Azulenoisoindigo: A building block for π-functional materials with reversible redox behavior and proton responsiveness  

作　　者：Bin Hou Jing Li Xiaodi Yang Jianwei Zhang Hanshen Xin Congwu Ge Xike Gao 

机构地区：[1]Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,Shanghai 200032,China [2]Experiment Center for Science and Technology,Shanghai University of Traditional Chinese Medicine,Shanghai 201203,China

出　　处：《Chinese Chemical Letters》2022年第4期2147-2150,共4页中国化学快报（英文版）

基　　金：financially supported by the National Natural Science Foundation of China (Nos. 21790362, 22075310 and21522209);the “Strategic Priority Research Program of Chinese Academy of Sciences”(No. XDB12010100);the Science and Technology Commission of Shanghai Municipality (Nos. 19XD1424700 and18JC1410600);SIOC. An early preprint of this work appeared on Chem Rxiv [47]。

摘　　要：Azulene, one of representative nonbenzenoid aromatic hydrocarbons, exhibits unique molecular structure and distinctive physical and chemical properties. Herein, azulenoisoindigo(Az II), an azulene-based isoindigo analogue, is designed and synthesized, which has a twisted molecular backbone and R/Sisomers in single crystals. Interestingly, Az II shows the characteristics of both isoindigo and azulene,such as reversible redox behavior and reversible proton responsiveness. UV-vis-NIR,^(1)H NMR and electron paramagnetic resonance(EPR) measurements were carried out to get insights into the possible mechanism of the proton-responsive property of Az II. The results demonstrated that only one azulenyl moiety of molecule of Az II was protonated and deprotonated, and the protonated Az II can be further oxidized to form azulenium cation radicals.

关 键 词：AZULENE Nonbenzenoid aromatic hydrocarbons Isoindigo π-Functional materials Proton responsiveness 

分 类 号：TB34[一般工业技术—材料科学与工程]