Structural and thermal properties of carboxylic acid functionalized polythiophenes
Mescoloto, Ariane de França; Pulcinelli, Sandra Helena; Santilli, Celso Valentin; Gonçalves, Vanessa Cristina
http://dx.doi.org/10.4322/polimeros.2014.049
Polímeros: Ciência e Tecnologia, vol.24, nEspecial, p.31-35, 2014
Abstract
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.
Keywords
Conjugated polymer, polythiophene, synthesis, thiophene-3-acetic acid
References
1. Skothein, T. A.; Reynolds, J. R.- "Handbook of Conducting Polymers", CRC Press, Boca Raton (2007).
2. Chan, H. S. O.; Ng, S. C.- Progress in Polymer Science, 23, n.7, (1998). 3. Perepichka, I. F.; Perepichka, D. F.; Meng, H.; Wudl, F.- Advanced Materials, 17, n.19, (2005).
4. Roncali, J.- Chemical Reviews, 92, n.4, (1992).
5. McCullough, R. D.- Advanced Materials, 10, n.2, (1998).
6. Niemi, V. M.; Knuuttila, P.; Osterholm, J. E.; Korvola, J.- Polymer, 33, n.7, (1992).
7. Schopf, G.; Kossmehl, G.- "Polythiophenes - Electrically conductive polymers- Introduction", Advances in Polymer Science (1997).
8. Nicho, M. E.; Hu, H. L.; Lopez-Mata, C.; Escalante, J.- Solar Energy Materials and Solar Cells, 82, n.1-2, (2004).
9. Qiao, X. Y.; Wang, X. H.; Mo, Z. S.- Synthetic Metals, 118, n.1-3, (2001).
10. Goncalves, V. C.; Balogh, D. T.- Sensors and Actuators B-Chemical, 142, n.1, (2009).
11. Ganapathy, H. S.; Kim, J. S.; Jin, S. H.; Gal, Y. S.; Lim, K. T.- Synthetic Metals, 156, n.1, (2006).
12. Kim, H. C.; Kim, J. S.; Baek, S.; Ree, M.- Macromolecular Research, 14, n.2, (2006).
13. He, J.; Su, Z. J.; Yan, B.; Xiang, L.; Wang, Y. H.- Journal of Macromolecular Science Part a-Pure and Applied Chemistry, 44, n.7-9, (2007).
14. Nicolas, M.; Guittard, F.; Geribaldi, S.- Journal of Polymer Science Part a- Polymer Chemistry, 45, n.20, (2007).
15. Osaka, I.; McCullough, R. D.- Accounts of Chemical Research, 41, n.9, (2008).
16. Wang, L.; Ji, J. S.; Lin, Y. J.; Rwei, S. P.- Synthetic Metals, 155, n.3, (2005).
17. Ji, J. S.; Lin, Y. J.; Lu, H. P.; Wang, L.; Rwei, S. P.- Thin Solid Films, 511, (2006).
18. Mukta, B.; Mahanta, D.; Patil, S.; Madras, G.- Journal of Solid State Chemistry, 180, p.2986 (2007).
19. Chang, Y. M.; Su, W. F.; Wang, L.- Macromolecular Rapid Communications, 29, p.1303 (2008).
20. Han, Z.; Zhang, J.; Yang, D.; Zhu, H.; Cao, W.- Journal of Materials Science: Materials in Electronics, 21, p.554 (2010).
21. Clement, S.; Tizit, A.; Desbief, S.; Mehdi, A.; De Winter, J.; Gerbaux, P.; Lazzaroni, R.; Boury, B.- Journal of Materials Chemistry, 21, p.2733 (2011).
22. Gonçalves, V. C.; Pulcinelli, S. H.; Santilli, C. V. “Polythiophene-silica hybrid films prepared by sol-gel process” - Synthetic Metals, (submitted 2012).
23. Della Casa, C.; Andreani, F.; Bizzari, P. C.; Salatelli, E.- Journal of Materials Chemistry, 4, n.7, p.1035 (1994).
24. Della Casa, C.; Salatelli, E.; Andreani, F.; Bizzarri, P. C.- Makromolekulare Chemie-Macromolecular Symposia, 59, (1992).
25. Lanzi, M.; Bertinelli, F.; Bizzarri, P. C.; Della Casa, C.- Polymers for Advanced Technologies, 9, p.334 (1998).
26. Lanzi, M.; Costa-Bizzarri, P.; Della-Casa, C.; Paganin, L.; Fraleoni, A.- Polymer, 44, n.3, (2003).
27. Liaw, D. J.; Liaw, B. Y.; Gong, J. P.; Osada, Y.- Synthetic Metals, 99, n.1, (1999).
28. Paganin, L.; Lanzi, I.; Costa-Bizzarri, P.; Bertinelli, F.; Masi, C.- Macromolecular Symposia, 218, (2004).
29. Goncalves, V. C.; Costa, L. M. M.; Cardoso, M. R.; Mendonca, C. R.; Balogh, D. T.- Journal of Applied Polymer Science, 114, n.2, (2009).
30. Gonçalves, V. C.; Balogh, D. T. “Chemical Polymerization of Different Polythiophene Derivatives with FeCl3 in a Chloroform/ Nitromethane Mixture” - European Polymer Journal, (submitted 2012).
31. Laakso, J.; Jarvinen, H.; Skagerberg, B.- Synthetic Metals, 55, n.2-3, (1993).
32. Colthup, N. B.; Daly, L. H.- "Introduction to Infrared and Raman Spectroscopy", Academic Press, San Diego (1990).
33. Amou, S.; Haba, O.; Shirato, K.; Hayakawa, T.; Ueda, M.; Takeuchi, K.; Asai, M.- Journal of Polymer Science Part a-Polymer Chemistry, 37, n.13, (1999).
Facebook
Google+
Twitter
LinkedIn
Mendeley
StumbleUpon
CiteULike
Reddit
Email