Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes

[Image: see text] An effective method for transition-metal-free postfunctionalization of thiazolo[3,2-c][1,3,5,2]oxadiazaborinine dyes via direct lithiation of the 1,3-thiazole ring was developed. The reaction allows valuable regioselective C–H modification of these N,O-chelated organoboron chromoph...

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Autores principales: Potopnyk, Mykhaylo A., Volyniuk, Dmytro, Luboradzki, Roman, Ceborska, Magdalena, Hladka, Iryna, Danyliv, Yan, Grazulevicius, Juozas V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7590982/
https://www.ncbi.nlm.nih.gov/pubmed/32271020
http://dx.doi.org/10.1021/acs.joc.0c00552
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author Potopnyk, Mykhaylo A.
Volyniuk, Dmytro
Luboradzki, Roman
Ceborska, Magdalena
Hladka, Iryna
Danyliv, Yan
Grazulevicius, Juozas V.
author_facet Potopnyk, Mykhaylo A.
Volyniuk, Dmytro
Luboradzki, Roman
Ceborska, Magdalena
Hladka, Iryna
Danyliv, Yan
Grazulevicius, Juozas V.
author_sort Potopnyk, Mykhaylo A.
collection PubMed
description [Image: see text] An effective method for transition-metal-free postfunctionalization of thiazolo[3,2-c][1,3,5,2]oxadiazaborinine dyes via direct lithiation of the 1,3-thiazole ring was developed. The reaction allows valuable regioselective C–H modification of these N,O-chelated organoboron chromophores incorporating different groups, including C-, Hal-, Si-, S-, Se-, and Sn-substituents. As a result, a library of novel fluorescent 1,3-thiazole-based organoboron complexes has been synthesized and characterized. The influence of the donor/acceptor strength of the substituent E on the photophysical properties has been established. The compound with a bulky lipophilic substituent (SnBu(3)) exhibits a relatively high solid-state photoluminescence quantum yield of 44%.
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spelling pubmed-75909822020-10-28 Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes Potopnyk, Mykhaylo A. Volyniuk, Dmytro Luboradzki, Roman Ceborska, Magdalena Hladka, Iryna Danyliv, Yan Grazulevicius, Juozas V. J Org Chem [Image: see text] An effective method for transition-metal-free postfunctionalization of thiazolo[3,2-c][1,3,5,2]oxadiazaborinine dyes via direct lithiation of the 1,3-thiazole ring was developed. The reaction allows valuable regioselective C–H modification of these N,O-chelated organoboron chromophores incorporating different groups, including C-, Hal-, Si-, S-, Se-, and Sn-substituents. As a result, a library of novel fluorescent 1,3-thiazole-based organoboron complexes has been synthesized and characterized. The influence of the donor/acceptor strength of the substituent E on the photophysical properties has been established. The compound with a bulky lipophilic substituent (SnBu(3)) exhibits a relatively high solid-state photoluminescence quantum yield of 44%. American Chemical Society 2020-04-09 2020-05-01 /pmc/articles/PMC7590982/ /pubmed/32271020 http://dx.doi.org/10.1021/acs.joc.0c00552 Text en This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Potopnyk, Mykhaylo A.
Volyniuk, Dmytro
Luboradzki, Roman
Ceborska, Magdalena
Hladka, Iryna
Danyliv, Yan
Grazulevicius, Juozas V.
Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
title Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
title_full Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
title_fullStr Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
title_full_unstemmed Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
title_short Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes
title_sort organolithium-mediated postfunctionalization of thiazolo[3,2-c][1,3,5,2]oxadiazaborinine fluorescent dyes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7590982/
https://www.ncbi.nlm.nih.gov/pubmed/32271020
http://dx.doi.org/10.1021/acs.joc.0c00552
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