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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.

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Authors and Affiliations

  1. Department of Physical and Macromolecular Chemistry, Faculty of Science, 128 43, Prague 2, Czech Republic

    Jaroslav Smitka, Eva Tesařová & José P. Da Silva

  2. CIQA, Faculdade de Ciências e Tecnologia, 8005-139, Faro, Portugal

    Américo Lemos

  3. Department of Chemical Engineering, Columbia University, New York, New York, 10027, USA

    Mintu Porel

  4. Department of Chemistry, Columbia University, New York, New York, 10027, USA

    Steffen Jockusch

  5. Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencias de los Materiales, Unidad Asociada al CSIC, Centro de Investigacioń en Química Sostenible (CIQSO), Campus de El Carmen s/n, Universidad de Huelva, 21007-, Huelva, Spain

    Tomás R. Belderrain

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  1. Jaroslav Smitka
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Correspondence to Jaroslav Smitka.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c3pp50336d

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Smitka, J., Lemos, A., Porel, M. et al. Phototransformation of benzimidazole and thiabendazole inside cucurbit[8]uril. Photochem Photobiol Sci 13, 310–315 (2014). https://doi.org/10.1039/c3pp50336d

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  • DOI: https://doi.org/10.1039/c3pp50336d

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