| Title |
Organolithium-mediated postfunctionalization of thiazolo[3,2-c][1,3,5,2]oxadiazaborinine fluorescent dyes |
| Authors |
Potopnyk, Mykhaylo A ; Volyniuk, Dmytro ; Luboradzki, Roman ; Ceborska, Magdalena ; Hladka, Iryna ; Danyliv, Yan ; Grazulevicius, Juozas V |
| DOI |
10.1021/acs.joc.0c00552 |
| Full Text |
|
| Is Part of |
Journal of organic chemistry.. Washington, DC : American Chemical Society. 2020, vol. 85, iss. 9, p. 6060-6072.. ISSN 0022-3263. eISSN 1520-6904 |
| Keywords [eng] |
large stokes shift ; C-H arylation ; BF2 complexes |
| Abstract [eng] |
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 (SnBu3) exhibits a relatively high solid-state photoluminescence quantum yield of 44%. |
| Published |
Washington, DC : American Chemical Society |
| Type |
Journal article |
| Language |
English |
| Publication date |
2020 |
| CC license |
|
