A Comparative Study of Redox-Active Dithiafulvenyl-Functionalized 1,3,6,8-Tetraphenylpyrene Derivatives,The Journal of Organic Chemistry

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A Comparative Study of Redox-Active Dithiafulvenyl-Functionalized 1,3,6,8-Tetraphenylpyrene Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-09-07 , DOI: 10.1021/acs.joc.1c01260
Farshid Shahrokhi ₁ , Maryam F Abdollahi ₁ , Yuming Zhao ₁

Affiliation

A series of 1,3,6,8-tetraphenylpyrene (TPPy) derivatives substituted with redox-active 1,4-dithiafulvenyl (DTF) groups was synthesized and characterized. The conformational properties of these DTF-TPPys and their TPPy precursors were assessed by X-ray single-crystal and nuclear magnetic resonance analyses. Their electronic and redox properties were examined by ultraviolet–visible absorption, fluorescence, and cyclic voltammetric analyses. The DTF substitution was found to strongly modify the absorption, emission, and electrochemical properties, while detailed effects can be linked to substitution patterns and alkyl side chains attached to the DTF groups. Furthermore, the DTF-TPPy derivatives showed sensitivity to acids; in particular, the vinylic proton of DTF group could undergo efficient proton/deuterium exchange with D₂O in an acidic medium.

中文翻译：

氧化还原活性二硫代富烯基官能化 1,3,6,8-四苯基芘衍生物的比较研究

合成并表征了一系列被氧化还原活性 1,4-二硫代富烯基 (DTF) 取代的 1,3,6,8-四苯基芘 (TPPy) 衍生物。这些 DTF-TPPy 及其 TPPy 前体的构象特性通过 X 射线单晶和核磁共振分析进行评估。通过紫外-可见吸收、荧光和循环伏安分析来检查它们的电子和氧化还原特性。发现 DTF 取代强烈地改变了吸收、发射和电化学性质，而详细的影响可以与取代模式和连接到 DTF 基团的烷基侧链有关。此外，DTF-TPPy 衍生物表现出对酸的敏感性；特别是，DTF 基团的乙烯基质子可以与 D ₂进行有效的质子/氘交换O 在酸性介质中。

更新日期：2021-09-17

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