Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability

The synthesis of 2,2&#8242;-bipyrroles substituted at positions 5,5&#8242; with pyrrolyl, <i>N</i>-methyl-pyrrolyl and thienyl groups and their application in the preparation of conducting polymers is reported herein. The preparation of these monomers consisted of two synthetic s...

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Main Authors: Robert Texidó, Gonzalo Anguera, Sergi Colominas, Salvador Borrós, David Sánchez-García
Format: Article
Language:English
Published: MDPI AG 2019-06-01
Series:Polymers
Subjects:
Online Access:https://www.mdpi.com/2073-4360/11/6/1068
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author Robert Texidó
Gonzalo Anguera
Sergi Colominas
Salvador Borrós
David Sánchez-García
author_facet Robert Texidó
Gonzalo Anguera
Sergi Colominas
Salvador Borrós
David Sánchez-García
author_sort Robert Texidó
collection DOAJ
description The synthesis of 2,2&#8242;-bipyrroles substituted at positions 5,5&#8242; with pyrrolyl, <i>N</i>-methyl-pyrrolyl and thienyl groups and their application in the preparation of conducting polymers is reported herein. The preparation of these monomers consisted of two synthetic steps from a functionalized 2,2&#8242;-bipyrrole: Bromination of the corresponding 2,2&#8242;-bipyrrole followed by Suzuki or Stille couplings. These monomers display low oxidation potential compared to pyrrole because of the extended length of their conjugation pathway. The resulting monomers can be polymerized through oxidative/electropolymerization. Electrical conductivity and electrochromic properties of the electrodeposited polymeric films were evaluated using 4-point probe measurements and cyclic voltammetry to evaluate their applicability in electronics.
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spelling doaj.art-e37686fc3ae8411f8e66c2d1ad49f90a2022-12-22T03:43:48ZengMDPI AGPolymers2073-43602019-06-01116106810.3390/polym11061068polym11061068Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored ProcessabilityRobert Texidó0Gonzalo Anguera1Sergi Colominas2Salvador Borrós3David Sánchez-García4Grup d’Enginyeria de Materials (GEMAT), Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, 08017 Barcelona, SpainGrup d’Enginyeria de Materials (GEMAT), Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, 08017 Barcelona, SpainElectrochemical Methods Laboratory—Analytical and Applied Chemistry Department at Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, 08017 Barcelona, SpainGrup d’Enginyeria de Materials (GEMAT), Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, 08017 Barcelona, SpainGrup d’Enginyeria de Materials (GEMAT), Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, 08017 Barcelona, SpainThe synthesis of 2,2&#8242;-bipyrroles substituted at positions 5,5&#8242; with pyrrolyl, <i>N</i>-methyl-pyrrolyl and thienyl groups and their application in the preparation of conducting polymers is reported herein. The preparation of these monomers consisted of two synthetic steps from a functionalized 2,2&#8242;-bipyrrole: Bromination of the corresponding 2,2&#8242;-bipyrrole followed by Suzuki or Stille couplings. These monomers display low oxidation potential compared to pyrrole because of the extended length of their conjugation pathway. The resulting monomers can be polymerized through oxidative/electropolymerization. Electrical conductivity and electrochromic properties of the electrodeposited polymeric films were evaluated using 4-point probe measurements and cyclic voltammetry to evaluate their applicability in electronics.https://www.mdpi.com/2073-4360/11/6/1068pyrrole2,2′-bipyrrolepolypyrroleconjugated polymerelectropolymerization
spellingShingle Robert Texidó
Gonzalo Anguera
Sergi Colominas
Salvador Borrós
David Sánchez-García
Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability
Polymers
pyrrole
2,2′-bipyrrole
polypyrrole
conjugated polymer
electropolymerization
title Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability
title_full Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability
title_fullStr Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability
title_full_unstemmed Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability
title_short Extended 2,2′-Bipyrroles: New Monomers for Conjugated Polymers with Tailored Processability
title_sort extended 2 2 bipyrroles new monomers for conjugated polymers with tailored processability
topic pyrrole
2,2′-bipyrrole
polypyrrole
conjugated polymer
electropolymerization
url https://www.mdpi.com/2073-4360/11/6/1068
work_keys_str_mv AT roberttexido extended22bipyrrolesnewmonomersforconjugatedpolymerswithtailoredprocessability
AT gonzaloanguera extended22bipyrrolesnewmonomersforconjugatedpolymerswithtailoredprocessability
AT sergicolominas extended22bipyrrolesnewmonomersforconjugatedpolymerswithtailoredprocessability
AT salvadorborros extended22bipyrrolesnewmonomersforconjugatedpolymerswithtailoredprocessability
AT davidsanchezgarcia extended22bipyrrolesnewmonomersforconjugatedpolymerswithtailoredprocessability