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Regioselectively ?- and ?-alkynylated BODIPY dyes via gold(I)-catalyzed direct C-H functionalization and their photophysical properties.

ABSTRACT: A series of ?- and ?-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C-H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting ?- and ?-substituted BODIPYs are notably altered. The lowest S0-S1 transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the ?-ethynylated derivatives are significantly lower than those of ?-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional ?-materials.

SUBMITTER: Shimada T 

PROVIDER: S-EPMC7136566 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C-H functionalization and their photophysical properties.

Shimada Takahide T   Mori Shigeki S   Ishida Masatoshi M   Furuta Hiroyuki H  

Beilstein journal of organic chemistry 20200401

A series of α- and β-ethynyl-substituted BODIPY derivatives (<b>3a</b>, <b>4a</b>, <b>5a, 5b</b>, <b>6a, 6b</b>) were synthesized by gold(I)-catalyzed direct C-H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S<sub>0</sub>-S<sub>1</sub  ...[more]

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