分析法测定豆类样品中钼（Ⅵ）含量徐艺凤，徐承娥，熊海涛*（陕西理工大学化学与环境科学学院，陕西汉中 723001）摘　要：本研究基于Mo （Ⅵ）对鲁米诺电还原发光信号的增敏作用，结合石墨烯与带正电荷的纳米金（（+）AuNPs ）的电信号放大作用，建立了一种灵敏且准确检测豆类种子中Mo （Ⅵ）含量的电化学发光新方法。

采用滴涂法先将Nafion-石墨烯修饰于玻碳电极表面，再通过静电组装及电化学聚合技术依次将（+）AuNPs 、鲁米诺修饰于电极表面，从而制得Nafion-石墨烯/（+）AuNPs/聚鲁米诺复合修饰电极。

通过循环伏安法与电化学发光技术对复合修饰电极进行了初步表征，并对测定Mo （Ⅵ）的实验条件进行了优化。

结果表明，在饱和硼砂缓冲溶液、电位扫描速率100 mV/s 、富集时间13 min 等优化实验条件下，Mo （Ⅵ）浓度在5.0×10−9~1.0×10−6 mol/L 范围内与复合修饰电极表面增敏的电还原发光信号呈现良好的线性关系，检出限（3σ）与相对标准偏差分别为2.1×10−9mol/L 及2.4%（C=1.0×10−7 mol/L ，n=11）。

