Aggregation-Induced Emission(AIE)Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes:Synthesis,Crystal Structure and Optical Properties  

聚集诱导发光活性氟硼吡啶肼醛腙燃料的合成、晶体结构及光学性质

作　　者：Gong Qingbao LüXiang Yu Changjiang Li Wanwan Zhao Quansheng Jiao Lijuan Hao Erhong 宫清宝;吕翔;于长江;李婉婉;赵全胜;焦莉娟;郝二红(皖南医学院脑科学研究院、皖南医学院第一附属医院/弋矶山医院神经外科,安徽芜湖241001;安徽师范大学化学与材料科学学院功能分子固体教育部重点实验室,安徽芜湖241002)

机构地区：[1]Department of Neurosurgery,The First Affiliated Hospital/Yijishan Hospital of Wannan Medical College,Institutes of Brain Science,Wannan Medical College,Wuhu,Anhui 241001 [2]Key Laboratory of Functional Molecular Solids,Ministry of Education,School of Chemistry and Materials Science,Anhui Normal University,Wuhu,Anhui 241002

出　　处：《有机化学》2024年第8期2545-2553,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.22271002);安徽省自然科学基金(Nos.2008085QB67,2308085J14);安徽省高等学校科学研究项目(Nos.2023AH050149,KJ2021A0126);安徽省教育厅高校优秀科研创新团队(No.2022AH010073)资助项目.

摘　　要：A new family of fluoroboronated pyridylhydrazinyl aldehyde hydrozone fluorophores named BOPAHs were developed via a simple one-pot two-step reaction from chloro-2-hydrazinylpyridine and aromatic aldehyde derivatives.They were well characterized by NMR,HRMS,and X-ray crystal structures.They exhibit main absorption from 400 nm to 600 nm and emission bands from 500 nm to 700 nm.The absorption/emission bands redshift with increased polarity of solvents indicate a distinct intramolecular charge transfer characteristic,further confirmed by density functional theory(DFT)calculations.These BOPAHs display weak fluorescence in solutions,but they exhibit obvious aggregation-induced emission properties,possibly resulting from weak intermolecular interactions by fixing the molecular conformations in aggregate states.通过简单易得的氯代2-肼基吡啶和芳香醛衍生物缩合与氟硼配位,一锅两步反应合成了系列新型的氟硼配位吡啶肼基醛腙染料,将其命名为BOPAHs.这些染料分子通过核磁共振、高分辨质谱和晶体结构进行了表征.其主吸收在400~600 nm范围内,发射波长在500~700 nm范围内.随着溶剂极性的增加,它们的吸收/发射峰逐渐红移,同时斯托克斯位移增大,表明这些分子具有明显的分子内电荷转移特性.同时,通过密度泛函理论计算进一步证实了这一特性.此外,这些BOPAHs在溶液中的荧光较弱,但它们都表现出明显的聚集诱导发射特性,可能是由于分子在聚集态下构象固定导致弱的分子间相互作用所致.

关 键 词：aggregation-induced emission organoboron dyes organic synthesis optical properties 

分 类 号：TQ617[化学工程—精细化工]