This paper reports the synthesis of a novel soluble poly(thienylene methylene) by a straightforward process based on the methanesulfonic acid-catalyzed self-condensation of 2-acetoxymethyl-3,4-dimethylthiophene. These macromolecules were found to generate in situ conjugated sequences consisting of thiophene and exounsaturated 2,5-dihydrothiophene moieties. The kinetics of these polycondensations, in which both the temperature and the monomer-to-catalyst molar ratio were varied, were followed by HPLC, as regards the rate of monomer consumption, and by GPC, as regards the evolution of the molecular weight of the growing chains. The ensuing polymers were characterized by FTIR, 1 H NMR, UV-vis spectroscopy, DSC, and TGA. † This contribution is dedicated to the fond memory of our dear friend and colleague Giovanna Costa, who died while this investigation was in progress.
This article reports a thorough spectroscopic characterization and the complete microstructural unravelling of a novel soluble poly(thienylene methylene) recently obtained by a straightforward process based on the methanesulfonic acidcatalyzed self-condensation of 2-acetoxymethyl-3,4-dimethylthiophene. These macromolecules were found to generate both in situ (in the acidic reaction medium) and ex situ (by the addition of appropriate dopants) conjugated sequences consisting of alternating aromatic-and quinoid-like thiophene rings, that is, conjugated thienylene methine sequences. The effect of different types of dopants on the electronic features of these polymers was assessed by the extent of bathochromic shifts they induced in the macromolecule UV-vis spectra. Doped films obtained by solution casting were characterized
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