C60 and its derivatives have been thoroughly probed as electron acceptors in fundamental electron transfer investigations with a variety of electron donors in covalent and noncovalent electron donor-acceptor systems. Molecular fragments of fullerenes may serve as model systems for their investigation, with the added value of their synthetic availability in pure form featuring a well defined molecular structure. The coordination of metal cations by fullerene fragments has been thoroughly studied, and they have also been used frequently to construct receptors for fullerenes, but their binding by other organic hosts has not been investigated thus far. Figure   1  : Chemical structures of 1 and 2 as well as the calculated structure (DFT) of the supramolecular associate 1�2.  Here, we present first insights into the supramolecular association of a fullerene fragment 2  (C30H12) with a bowl shaped electron donor molecule 1  . 1  is based on a truxene core, to which three dithiole rings are covalently attached (truxTTF) � figure 1. UV/Vis titrations and DFT calculations support formation of the supramolecular associate 1  ?  2  , for which an association constant of log Ka=3.6 is calculated in CHCl3 at RT. Remarkably, electron transfer from 1  to 2  to form the fully charge-separated species takes place upon irradiation of 1  ?  2  with light, constituting the first example, in which a fullerene fragment mimics the electron-accepting behavior of fullerenes within a supramolecular complex.[1][1] Gallego et al. Angew. Chem. Int. Ed. 2014  , 53, 1 � 7

Electron transfer in a supramolecular associate of a fullerene fragment

248th National Meeting (2014)

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