Influence of Configuration on Photoinduced Electron-transfer Mechanism in Sulfonyl Amidine Linked Porphyrin-fullerene Dyad

doi:10.3969/j.issn.0251-0790.2012.06.015

Abstract

Abstract: A novel sulfonyl amidine linked porphyrin-fullerene dyad ZnP-H-C₆₀ was facilely synthesized via a three components one-pot coupling reaction. There are two isomers(Z- and E-) in the dyad solution in low-polarity solvents, such as chloroform and toluene. We found that the photoinduced electron-transfer(PET) process could occur in two isomers, but the electron-transfer mechanism was different from each other. The electron transfer process was mediated by the intramolecular hydrogen-bond in (Z-)ZnP-H-C₆₀; and in (E-)ZnP-H-C₆₀, the porphyrin-fullerene exciplex was the precursor of the charge separation(CS) state due to the closer distance between porphyrin and fullerene entities.

Key words: Porphyrin, Fullerene, Photoinduced electron-transfer, Hydrogen-bond

CLC Number:

O621

TrendMD:

HE Lin, CHEN Chen, LI Fei, ZHU Yi-Zhou, ZHENG Jian-Yu. Influence of Configuration on Photoinduced Electron-transfer Mechanism in Sulfonyl Amidine Linked Porphyrin-fullerene Dyad[J]. Chem. J. Chinese Universities, 2012, 33(06): 1205.

