Abstract
The results of the authors’ studies on the [2+3] cycloaddition of azomethine and nitrile ylides generated from picolylamine and benzylamine derivatives to fullerenes are systematized and new experimental data are considered. Catalysts and microwave radiation promoting the formation of ylides and their addition to fullerenes were successfully used for the first time. A large series of new pyrrolidine and pyrroline derivatives of fullerenes C60 and C70 were synthesized and characterized. The proposed procedures afford the reaction products in yields twice as high (80–85%) as those attained by the classical Prato reaction. The reactions proceed with virtually complete regio- (in the case of C70) and stereoselectivity to afford only cis-2′,5′-disubstituted and trans-1′,2′,5′-trisubstituted pyrrolidinofullerenes. Pyridyl-substituted pyrrolidinofullerenes react with metalloporphyrins and phthalocyanines to form self-ordered coordination complexes. The latter are analogs of natural photosynthetic antenna systems due to photoinduced charge separation that occurs in these complexes upon exposure to light.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
A. Hirsch, M. Brettreich, Fullerenes Chemistry and Reactions, Wiley—VCH, London, 2004.
A. Hirsch, Top. Curr. Chem., 1999, 199, 1.
S. Bosi, T. Da Ross, G. Spalluto, M. Prato, Eur. J. Med. Chem., 2003, 38, 913.
T. Da Ros, M. Prato, Chem. Commun., 1999, 663.
N. Tagmatarchis, H. Shinohara, Mini Rev. Med. Chem., 2001, 1, 339.
P. Mroz, G. P. Tegos, H. Gali, T. Wharton, T. Sarna, M. R. Hamblin, Photochem. Photobiol. S., 2007, 6, 1139.
S. Bosi, T. Da Ros, S. Castellano, E. Bafni, M. Prato, Bioorg. Med. Chem. Lett., 2000, 10, 1043.
J. E. Kim, M. Lee, Biochem. Biophys. Res. Commun., 2003, 303, 576.
L. L. Dugan, E. G. Lovett, K. L. Queick, J. Lotharius, T. T. Lin, K. L. O’Malley, Parkinsonism and Related Disorders, 2001, 7, 243.
S. H. Friedman, D. L. DeCamp, R. P. Sijbesma, G. Srdanov, F. Wudl, G. L. Kenyon, J. Am. Chem. Soc., 1993, 115, 6506.
T. B. Singh, N. S. Sariciftci, Ann. Rev. Mater. Res., 2006, 36, 199.
B. T. Singh, N. Marjanovic, G. Matt, S. Guenes, N. S. Sariciftci, A. Montaigne, A. Andreev, H. Sitter, R. Schoediauer, S. Bauer, Org. Electron., 2005, 6, 105.
C. Waldauf, P. Schilinsky, M. Perisutti, J. Hauch, C. J. Brabec, Adv. Mater., 2003, 15, 2084.
T. Antopoulos, F. B. Kooistra, H. J. Wondergem, D. Kronholm, J. C. Hummelen, D. M. de Leeuw, Adv. Mater., 2006, 18, 1679.
J. W. Lee, J. H. Kwong, Apll. Phys. Lett., 2005, 86, 063514.
X. D. Feng, C. J. Huang, V. Lui, R. S. Khangura, Z. H. Lu, Apll. Phys. Lett., 2005, 86, 143511.
M. A. Green, K. Emery, D. L. King, Y. Hishikawa, W. Warta, Prog. Photovoltaics: Res. Appl., 2006, 14, 455.
J. Y. Kim, K. Lee, N. E. Coates, D. Moses, T.-Q. Nguyen, M. Dante, A. J. Heeger, Science, 2007, 317, 222.
M. E. El-Khouly, O. Ito, P. M. Smith, F. D’souza, J. Photochem. Photobiol. C, 2004, 5, 79.
www.solennebv.com, www.adsdyes.com/fullerenes.html, http://www.sesres.com/FullerenesPrices.asp.
F. Conti, C. Corvaja, M. Maggini, G. Scorrano, P. Ceroni, F. Paolucci, S. Roffia, Phys. Chem. Chem. Phys., 2001, 3, 3518.
