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Issue 2, 2014
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Phototransformation of benzimidazole and thiabendazole inside cucurbit[8]uril

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Abstract

The phototransformation of benzimidazole (BZ) and of the benzimidazole pesticide thiabendazole (TBZ) was investigated in aqueous solution in the absence and presence of the supramolecular host cucurbit[8]uril (CB8). ESI-MS and NMR reveal that both compounds form stable 1 : 2 host–guest complexes with CB8 (BZ2@CB8, TBZ2@CB8). The phototransformation of free BZ leads to dehydrodimerization, while for TBZ the photoreactivity leads to BZ, benzimidazole-2-carboximide and 2-acetylbenzimidazole. Inside CB8, BZ undergoes photohydrolysis to form 2-aminoformanilide, while for TBZ2@CB8 additional photoproducts were observed which are pH dependent. At pH 1.2 photolysis of TBZ2@CB8 leads to new red-shifted photoproducts with extended π conjugation.

Graphical abstract: Phototransformation of benzimidazole and thiabendazole inside cucurbit[8]uril

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Supplementary files

Article information


Submitted
19 Sep 2013
Accepted
01 Nov 2013
First published
01 Nov 2013

Photochem. Photobiol. Sci., 2014,13, 310-315
Article type
Paper

Phototransformation of benzimidazole and thiabendazole inside cucurbit[8]uril

J. Smitka, A. Lemos, M. Porel, S. Jockusch, T. R. Belderrain, E. Tesařová and J. P. Da Silva, Photochem. Photobiol. Sci., 2014, 13, 310
DOI: 10.1039/C3PP50336D

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