槲皮素分子印迹聚邻苯二胺敏感膜电化学传感器王微;孙红;赫春香【摘要】以槲皮素为模板分子，邻苯二胺为功能单体，采用循环伏安法制备了槲皮素分子印迹薄膜修饰电极，并将其用于槲皮素的检测.在HAc-NH4Ac缓冲溶液(pH 4.0)中，以微分脉冲伏安法为电化学激发信号，槲皮素在0.37 V(VS.SCE)处产生一个灵敏的氧化峰，峰电流与其浓度在8.00×10-8~1.00×10-3 mol/L 范围内呈线性关系，实验检出限为5.00×10-8 mol/L.将新方法应用于2种银杏叶类药物中槲皮素的测定，回收率在99.2%~102%之间.【期刊名称】《高师理科学刊》【年(卷),期】2012(000)006【总页数】3页(P50-52)【关键词】槲皮素;邻苯二胺;分子印迹膜;微分脉冲伏安法【作者】王微;孙红;赫春香【作者单位】辽宁师范大学化学化工学院,辽宁大连 116029;辽宁师范大学化学化工学院,辽宁大连 116029;辽宁师范大学化学化工学院,辽宁大连 116029【正文语种】中文【中图分类】O657.1槲皮素（Quercetin，Qu）具有多种药用价值，因而在黄酮类化合物中占有重要的地位[1]，其测定方法的研究在鉴定生产原料品质、评价生物制剂工艺以及药代动力学分析等方面具有重要意义.目前，检测槲皮素的方法主要有毛细管电泳法[2]、高效液相色谱法[3]、荧光法[4]和电化学检测方法[5-7].将分子印迹技术应用于传感器的研制是近年来出现的新技术[8].邻苯二胺（o-pheny-lenediamine，OPD）是制备分子印迹电化学传感器常用的功能单体，采用电化学方法可以直接在基体电极表面聚合成带有模板印迹的聚合物[9].这种分子印迹技术不需要交联剂和致孔剂，具有简便、快速的优点.本文以槲皮素为模板分子，邻苯二胺为功能单体，制备了槲皮素分子印迹电化学传感器，并建立了微分脉冲伏安法测定槲皮素的新方法.本方法具有灵敏度高、选择性好、方法简便等优点.LK9805电化学分析仪（天津市兰力科电子科技发展有限公司）；三电极系统：以石墨（SG）、聚邻苯二胺/石墨、槲皮素/邻苯二胺/石墨分子印迹修饰电极为工作电极，饱和甘汞电极为参比电极（文中全部电位均相对于饱和甘汞电极），铂丝电极为辅助电极.槲皮素、芦丁、桑色素、葛根素和山奈酚（由西安天本生物工程有限公司提供，纯度>98%）.除指明外其它化学试剂均为分析纯.实验用水为石英亚沸二次蒸馏水. 1.2.1 分子印迹修饰电极的制备将光谱纯石墨棒制成蜡浸石墨电极（SG），并清洗至洁净[10].以SG为工作电极，含有1.00×10-2 mol/L OPD，4.00×10-4mol/L Qu，0.10 mol/L KCl的混合溶液为修饰剂，在+1.50 ~-1.00 V电位范围内，以0.05 V/s的扫速连续循环伏安扫描30圈.取出电极，用水冲洗，再置于pH 7.0 的磷酸盐缓冲溶液（PBS）中，循环扫描30圈，得到具有槲皮素印迹的聚邻苯二胺石墨修饰电极（MIPCME）.不加入模板分子（槲皮素）制备非分子印迹修饰电极（NIPCME）.1.2.2 槲皮素的测定以MIPCME为工作电极，静置吸附300 s，-0.30 V为起点电位，在-0.30~0.60 V电位范围内记录微分脉冲伏安曲线，根据 0.37 V 处的峰电流进行定量分析.分别以SG，NIPCME，MIPCME为工作电极，测定5 mmol/L K3Fe（CN）6（0.1 mol/L KNO3中）的循环伏安曲线（见图1）.结果表明，K3Fe（CN）6在NIPCME电极上没有电化学响应，在MIPCME上出现氧化还原峰，但是峰电流明显小于其在SG电极上的响应.说明NIPCME是电惰性的，而MIPCME上存在空穴.分别以SG，MIPCME，NIPCME为工作电极，按照实验方法测定5.00×10-5 mol/L槲皮素.结果表明，槲皮素在MIPCME上的峰电流远远大于在SG电极上电流响应（见图2）.分别试验了槲皮素在HAc-NH4Ac（pH 4.00~6.00 ），NH3-NH4Cl（pH8.00~10.00），PBS（pH 4.00~10.00）中的电化学响应.结果表明，以pH 4.0 的HAc -NH4Ac缓冲溶液作为支持电解质时峰电流最大.实验发现，吸附时间对峰电流有明显的影响，最佳吸附时间为300 s.在8.00×10-8~1.00×10-3mol/L范围内，槲皮素的浓度与峰电流呈线性关系，回归方程ip（μA）= 3.14 c（μmol/L）+ 4.33（r=0.998），实验检出限5.00×10-8 mol/L.