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Synthesis and Spectroscopic and Electrochemical Characterisation of a Conducting Polythiophene Bearing a Chiral β ‐Substituent: Polymerisation of (+)‐4,4′‐Bis[( S )‐2‐methylbutylsulfanyl]‐2,2′‐bithiophene
Author(s) -
Iarossi Dario,
Mucci Adele,
Parenti Francesca,
Schenetti Luisa,
Seeber Renato,
Zanardi Chiara,
Forni Arrigo,
Tonelli Massimo
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010202)7:3<676::aid-chem676>3.0.co;2-2
Subject(s) - polythiophene , substituent , electrochemistry , polymerization , bearing (navigation) , chemistry , polymer chemistry , materials science , combinatorial chemistry , conductive polymer , organic chemistry , polymer , electrode , physics , astronomy
A regioregular head‐to‐head / tail‐to‐tail poly( β , β ′‐disubstituted bithiophene) P 1 was synthesised by chemical and electrochemical polymerisation of 2,2′‐bithiophene that bears ( S )‐2‐methylbutylsulfanyl chains in the β and β ′‐positions. The polymer was characterised by GPC, NMR and UV/Vis spectroscopy, CD, AFM and by electrochemical and conductivity measurements. The CD spectra of P 1 in solutions in which poor solvents are present show interesting features and allow the presence of different optically active species to be distinguished. Upon varying the casting conditions of P 1 , different relative amounts of grainy and homogeneous aggregated phases were observed in AFM micrographies of films and corresponding negative or positive first Cotton effects were found in the CD spectra. AFM, CD and UV/Vis characterisations were also performed on an electrogenerated optically active polymer PE 1 , in order to make a comparison with the chemically synthesised one. The interesting, small band gap of P 1 allows for easy p‐ and n‐electrochemical doping.