Issue 46, 2019

ZnO-NP assisted synthesis of fluorescent β-carboline C-1 tethered benzimidazole/benzothiazole/benzoxazole derivatives and assessment of their photophysical properties

Abstract

A facile transformation of 1-formyl β-carboline into fluorescent β-carboline C-1 tethered benzazole derivatives is described under the catalysis of ZnO nanoparticles. The reaction proceeded with the reaction of 1-formyl β-carboline and substituted o-diaminobenzene/2-aminobenzenethiol/2-aminophenol, which results in formation of a Schiff base, followed by an intramolecular cylization reaction to generate β-carboline linked benzimidazole, benzothiazole and benzoxazole derivatives. This appraoch displayed a wide substrate scope and high regioselectivity to yield the desired products in moderate to good yields. The photophysical properties of the synthesized derivatives were also evaluated and they exhibited excellent fluorescence properties. Among these β-carboline substituted azoles, the benzothiazole derivative displayed the maximum quantum yield (ΦF up to 28%).

Graphical abstract: ZnO-NP assisted synthesis of fluorescent β-carboline C-1 tethered benzimidazole/benzothiazole/benzoxazole derivatives and assessment of their photophysical properties

Supplementary files

Article information

Article type
Paper
Submitted
16 Aug 2019
Accepted
21 Oct 2019
First published
24 Oct 2019

New J. Chem., 2019,43, 18304-18315

ZnO-NP assisted synthesis of fluorescent β-carboline C-1 tethered benzimidazole/benzothiazole/benzoxazole derivatives and assessment of their photophysical properties

V. Kumar, D. Singh, A. K. Paul, R. Shrivastava and V. Singh, New J. Chem., 2019, 43, 18304 DOI: 10.1039/C9NJ04256C

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