一支电极平行测定6组同浓度的槲皮素，响应值的相对标准偏差（RSD）为1.2 %；平行制备4支电极，RSD为3.3 %.在允许存在10 % 误差的前提下，桑色素、葛根素和山奈酚不干扰测定.芦丁对本方法有一定的干扰，最大共存量为槲皮素的60倍.此外，实验还表明，测定体系中允许共存300倍的十二烷基磺酸钠，150倍的抗坏血酸，100倍的聚乙烯醇，50倍的草酸和柠檬酸钠.其它常见金属离子均不干扰测定.测定了舒血宁注射液（1#）和银杏叶分散片（2#）中槲皮素的质量分数.银杏叶中黄酮苷的代表成分是槲皮苷、山萘酚苷、芦丁苷和鼠李糖苷[11].据此对药品进行预处理：将试样溶液与 50 mL 0.5 % 的硫酸和45 mL无水乙醇混合，加热回流1 h，冷却，用无水乙醇定容至100 mL.处理后槲皮苷转化成槲皮素，芦丁水解转化成槲皮素，结果见表1，平均回收率（n=3）分别为99.2%，102%.表明此方法适用于实际样品中槲皮素的测定.【相关文献】[1] Luo Yiping.Advances in Pharmacological Research of Flavonoids[J].Asia-Pacific Traditional Medicine，2010（4）：132-134[2] Dadakova E，Kalinova J.Determination of quercetin glycosides and free quercetin in buckwheat by capillary micellar electrokimetic chromatography[J].Journal of Separation Science，2010，33：1633-1638[3] Du FY，Xiao XH.Lonic lipquid aqueous solvent-based microwave-assisted hydrolysis for the extraction and HPLC determination of myricetin and quercetin from Myrica rubra leaves[J].Biomedical Chromatography，2011，25：472-478[4] Chen Daiwu，Xie Qingji.Fluorescent Studies on the Interactions of Quercetin with Aminoacid[J].Chemical Research，2009（4）：78- 81[5] 轩卫华，曹红，龚晓武，等.槲皮素在悬汞电极上的伏安行为研究[J].分析试验室，2011，29（11）：32-35[6] Ziyatdinova G，Aytuganova I，Nizamova A，et al.Cyclic voltammetry of natural flavonoids mwnt-modified electrode and their determination inpharmaceuticals[J].Collection of Czechoslovak chemical communications，2011，76：1619-1631[7] 王明艳，许兴友，马卫兴，等.4-（3-吡啶基）-2-巯基咪唑修饰金电极一阶微分线性扫描伏安法直接测定复方鱼腥草片中槲皮素[J].理化检验：化学分册，2010，46（10）：1125-1128，1131[8] 朱玲艳，王宗花，陈小印，等.聚吡咯/碳纳米管分子印迹修饰电极对槲皮素的选择性测定[J].分析测试学报，2011，30（1）：18-23[9] Tanji Y， Wanzhi W，Jinxiang Z. Selective detection of dopamine in the presence of ascorbic acid by use of glassy-carbon electrodes modified with both polyaniline film and multi-walled carbon nanotubes with incorporated β-cyclodextrin[J].Analytical and Bioanalytical Chemistry，2006，386：2087-2094[10] 李晓娟，赫春香.铁氰化镍/银复合修饰电极的制备及对氟康唑的电吸附作用[J].高师理科学刊，2009，29（1）：68-71[11] 唐于平，王颖，楼凤昌，等.银杏叶中的黄酮醇苷类成分[J].药学学报，2000，35（5）：363-366。

