Hostname: page-component-7479d7b7d-m9pkr Total loading time: 0 Render date: 2024-07-12T11:44:03.727Z Has data issue: false hasContentIssue false

Synthesis and Physicochemical Characterization of New Polythiophenes Based on Three Different Monomers

Published online by Cambridge University Press:  16 March 2015

Karla K. Guzmán-Rabadán
Affiliation:
Centro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp), Universidad Autónoma del Estado de Morelos (UAEM). Av. Universidad No. 1001, Col. Chamilpa, C.P. 62209, Cuernavaca, Morelos, México.
Marco A. Ramírez-Gómez
Affiliation:
Centro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp), Universidad Autónoma del Estado de Morelos (UAEM). Av. Universidad No. 1001, Col. Chamilpa, C.P. 62209, Cuernavaca, Morelos, México.
Marisol Güizado-Rodríguez
Affiliation:
Centro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp), Universidad Autónoma del Estado de Morelos (UAEM). Av. Universidad No. 1001, Col. Chamilpa, C.P. 62209, Cuernavaca, Morelos, México.
Jorge A. Guerrero-Álvarez
Affiliation:
Centro de Investigaciones Químicas (CIQ), Universidad Autónoma del Estado de Morelos (UAEM). Av. Universidad No. 1001, Col. Chamilpa, C.P. 62209, Cuernavaca, Morelos, México.
Víctor Barba
Affiliation:
Centro de Investigaciones Químicas (CIQ), Universidad Autónoma del Estado de Morelos (UAEM). Av. Universidad No. 1001, Col. Chamilpa, C.P. 62209, Cuernavaca, Morelos, México.
Miguel A. Basurto-Pensado
Affiliation:
Centro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp), Universidad Autónoma del Estado de Morelos (UAEM). Av. Universidad No. 1001, Col. Chamilpa, C.P. 62209, Cuernavaca, Morelos, México.
Rosario Galindo
Affiliation:
Centro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, C.P. 37150, León, Guanajuato, México.
Mario Rodríguez
Affiliation:
Centro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, C.P. 37150, León, Guanajuato, México.
José L. Maldonado
Affiliation:
Centro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, C.P. 37150, León, Guanajuato, México.
Get access

Abstract

The chemical synthesis of the copolymers poly(3-HT-co-EDOT-co-fluorene) and poly(3-HT-co-EDOT-co-TDR1) is reported. The first copolymer is derived of 3-hexylthiophene (3-HT), 3,4-ethylenedioxythiophene (EDOT) and 2,2'- (9,9-dioctyl-9H-fluorene-2,7-diyl) bisthiophene (fluorene). The second copolymer is derived of 3-hexylthiophene (3-HT), 3,4-ethylenedioxythiophene (EDOT) and (E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethyl 2-(thiophen-3-yl)acetate (TDR1). Their physicochemical characterization by 1H NMR, FT-IR, DSC-TGA, GPC, UV-vis, cyclic voltammetry was carried out. These copolymers combine the high electron density and low oxidation potential of EDOT with the high charge mobility and processability of 3-HT. These are candidates for applications as active or barrier layer in electronic devices (bulk heterojuntion organic solar cells) or as functional membranes (e.g., sensors).

Type
Articles
Copyright
Copyright © Materials Research Society 2015 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

