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5-(1H-Indol-3-yl)-pyrazolyl derivatives as colorimetric sensor for anions

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Abstract

The synthesis, characterisation and binding and deprotonation studies with anions for four 5-(1H-indol-3-yl)-pyrazolyl derivatives (2–5) have been described. It is worthy to mention that sensor 2 shows a drastic change in absorption spectrum (ca. 335 nm) and colour (colourless to blue) upon addition of F− in DMSO solution due to the deprotonation of indole –NH proton, as confirmed by 1H NMR titration. Sensor 4 recognizes F− and CN− ions by deprotonation mechanism with visible colour change of the solution in a similar manner to that of 2. However, in contrary to 2 and 4, sensor 3 binds with F−, CN−, H2PO4 −, AcO− and PhCOO− ions exploiting hydrogen-bonding interaction with the shifting of absorption band to longer wavelength and subsequent colour change of the solution. Compound 5 recognizes F− without any visual colour change and its binding is studied by 1H NMR titration to acquire the important information about the nature of binding between F− and 5.

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Acknowledgments

I.A. and T.G. thank the Department of Science and Technology, New Delhi, India for JRF (IA) and financial support for this work (SR/FT/CS-028/2008). The authors gratefully acknowledge the instrumental facility provided by Analytical Science Discipline, Central Salt & Marine Chemicals Research Institute, Bhavnagar, India.

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Authors and Affiliations

  1. Department of Chemistry, Motilal Nehru National Institute of Technology, Allahabad, 211004, India

    Israr Ahmad & Tamal Ghosh

  2. Analytical Research Division, Nector Lifesciences Ltd., Unit-II, Derabassi, Mohali, 140507, Punjab, India

    Neeraj Kumar Mishra

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  1. Israr Ahmad
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Correspondence to Tamal Ghosh.

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10847_2012_188_MOESM1_ESM.doc

Supplementary Material: Equations used for calculation of binding constant and deprotonation constant, stoichiometric analysis of 2 with F− ion by Job’s plot in DMSO, stoichiometric analysis of 4 with F− ion by Job’s plot in CH3CN, 1H NMR titration of 2 with TBAF in (CD3)2SO (including the –NH2 signal). These materials are available on the web. (DOC 2120 kb)

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Ahmad, I., Mishra, N.K. & Ghosh, T. 5-(1H-Indol-3-yl)-pyrazolyl derivatives as colorimetric sensor for anions. J Incl Phenom Macrocycl Chem 76, 183–191 (2013). https://doi.org/10.1007/s10847-012-0188-7

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