Nonalternant isomer of pentacene fusing two azulene units

作     者：Bo Yu Pengchen Du Jianwen Guo Hanshen Xin Jianhua Zhang Bo Yu;Pengchen Du;Jianwen Guo;Hanshen Xin;Jianhua Zhang

作者机构：Department of ChemistryCollege of SciencesShanghai UniversityShanghai 200444China School of MicroelectronicsShanghai UniversityShanghai 201800China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2024年第35卷第5期

页      面：244-248页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：financially supported by the National Natural Science Foundation of China(No.22101170) 

主　　题：Azulene Isomer Polycyclic aromatic hydrocarbon Nickel(0)-catalyzed Photo-oxidative stability 

摘      要：Azulene is a promising building block for creating innovative polycyclic aromatic hydrocarbons. This study involved the construction of three nonalternant isomers of pentacene by fusing two azulene units, named Az-PH1/2/3. Az-PH1 was initially developed through the rhodium(Ⅱ)-catalyzed cyclization of bis(N-tosylhydrazone)s. Intriguingly, Az-PH1 was also unexpectedly obtained during a nickel(0)-catalyzed one-step tandem reaction. We investigated the optical and electrochemical properties, aromaticity, and photo-oxidative stability of Az-PH1, comparing it with the well-known pentacene using density functional theory, electrochemical, and photophysical tests. Our results showed that the azulene-fusing strategy resulted in a molecule with narrow optical bandgaps(2.046 eV) and a long half-life time under ambient air conditions.