Double [5]carbohelicene: facile synthesis, chiroptical properties,isomerization study, and lasing application
作者机构：State Key Laboratory of Petroleum Molecular & Process Engineering Shanghai Key Laboratory of Green Chemistry and Chemical ProcessesSchool of Chemistry and Molecular Engineering East China Normal University School of Physics and Optoelectronics South China University of Technology Institute of Polymer Optoelectronic Materials & Devices State Key Laboratory of Luminescent Materials & Devices South China University of Technology School of Physics and Electronic Science Engineering Research Center of Nanophotonics & Advanced Instrument Ministry of EducationEast China Normal University State Key Laboratory of Precision Spectroscopy School of Physics and Electronic Science East China Normal University
出 版 物：《Science China Chemistry》 (中国科学:化学(英文版))
年 卷 期：2025年第68卷第1期
页 面：233-240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：supported by the National Natural Science Foundation of China (22071061) the Shanghai Natural Science Foundation (22ZR1420600) the Fundamental Research Funds for the Central Universities
主 题：double carbohelicene optical resolution organic laser isomerization X-ray diffraction
摘 要：Double carbohelicenes have attracted considerable attention due to their aesthetic structures, distinct π-conjugation extension, inherent chirality, and intriguing optical and electronic properties. Herein, the concise de novo synthesis of a new double[5]carbohelicene 1 together with its chiroptical properties, isomerization process and lasing application is presented. 1 was synthesized by a simple protocol involving the formation of a 6,6′-bipentacene as the key intermediate. It is worth noting that1 existed as two diastereomers 1-PP/MM and 1-PM, which were successfully isolated and unambiguously confirmed by Xray crystallography. The optical resolution of the racemic 1-PP/MM was successfully achieved by chiral-phase highperformance liquid chromatography（HPLC）, and 1-PP and 1-MM were characterized by circular dichroism. Interestingly, it was found that 1-PP/MM could be completely isomerized to 1-PM upon heating, and the detailed thermodynamics and kinetics of the isomerization process were systematically investigated. 1-PM exhibited deep-red luminescence with emission maximum at 723 nm and fluorescence quantum yield as high as 32.95%. Consequently, we can showcase the lasing application of 1-PM by doping with epoxy resin to assemble a bottle microlaser spontaneously, which the lasing wavelength is 796.6 nm at a threshold of 0.8 m J cm-2. We believe that our studies, including the facile synthesis methodology, detailed isomerization studies, and lasing application, will shed some light on the design and synthesis of novel carbohelical systems with more functions.
同方期刊数据库