This paper describes a new easy and straight-forward synthetic pathway leading to a thiophenic monomer functionalized with a second-order NLO chromophore and with an alkylic plastifying chain, namely the 3-{6-[4-(40- nitrophenylazo)-N-ethyl-N-phenylamino]hexyl}-4-hexylthiophene. The corresponding polymers obtained by direct oxidative polymerization and by post-polymerization functionalization of a polymeric precursor are soluble in common organic solvents even if their chromophore content is 100%. The final materials have been characterized by using 1Hand 13C-NMR spectrometry, FT-IR spectroscopy, SEC, DSC analysis and conductivity measurements. The thermal characteristics and the electrical behaviour of the ‘‘self-plastifying’’ polymers are comparable to those of the alkylthiophene/ chromophorized-alkylthiophene copolymers, but the presence of the highest content in NLO chromophoric substituent in the new synthesized homopolymers makes them particularly interesting for optoelectronic applications.

Synthesis and polymerization of a new thiophene functionalized with both NLO-active chromophore and an alkylic self-plastifying chain

LANZI, MASSIMILIANO;PAGANIN, LUISA;COSTA BIZZARRI, PAOLO
2004

Abstract

This paper describes a new easy and straight-forward synthetic pathway leading to a thiophenic monomer functionalized with a second-order NLO chromophore and with an alkylic plastifying chain, namely the 3-{6-[4-(40- nitrophenylazo)-N-ethyl-N-phenylamino]hexyl}-4-hexylthiophene. The corresponding polymers obtained by direct oxidative polymerization and by post-polymerization functionalization of a polymeric precursor are soluble in common organic solvents even if their chromophore content is 100%. The final materials have been characterized by using 1Hand 13C-NMR spectrometry, FT-IR spectroscopy, SEC, DSC analysis and conductivity measurements. The thermal characteristics and the electrical behaviour of the ‘‘self-plastifying’’ polymers are comparable to those of the alkylthiophene/ chromophorized-alkylthiophene copolymers, but the presence of the highest content in NLO chromophoric substituent in the new synthesized homopolymers makes them particularly interesting for optoelectronic applications.
M. Lanzi; L. Paganin; P. Costa Bizzarri
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/5581
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