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Pyrene-1-Carboxylate in Water and Glycerol Solutions: Origin of the Change of pK Upon Excitation

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Abstract

Pyrene-1-carboxy acid has a pK of 4 in the ground state, and a pK of 8 in the excited state. Fluorescence spectra of the acid and base forms are presented as a function of solvent and temperature. Ab initio quantum calculations indicate that the bond between the ring system and the carboxyl group has aromatic character that becomes stronger upon excitation. This stabilization helps to account for the increase in pK upon excitation.

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Acknowledgements

This work was supported by NIH grant PO1 GM48130 and fellowship grant NIH F31 NSO53399 to NVN.

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Authors and Affiliations

  1. Department of Biochemistry and Biophysics, School of Medicine, University of Pennsylvania, Philadelphia, PA, 19104, USA

    Nathaniel V. Nucci, Bogumil Zelent & Jane M. Vanderkooi

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  1. Nathaniel V. Nucci
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  2. Bogumil Zelent
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  3. Jane M. Vanderkooi
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Correspondence to Jane M. Vanderkooi.

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Nucci, N.V., Zelent, B. & Vanderkooi, J.M. Pyrene-1-Carboxylate in Water and Glycerol Solutions: Origin of the Change of pK Upon Excitation. J Fluoresc 18, 41–49 (2008). https://doi.org/10.1007/s10895-007-0233-x

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  • DOI: https://doi.org/10.1007/s10895-007-0233-x

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