Electron donor-acceptor interactions in regioselectively synthesized exTTF2-C70(CF3)10 dyads

Journal article
(Original article)

Publication Details

Author(s): Takano Y, Angeles Herranz M, Martin N, De Miguel Rojas G, Guldi DM, Kareev IE, Strauss SH, Boltalina OV, Tsuchiya T, Akasaka T
Journal: Chemistry - A European Journal
Publisher: Wiley-VCH Verlag
Publication year: 2010
Volume: 16
Journal issue: 18
Pages range: 5343-5353
ISSN: 0947-6539


The decakis(trifluoromethyl)fullerene C-CO(CF ) in which the CF groups are arranged on a para-meta-para ribbon of C(CF) edge-sharing hexagons, and which has now been prepared in quantities of hundreds of milligrams, was reacted under standard Bingel-Hirsch conditions with a bis-π-extended tetrathiafulvalene (exTTF) malonate derivative to afford a single cxTTF-C(CF) regioisomer in 80% yield based on consumed starting material. The highly soluble hybrid was thoroughly characterized by using ID H, C, and F NMR, 2D NMR, and UV/Vis spectroscopy; matrix-assisted laser desorption ionization (MALDI) mass spectrometry; and electrochemistry. The cyclic voltammogram of the exTTFC(CF) dyad revealed an irreversible second reduction process, which is indicative of a typical retro-Bingel reaction; whereas the usual phenomenon of exTTF inverted potentials (E>E), resulting in a single, two-electron oxidation process, was also observed. Steady-state and time-resolved photolytic techniques demonstrated that the C-C(CF)singlet excited state is subject to a rapid electron-transfer quenching. The resulting charge-separated states were identified by transient absorption spectroscopy, and radical pair lifetimes of the order of 300 ps in toluene were determined. The exTTFC(CF), dyad represents the first example of exploitation of the highly soluble trifluoromethylated fullerenes for the construction of systems able to mimic the photosynthetic process, and is therefore of interest in the search for new materials for photovoltaic applications. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA,.

FAU Authors / FAU Editors

Guldi, Dirk Michael Prof. Dr.
Lehrstuhl für Physikalische Chemie I

External institutions with authors

Colorado State University
Russian Academy of Sciences / Росси́йская акаде́мия нау́к (RAS)
Universidad Complutense de Madrid (UCM)
University of Tsukuba / 筑波大学

How to cite

Takano, Y., Angeles Herranz, M., Martin, N., De Miguel Rojas, G., Guldi, D.M., Kareev, I.E.,... Akasaka, T. (2010). Electron donor-acceptor interactions in regioselectively synthesized exTTF2-C70(CF3)10 dyads. Chemistry - A European Journal, 16(18), 5343-5353. https://dx.doi.org/10.1002/chem.200902336

Takano, Yuta, et al. "Electron donor-acceptor interactions in regioselectively synthesized exTTF2-C70(CF3)10 dyads." Chemistry - A European Journal 16.18 (2010): 5343-5353.


Last updated on 2019-13-04 at 21:51