一种氟雷拉纳的合成方法引言氟雷拉那是一类广泛应用于药物合成和材料科学领域的有机化合物。

本文将介绍一种高效、环境友好的氟雷拉那合成方法，该方法基于催化剂的应用，可以实现高产率和高选择性的合成反应。

1.催化剂的选择合成氟雷拉那的第一步是选择合适的催化剂。

通常，有机钯催化剂被广泛应用于氟化反应中。

例如，P d(OA c)2、Pd Cl2和Pd2(db a)3等催化剂都具有良好的活性和选择性。

同时，添加相应的配体，如Ph o sp hi ne 类配体或N-he te roc y cl ic ca rb en e（NH C）配体，可以进一步改善反应效果。

2.底物选择和反应条件优化在氟雷拉那的合成中，底物的选择至关重要。

一般来说，苯环上的取代基会对反应活性和选择性产生重要影响。

选择底物时，应考虑其电子效应和立体效应。

此外，还需优化反应条件，如温度、溶剂和反应时间等。

合理的选择和优化可以提高产率和选择性。

3.合成策略基于上述的催化剂选择和反应条件优化，下面将介绍一种具体的合成策略。

3.1预处理步骤首先，将底物A与催化剂[P d（催化剂）]配体进行预处理。

预处理步骤一般包含反应物体系的净化和活化。

净化可通过适当的萃取和柱层析等手段进行。

活化则包括催化剂与配体的预活化处理。

3.2氟化反应步骤在反应体系中加入预处理后的底物A和适量的催化剂[P d（催化剂）]，并在适当的温度下进行搅拌反应。

反应的时间通常为几小时至数十小时。

反应完成后，通过简单的过滤或提取等操作，获得氟雷拉那产物。

3.3产物纯化步骤为了得到高纯度的产物，对反应混合物进行纯化是必要的。

一种常见的纯化方法是使用柱层析。

通过选择合适的柱填料和洗脱溶剂，可以分离目标产物并去除杂质。

最后，通过减压蒸馏等方法去除溶剂，获得纯净的氟雷拉那产物。

结论通过以上的合成方法和策略，我们可以高效、环境友好地合成氟雷拉那。

该方法基于催化剂的应用，具有高产率和高选择性。

通过进一步优化催化剂的选择以及反应条件的调控，我们相信该方法的研究和应用前景将更加广阔。

Friedländer喹啉合成反应此反应是指邻胺基芳基醛或酮与另一分子有α-亚甲基的酮反应得到喹啉的反应。

反应中两个底物先缩合，得到的中间体经过酸或碱催化环脱水得到喹啉。

反应机理：最新文献Rapid and efficient synthesis of poly-substituted quinolines assisted by p-toluene sulphonic acid under solvent-free conditions: comparative study of microwave irradiation versus conventional heatingC.-S. Jia, Z. Zhang, S.-J. Tu, G.-W. Wang, Org. Biomol. Chem., 2006, 4, 104-110.Molecular iodine: a highly efficient catalyst in the synthesis of quinolines via Friedländer annulationJ. Wu, H.-G. Xia, K. Gao, Org. Biomol. Chem., 2006, 4, 126-129.Transition-Metal-Free Indirect Friedländer Synthesis of Quinolines from AlcoholsR. Martínez, D. J. Ramón, M. Yus,J. Org. Chem., 2008, 73, 9778-9780.Silver Phosphotungstate: A Novel and Recyclable Heteropoly Acid for Friedländer Quinoline SynthesisJ. S. Yadav, B. V. S. Reddy, P. Sreedhar, R. S. Rao, K. Nagaiah, Synthesis, 2004, 2381-2385.Efficient and Rapid Friedlander Synthesis of Functionalized Quinolines Catalyzed by Neodymium(III) Nitrate Hexahydrate R. Varala, R. Enugala, S. R. Adapa, Synthesis, 2006, 3825-3830.Ionic Liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines S. S. Palimkar, S. A. Siddiqui, T. Daniel, R. J. Lahoti, K. V. Srinivasan, J. Org. Chem., 2003, 68, 9371-9378.Synthesis of Quinolines via Friedländer Reaction in Water and under Catalyst-Free ConditionsQ. Shen, L. Wang, J. Yu, M. Liu, J. Qiu, L. Fang, F. Guo, J. Tang, Synthesis, 2012, 44, 389-392.One-Pot Friedländer Quinoline Synthesis: Scope and LimitationsA.-H. Li, D. J. Beard, H. Coate, A. Honda, M. Kadablbajoo, A.Kleinberg, R. Laufer, K. M. Mulvihill, A. Nigro, P. Rastogi, M. W. Siu, A. G. Steinig, T. Wang, D. Werner, A. P. Crew, M. J. Mulvihill,Synthesis, 2010, 1629-1632.Highly Regioselective Friedländer Annulations with Unmodified Ketones Employing Novel Amine Catalysts: Syntheses of 2-Substituted Quinolines, 1,8-Naphthyridines, and Related HeterocyclesP. G. Dormer, K. K. Eng, R. N. Farr, G. H. Humphrey, J. C. McWilliams, P. J. Reider, J. W. Sager, R. P. Volante, J. Org. Chem., 2003, 68, 467-477.Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as OrganocatalystsA. Bañón-Caballero, G. Guillena, C. Nájera,J. Org. Chem., 2013, 78, 5349-5356.编译自：有机化学门户邻氨基芳基醛或酮与另一分子至少含有一个与羰基相连的亚甲基的醛或酮反应得到取代喹啉的反应。

硕士学位论文（2012届）烯胺酮参与的多组分反应吲哚及其衍生物合成Enaminones-Based Multicomponent reation for the Synthesis of Indole and Its derivatives作者伊绵帅导师李桂根教授江苏师范大学化学化工学院二一二年五月〇江苏师范大学学位论文版权使用授权书本学位论文作者完全了解江苏师范大学有权保留并向国家有关部门或机构送交论文的复印件和电子版，允许论文被查阅和借阅。

