Synthesis and Photoinduced Electron-Transfer Reactions in a La2@Ih-C80–Phenoxazine Conjugate

Akasaka T, Nakata A, Rudolf M, Wang WW, Yamada M, Suzuki M, Maeda Y, Aoyama R, Tsuchiya T, Nagase S, Guldi DM (2017)

Publication Type: Journal article

Publication year: 2017

Journal

ChemPlusChem Wiley

Book Volume: 82

Pages Range: 1067-1072

Journal Issue: 7

DOI: 10.1002/cplu.201600391

Abstract

A newly designed electron donor–acceptor conjugate consisting of an endohedral dimetallofullerene (La2@Ih-C80) and phenoxazine (POZ) was successfully synthesized under Prato conditions. Our results document that the 1,3-dipolar cycloaddition took place across the [5,6] junction to afford exclusively the corresponding [5,6] cycloadduct. The structure of the conjugate was characterized by means of NMR spectroscopy, absorption spectroscopy, and electrochemical studies. Computational calculations suggest that the electron density of the highest occupied molecular orbital (HOMO) is distributed on the POZ moiety, whereas that of the lowest unoccupied molecular orbital (LUMO) is located at the endohedral La atoms, leading to efficient separation of the HOMO and LUMO in the conjugate. Time-resolved absorption spectroscopic investigations and spectroelectrochemical measurements corroborate the formation of the energetically low-lying (La2@Ih-C80).−–(POZ).+ radical-ion-pair state by means of ultrafast through-space electron transfer.

Authors with CRIS profile

Marc Rudolf Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

University of Tsukuba / 筑波大学 JP Japan (JP) Kyoto University / 京都大学 Kyōto daigaku JP Japan (JP) Tokyo Gakugei University JP Japan (JP)

How to cite

APA:

Akasaka, T., Nakata, A., Rudolf, M., Wang, W.-W., Yamada, M., Suzuki, M.,... Guldi, D.M. (2017). Synthesis and Photoinduced Electron-Transfer Reactions in a La2@Ih-C80–Phenoxazine Conjugate. ChemPlusChem, 82(7), 1067-1072. https://doi.org/10.1002/cplu.201600391

MLA:

Akasaka, Takeshi, et al. "Synthesis and Photoinduced Electron-Transfer Reactions in a La2@Ih-C80–Phenoxazine Conjugate." ChemPlusChem 82.7 (2017): 1067-1072.

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