Donor-acceptor conjugates of lanthanum endohedral metallofullerene and π-extended tetrathiafulvalene

Takano Y, Angeles Herranz M, Martin N, Radhakrishnan SG, Guldi DM, Tsuchiya T, Nagase S, Akasaka T (2010)

Publication Type: Journal article, Original article

Publication year: 2010

Journal

Journal of the American Chemical Society American Chemical Society

Original Authors: Takano Y., Herranz M.A., Martin N., Radhakrishnan S.G., Guldi D.M., Tsuchiya T., Nagase S., Akasaka T.

Publisher: American Chemical Society

Book Volume: 132

Pages Range: 8048-8055

Journal Issue: 23

DOI: 10.1021/ja100665q

Abstract

Stable donor-acceptor conjugates (2, 3) involving an endohedral metallofullerene, La @I -C , and π-extended tetrathiafulvalene (exTTF) have been synthesized by highly regioselective 1,3-dipolar cycloadditions of exTTF-containing azomethine ylides to the endofullerene, yielding exclusively [5,6] metallofulleropyrrolidines with C symmetry in high yields (68-77%). The cyclic voltammograms (CVs) of the conjugates reveal the redox active character of the system due to the presence of both donor and acceptor groups, that is, exTTF and La @I -C , respectively. Furthermore, the electrochemically reversible character of the endofullerene confirms the presence of the [5,6] adduct. Despite the relatively close proximity between the exTTF and the endohedral metallofullerene (EMF), only a weak electronic interaction was observed in the ground state, as evidenced by absorption spectroscopy and CV measurements of 2 and 3. On the other hand, in the excited state the fast formation of a radical ion-pair state (i.e., 6.0 × 10 s ), that is, the reduction of the electron accepting La @C and the oxidation of exTTF, evolves with lifetimes as long as several ns (3.0 × 10 s ) in toluene. Transient absorption spectroscopy experiments confirmed these observations. © 2010 American Chemical Society.

Authors with CRIS profile

Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Complutense de Madrid (UCM) ES Spain (ES) University of Tsukuba / 筑波大学 JP Japan (JP) National Institute of Natural Sciences (NINS) / 自然科学研究機構 JP Japan (JP)

How to cite

APA:

Takano, Y., Angeles Herranz, M., Martin, N., Radhakrishnan, S.G., Guldi, D.M., Tsuchiya, T.,... Akasaka, T. (2010). Donor-acceptor conjugates of lanthanum endohedral metallofullerene and π-extended tetrathiafulvalene. Journal of the American Chemical Society, 132(23), 8048-8055. https://doi.org/10.1021/ja100665q

MLA:

Takano, Yuta, et al. "Donor-acceptor conjugates of lanthanum endohedral metallofullerene and π-extended tetrathiafulvalene." Journal of the American Chemical Society 132.23 (2010): 8048-8055.

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