An effective method for transition-metal-free postfunctionalization of thiazolo[3,2-][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) exhibits a relatively high solid-state photoluminescence quantum yield of 44%.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7590982 | PMC |
| http://dx.doi.org/10.1021/acs.joc.0c00552 | DOI Listing |
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Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-][1,3,5,2]oxadiazaborinine Fluorescent Dyes.
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An effective method for transition-metal-free postfunctionalization of thiazolo[3,2-][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.
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