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A new benzimidazolium incorporated chemodosimeter affording dual chromogenic and fluorescence switch-on signaling for the selective targeting of cyanide

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Abstract

We have designed and synthesized a new chemodosimeter, Benzolin-A, which selectively responds to toxic cyanide by dual colorimetric and fluorescence turn-on responses in buffered aqueous DMSO. In the presence of cyanide, we observe absorbance red shift of 108 nm (color changing from colorless to yellow) and fivefold fluorescence enhancement. The 1H NMR studies confirm the nucleophilic addition mechanism, and consistent with the experimental findings, the computational work predicts the feasibility of photoelectron transfer or energy transfer process in the native probe, as well as enhanced internal charge transfer in the Benzolin-A-cyanide adduct. Noteworthily, several background anions, such as F−, Cl−, AcO−, SCN−, HSO4 −, NO3 −, Br−, I− and H2PO4 − exhibit none or insignificant optical perturbations.

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  1. Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (E), Mumbai, 400098, India

    Sabir H. Mashraqui, Rupesh Betkar & Sushil Ghorpade

  2. Department of Quimica, Universitat de les Illes Balears, Crta. De Valldemossa km 7.5, 07122, Palma, Baleares, Spain

    Antonio Frontera

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  1. Sabir H. Mashraqui
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10847_2012_198_MOESM1_ESM.doc

Supporting Information: Spectral data of compound 3 and Benzolin-A, H NMR spectra of Benzolin-A without and with added tetra-n-butylammonium cyanide, comparative fluorescence enhancements of Benzolin-A in the presence of various anions are available online. (DOC 886 kb)

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Mashraqui, S.H., Betkar, R., Ghorpade, S. et al. A new benzimidazolium incorporated chemodosimeter affording dual chromogenic and fluorescence switch-on signaling for the selective targeting of cyanide. J Incl Phenom Macrocycl Chem 76, 293–300 (2013). https://doi.org/10.1007/s10847-012-0198-5

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