%0 Generic %A Potopnyk, Mykhaylo A. %A Volyniuk, Dmytro %A Luboradzki, Roman %A Ceborska, Magdalena %A Hladka, Iryna %A Danyliv, Yan %A Gražulevičius, Juozas Vidas %D 2019 %T 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 %U https://acs.figshare.com/articles/dataset/Application_of_the_Suzuki_Miyaura_Reaction_for_the_Postfunctionalization_of_the_Benzo_4_5_thiazolo_3_2_i_c_i_1_3_5_2_oxadiazaborinine_Core_An_Approach_toward_Fluorescent_Dyes/8041052 %R 10.1021/acs.joc.9b00566.s008 %2 https://acs.figshare.com/ndownloader/files/14985740 %K benzothiazole unit %K Suzuki %K regioselective postfunctionalization %K 4- cyanophenyl group %K 4- C 6 H 4 CN %K Fluorescent Dyes %K target complexes %K oxadiazaborinine %K fluorescence quantum %K fluorescence quantum yields %X 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. %I ACS Publications