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Absorption and Fluorescence Emission Attributes of a Fluorescent dye: 2,3,5,6-Tetracyano-p-Hydroquinone

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Abstract

Four cyano groups have been substituted on the aromatic ring of p-hydroquinone (2,3,5,6-tetracyanohydroquinone) in order to study the enhanced photoacidity of this molecule. The acid-base equilibria have been studied using absorption (for ground state pKa) and fluorescence (excited state pKa) spectra. Three distinct species (neutral, anionic and dianionic forms) were observed in the ground state and only two species (anionic and dianionic forms) were found in the excited state when studied at different pH/Ho in water. Absorption and emission characteristics were studied in various organic solvents, including protic and aprotic solvents. Deprotonation was also investigated using binary mixtures. It has been revealed that absorption and emission spectra are considerably changed with change in media. Proton transfer to the solvent has been observed in various solvents.

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Acknowledgments

We would like to thank Dr. Stephan Landgraf, Dr. Arnulf Rosspeintner, Dr. Gonzalo Angulo and Prof. Dr. Patrice Jacques for their guidance and helpful discussions. The author acknowledges financial support from the Higher Education Commission Pakistan.

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Authors and Affiliations

  1. Department of Chemistry & Biochemistry, University of Agriculture Faisalabad, Faisalabad, Pakistan

    Muhammad Zahid, Ijaz Ahmad Bhatti & Sadia Asim

  2. Institute of Physical and Theoretical Chemistry, Graz University of Technology, Graz, Austria

    Günter Grampp

  3. Department of Chemistry, GC University Faisalabad, Faisalabad, Pakistan

    Asim Mansha

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  1. Muhammad Zahid
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  2. Günter Grampp
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Correspondence to Muhammad Zahid.

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Zahid, M., Grampp, G., Mansha, A. et al. Absorption and Fluorescence Emission Attributes of a Fluorescent dye: 2,3,5,6-Tetracyano-p-Hydroquinone. J Fluoresc 23, 829–837 (2013). https://doi.org/10.1007/s10895-013-1197-7

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