References

[1] Gust D., Moore T. A., Moore A. L.. Acc. Chem. Res.[J], 2009, 42(12): 1890-1898 [2] Armaroli N., Accorsi G., Song F. Y., Palkar A., Echegoyen L., Bonifazi D., Diederich F.. Chem. Phys. Chem.[J], 2005, 6(44): 732-743 [3] Imahori H., Sakata Y.. Eur. J. Org. Chem.[J], 1999, (10): 2445-2457 [4] Imahori H., Mori Y., Matano Y. J.. Photochem. Photobio. C: Photochem. Rev.[J], 2003, 4: 51-83 [5] Imahori H.. Org. Biomol. Chem.[J], 2004, 2: 1425-1433 [6] Hasobe T.. Phys. Chem. Chem. Phys.[J], 2010, 12(1): 44-57 [7] D’Souza F., Ito O.. Coord. Chem. Rev.[J], 2005, 249(13/14): 1410-1422 [8] YANG Sen-Gen(杨森根), LIU Jian-Yong(刘见永), WU Zhen-Yi(吴振奕), TIAN Ling(田玲), FAN Su-Hua(凡素华), ZHAN Meng-Xiong(詹梦熊). Chem. J. Chinese Universites(高等学校化学学报)[J], 2005, 26(7): 1202-1205 [9] Yamanaka K.. Bull. Chem. Soc. Jpn.[J], 2009, 82(3): 316-332 [10] Imahori H., Yamada H., Guldi D. M., Endo Y., Shimomura A., Kundu S., Yamada K., Okada T., Sakata Y., Fukuzumi S.. Angew. Chem. Int. Ed.[J], 2002, 41(13): 2344-2347 [11] Imahori H., El-Khouly M. E., Fujitsuka M., Ito O., Sakata Y., Fukuzumi S.. J. Phys. Chem. A[J], 2001, 105(2): 325-332 [12] Schuster D. I., Li K., Guldi D. M., Palkar A., Echegoyen L., Stanisky C., Cross R. J., Niemi M., Tkachenko N. V., Lemmetyi-nen H.. J. Am. Chem. Soc.[J], 2007, 129(51): 15973-15982 [13] Tkachenko N. V., Lemmetyinen H., Sonoda J., Ohkubo K., Sato T., Imahori H., Fukuzumi S.. J. Phys. Chem. A[J], 2003, 107(42): 8834-8844 [14] Vail S. A., Schuster D. I., Guldi D. M., Isosomppi M., Tkachenko N., Lemmetyinen H., Palkar A., Echegoyen L., Chen X., Zhang J. Z. H.. J. Phys. Chem. B[J], 2006, 110(29): 14155-14166 [15] Davis W. B., Svec W. A., Ratner M. A., Wasielewski M. R.. Nature[J], 1998, 396: 60-63 [16] Vail S. A., Krawczuk P. J., Guldi D. M., Palkar A., Echegoyen L., Tom J. P. C., Fazio M. A., Schuster D. I.. Chem. Eur. J.[J], 2005, 11: 3375-3388 [17] Tashiro K., Sato A., Yuzawa T., Aida T., Yamanaka K. I., Fujitsuka M., Ito O.. Chem. Lett.[J], 2006, 35(5): 518-519 [18] Torre G. de la, Giacalone F., Segura J. L., Mart N., Guldi D. M.. Chem. Eur. J.[J], 2005, 11: 1267-1280 [19] Tsuji H., Sasaki M., Shibano Y., Toganoh M., Kataoka T., Araki Y., Tamao K., Ito O.. Bull. Chem. Soc. Jpn.[J], 2006, 79(9): 1338-1346 [20] Kesti T. J., Tkachenko N. V., Vehmanen V., Yamada H., Imahori H., Fukuzumi S., Lemmetyinen H.. J. Am. Chem. Soc.[J], 2002, 124(27): 8067-8077 [21] Imahori H., Tkachenko N. V., Vehmanen V., Koichi Tamaki, Lemmetyinen H., Sakata Y., Fukuzumi S.. J. Phys. Chem. A[J], 2001, 105(10): 1750-1756 [22] Imahori H., Hagiwara K., Aoki M., Akiyama T., Taniguchi S., Okada T., Shirakawa M., Sakata Y.. J. Am. Chem. Soc.[J], 1996, 118(47): 11771-11782 [23] D’Souza F., Maligaspe E., Karr P. A., Schumacher A. L., El Ojaimi M., Gros C. P., Barbe J. M., Ohkubo K., Fukuzumi S.. Chem. Eur. J.[J], 2008, 14: 674-681 [24] Guldi D. M.. Chem. Soc. Rev.[J], 2002, 31(1): 22-36 [25] Nicola A., Marconi G., Echegoyen L., Bourgeois J. P., Diederich F.. Chem. Eur. J.[J], 2000, 6: 1629-1645 [26] Dietel E., Hirsch A., Eichhorn E., Rieker A., Hackbarth S., Rder B.. Chem. Commun.[J], 1998: 1981-1982 [27] Turrd C., Chang C. K., Leroi G. E., Cukier R. I., Nocera D. G.. J. Am. Chem. Soc.[J], 1992, 114(10): 4013-4015 [28] Osuka A., Yoneshima R., Shiratori H., Okada T., Taniguchi S., Mataga N.. Chem. Commun.[J], 1998: 1567-1568 [29] Kirby J. P., Roberts J. A., Nocera D. G.. J. Am. Chem. Soc.[J], 1997, 119(39): 9230-9236 [30] Gadde S, Islam D. M. S., Wijesinghe C. A., Subbaiyan N. K., Zandler M. E., Araki Y., Ito O., D’Souza F.. J. Phys. Chem. C[J], 2007, 111(34): 12500-12503 [31] D’Souza F., Deviprasad G. R., Zandler M. E., El-Khouly M. E., Fujitsuka M., Ito O.. J. Phys. Chem. A[J], 2003, 107(24): 4801-4807 [32] Liu Y., Xiao S., Li H., Li Y., Liu H., Lu F., Zhuang J., Zhu D.. J. Phys. Chem. B[J], 2004, 108(20): 6256-6260 [33] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery Jr. J. A., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A.. Gaussian 03: Revision B.04, Wallingford CT: Gaussian, Inc., 2004 [34] Chaignon F., Torroba J., Blart E., Borgstrm M., Hammarstrm L., Odobel F.. New J. Chem.[J], 2005, 29: 1272-1284 [35] Armarego W. L. F., Chai C. L. L.. Purification of Laboratory Chemicals(Fifth Edition)[M], Berlin Dayton: Elsevier, 2003 [36] Laurence C., Nicolet P., Dalati M. T.. J. Phys. Chem.[J], 1994, 98: 5807-5816 [37] Schuster D. I., Cheng P., Jarowski P. D., Guldi D. M., Luo C., Echegoyen L., Pyo S., Holzwarth A. R., Braslavsky S. E., Williams R. M., Klihm G.. J. Am. Chem. Soc.[J], 2004, 126(23): 7257-7270 [38] Schuster D. I., MacMahon S., Guldi D. M., Echegoyen L., Braslavsky S. E.. Tetrahedron[J], 2006, 62(9): 1928-1936 [39] Schuster D. I.. Carbon[J], 2000, 38(11/12): 1607-1614