The search for molecular receptors for fullerenes that form complexes of high stability is a very active area of investigation. To date, the highest binding constants have been obtained utilizing metalloporphyrins as recognizing units. Here, we describe the synthesis of a collection of exTTF-based macrocyclic hosts and their binding abilities towards both C60 and C70 (JACS 2010 and 2011). Our macrocyclic receptors include two hosts capable of binding C70 with micromolar affinity, and one of the best hosts for C60 reported to date, with a log Ka = 7.5 (PhCN, r.t.). We also report insights into the thermodynamic nature of the association event, and its influence on the electronic properties of the host-guest systems. We have found that small variations in the structure of the host lead to very significant changes in affinity towards the fullerene guest, and in some cases even in the stoichiometry of the associates.

One size fits ball: Macrocyclic hosts for fullerenes with micromolar affinity

243rd National Meeting (2012)

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