本人授权江苏师范大学可以将本学位论文的全部或部分内容编入有关数据库进行检索和传播，可以采用影印、缩印或扫描等手段保存、汇编、出版本学位论文。

保密的学位论文在解密后适用本授权书。

作者签名：导师签名：年月日年月日中图分类号：o629 单位代码：10320UDC：密级：硕士学位论文烯胺酮参与的多组分反应吲哚及其衍生物合成Enaminones-Based Multicomponent reation for the Synthesis of Indole and Its derivatives作者伊绵帅导师李桂根教授申请学位理学硕士培养单位江苏师范大学学科专业有机化学研究方向有机合成答辩委员会主席韩相恩评阅人二〇一二年五月致 谢谨以此文，向我的导师屠树江教授、李桂根教授表示衷心的感谢，感谢老师在我攻读硕士学位期间给我的指导和关心。

老师三年来给我的在科学研究、做人做事方面的教诲使我受益匪浅；先生踏实的工作作风、严谨的治学态度、谦厚的待人风格、踏实的工作作风、开阔的思维方式将使我受益终生。

感谢吴翚教授、王香善教授、史延慧教授、曹昌盛教授、姚昌盛教授、冯友健教授等有机组所有老师，感谢石枫老师， 毫无保留的向我传授知识，细心解答问题，给了我很大的帮助。

特别感谢姜波老师对于我学术上耐心的指导和帮助。

感谢李超师兄、王翔师兄、程闯师兄、刘银平师姐、吴飞跃师姐和丁洁师姐给予我的帮助。

VarinderK.Aggarw...有机硼化合物因其C-B键具有独特的反应性能，因此在有机合成中发挥着重要的作用。

利用过渡金属催化1,2-双硼酸酯的选择性脱硼偶联反应是合成多样官能团化有机硼化物的重要手段。

然而，此类反应主要局限在位阻相对较小的一级硼酸酯位点处发生偶联。

而在位阻较大的二级或三级硼酸酯位点处实现偶联则具有较大的挑战性。

最近，英国布里斯托大学Varinder K. Aggarwal课题组发展镍/光共催化芳基卤化物和1,2-双硼酸酯的选择性交叉偶联反应。

反应可以实现1,2-双硼酸酯选择性地在位阻较大的二级或三级硼酸酯位点处与芳基卤化物发生偶联，实现一系列β-芳基硼酸酯的合成。

相关成果发表在Angew. Chem. Int. Ed., 2022, DOI: 10.1002/anie.202207988上（Scheme 1）。

（图片来源：Angew. Chem. Int. Ed.）作者首先选择由1,2-双硼酸酯1a衍生来的硼络合物2a和对溴苯腈5a作为模板底物进行探索（Table 1）。

经过一系列条件筛选，作者发现当使用4CzIPN（5 mol%），Ni(TMHD)2（10 mol%），DMF 作溶剂，蓝光照射室温下反应16小时，可以以81%的分离产率（r.r. = 20:1）得到相应的β-芳基硼酸酯6aa（Table 1，entry 11）。

（图片来源：Angew. Chem. Int. Ed.）在得到了最优反应条件后，作者对此反应的底物范围进行探索。

实验结果表明，不同取代的芳基溴化物5（Table 2）和1,2-双硼酸酯1（Table 3）的反应均具有较好的选择性、底物适应性以及官能团兼容性。

值得注意的是，除了芳基溴化物外，芳基碘化物、杂芳基卤化物和烯基溴化物均可在此体系中兼容。

此外，作者还可以利用此方法对进行克级合成，可以以71%的产率和19:1的r.r.值得到目标产物6aa。

（图片来源：Angew. Chem. Int. Ed.）（图片来源：Angew. Chem. Int. Ed.）为了深入了解反应机理，作者进行了机理探索实验（Scheme 1）。