Sn-fused perylene diimides: Synthesis, mechanism, and properties  

作　　者：Wenzhong Zhang Zirui Yan Lingcheng Chen Yi Xiao 

机构地区：[1]State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian 116024,China

出　　处：《Chinese Chemical Letters》2024年第10期244-248,共5页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.21406027,21875027,and 22174009);the Medical and Engineering Joint Project of Natural Science Foundation of Liaoning Province(No.2021-YGJC-17);Supercomputing Center of Dalian University of Technology。

摘　　要：The first example of metal Sn-fused perylene diimides(PDI)derivative(Sn-PDI)was designed,synthesized,and investigated.To obtain this type compound,a simple one-pot synthesis,named stannylative cycloaddition reaction,has been successfully developed via a palladium-based catalyst system.The novel mechanism exhibits that the reaction experiences oxidative addition,Pd-cyclization,stannylation,Pd-Sn-cyclization,and reductive elimination processes successively.This stannylative cycloaddition does realize uniqueσ-πhyperconjugation effect and therefore significantly influencing on the photophysical,electrochemical and excited state properties.Compared with those of PDI,both of the absorption and fluorescence spectra of Sn-PDI display large red-shifts over 20 nm.The electron energy levels of Sn-PDI have changed with an uncommon regulation.And Sn-PDI gives a considerably raised highest occupied molecular orbital(HOMO)level of-6.00 eV More importantly,the singlet excitons of Sn-PDI could efficiently intersystem cross(ISC)into triplet state with a long lifetime of 17.8μs,which is far longer than that(4.4 ns)of PDI.

关 键 词：Functional dyes Perylene diimides Organometallic heterocyclics HYPERCONJUGATION Triplet state 

分 类 号：TQ610.1[化学工程—精细化工]