BODIPYs with Chalcogenophenes at Boron: Synthesis and Properties

被引：5

作者：

Campbell, Jacob W. ^{[1
]}

Tung, Matthew T. ^{[2
]}

Robertson, Katherine N. ^{[3
]}

Beharry, Andrew A. ^{[2
]}

Thompson, Alison ^{[1
]}

机构：

[1] Dalhousie Univ, Dept Chem, POB 15000, Halifax, NS B3H 4J3, Canada

[2] Univ Toronto, Dept Chem & Phys Sci, Mississauga, ON L5L 1C6, Canada

[3] St Marys Univ, Dept Chem, Halifax, NS B3H 3C3, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

FLUORESCENT-PROBE; SUBSTITUTED BORON; MOLECULAR DESIGN; DYES; DIPYRROMETHENE; LUMINESCENT; DIPYRRIN; SERIES; LIGHT; CU2+;

D O I：

10.1021/acs.joc.3c00708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein are the synthesis and characterizationof BODIPYsbearing heterocycles at boron. To synthesize this series, variouschalcogenophenes (furan, thiophene, selenophene, and tellurophene)were lithiated and then used as nucleophiles to attack the boron centerof a parent F-BODIPY. Compounds in the series werecompared with respect to their photophysical and structural properties,and trends were discussed. By virtue of the "heavy atom effect",as the mass of the heterocycle appended to the BODIPY core increases,compounds exhibit a higher singlet oxygen quantum yield. The BODIPYwith tellurophene at boron exhibits the highest quantum yield (& phi;(& UDelta;) = 0.68) in the series and reduced emission (& phi;(f) = 0.01).

引用

页码：10655 / 10661

页数：7

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