Influence of pH on photophysical properties of (E)-1-(4-chlorobenzyl)-4-(4-hydroxystyryl)pyridinium chloride

Dorota Prukała; Wiesław Prukała; Mateusz Gierszewski; Jerzy Karolczak; Igor Khmelinskii; Marek Sikorski

doi:10.1039/C2PP25063B

Influence of pH on photophysical properties of (E)-1-(4-chlorobenzyl)-4-(4-hydroxystyryl)pyridinium chloride

Dorota Prukała,*^a Wiesław Prukała,^a Mateusz Gierszewski,^a Jerzy Karolczak,^b^c Igor Khmelinskii^d and Marek Sikorski^a

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* Corresponding authors

^a Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
E-mail: dprukala@amu.edu.pl
Fax: +48 61 8658008
Tel: +48 61 8291309

^b Faculty of Physics, A. Mickiewicz University, Umultowska 85, 61-614 Poznań, Poland

^c Centre of Ultrafast Laser Spectroscopy, A. Mickiewicz University, Umultowska 85, 61-614 Poznań, Poland

^d Universidade do Algarve, FCT, DQF and CIQA, Campus de Gambelas, 8005-139 Faro, Portugal

Abstract

The protonation/deprotonation equilibrium was investigated for N-p-chlorobenzyl-substituted (E)-4′-hydroxy stilbazolium halide, namely (E)-1-(4-chlorobenzyl)-4-(4-hydroxystyryl)pyridinium chloride (EPC). Absorption, emission and synchronous scanning spectra were used to explain the observed phenomena. The excited state lifetimes of the protonated and deprotonated forms of EPC were measured and discussed. Absorption spectra were used to determine its pK_a value in the ground state. We conclude that the protonation/deprotonation equilibrium is not attained in the first excited state of EPC, for kinetic reasons. The quinoid and benzenoid structures of EPC in the ground and excited state are discussed in acidic and basic range of pH. Aqueous solutions of EPC were yellow at pH < 7 and red at pH > 7, and addition of alcohols (methanol or 2-propanol) enhanced this change. Therefore, quaternary stilbazolium salts were investigated for application as acid–base indicators.

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Publication details

The article was received on 30 Jan 2012, accepted on 07 Jun 2012 and first published on 13 Jun 2012

Article type: Paper

DOI: 10.1039/C2PP25063B

Citation: Photochem. Photobiol. Sci., 2012,11, 1454-1464

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Influence of pH on photophysical properties of (E)-1-(4-chlorobenzyl)-4-(4-hydroxystyryl)pyridinium chloride

D. Prukała, W. Prukała, M. Gierszewski, J. Karolczak, I. Khmelinskii and M. Sikorski, Photochem. Photobiol. Sci., 2012, 11, 1454
DOI: 10.1039/C2PP25063B
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Photochemical & Photobiological Sciences

Influence of pH on photophysical properties of (E)-1-(4-chlorobenzyl)-4-(4-hydroxystyryl)pyridinium chloride

Abstract

Supplementary files

Publication details

Influence of pH on photophysical properties of (E)-1-(4-chlorobenzyl)-4-(4-hydroxystyryl)pyridinium chloride

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