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Synthesis, Characterization, Tautomeric Structure and Solvatochromic Behavior of Novel 4-(5-Arylazo-2-Hydroxystyryl)-1-Methylpyridinium Iodide as Potential Molecular Photoprobe

1
Department of Measurements and Environmental Applications, National Institute of Laser Enhanced Sciences (NILES), Cairo University, Giza 12613, Egypt
2
Department of Chemistry, University College of Duba, Tabuk University, Duba 71911, Saudi Arabia
3
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
4
Department of Physics, Faculty of Science, Ain Shams University, Cairo 11566, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Lioz Etgar
Materials 2016, 9(12), 1022; https://doi.org/10.3390/ma9121022
Received: 21 October 2016 / Revised: 7 December 2016 / Accepted: 12 December 2016 / Published: 19 December 2016
A novel series of the title compound 4-(5-arylazo-2-hydroxystyryl)-1-methylpyridinium iodide 6 has been synthesized via condensation reactions of the arylazosalicylaldehyde derivatives 4ai with 1-methyl-picolinium iodide 5. The structures of the new arylazo compounds were characterized by 1H NMR, IR, mass spectroscopy, as well as spectral and elemental analyses. The electronic absorption spectra of arylazomerocyanine compounds 6 were measured in different buffer solutions and solvents. The pK′s and pK*′s in both the ground and excited states, respectively, were determined for the series and their correlations with the Hammett equation were examined. The results indicated that the title arylazomerocyanine dyes 6 exist in the azo form 6A in both ground and excited states. The substituent and solvent effects (solvatochromism) of the title compound arylazomerocyanine dyes were determined using the Kamlet-Taft equation and subsequently discussed. View Full-Text
Keywords: arylazomerocyanine; acidity constants; azo-hydrazonetautomerism; solvatochromism arylazomerocyanine; acidity constants; azo-hydrazonetautomerism; solvatochromism
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MDPI and ACS Style

Altalbawy, F.; Darwish, E.; Medhat, M.; El-Zaiat, S.; Saleh, H. Synthesis, Characterization, Tautomeric Structure and Solvatochromic Behavior of Novel 4-(5-Arylazo-2-Hydroxystyryl)-1-Methylpyridinium Iodide as Potential Molecular Photoprobe. Materials 2016, 9, 1022.

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