Synthesis Of C 60-containing Polymers By Ring-opening Metathesis Co-polymerization Of A C 60-cyclopentadiene Cycloadduct And N-(cycloheptyl)-endo-norbornene-5, 6-dicarboximide And Their Application In A Photovoltaic Device

Abstract

A C 60-cyclopentadiene cycloadduct and N-(cycloheptyl)-endo- norbornene-5,6- dicarboximide were utilized as co-monomers in ring-opening metathesis polymerization (ROMP) reactions to afford a series of polymers containing C 60 in varying ratios. The polymerization reactions were catalyzed by the Grubbs second-generation ruthenium catalyst, and the co-polymers formed were investigated by spectroscopic and thermal techniques. The photovoltaic behavior of the new materials was studied by the construction of a simple sandwich-type photovoltaic cell. Under irradiation we concluded that the C 60 in the copolymers simultaneously accelerated both the charge separation in the polymer and the charge recombination between the electrons in the TiO2 and the electrolyte. Copyright © Taylor & Francis Group, LLC.213198212Giacalone, F., Martín, N., (2006) Chem. Rev., 106, p. 5136Wang, C., Guo, Z.-X., Fu, S., Wu, W., Zhu, D., (2004) Prog. Polym. Sci., 29, p. 1079Geckeler, K.E., Samal, S., (1999) Polym. Int., 48, p. 743Prato, M., (1997) J. Mater. Chem., 7, p. 1097Shi, S., Khemani, K.C., Li, Q.C., Wudl, F., (1992) J. Am. Chem. Soc., 114, p. 10656Song, T., Goh, S.H., Lee, S.Y., (2003) Polymer, 44, p. 2563Ma, C.-C.M., Sung, S.-C., Wang, F.-Y., Chiang, L.Y., Wang, L.Y., Chiang, C.-L., (2001) J. Polym. Sci., Part B: Polym. Phys., 39, p. 2436. , and references cited thereinImahori, H., Hagiwara, K., Akiyama, T., Aoki, M., Taniguchi, S., Okada, T., Shirakawa, M., Sakata, Y., (1996) Chem. Phys. Lett., 263, p. 545Yu, G., Gao, Y., Hummelen, J.C., Wudl, F., Heeger, A.J., (1995) Science, 270, p. 1789Sariciftci, N.S., Smilowitz, L., Heeger, A.J., Wudl, F., (1992) Science, 258, p. 1474. , 7Imahori, H., Sakata, Y., (1999) Eur. J. Org. Chem., p. 2445Gust, D., Moore, T.A., Moore, A.L., (2001) Acc. Chem. Res., 34, p. 40Roncali, (2005) J. Chem. Soc. Rev., 34, p. 483Bazaco, R.B., Segura, J.L., Seoane, C., (2009) Collect. Czech. Chem. Commun., 74, p. 857Hiorns, R.C., Cloutet, E., Ibarboure, E., Khoukh, A., Bejbouji, H., Vignau, L., Cramail, H., (2010) Macromolecules, 43, p. 6033Hilf, S., Kilbinger, A.F.M., (2009) Macromolecules, 42, p. 1099Sharma, G.D., Balraju, P., Mikroyannidis, J.A., Stylianakis, M.M., (2009) Sol. Energy Mater. Sol. Cells, 93, p. 2025Jin, Y., Jee, J., Kim, H., Song, S., Park, S.H., Kim, J., Kang, S.-W., Suh, H., (2009) Synth. Met.,., 159, p. 1529Mozer, A.J., Sariciftci, N.S., (2006) C.R. Chimie, 9, p. 568Sakai, J., Taima, T., Saito, K., (2008) Org. Electron., 9, p. 582Zhang, N., Schricker, S.R., Wudl, F., Prato, M., Maggini, M., Scorrano, G., (1995) Chem. Mater., 7, p. 441Ball, Z.T., Sivula, K., Fréchet, J.M.J., (2006) Macromolecules, 39, p. 70De La Escosura, A., Martínez-Díaz, M.V., Torres, T., Grubbs, R.H., Guldi, D.M., Neugebauer, H., Winder, C., Sariciftci, N.S., (2006) Chem. Asian J., 1-2, p. 148Sivula, K., Ball, Z.T., Watanabe, N., Fréchet, J.M.J., (2006) Adv. Mater., 18, p. 206Liu, X., Basu, A., (2006) J. Organomet. Chem., 691, p. 5148Gómez, F.J., Chen, J., Wang, D., Waymouth, R.R.M., Dai, H., (2003) Chem. Commun., p. 190Liu, Y., Andronov, A., (2004) Macromolecules, 37, p. 4755Mamo, M.A., Coville, N.J., Van Otterlo, W.A.L., (2007) Fullerenes, Nanotubes and Carbon Nanostructures, 15, p. 341. , 15Trnka, T.M., Grubbs, R.H., (2001) Acc. Chem. Res., 34Morgans, G.L., Ngidi, E.L., Madeley, L.G., Khanye, S.D., Michael, J.P., De Koning, C.B., Van Otterlo, W.A.L., (2009) Tetrahedron, 65, p. 10650Scalzullo, S.M., Uislam, U., Morgans, G.L., Michael, J.P., Van Otterlo, W.A.L., (2008) Tetrahedron Lett., 49, p. 7403Panayides, J.