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1,3-dinitrobenzene containing Indole-based Schiff bases as chromogenic receptors for F− anions

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Abstract

Two colorimetric indole-based Schiff base receptors containing electron-deficient 1,3-dinitrobenzene motif, R1 and R2 were developed as a potential receptors for F− anion. Detailed UV-visible and 1H NMR studies revealed that the interactions of the receptor R2 with F− anions were driven by H-bonding followed by anion-induced deprotonation. The anion-receptor interactions produced distinct colorimetric changes in solution, which was visible to the naked eye.

Graphic abstract

Two colorimetric Shiff base receptors, R1 and R2, have been developed containing the electron deficient 1,3-dinitrobenzene moiety and indole group for specific detection of F− anion. The anion-receptor interactions involving F− produced distinct colorimetric changes in solution which could be monitored by UV-visible spectroscopy, as well as the naked eye. Detailed 1H NMR and DFT computational studies revealed that the interactions of the receptor R2 with F− anions were driven by hydrazone N–H…F− H-bonding along with a charge transfer (CT) from the F− anion to the electron-deficient 1,3-dinitrobenzene moiety. Subsequently, the receptor R2 could be developed as a potential paper-based chemosensor for F− anion.

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Acknowledgements

We thank the Department of Science & Technology (DST) India for funding under Fast Track Scheme (SR/FTP/CS-102/2007). We gratefully acknowledge DST-FIST and UGC (DSA) for providing departmental infrastructure facilities.

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Authors and Affiliations

  1. Department of Chemistry, Gauhati University, Guwahati, Assam, 781014, India

    Barnali Deka & Rupam J Sarma

  2. Department of Chemistry, Handique Girls’ College, Guwahati, Assam, 781001, India

    Barnali Deka

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  1. Barnali Deka
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Correspondence to Barnali Deka.

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Deka, B., Sarma, R.J. 1,3-dinitrobenzene containing Indole-based Schiff bases as chromogenic receptors for F− anions. J Chem Sci 133, 62 (2021). https://doi.org/10.1007/s12039-021-01932-3

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