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Synthesis and Electrochromic Properties of Conducting Polymers Based on Highly Planar 2,7‐Disubstituted Xanthene Derivatives
Author(s) -
Olech Kamila,
Gutkowski Ramona,
Kuznetsov Volodymyr,
Roszak Szczepan,
Sołoducho Jadwiga,
Schuhmann Wolfgang
Publication year - 2015
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201402349
Subject(s) - xanthene , electrochromism , copolymer , materials science , monomer , polymer , thiophene , electrochemistry , alkyl , polymerization , polymer chemistry , density functional theory , conductive polymer , combinatorial chemistry , chemistry , photochemistry , organic chemistry , computational chemistry , electrode , composite material
Abstract On the basis of preliminary DFT calculations, p‐type semiconducting polymers based on 2,7‐substituted xanthene building blocks that show a high degree of planarity were designed. The synthesis, electrochemical characterization, and theoretical modeling of 2,7‐bis(thiophen‐2‐yl)‐9,9‐dimethylxanthene ( 1 ) and 2,7‐bis(3‐hexylthiophen‐2‐yl)‐9,9‐dimethylxanthene ( 2 ) is described. The synthetic procedure is based on the incorporation of thiophene rings by means of Pd‐catalyzed cross‐coupling reactions, which lead to monomers 1 and 2 . Copolymers P1 and P2 obtained by means of anodic polymerization have been characterized by spectroscopic and electrochemical methods. Electrochromism was observed for both polymers. The experimental data supported by density functional theory modeling explain the influence of alkyl chain substitution on the properties of the investigated copolymers.