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首页> 外文期刊>Chemistry: A European journal >Synthesis of redox-active, intramolecular charge-transfer chromophores by the [2+2] cycloaddition of ethynylated 2H-Cyclohepta[b]furan-2-ones with tetracyanoethylene
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Synthesis of redox-active, intramolecular charge-transfer chromophores by the [2+2] cycloaddition of ethynylated 2H-Cyclohepta[b]furan-2-ones with tetracyanoethylene

机译：乙氧基化2H-环庚基[b]呋喃-2-酮与四氰基乙烯的[2 + 2]环加成反应合成氧化还原活性分子内电荷转移发色团

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摘要

Ethynylated 2H-cyclohepta[b]furan-2-ones 5-15 have been prepared by Pd-catalyzed alkynylation of 3-iodo-5-isopropyl-2H-cyclohepta[b]furan-2-one (2) with the corresponding ethynylarenes or the reaction of 2-iodothiophene with 3-ethynyl-5-isopropyl-2H-cyclohepta[b]furan-2-one (4) under Sonogashira-Hagihara conditions. Compounds 5-15 reacted with tetracyanoethylene in a formal [2+2] cycloaddition reaction, followed by ring opening of the initially formed [2+2] cycloadducts, cyclobutenes, to afford the corresponding 1,1,4,4- tetracyanobutadienyl (TCBD) chromophores 16-26 in excellent yields. The intramolecular charge-transfer interactions between the 2H-cyclohepta[b]furan-2- one ring and TCBD acceptor moiety were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of the novel TCBD derivatives 16-26 was examined by cyclic voltammetry and differential pulse voltammetry, which revealed multistep electrochemical reduction properties, depending on the number of TCBD units in the molecule. Moreover, a significant color change was observed by UV/Vis spectroscopy under electrochemical reduction conditions.
机译：乙炔化2H-环庚[b]呋喃-2-酮5-15是通过Pd催化3-碘-5-异丙基-2H-环庚[b]呋喃-2-酮（2）与相应的乙炔基炔烃进行炔化反应制得的或2-碘代噻吩在Sonogashira-Hagihara条件下与3-乙炔基-5-异丙基-2H-环庚[b]呋喃-2-酮（4）的反应。化合物5-15在正式的[2 + 2]环加成反应中与四氰基乙烯反应，然后将最初形成的[2 + 2]环加合物环丁烯开环，得到相应的1,1,4,4-四氰基丁二烯基（TCBD ）发色团16-26的产率很高。通过UV / Vis光谱和理论计算研究了2H-环庚[b]呋喃-2-一环和TCBD受体部分之间的分子内电荷转移相互作用。通过循环伏安法和差分脉冲伏安法检查了新型TCBD衍生物16-26的氧化还原行为，这揭示了多步电化学还原性质，具体取决于分子中TCBD单元的数量。此外，在电化学还原条件下，通过UV / Vis光谱观察到显着的颜色变化。

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