G. Schick, M. Levitus, L. Kvetko, B. A. Johnson, I. Lamparth, R. Lunkwitz, B. Ma, S. I. Khan, M. A. Garsia-Garibay, Y. Rubin, J. Am. Chem. Soc., 1999, 121, 3246.
X. Tan, D. Schuster, S. Wilson, Tetrahedron Lett., 1998, 39, 4187.
M. E. El-Khouly, S. Gadde, G. R. Deviprasad, M. Fudjutsuka, O. Ito, F. D’souza, J. Porphyrins Phthalocyanines, 2003, 7, 1.
M. Prato, M. Maggini, Acc. Chem. Res., 1998, 31, 519.
M. A. Yurovskaya, I. V. Trushkov, Izv. Akad. Nauk, Ser. Khim., 2002, 343 [Russ. Chem. Bull., Int. Ed., 2002, 51, 367].
M. Prato, M. Maggini, C. Giacometti, G. Scorrano, G. Sandona, G. Farnia, Tetrahedron, 1996, 52, 5221.
O. Tsuge, S. Kanemasa, in Adv. Heterocycl. Chem., Ed. A. R. Katritzky, Academic Press, San Diego-New York-Berkeley-Boston-London-Sydney-Tokyo-Toronto, 1989, 45.
S. H. Wu, W. Q. Sun, D. W. Zhang, L. H. Shu, H. M. Wu, J. F. Xu, X. F. Lao, J. Chem. Soc., Perkin Trans. 1, 1998, 1733.
A. Bianco, T. Da Ros, M. Prato, C. Toniollo, J. Peptide Sci., 2001, 7, 208.
D. Pantarotto, N. Tagmatarchis, A. Bianco, M. Prato, Mini Rev. Med. Chem., 2004, 4, 805.
P. A. Troshin, R. N. Lyubovskaya, Fuller. Nanotub. Carb. Nanostruct., 2005, 13, 345.
S. Zhang, L. Gan, C. Huang, M. Lu, J. Pan, X. He, J. Org. Chem., 2002, 67, 883.
L. Gan, D. Zhou, C. Luo, H. Tan, C. Huang, M. Lu, J. Pan, Y. Wu, J. Org. Chem., 1996, 61, 1954.
R. Grigg, H. Q. N. Gunaratne, V. Sridharan, S. Thianpatanagul, M. X. Tute, Tetrahedron Lett., 1983, 24, 4363.
P. A. Troshin, S. I. Troyanov, G. N. Boiko, R. N. Lyubovskaya, A. N. Lapshin, N. F. Goldshleger, Fuller. Nanotub. Carb. Nanostruct., 2004, 12, 435.
P. A. Troshin, A. S. Peregudov, D. Muhlbacher, R. N. Lyubovskaya, Eur. J. Org. Chem., 2005, 14, 3064.
N. F. Gol’dshleger, A. N. Lapshin, E. I. Yudanova, N. M. Alpatova, E. V. Ovsyannikova, Elektrokhimiya, 2006, 42, 19 [Russ. J. Electrochem., 2006, 42, 16 (Engl. Transl.)].
A. Ikeda, C. Fukuhara, M. Kawaguchi, M. Numata, S. Shinkai, S.-G. Liu, L. Echegoyen, J. Chem. Soc., Perkin Trans. 2, 2000, 307.
A. Skiebe, A. Hirsch, H. Ktos, B. Gotsehy, Chem. Phys. Lett., 1994, 220, 138.
A. B. Kornev, P. A. Troshin, A. S. Peregudov, R. N. Lyubovskaya, 7th Biennial Int. Workshop “Fullerenes and Atomic Clusters” (St. Petersburg, June 27–July 1, 2005), Book of Abstracts, St. Petersburg, 2005, 120.
