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Vol. 26 No. 18 (2014): Vol 26 Issue 18

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Synthesis and Electropolymerization of New Phenylene-Substituted Dipyrridyls: Electrochemical and Spectroscopic Characterization

https://doi.org/10.14233/ajchem.2014.16351
Abdou Karim Diagne Diaw
Laboratoire de Chimie Physique Organique et d'Analyses Environnementales (LCPOAE), Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar-Fann, Sénégal
Modou Fall
Laboratoire de Chimie Physique Organique et d'Analyses Environnementales (LCPOAE), Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar-Fann, Sénégal
Diariatou Gningue-Sall
Laboratoire de Chimie Physique Organique et d'Analyses Environnementales (LCPOAE), Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar-Fann, Sénégal
Jean-Jacques Aaron
Université Paris-Est, Laboratoire Géomatériaux et Environnement (EA 4508), UPEMLV, 77454 Marne-la-Vallée, France
Abderrahim Yassar
LPICM (UMR 7647), Ecole Polytechnique, Route de Saclay, 91128 Palaiseau, France

Corresponding Author(s) : Modou Fall

modou.fall@ucad.edu.sn

Asian Journal of Chemistry, Vol. 26 No. 18 (2014): Vol 26 Issue 18

Abstract

The present paper sets out the synthesis and electropolymerization process of 1,1'-phenylenedipyrridyl and 1,1'-diphenylenedipyrridyl. These compounds are prepared by Clauson-Kaas methods with 35 or 71 % yield and characterized. UV-visible electronic absorption spectra and electrochemical methods were used to examine the effects of the electronic p-system extension in 1,1'-phenylenedipyrridyl and 1,1'-diphenylenedipyrridyl structures on the monomer properties relative to N-phenylpyrrole. Also, 1,1'-phenylenedipyrridyl and 1,1'-diphenylenedipyrridyl were electropolymerized on platinum electrode by anodic oxidation in 0.1 M tetrabutylammonium hexafluorophosphate (Bu4NPF6) acetonitrile or dichloromethane solutions and characterized by electrochemical and spectroscopic techniques. The electronic p-system extension effects on the poly(1,1'-phenylenedipyrridyl) physico-chemical properties and structure were investigated by cyclic voltammetry, FT-IR, UV-visible and XPS spectroscopy and scanning electron microscopy (SEM). Cyclic voltammetry of the poly(1,1'-phenylenedipyrridyl) films indicated a good redox behaviour and an improvement of the electrochemical properties. FT-IR spectral studies indicated a linear structure of this polymer with 2, 5 coupling on the pyrrole ring. SEM analysis showed that polymer film morphology changed between the oxidized and reduced states. The solid-state UV-visible spectra of the poly(1,1'-phenylenedipyrridyl) films on ITO were characterized by a significant red-shift of the absorption maximum, as compared to poly(1,1'-phenylenedipyrridyl) film. Moreover, the very low amount of poly(1,1'-diphenylenedipyrridyl) film obtained during the electropolymerization process and electrochemical studies of electrosynthesized poly(1,1'-diphenylenedipyrridyl) showed that the polymer properties modulated by extension of the monomer electronic p-system can be limited by steric effects.

Keywords

Synthesis Phenylpyrrole and derivatives Electropolymerization Electrocatalytic effect
Karim Diagne Diaw, A., Fall, M., Gningue-Sall, D., Aaron, J.-J., & Yassar, A. (2014). Synthesis and Electropolymerization of New Phenylene-Substituted Dipyrridyls: Electrochemical and Spectroscopic Characterization. Asian Journal of Chemistry, 26(18), 5973–5980. https://doi.org/10.14233/ajchem.2014.16351
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