Alcazar, D., Wang, F., Swager, T. M., Thomas, E. L., Macromolecules 41, 9863 (2008).CrossRefGoogle Scholar
Ng, S. C., Ding, M., Chan, H. S. O., Yu, W. L., Macromol. Chem. Phys. 202, 8 (2001).3.0.CO;2-U>CrossRefGoogle Scholar
Zagórska, M., Kulszewicz-Bajer, I., Proń, A., Raimond, P., Kajzar, F., Attias, A.-J., Synth. Met. 102, 1141 (1999).CrossRefGoogle Scholar
Samyn, C., Verbiest, T., Persoons, A., Macromol. Rapid. Comun. 21, 1 (2000).3.0.CO;2-X>CrossRefGoogle Scholar
Della-Casa, C., Fraleoni, A., Costa-Bizzarri, P., Lanzi, M., Synth. Met. 124, 467 (2001).CrossRefGoogle Scholar
Abd-EI-Aziz, A. S., Afifi, T. H., Budakowski, W. R., Friesen, K. J., Todd, E. K., Macromolecules 35 (24), 8929 (2002).CrossRefGoogle Scholar
Lanzi, M., Paganin, L., Costa-Bizarri, P., Della-Casa, C., Fraleoni, A., Macromol. Rapid Commun. 23, 630 (2002).3.0.CO;2-9>CrossRefGoogle Scholar
Della-Casa, C., Costa-Bizzarri, P., Lanzi, M., Paganin, L., Bertinelli, F., Pizzoferrato, R., Sarcinelli, F., Casalboni, M., Synth. Met. 138, 409 (2003).CrossRefGoogle Scholar
Lanzi, M., Paganin, L., Costa-Bizzarri, P., Eur. Polym. J. 40, 2117 (2004).CrossRefGoogle Scholar
Della-Casa, C., Fraleoni-Morgera, A., Lanzi, M., Costa-Bizzarri, P., Paganin, L., Bertinelli, F., Schenetti, L., Mucci, A., Casalboni, M., Sarcinelli, F., Quatela, A., Eur. Polym. J. 41, 2360 (2005).CrossRefGoogle Scholar
Gonҫalves, V. C., Balogh, D. T., Eur. Polym. J. 42, 3303 (2006).CrossRefGoogle Scholar
Lanzi, M., Bertinelli, F., Paganin, L., Costa-Bizzarri, P., Cesari, G., Macromol. Chem. Phys. 207, 1253 (2006).CrossRefGoogle Scholar
Caruso, U., Diana, R., Fort, A., Panunzi, B., Roviello, A., Macromol. Symp. 234, 87 (2006).CrossRefGoogle Scholar
Batista, R. M. F., Costa, S. P. G., Belsley, M., Raposo, M. M. M., Tetrahedron 63, 9842 (2007).CrossRefGoogle Scholar
Kim, D. W., Choi, J. J., Lim, J.-S., Lee, Ch., Mol. Cryst. Liq. Cryst. 463, 43/[325]-53/[335] (2007).Google Scholar
Ma, X., Liang, R., Yang, F., Zhao, Z., Zhang, A., Song, N., Zhou, Q., Zhang, J., J. Mater. Chem. 18, 1756 (2008).CrossRefGoogle Scholar
Shi, Z., Zhang, X., Cui, Z., J. of Nonlinear Optical Physics & Materials 17(3), 243 (2008).CrossRefGoogle Scholar
Zhang, B.-z., Zhao, X.-y., J. Mater. Sci. 44, 2765 (2009).CrossRefGoogle Scholar
Sonmez, G., Shen, C. K. F., Rubin, Y., Wudl, F., Angew. Chem. Int. Ed. 43, 1498 (2004).CrossRefGoogle Scholar
Dore, K., Dubus, S., Ho, H. A., Levesque, I., Leclerc, M., J. Am. Chem. Soc. 126, 4240 (2004).CrossRefGoogle Scholar
Villers, D., Jobin, D., Soucy, C., Cossement, D., Chahine, R., Breau, L., Belanger, D., J. Electrochem. Soc. A 150, 747 (2003).CrossRefGoogle Scholar
Tüken, T., Yazici, B., Erbil, M., Prog. Org. Coat. 51, 205 (2004).CrossRefGoogle Scholar
Ong, B. S., Wu, Y. L., Liu, P., Gardner, S., Adv. Mater. 17, 1141 (2005).CrossRefGoogle Scholar
Yang, H. C., Shin, T. J., Yang, L., Cho, K., Ryu, C. Y., Bao, Z. N., Adv. Funct. Mater. 15, 671 (2005).CrossRefGoogle Scholar
Ong, B. S., Wu, Y., Liu, P., Gardner, S., J. Am. Chem. Soc. 126, 3378 (2004).CrossRefGoogle Scholar
Breggren, M., Inganas, O., Rasmusson, J., Gustafsson, G., Andersson, M. R., Wennerstrom, O., Hjertberg, T., Nature 372, 444 (1994).CrossRefGoogle Scholar
Ahn, S. H., Czae, M., Kim, E. R., Lee, H., Han, S. H., Noh, J., Hara, M., Macromolecules 34, 2522 (2001).CrossRefGoogle Scholar
Brabec, C., J. Sol. Energy Mater. Sol. Cells 83, 273 (2004).CrossRefGoogle Scholar
Zhang, Y., Tajima, K., Hirota, K., Hashimoto, K., J. Am. Chem. Soc. 130, 7812 (2008).CrossRefGoogle Scholar
Ohshimizu, K., Ueda, M., Macromolecules 41, 5289 (2008).CrossRefGoogle Scholar
Wang, H.-S., Su, M.-S., Wei, K.-H., J. Polym. Sci. Polym. Chem. 48, 3331 (2010).CrossRefGoogle Scholar
Li, Y., Xue, L., Xia, H., Xu, B., Wen, S., Tian, W., J. Polym. Sci. Polym. Chem. 46, 3970 (2008).CrossRefGoogle Scholar
Miozzo, L., Battaglini, N., Braga, D., Kergoat, L., Suspène, C., Yassar, A., J. Polym. Sci. Polym. Chem., 50, 534 (2012).CrossRefGoogle Scholar