One-Pot Synthesis of Brightly Fluorescent Mes2B-Functionalized Indolizine Derivatives via Cycloaddition Reactions

被引：40

作者：

Yang, Deng-Tao ^{[1
]}

Radtke, Julian ^{[2
]}

Mellerup, Soren K. ^{[1
]}

Yuan, Kang ^{[1
]}

Wang, Xiang ^{[1
]}

Wagner, Matthias ^{[2
]}

Wang, Suning ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

[2] Goethe Univ Frankfurt, Inst Anorgan & Analyt Chem, D-60438 Frankfurt, Germany

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 10期

基金：

加拿大自然科学与工程研究理事会;

关键词：

LIGHT-EMITTING-DIODES; FIELD-EFFECT TRANSISTORS; ORGANOBORON COMPOUNDS; CONJUGATED POLYMERS; 1,3-DIPOLES; PERFORMANCE; ELECTRONICS; MOLECULES; TRANSPORT; MOIETIES;

D O I：

10.1021/acs.orglett.5b00994

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four new BMes(2)-functionalized indolizine derivatives (Mes = mesityl) have been prepared via the cycloaddition reaction between pyrido[2,1-a]isoindole (A) or pyrrolo[1,2-a]pyridine (B) and BMes2-containing alkynes. All four compounds are brightly blue or blue-green fluorescent with lambda(em) = 428-495 nm and Phi = 0.27-0.68, depending on the substitution position of the BMes(2) group. Experimental and TD-DFT computational data indicated that the primary electronic transitions responsible for the fluorescence of 1-4 are from HOMO to LUMO (pi -> pi*) rather than charge transfer from N -> B, which is in agreement with previous findings suggesting that the lone-pair on N is delocalized throughout the N-heterocycles.

引用

页码：2486 / 2489

页数：4

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