Synthesis of a C₆₀-oligophenylenevinylene hybrid and its incorporation in a photovoltaic device

Abstract

A fulleropyrrolidine derivative bearing an oligophenylenevinylene substituent has been prepared by 1,3-dipolar cycloaddition of an azomethine ylide to C₆₀ and incorporated in a photovoltaic device.

References

1. A. Hirsch, Adv. Mater., 1993, 5, 859; F. Diederich and C. Thilgen, Science, 1996, 271, 317; M. Prato, J. Mater. Chem., 1997, 7, 1097; L. Echegoyen and L. E. Echegoyen, Acc. Chem. Res., 1998, 31, 593; F. Diederich and M. Gomez-Lopez, Chimia, 1998, 52, 551.
2. N. S. Sariciftci, L. Smilowitz, A. J. Heeger and F. Wudl, Science, 1992, 258, 1474; N. S. Sariciftci, D. Braun, C. Zhang, V. Srdanov, A. J. Heeger, G. Stucky and F. Wudl, Appl. Phys. Lett., 1993, 62, 585; R. A. J. Janssen, M. P. T. Christiaans, K. Pakbaz, D. Moses, J. C. Hummelen and N. S. Sariciftci, J. Chem. Phys., 1995, 102, 2628; R. A. J. Jansen, J. C. Hummelen, K. Lee, K. Pakbaz, N. S. Sariciftci, A. J. Heeger and F. Wudl, J. Chem. Phys., 1995, 103, 788; G. Yu, J. Gao, J. C. Hummelen, F. Wudl and A. J. Heeger, Science, 1995, 270, 1789; B. Kraabel, J. C. Hummelen, D. Vacar, D. Moses, N. S. Sariciftci, A. J. Heeger and F. Wudl, J. Chem. Phys., 1996, 104, 4267; L. S. Roman, M. R. Andersson, T. Yohannes and O. Inganäs, Adv. Mater., 1997, 9, 1164.
3. S. I. Khan, A. M. Olivier, M. N. Paddon-Row and Y. Rubin, J. Am. Chem. Soc., 1993, 115, 4919; R. M. Williams, J. M. Zwier and J. W. Verhoeven, J. Am. Chem. Soc., 1995, 117, 4093; D. Armspach, E. C. Constable, F. Diederich, C. E. Housecroft and J.-F. Nierengarten, Chem. Commun., 1996, 2009; H. Imahori and Y. Sakata, Adv. Mater., 1997, 9, 537; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; N. Martin, L. Sanchez, B. Illescas and I. Perez, Chem. Rev., 1998, 98, 2527; F. Effenberger and G. Grube, Synthesis, 1998, 1372; S. Llacay, J. Veciana, J. Vidal-Gancedo, J. L. Bourdelande, R. Gonzalez-Moreno and C. Rovira, J. Org. Chem., 1998, 63, 5201; J. M. Lawson, A. M. Olivier, D. F. Rotherfluh, Y.-Z. An, G. A. Ellis, M. G. Ranasinghe, S. I. Khan, A. G. Franz, P. S. Ganapathi, M. J. Shephard, M. N. Paddon-Row and Y. Rubin, J. Org. Chem., 1996, 61, 5032; R. M. Williams, M. Koeberg, J. M. Lawson, Y.-Z. An, Y. Rubin, M. N. Padden-Row and J. W. Verhoeven, J. Org. Chem., 1996, 61, 5055.
4. N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker and J.-P. Sauvage, Angew. Chem., Int. Ed. Engl., 1996, 35, 906.
5. J.-F. Nierengarten and J.-F. Nicoud, Tetrahedron Lett., 1997, 38, 7737.
6. G. Zerban and H. Meier, Z. Naturforcsh. Teil B, 1993, 48, 171.
7. M. Prato and M. Maggini, Acc. Chem. Res., 1998, 31, 519 and references therein.