高等学校化学学报2018，Vol.39Issue(7)：1449-1454,6.DOI:10.7503/cjcu20180145
含噻吩和吡啶基的插烯式四硫富瓦烯衍生物的合成、结构和电化学性质
Synthesis,Structure and Electrochemistry of Tetrathiafulvalene Vinylogues Bearing Thienyl and Pyridyl Groups
摘要
Abstract
Through triethylphosphite-mediated cross-coupling reaction,4,5-bis(pyridin-2-ylthio)-1,3-dithi-ole-2-thione(1)reacted with 2-thiophenecarboxaldehyde(2a)or 3-thiophenecarboxaldehyde(2b)to give 2,2'-[(2-(thiophen-2-ylmethylene)-1,3-dithiole-4,5-diyl)bis(sulfanediyl)] dipyridine(3a)and 2,2'-[(2-(thiophen-3-ylmethylene)-1,3-dithiole-4,5-diyl)bis(sulfanediyl)] dipyridine(3b)with the yields of 64% and 59%,respectively.The dithiafulvalene compounds possessing thienyl and pyridyl groups 3a and 3b were subjected to an iodine-induced oxidative dimerization reactions and then a brief reductive aqueous workup with Na2S2O3 to gain tetrathiafulvalene vinylogues 1,2-bis(4,5-bis(pyridin-2-ylthio)-1,3-dithiol-2-ylidene)-1,2-di(thiophen-2-yl)ethane(4a)and 1,2-bis(4,5-bis(pyridin-2-ylthio)-1,3-dithiol-2-ylidene)-1,2-di(thiophen-3-yl)ethane(4b)with the yields of 24% and 22%,respectively.All novel compounds were identi-fied by the nuclear magnetic resonance spectroscopy(NMR),fourier transform infrared spectroscopy(FTIR)and mass spectroscopy(MS)methods.Meanwhile,the structures of compounds 3a,3b,4a and 4b were char-acterized by X-ray diffraction analysis.The cyclic voltammograms showed that the tetrathiafulvalene vinylogues 4a and 4b displayed quasi-reversible one two-electron redox processes.Combined with quantum chemical cal-culations,effects of the different thienyl and pyridyl groups substituted tetrathiafulvalene vinylogues 4a and 4b on electrochemical potentials were analysised.关键词
插烯式四硫富瓦烯/噻吩/吡啶/循环伏安/量子化学计算Key words
Tetrathiafulvalene vinylogue/Thiophene/Pyridine/Cyclic voltammetry/Quantum chemical calculation分类
化学化工引用本文复制引用
赵邦屯,陶晶晶,陈小纪,付慧敏,朱卫民..含噻吩和吡啶基的插烯式四硫富瓦烯衍生物的合成、结构和电化学性质[J].高等学校化学学报,2018,39(7):1449-1454,6.基金项目
国家自然科学基金(批准号:21172105)资助.Supported by the National Natural Science Foundation of China(No.21172105). （批准号:21172105）
