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Ethynylene-Linked Oligomers Based on Benzodithiophene:Synthesis and Photoelectric Properties

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Chinese Journal of Chemistry 2014年第4期32卷 298-306页

作者： Songyang Jiang Yuwen Ma Yingyi Wang Chengyun Wang yongjia shen Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and TechnologyShanghai 200237China

Two conjugated ethynyl-linked oligomers,oligo(benzodithiophene-ethynylene-benzothiadiazole)(O1)and oligo(benzodithiophene-ethynylene-carbazole)(O2),were synthesized by Sonogashira coupling *** de-grees of polymerization were 7 and 10,*** photophysical and electrochemical properties were in-vestigated.O1 exhibitd two strong absorption bands at 404 nm and 483 nm,and O2 at 401 nm and 429 *** re-sults of UV-Vis,cyclic voltammetry(CV)and theoretical calculations showed that O1 has a narrower band gap than *** conductivities of O1 and O2 were 1.05×10^(−15) and 6.98×10^(−16) S/cm,respectively,and would increase to 1.23×10^(−10) and 1.05×10^(−10) S/cm after doping with iodine.

关键词： benzodithiophene conjugated polymer Sonogashira reaction photoelectric property conductivity

Synthesis, Structure and Photophysical Properties of Silole-Oxadiazole Copolymers

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Chinese Journal of Chemistry 2013年第6期31卷 779-786页

作者： Tingting Zhang Chaoqiang Zhu Yuwen Ma Chengyun Wang yongjia shen Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and Technology 130 Meilong Road Shanghai 200237 China

A new conjugated copolymer （PTST-DyOXD） derived from 1,1-dimethyl-3,4-diphenyl-2,5-bis（5-bromo-2- thienyl）-silole （TST） and 2,5-bis（4-ethynylphenyl）-l,3,4-oxadiazole （DyOXD） was synthesized by Pd（0）-catalyzed Sonogashira coupling reaction. For comparison, another copolymer without acetenyl group （PTST-OXD） was also synthesized by Pd（0）-catalyzed Suzuki coupling reaction. Chemical structures and optoelectronic properties of the copolymers were characterized by IH NMR, 13C NMR, IR, UV-vis absorption, photoluminescence and cyclic voltammetry. The number-average molecular weight （Mn） is 4010 Da for PTST-DyOXD and 3890 Da for PTST-OXD, respectively. The thermogravimetric analysis （TGA） measurements show that they have good thermal stability with decomposition temperature at 312 and 318 ~C, respectively. The optical band gap is 2.21 eV for PTST-DyOXD and 2.10 eV for PTST-OXD based on the absorption onset. CV analysis revealed the LUMO level of PTST-DyOXD is -3.04 eV, lower than that of PTST-OXD （about -2.89 eV）, which is attributed to the introduction of acetylene group in PTST-DyOXD, increasing the system of the conjugate chain length.

关键词： 2,5-bis(5-bromo-2-thienyl)silole 2,5-bis(4-ethynylphenyl)-1,3,4-oxadiazole Sonogashira reaction Suzuki reaction conjugated polymer

Siloles and Acetenyl Aromatics Copolymers: Synthesis, Characterization and Photophysical Properties

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Chinese Journal of Chemistry 2015年第5期33卷 550-558页

作者： Zhenhua He Guoqiao Lai Zhifang Li Xiao Yuan yongjia shen Chengyun Wang Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and TechnologyShanghai 200237China Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal UniversityHangzhouZhejiang 310012China

Two copolymers,poly(1,1-dimethyl-3,4-diphenylsilole-alt-N-hexyl-3,6-diethynylcarbazole)(PS-DyCz)and poly-(1,1-dimethyl-3,4-diphenylsilole-alt-2,7-diethynyl-9,9'-dihexylfluorene)(PS-DyF),were synthesized by Sonogashira coupling reaction of 2,5-dibromo-1,1-dimethyl-3,4-diphenylsilole and N-hexyl-3,6-diethynylcarbazole or 2,7-diethynyl-9,9'-dihexylfluorene,*** chemical structures of the copolymers were characterized by NMR,FT-IR *** thermal and photophysical properties were evaluated by TGA,DSC,UV-Vis and fluorescence spectroscopy,*** weight-averaged molecular weights(Mw)of PS-DyCz and PS-DyF are 1.20×10^(4) and 3.83×10^(4) Da,*** degree of polymerization is 8 and 22 ***π-conjugated polymers exhibited lower band-gap of 2.25 and 2.70 eV due to the presence of silole rings and C≡C triple bonds in their backbone,the results were consistent with the density functional(DFT)calculations at the B3LYP/6-31G^(*)level.

