jo9b00566_si_008.cif (14.96 kB)
Application of the Suzuki–Miyaura Reaction for the Postfunctionalization of the Benzo[4,5]thiazolo[3,2‑c][1,3,5,2]oxadiazaborinine Core: An Approach toward Fluorescent Dyes
dataset
posted on 2019-04-16, 00:00 authored by Mykhaylo A. Potopnyk, Dmytro Volyniuk, Roman Luboradzki, Magdalena Ceborska, Iryna Hladka, Yan Danyliv, Juozas Vidas GražulevičiusA 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.