Multifunctional 2-(2-hydroxyphenyl)benzoxazoles: Ready synthesis,mechanochromism, fluorescence imaging, and OLEDs  

作　　者：Kangmin Wang Liqiu Wan Jingyu Wang Chunlin Zhou Ke Yang Liang Zhou Bijin Li 

机构地区：[1]Chongqing Key Laboratory of Natural Product Synthesis and Drug Research,School of Pharmaceutical Sciences,Chongqing University,Chongqing 401331,China [2]jiangsu Key Laboratory of Advanced Catalytic Materials&Technology,School of Petrochemical Engineering,Changzhou University,Changzhou 213164,China [3]State Key Laboratory of Rare Earth Resource Utilization,Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China

出　　处：《Chinese Chemical Letters》2024年第10期223-227,共5页中国化学快报（英文版）

基　　金：Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology(No.BM2012110);the fundamental research funds for the central universities(No.2023CDJYGRH-YB17);the Venture&Innovation Support Program for Chongqing Overseas Returnees(No.cx2022061);the Natural Science Foundation of Chongqing(No.CSTB2022NSCQ-MSX1123);the Chongqing Talents:Exceptional Young Talents Project(No.cstc2021ycjh-bgzxm0067);Changzhou University,Advanced Catalysis and Green Manufacturing Collaborative Innovation Center(No.ACGM2022–10–10);National Natural Science Foundation of China(Nos.21702019,62174160)for financial support。

摘　　要：Triphenylamine(TPA)-containing 2-(2-hydroxyphenyl)benzoxazoles(2a-2c)have been synthesized via a highly efficient rhodium-catalyzed C–H/C–H cross-coupling reaction.Compound 2a is a novel mechanofluorochromic material with blue-shifted mechanochromic properties.Compounds 2b and 2c presented opposite mechanochromic trends.For 2b,the enol-form emission enhanced,and the ketoform emission blue-shift after grinding.In contrast,2c exhibited the weak enol-form emission disappeared and the keto-form emission slightly red-shift after grinding treatments.The estrone-containing2b-based water-dispersed nanoparticles(NPs)exhibit apparent dual-emission and were applied for fluorescence images.In addition,bis(TPA)-containing 2c-based devices exhibit dual-emission with good performance and a singlet exciton yield of 92%,which breaks through the theoretical upper limit of 25%in conventional fluorescent OLEDs.This is one of the highest exciton utilization values recorded for the ESIPT molecules with a dual emission system.

关 键 词：RHODIUM-CATALYZED 2-(2'-Hydroxyphenyl)benzoxazoles Mechanochromism Fluorescence images OLEDS 

分 类 号：O626[理学—有机化学] TN383.1[理学—化学]