期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 9, 页码 5614-5626出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00566
关键词
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资金
- Institute of Organic Chemistry of the Polish Academy of Sciences
- European Social Fund [09.3.3-LMT-K-712]
- Institute of Physical Chemistry of the Polish Academy of Sciences
A fluorescent dye based on the 8-brominated benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinine core was synthesized from benzo[d]thiazol-2-amine. The new boron complex can be effectively modified by a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with (het)arylboronic acids. This reaction allows a valuable regioselective postfunctionalization of 1,3,5,2-oxadiazaborinine chromophores with different aromatic substituents. The solutions of obtained target complexes in organic solvents demonstrate high fluorescence quantum yields. The compound with a 4-cyanophenyl group at benzothiazole unit (Ar = 4-C6H4CN) exhibits a comparatively high fluorescence quantum yield of 0.31 in the solid state.
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