Structural and thermal properties of carboxylic acid functionalized polythiophenes
Polythiophenes functionalized with polar groups at the end of side-chain have emerged as an alternative method to obtain good compatibility between this class of conjugated polymers and electron acceptor compounds. The aim is to prevent phase segregation and to improve the efficiency of the polythio...
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Associação Brasileira de Polímeros
2014-01-01
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doaj-2a4392469e8746518c477cbcaf5c78972020-11-24T22:45:10ZengAssociação Brasileira de PolímerosPolímeros1678-51692014-01-0124spe253010.4322/polimeros.2014.049S0104-14282014000700007Structural and thermal properties of carboxylic acid functionalized polythiophenesAriane de França Mescoloto0Sandra Helena Pulcinelli1Celso Valentim Santilli2Vanessa Cristina Gonçalves3Universidade Estadual PaulistaUniversidade Estadual PaulistaUniversidade Estadual PaulistaInstituto Federal de Educação, Ciência e Tecnologia de São PauloPolythiophenes functionalized with polar groups at the end of side-chain have emerged as an alternative method to obtain good compatibility between this class of conjugated polymers and electron acceptor compounds. The aim is to prevent phase segregation and to improve the efficiency of the polythiophene technological devices. However, homopolymers synthesized from thiophene rings with high polar groups at the end of the side-chain, such as hydroxyl and carboxylic acid groups, are poorly soluble in common volatile organic solvents. We report on a systematic preparation of copolymers of 3-hexylthiophene (HT) and thiophene-3-acetic acid (TAA), using different feed ratios. The chemical structures of the copolymers were confirmed by FTIR and ¹H-NMR. The TAA content in these copolymers were 33, 38 and 54 mol %. HPSEC results did not show any remarkable correlation with TAA contents in the copolymers. In contrast, the thermal analyses showed a decrease in the thermal stability and an increase in rigidity of their backbones, for the copolymers with high amounts of TAA. The solubility and optical property of copolymers were also related to the TAA contents. Thus, the properties of these copolymers can be modulated by a simple control of feed ratio of TAA in the copolymerization.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0104-14282014000700007&lng=en&tlng=enConjugated polymerpolythiophenesynthesisthiophene-3-acetic acid |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Ariane de França Mescoloto Sandra Helena Pulcinelli Celso Valentim Santilli Vanessa Cristina Gonçalves |
spellingShingle |
Ariane de França Mescoloto Sandra Helena Pulcinelli Celso Valentim Santilli Vanessa Cristina Gonçalves Structural and thermal properties of carboxylic acid functionalized polythiophenes Polímeros Conjugated polymer polythiophene synthesis thiophene-3-acetic acid |
author_facet |
Ariane de França Mescoloto Sandra Helena Pulcinelli Celso Valentim Santilli Vanessa Cristina Gonçalves |
author_sort |
Ariane de França Mescoloto |
title |
Structural and thermal properties of carboxylic acid functionalized polythiophenes |
title_short |
Structural and thermal properties of carboxylic acid functionalized polythiophenes |
title_full |
Structural and thermal properties of carboxylic acid functionalized polythiophenes |
title_fullStr |
Structural and thermal properties of carboxylic acid functionalized polythiophenes |
title_full_unstemmed |
Structural and thermal properties of carboxylic acid functionalized polythiophenes |
title_sort |
structural and thermal properties of carboxylic acid functionalized polythiophenes |
publisher |
Associação Brasileira de Polímeros |
series |
Polímeros |
issn |
1678-5169 |
publishDate |
2014-01-01 |
description |
Polythiophenes functionalized with polar groups at the end of side-chain have emerged as an alternative method to obtain good compatibility between this class of conjugated polymers and electron acceptor compounds. The aim is to prevent phase segregation and to improve the efficiency of the polythiophene technological devices. However, homopolymers synthesized from thiophene rings with high polar groups at the end of the side-chain, such as hydroxyl and carboxylic acid groups, are poorly soluble in common volatile organic solvents. We report on a systematic preparation of copolymers of 3-hexylthiophene (HT) and thiophene-3-acetic acid (TAA), using different feed ratios. The chemical structures of the copolymers were confirmed by FTIR and ¹H-NMR. The TAA content in these copolymers were 33, 38 and 54 mol %. HPSEC results did not show any remarkable correlation with TAA contents in the copolymers. In contrast, the thermal analyses showed a decrease in the thermal stability and an increase in rigidity of their backbones, for the copolymers with high amounts of TAA. The solubility and optical property of copolymers were also related to the TAA contents. Thus, the properties of these copolymers can be modulated by a simple control of feed ratio of TAA in the copolymerization. |
topic |
Conjugated polymer polythiophene synthesis thiophene-3-acetic acid |
url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0104-14282014000700007&lng=en&tlng=en |
work_keys_str_mv |
AT arianedefrancamescoloto structuralandthermalpropertiesofcarboxylicacidfunctionalizedpolythiophenes AT sandrahelenapulcinelli structuralandthermalpropertiesofcarboxylicacidfunctionalizedpolythiophenes AT celsovalentimsantilli structuralandthermalpropertiesofcarboxylicacidfunctionalizedpolythiophenes AT vanessacristinagoncalves structuralandthermalpropertiesofcarboxylicacidfunctionalizedpolythiophenes |
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1725689831060668416 |