%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