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Highly selective colorimetric detection of cyanide anions in aqueous media by triphenylamine and phenanthro(9,10-d)imidazole based probes

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Abstract

Two novel fluorescent probes based on triphenylamine (TPC) and phenanthro(9,10-d-imidazole) (PITP) have been synthesized and studied as cyanide selective indicators in aqueous media. Complete colour bleaching was observed due to the nucleophilic addition of cyanide to the 2-vinylmalononitrile of TPC, which results in the disruption of the extended conjugation and turns off the intramolecular charge transfer (ICT) process. Furthermore, a visible color change was observed with a large Stokes shift (108 nm) upon the addition of cyanide anions to PITP, due to the formation of hydrogen bonding between the CN− anion and -NH of PITP, which increased the electron density on the donor moiety and induced strong ICT.

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Authors and Affiliations

  1. School of Chemistry, Madurai Kamaraj University, Madurai-21, Tamilnadu, India

    Arockiam Jesin Beneto & Ayyanar Siva

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  1. Arockiam Jesin Beneto
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  2. Ayyanar Siva
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Correspondence to Ayyanar Siva.

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Electronic supplementary information (ESI) available: Experimental procedures, spectral data, copies of 1H & 13C NMR and ESI-MS.

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Beneto, A.J., Siva, A. Highly selective colorimetric detection of cyanide anions in aqueous media by triphenylamine and phenanthro(9,10-d)imidazole based probes. Photochem Photobiol Sci 16, 255–261 (2017). https://doi.org/10.1039/c6pp00345a

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