关键词： silole acetylene carbazole fluorene conjugated polymer density functional theory

Synthesis, spectroscopic, and electrochemical properties of two dyads consisted of tetrathiafulvalene and carbazole

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Frontiers of Chemical Science and Engineering 2009年第2期3卷 192-195页

作者： Guoqiao LAI Yibo LIU Meijiang LI yongjia shen Key Lab of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal UniversityHangzhou 310012China Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science&TechnologyShanghai 200237China

Two donor-σ-acceptor molecules containing tetrathiafulvalene(TTF)and carbazole moieties were synthesized bythe reactionof 9-(4-bromo-butyl)-carbazole(1)with 2,6-bis(hexylthio)-3-(2-cyanoethylthio)-7-(methylthio)-tetrathiafulvalene(2)or2,6-bis(2-cyanoethylthio)-3,7-bis(methylthio)tetrathiafulvalene(3)in the presence of CsOH·H_(2)O,*** structures of the molecules were characterized by 1 H NMR,13 C NMR,MS,and elemental *** showed negligible intramolecu-lar charge-transfer interaction in their ground states as indicated by their UV-Vis spectroscopics and cyclic voltammetry *** with carbazole,their fluorescence was strongly quenched,which implied that a photo induced electron transfer(PET)interaction between TTF and carbazole moieties occurred.

关键词： donor-σ-acceptor molecule intramolecular charge transfer interaction photo induced electron transfer tetrathiafulvalene carbazole

A Benzodithiophene-Based Fluorescence Probe for Rapid Detection of Fluoride Ion

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Chinese Journal of Chemistry 2016年第8期34卷 809-813页

作者： Wenbin Tan Taohua Leng Guoqiao Lai Zhifang Li JiefeiWu yongjia shen Chengyun Wang Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and Technology Shanghai 200237 China National Food Quality Supervision and Inspection Center (Shanghai)/Shanghai Institute of Quality Inspection and Technical Research Shanghai 200233 China Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Nor- mal University Hangzhou Zhejiang 310012 China

A novel and simple fluorescence probe was synthesized from benzo[1,2-b:4,5-b′]dithiophene (BDT) and trimethylsilylethyne via Sonogashira reaction, and showed highly selective and sensitive fluorescence decreasing response towards F−. The probe molecule turned to a weakly fluorescent terminal alkyne moiety because its trimethylsilyl (TMS) group was cleaved by fluoride, which was proved by 1H NMR titration. Whereas no distinct fluorescent changes were observed with the addition of other anions, such as Cl−, Br−, I−, AcO− and H2PO4−. Upon the addition of F−, the maximum fluorescence emission wavelength shifted from 460 nm to 450 nm with a decrease of fluorescence intensity by 40% within 20 s. Moreover, the detection limit towards F− was calculated to be as low as 73.5 nmol/L.

关键词： fluorescent probe benzodithiophene fluoride anion trimethylsilylethynyl group

Synthesis and properties of tetrathiafulvalene-porphyrin assemblies

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Frontiers of Chemical Science and Engineering 2011年第4期5卷 422-428页

作者： Meijiang LI Rui HUANG Changzhi WU Hujin ZUO Guoqiao LAI yongjia shen Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal UniversityHangzhou 310012China Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science&TechnologyShanghai 200237China

Two donor-σ-acceptor molecular systems incorporating tetrathiafulvalene(TTF)and tetraphenylpor-phyrin(TPP)units,TTF-TPP(dyad 1)and TTF-TPP-TTF(triad 2),were *** dyad 1 and triad 2 and their synthetic intermediates have been characterized by 1H nuclear magnetic resonance(1H NMR)and mass spectro-graphy(MS).Their ultraviolet and visible spectroscopy(UV-Vis)and cyclic voltammetry(CV)showed negligible intramolecular charge transfer interaction in their ground ***ﬂuorescence intensity was strongly quenched compared with TPP,which implied the photoinduced electron transfer occurred from the TTF unit to the TPP unit in the excited *** the other hand,theirﬂuorescence intensity could be modulated by sequential oxidation of the TTF unit using chemical methods,which exhibited their potential application inﬂuorescence molecular switch.