S. R. Wilson, Q. Lu, J. Org. Chem., 1995, 60, 6496.
F. Langa, P. de la Cruz, A. de la Hoz, E. Espildora, F. P. Cossio, B. Lecea, J. Org. Chem., 2000, 65, 2499.
P. A. Troshin, A. S. Peregudov, S. M. Peregudova, R. N. Lyubovskaya, Eur. J. Org. Chem., 2007, 5861.
C. C. Henderson, C. M. Rohfing, K. T. Gillen, P. Cahil, Science, 1994, 264, 397.
Z. Wang, M. S. Meier, J. Org. Chem., 2003, 68, 3043.
O. A. Troshina, P. A. Troshin, A. S. Peregudov, V. I. Kozlovskiy, R. N. Lyubovskaya, Eur. J. Org. Chem., 2006, 5243.
P. A. Troshin, A. B. Kornev, A. S. Peregudov, S. M. Peregudova, R. N. Lyubovskaya, Mendeleev Commun., 2007, 17, 116.
J. Averburg, E. Albrecht, J. Lauterwein, H. Luftman, J. Mattey, H. Mohn, W. H. Muller, H.-U. ter Meer, Chem. Ber., 1994, 127, 787.
K. D. Kampe, N. Egger, M. Vogel, Angew. Chem., Int. Ed., 1993, 32, 1174.
J. Avenburg, J. Mattey, Tetrahedron, 1996, 52, 5407.
Y. Tsunenishi, H. Ishida, K. Itoh, M. Ohno, Synlett, 2000, 1318.
G. Naxakis, P. Sofou, Y. Elemes, Fuller. Nanotub. Carbon Nanostruct., 2004, 12, 781.
G. E. Ball, G. A. Burley, L. Chaker, B. C. Hawkins, J. R. Williams, P. A. Keller, S. G. Pyne, J. Org. Chem., 2005, 70, 8572.
A. A. Ovcharenko, V. A. Chertkov, A. V. Karchava, M. A. Yurovskaya, Tetrahedron Lett., 1997, 38, 6933.
G.-W. Wang, H.-T. Yang, Tetrahedron Lett., 2007, 48, 4635.
N. Martín, L. Sanchez, B. Illescas, I. Perez, Chem. Rev., 1998, 98, 2527.
D. M. Guldi, Chem. Soc. Rev., 2002, 31, 22.
M. Meijer, G. P. van Klink, G. van Koten, Coord. Chem. Rev., 2002, 230, 141.
F. D’souza, G. R. Deviprasad, M. E. Zandler, V. T. Hoang, A. Klykov, M. VanStipdonk, A. Perera, M. E. El-Khouly, M. Fujitsuka, O. Ito, J. Phys. Chem. A, 2002, 106, 3243.
A. Bagno, S. Claeson, M. Maggini, M. L. Martini, M. Prato, G. Scorrano, Chem. Eur. J., 2002, 8, 1015.
A. N. Lapshin, V. A. Smirnov, R. N. Lyubovskaya, N. F. Gol’dshleger, Izv. Akad. Nauk, Ser. Khim., 2005, 2265 [Russ. Chem. Bull., Int. Ed., 2005, 54, 2338].
I. A. Mochalov, A. N. Lapshin, V. A. Nadtochenko, V. A. Smirnov, N. F. Gol’dshleger, Izv. Akad. Nauk, Ser. Khim., 2006, 1541 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1598].
R. Koeppe, P. A. Troshin, R. N. Lyubovskaya, N. S. Sariciftci, Appl. Phys. Lett., 2005, 87, 244102.
R. Koeppe, P. A. Troshin, A. Fuchsbauer, R. N. Lyubovskaya, N. S. Sariciftci, Fuller. Nanotub. Carb. Nanostruct., 2006, 14, 441.
P. A. Troshin, R. Koeppe, A. S. Peregudov, S. M. Peregudova, M. Egginger, R. N. Lyubovskaya, N. S. Sariciftci, Chem. Mater., 2007, 19, 5363.
J. Drechsel, B. Mannig, F. Kozlovski, D. Gebeyehu, A. Werner, M. Koch, K. Leo, M. Pfeiffer, Thin Solid Films, 2004, 451, 515.
A. A. Gershkovich, V. K. Kibirev, Khimicheskii sintez peptidov [Chemical Peptide Synthesis], Naukova dumka, Kiev, 1992, 137 (in Russian).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 873–898, May, 2008.
Rights and permissions
About this article
Cite this article
Troshin, P.A., Peregudov, A.S., Troyanov, S.I. et al. New pyrrolidine and pyrroline derivatives of fullerenes: from the synthesis to the use in light-converting systems. Russ Chem Bull 57, 887–912 (2008). https://doi.org/10.1007/s11172-008-0126-4
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-008-0126-4