Synthesis of fluorescent multisubstituted polyquinolines by cascade C–H activation-based polyannulations of isonicotinamides and diynes  

作　　者：Dongyang Fan Fei Zhang Jie Cui Dong Wang Ting Han Ben Zhong Tang 

机构地区：[1]Center for AIE Research,Shenzhen Key Laboratory of Polymer Science and Technology,Guangdong Research Center for Interfacial Engineering of Functional Materials,College of Materials Science and Engineering,Shenzhen University,Shenzhen 518060,China [2]College of Physics and Optoelectronic Engineering,Shenzhen University,Shenzhen 518060,China [3]School of Science and Engineering,Shenzhen Institute of Aggregate Science and Technology,The Chinese University of Hong Kong,Shenzhen 518172,China

出　　处：《Science China Chemistry》2023年第4期1139-1149,共11页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(22271197,21905176);the Natural Science Foundation for Distinguished Young Scholars of Guangdong Province(2020B1515020011);the Science and Technology Plan of Shenzhen(JCYJ20190808142403590,JCYJ20190808153415062);the Instrumental Analysis Center of Shenzhen University。

摘　　要：The development of new and efficient polymerization strategies for the synthesis of multisubstituted fused heterocyclic polymers with attractive properties is of great significance.Herein,a rhodium-catalyzed polyannulation route is developed for the in situ generation of multisubstituted polyquinolines with efficient aggregate-state fluorescence.Based on the cascade C-H activation of isonicotinamides and their annulations with internal diynes,a series of high molecular weight polyquinolines are efficiently produced in high yields of up to 99%in a facile and atom-economical manner.Unlike conventional two-component stepwise polymerizations,these polyannulation reactions are tolerant to monomer non-stoichiometric conditions and proceed even more thoroughly in the presence of an excess amount of the isonicotinamide monomer.Benefiting from the unique multisubstituted polyquinoline structures,the obtained polymers show high thermal and morphological stability,useful aggregation-induced emission(AIE)properties,and tunable aggregated-state fluorescence behaviors.The AIE-active polyquinoline is demonstrated to be a good lysosome-specific fluorescent probe with low cytotoxicity and excellent photostability.

关 键 词：fused heterocyclic polymers polyannulation POLYQUINOLINES aggregation-induced emission BIOIMAGING 

分 类 号：TQ317[化学工程—高聚物工业]