I2/H2O2 mediated synthesis and photophysical properties of imidazole-fused heterocycles via [4+1] cyclization approach

Submitting author affiliation:
Zhengzhou University, Zhengzhou, China

Beilstein Arch. 2024, 20248. https://doi.org/10.3762/bxiv.2024.8.v1

Published 07 Feb 2024

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An efficient I2 (10 mmol%)/H2O2 mediated oxidative formal [4+1] cyclization of 2-pyridinemethylamine or o-phenylenediamine (2-aminobenzenethiol) with benzaldehyde via C-N bond formation has been developed. This strategy offers a straightforward approach to imidazo[1,5-a]pyridine and benzimidazole (benzothiazole) derivatives in 65% to 98% yields. Several heterocyclic products exhibit promising blue luminous performance with satisfactory fluorescence quantum yields of up to 64%, large Stokes shifts, and a longer lifetime (7.35 ns). The band gap energies obtained from DFT are also consistent with the absorption spectra.

Keywords: [4+1] cyclization; I2/H2O2 mediated; Imidazo-fused Heterocycles; Photophysical properties; DFT calculations

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Li, H.; Gao, C.; Liu, Q.; Guo, Y.; Cao, S.; Zhao, Y. Beilstein Arch. 2024, 20248. doi:10.3762/bxiv.2024.8.v1

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