Electrochemistry of Secondary Amine Substituted 2,5-di(2-thienyl)pyrrole Derivative and Its Copolymer

Since the discovery of conductive polymers, one of the most promising innovations in the field of polymer chemistry, these materials have been used in many practical applications. However, new monomers are being designed to overcome some of the disadvantages of conductive polymers, such as their inherent stability, low optical and electrical properties. It is known that minor arrangement on the monomer structure lead to very large changes in the polymer properties. In this study, a thienyl pyrrole monomer, one of the most studied monomers in the field of conductive polymers, has been produced using hydrazine derivatives instead of amines. For this purpose, the model monomer, N-phenyl-2,5-di(thiophen-2-yl)-1H-pyrrol-1-amine, was synthesized and the optical, electrochemical and electrochromic properties of its conductive polymer were investigated. Furthermore, copolymer studies with 3,4-ethylenedioxythiophene (EDOT) have been done to emphasize the importance of copolymerization on electrochromic properties of the conducting polymers. Effects of the feed ratio of the monomers and applied potential for copolymerization on optical and electrochemical properties of the electrochemically synthesized copolymers were investigated in detail.

[1]  A. Koca,et al.  Enhancing biosensor properties of conducting polymers via copolymerization: Synthesis of EDOT-substituted bis(2-pyridylimino)isoindolato-palladium complex and electrochemical sensing of glucose by its copolymerized film. , 2017, Biosensors & bioelectronics.

[2]  M. Ak,et al.  High contrast electrochromic polymer and copolymer materials based on amide-substituted poly(dithienyl pyrrole) , 2017 .

[3]  M. Ak,et al.  A soluble and fluorescent new type thienylpyrrole based conjugated polymer: optical, electrical and electrochemical properties. , 2016, Physical chemistry chemical physics : PCCP.

[4]  C. Freire,et al.  High-Performance Electrochromic Devices Based on Poly[Ni(salen)]-Type Polymer Films. , 2016, ACS applied materials & interfaces.

[5]  M. Karakus,et al.  The effect of the monomer feed ratio and applied potential on copolymerization: investigation of the copolymer formation of ferrocene-functionalized metallopolymer and EDOT , 2016 .

[6]  M. Ak,et al.  Processable Amide Substituted 2,5-Bis(2-thienyl)pyrrole Based Conducting Polymer and Its Fluorescent and Electrochemical Properties , 2016 .

[7]  M. Ak,et al.  Smart window application of a new hydrazide type SNS derivative , 2016 .

[8]  S. Timur,et al.  Comparative investigation of spectroelectrochemical and biosensor application of two isomeric thienylpyrrole derivatives , 2015 .

[9]  Suna Timur,et al.  A novel organic–inorganic hybrid conducting copolymer for mediated biosensor applications , 2014 .

[10]  S. Timur,et al.  New class of 2,5-di(2-thienyl)pyrrole compounds and novel optical properties of its conducting polymer , 2013 .

[11]  P. Camurlu,et al.  Clickable, versatile poly(2,5-dithienylpyrrole) derivatives , 2013 .

[12]  C. Bignozzi,et al.  Strong π-delocalization and substitution effect on electronic properties of dithienylpyrrole-containing bipyridine ligands and corresponding ruthenium complexes. , 2012, Dalton transactions.

[13]  P. Camurlu,et al.  Novel ferrocene derivatized poly(2,5-dithienylpyrrole)s: Optoelectronic properties, electrochemical copolymerization , 2012 .

[14]  P. Camurlu,et al.  Fast switching, high contrast multichromic polymers from alkyl-derivatized dithienylpyrrole and 3,4-ethylenedioxythiophene , 2012 .

[15]  Levent Toppare,et al.  Electrochromic conjugated polyheterocycles and derivatives--highlights from the last decade towards realization of long lived aspirations. , 2012, Chemical communications.

[16]  Cheng Zhang,et al.  Multicolored electrochromic copolymer based on 1,4-di(thiophen-3-yl)benzene and 3,4-ethylenedioxythiophene , 2011 .

[17]  J. Harrowfield,et al.  Synthesis and electropolymerization of N-(4' -carboxyphenyl)-2,5-di(2" -thienyl)pyrrole , 2010 .

[18]  A. Cihaner,et al.  A new conducting polymer bearing 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) subunit: Synthesis and characterization , 2008 .

[19]  Vincenzo Palermo,et al.  Photovoltaic charge generation visualized at the nanoscale: a proof of principle. , 2008, Journal of the American Chemical Society.

[20]  C. Tanyeli,et al.  A soluble conducting polymer of 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)benzenamine and its multichromic copolymer with EDOT , 2008 .

[21]  A. Kavitha,et al.  Atom-Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally-Amendable Copolymer , 2007 .

[22]  Jean Roncali,et al.  Effect of Structural Factor on the Electropolymerization of Bithiophenic Precursors Containing a 3,4-Ethylenedisulfanylthiophene Unit , 2005 .

[23]  Benjamin D. Reeves,et al.  Spray Coatable Electrochromic Dioxythiophene Polymers with High Coloration Efficiencies , 2004 .

[24]  P. Lacaze,et al.  Synthesis of 2,5-di(2-thienyl)-1H-pyrrole N-linked with conjugated bridges , 2002 .

[25]  R. Friend,et al.  Self-organized discotic liquid crystals for high-efficiency organic photovoltaics. , 2001, Science.

[26]  Roger J. Mortimer,et al.  Organic electrochromic materials , 1999 .

[27]  Arno Kraft,et al.  Electroluminescent Conjugated Polymers-Seeing Polymers in a New Light. , 1998, Angewandte Chemie.

[28]  Gilles Horowitz,et al.  Organic Field‐Effect Transistors , 1998 .

[29]  P. Bajaj,et al.  Acrylonitrile-acrylic acids copolymers. I: Synthesis and characterization , 1993 .