关键词： tetrathiafulvalene tetraphenylporphyrin dyad triad ﬂuorescence molecular switch

Synthesis and properties of tetrathiafulvalene-fluorescein dyads

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Frontiers of Chemical Science and Engineering 2009年第3期3卷 314-317页

作者： Guoqiao LAI Yibo LIU Yu ZHANG Jun RUAN Meijiang LI yongjia shen Key Lab of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal UniversityHangzhou 310012China Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and TechnologyShanghai 200237China

Two donor-acceptor molecular systems con-sisted of tetrathiafulvalene(TTF)and fluorescein were designed and *** target compounds and their key intermediates were characterized by 1H NMR,mass spectrography,and infrared spectroscopy,*** UV-vis spectra implied intramolecular interaction in their ground *** spectra and fluorescence lifetimes indicated the photoinduced charge transfer(PET)interaction between the TTF and fluorescein units in their excited states.

关键词： TTF fluorescein charge transfer

两种新型四硫代富瓦烯衍生物的合成与光电性能

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华东理工大学学报（自然科学版） 2019年第4期45卷 563-569页

作者：王雪黄睿沈永嘉华东理工大学结构可控先进功能材料及其制备教育部重点实验室精细化工研究所

聚噻吩类衍生物是导电聚合物中重要的一部分.不带有任何取代基的聚噻吩溶解性能极差,如果在噻吩单体的3,4位引入取代基,则可以有效提高其溶解度.将含羧基的四硫代富瓦烯衍生物(TTF-COOH)和含两个羟基的噻吩衍生物ProDOT(CH2OH)2,通过Ste... 详细信息

聚噻吩类衍生物是导电聚合物中重要的一部分.不带有任何取代基的聚噻吩溶解性能极差,如果在噻吩单体的3,4位引入取代基,则可以有效提高其溶解度.将含羧基的四硫代富瓦烯衍生物(TTF-COOH)和含两个羟基的噻吩衍生物ProDOT(CH2OH)2,通过Steglich酯化反应组合起来,从而得到两种新型衍生物ProDOT(CH2O-TTF)2及ProDOT(CH2OH)(CH2O-TTF).经1H-NMR、UV-Vis和循环伏安法(CV)表征这两种新型衍生物的结构及电化学性质发现:前者衍生物是含有两个TTF片段的ProDOT单体,具有电荷转移现象;后者则具备活性位点,可以进一步发生其他反应.

关键词： Steglich酯化反应 ProDOT 四硫代富瓦烯电化学

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恶霉灵为活性组分的聚合杀菌剂的合成

有机化学 2002年第6期22卷 428-432页

作者：台立民刘冬雪沈永嘉司乃国华东理工大学精细化工研究所上海200237 沈阳化工研究院沈阳110021

由 3 羟基 5 甲基异唑 (恶霉灵 )与甲苯 1,4 二异氰酸酯合成了 3 (3′ 异氰酸酯基 4′ 甲基苯胺基羰基 )氧基 5 甲基异唑 ,以苯乙烯马来酸酐的交替共聚物为化学载体 ,经乙二胺搭桥合成了以恶霉灵为活性组分的聚合杀菌剂 .... 详细信息

由 3 羟基 5 甲基异唑 (恶霉灵 )与甲苯 1,4 二异氰酸酯合成了 3 (3′ 异氰酸酯基 4′ 甲基苯胺基羰基 )氧基 5 甲基异唑 ,以苯乙烯马来酸酐的交替共聚物为化学载体 ,经乙二胺搭桥合成了以恶霉灵为活性组分的聚合杀菌剂 .用IR光谱、1HNMR、质谱和元素分析等表征了化学结构。

关键词：活性组分合成 3-羟基-5-甲基异恶唑恶霉灵聚合杀菌剂苯乙烯-马来酸酐交替共聚物