-L., Pathak, R., Panagiotopoulos, H., Davids, H., Fernandes, M.A., De Koning, C.B., Van Otterlo, W.A.L., (2007) Tetrahedron, 63, p. 4737Panayides, J.-L., Pathak, R., De Koning, C.B., Van Otterlo, W.A.L., (2007) Eur. J. Org. Chem., 4953Coyanis, E.M., Panayides, J.-L., Fernandes, M.A., De Koning, C.B., Van Otterlo, W.A.L., (2006) J. Organomet. Chem., 691, p. 5222Yadav, D.B., Morgans, G.L., Aderibigbe, B.A., Madeley, L.G., Fernandes, M.A., Michael, J.P., De Koning, C.B., Van Otterlo, W.A.L., (2011) Tetrahedron, 67, p. 2991Contreras, A.P., Tlenkopatchev, M.A., Del Mar López-González, M., Riande, E., (2002) Macromolecules, 35, p. 4677For related work concerning N-alkylated norbornene dicarboximides and their application in ROMP, see the following representative publications:Matson, J.B., Grubbs, R.H., (2010) Macromolecules, 43, p. 213Hilf, S., Grubbs, R.H., Kilbinger, A.F.M., (2008) J. Am. Chem. Soc., 130, p. 11040Vargas, J., Santiago, A.A., Gaviño, R., Cerda, A.M., Tlenkopatchev, M.A., (2007) Express Polym. Lett., 1, p. 274Santiago, A.A., Vargas, J., Gaviño, R., Cerda, A.M., Tlenkopatchev, M.A., (2007) Macromol. Chem. Phys., 208, p. 1085Hilf, S., Kilbinger, A.F.M., (2007) Macromol. Rapid Commun., 28, p. 1225Thomas, C.C., Ezat, K., Lian, R.H., (2006) Macromolecules, 39, p. 5639Castle, T.C., Khosravi, E., Hutchings, L.R., (2006) Macromolecules, 39, p. 5639Madan, R., Anand, R.C., Varma, I.K., (1997) J. Polym. Sci.: Part A: Polym. Chem., 35, p. 2917Rotello, V.M., Howard, J.B., Yadav, T., Conn, M.M., Viani, E., Giovane, L.M., Lafleur, A.L., (1993) Tetrahedron Lett., 34, p. 1561Wilson, S.R., Yurchenko, M.E., Schuster, D.I., Khong, A., Saunders, M., (2000) J. Org. Chem., 65, p. 2619Schwenninger, R., Müller, T., Kräutler, B., (1997) J. Am. Chem. Soc., 119, p. 9317Nie, B., Rotello, V.M., (1996) J. Org. Chem., 61, p. 1870Yurovskaya, M.A., Trushkov, I.V., (2002) Russ. Chem. Bull. Int. Ed., 51, p. 367Hudhomme, P., (2006) C.R. Chimie, 9, p. 881Taylor, R., (2006) C.R. Chimie, 9, p. 982Yli-Kauhaluoma, J., (2001) Tetrahedron, 57, p. 7053Goh, H.W., Goh, S.H., Xu, G.Q., (2002) J. Polym. Sci. Part A: Polym. Chem., 40, p. 1157Zhang, X., Sieval, A.B., Hummelen, J.C., Hessen, B., (2005) Chem. Commun., p. 1616Geckeler, K.E., Hirsch, A., (1993) J. Am. Chem. Soc., 115, p. 3850Suzuki, T., Li, Q., Khemani, K.C., Wudl, F., (1992) J. Am. Chem. Soc., 114, p. 7301Li, W.J., Liang, W.J., (2007) Spectrochim. Acta Part A, 67, p. 1346Tang, B.Z., Leung, S.M., Peng, H., Yu, N.-T., Su, K.C., (1997) Macromolecules, 30, p. 2848Chu, C.-C., Ho, T.-I., Wang, L., (2006) Macromolecules, 39, p. 5657Xiao, S., Li, Y., Li, Y., Li, H., Zhuang, J., Liu, Y., Lu, F., Zhu, D., (2004) Tetrahedron Lett., 45, p. 3975Kraus, A., Mullen, K., (1999) Macromolecules, 32, p. 4214Camp, A.G., Lary, A., Ford, W.T., (1995) Macromolecules, 28, p. 7959Chiang, L.Y., Wang, L.Y., Kuo, C.-S., (1995) Macromolecules, 28, p. 7574Dai, L., Mau, A.W.H., Griesser, H.J., Spurling, T.H., (1995) J. Phys. Chem., 99, p. 17302MacHado, W., Athayde, P., Mamo, M.A., Van Otterlo, W.A.L., Coville, N.J., Hümmelgen, I.A., (2010) Org. Electron., 11, p. 1736Mamo, M.A., MacHado, W.S., Van Otterlo, W.A.L., Coville, N.J., Hümmelgen, I.A., (2010) Org. Electron., 11, p. 1858De Freitas, J.N., Mamo, M.A., Maubane, M., Van Otterlo, W.A.L., Coville, N.J., Nogueira, A.F., (2012) J. Power Sources, , DOI 10.1016/j. jpowsour.2012.04.066Ohmori, Y., Itoh, E., Miyairi, K., (2006) Thin Solid Films, 499, p. 36