Doublecarbohelicene:facile synthesis,chiroptical properties,isomerization study,and lasing application

作     者：Peipei Liu Yantong Li Meng-Xiang Wu Hao Kang Xiao-Li Zhao Lin Xu Linlin Liu Xiaodong Li Junfeng Fang Zhiwei Fang Ya Cheng Hai-Bo Yang Huakang Yu Xueliang Shi 

作者机构：State Key Laboratory of Petroleum Molecular&Process EngineeringShanghai Key Laboratory of Green Chemistry and Chemical ProcessesSchool of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China School of Physics and OptoelectronicsSouth China University of TechnologyGuangzhou 510640China School of Physics and Electronic ScienceEngineering Research Center of Nanophotonics&Advanced InstrumentMinistry of EducationEast China Normal UniversityShanghai 200241China State Key Laboratory of Precision SpectroscopySchool of Physics and Electronic ScienceEast China Normal UniversityShanghai 200241China Institute of Polymer Optoelectronic Materials&DevicesState Key Laboratory of Luminescent Materials&DevicesSouth China University of TechnologyGuangzhou 510640China 

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,distinctπ-conjugation extension,inherent chirality,and intriguing optical and electronic ***,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 *** is worth noting that1 existed as two diastereomers 1-PP/MM and 1-PM,which were successfully isolated and unambiguously confirmed by Xray *** 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 ***,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.