N,O π-Conjugated 4-Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties

Mykhaylo A. Potopnyk; Roman Lytvyn; Yan Danyliv; Magdalena Ceborska; Oleksandr Bezvikonnyi; Dmytro Volyniuk; Juozas Vidas Gražulevičius

doi:10.1021/acs.joc.7b02239

N,O π-Conjugated 4-Substituted 1,3-Thiazole BF₂ Complexes: Synthesis and Photophysical Properties

Mykhaylo A. Potopnyk^*
, Roman Lytvyn
, Yan Danyliv
, Magdalena Ceborska
, Oleksandr Bezvikonnyi
, Dmytro Volyniuk
, Juozas Vidas Gražulevičius

^*Corresponding author for this work

Institute of Organic Chemistry of the Polish Academy of Sciences
Kaunas University of Technology
Ivan Franko National University of L'viv
Institute of Physical Chemistry of the Polish Academy of Sciences

Research output: Contribution to journal › Article › peer-review

47 Citations (Scopus)

Abstract

A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)benzoyl chloride and the subsequent BF₂ complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo[3,2-c][1,3,5,2]oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π-π/π-n interactions in the molecular packing.

Original language	English
Pages (from-to)	1095-1105
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	83
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.7b02239
Publication status	Published - 2 Feb 2018
Externally published	Yes

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title = "N,O π-Conjugated 4-Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties",

abstract = "A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo[3,2-c][1,3,5,2]oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94\%) in the solid state because of the inhibition of π-π/π-n interactions in the molecular packing.",

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doi = "10.1021/acs.joc.7b02239",

language = "English",

volume = "83",

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TY - JOUR

T1 - N,O π-Conjugated 4-Substituted 1,3-Thiazole BF2 Complexes

T2 - Synthesis and Photophysical Properties

AU - Potopnyk, Mykhaylo A.

AU - Lytvyn, Roman

AU - Danyliv, Yan

AU - Ceborska, Magdalena

AU - Bezvikonnyi, Oleksandr

AU - Volyniuk, Dmytro

AU - Gražulevičius, Juozas Vidas

PY - 2018/2/2

Y1 - 2018/2/2

N2 - A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo[3,2-c][1,3,5,2]oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π-π/π-n interactions in the molecular packing.

AB - A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo[3,2-c][1,3,5,2]oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π-π/π-n interactions in the molecular packing.

UR - https://www.scopus.com/pages/publications/85041562409

U2 - 10.1021/acs.joc.7b02239

DO - 10.1021/acs.joc.7b02239

M3 - Article

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AN - SCOPUS:85041562409

SN - 0022-3263

VL - 83

SP - 1095

EP - 1105

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

N,O π-Conjugated 4-Substituted 1,3-Thiazole BF₂ Complexes: Synthesis and Photophysical Properties

Abstract

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