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Issue 19, 2012
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Advanced buckyball joints: synthesis, complex formation and computational simulations of centrohexaindane-extended tribenzotriquinacene receptors for C60 fullerene

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Abstract

The synthesis of a structurally optimized tribenzotriquinacene receptor 9 is described, which is extended by centrohexaindane moieties to give rise to a half-round concave ball bearing, with optimum shape complementarity towards C60 fullerene. Spectroscopic investigations reveal that this novel host forms a 1 : 1 host–guest complex with C60 with a complex stability constant of K1 = 14 550 ± 867 M−1, which is considerably higher than those reported for structurally related tribenzotriquinacene hosts reported previously. Both the suppression for binding of a second receptor (i.e. formation of a 2 : 1 host–guest complex) as well as the increase of complex stability of the 1 : 1 complex can be rationalized in terms of multiple additive van der Waals and π–π interactions between C60 and the aromatic groups of the receptor, as revealed by DFT + D and force-field calculations. Combining results from spectroscopic and theoretical investigations leads to predictions in light of future receptor designs, which – apart from shape complementarity – will have to consider an optimized electronic match (i.e. partial charge transfer) between the receptor and the fullerene host.

Graphical abstract: Advanced buckyball joints: synthesis, complex formation and computational simulations of centrohexaindane-extended tribenzotriquinacene receptors for C60 fullerene

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Publication details

The article was received on 16 Dec 2011, accepted on 21 Mar 2012 and first published on 22 Mar 2012


Article type: Paper
DOI: 10.1039/C2DT12435A
Citation: Dalton Trans., 2012,41, 5995-6002
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    Advanced buckyball joints: synthesis, complex formation and computational simulations of centrohexaindane-extended tribenzotriquinacene receptors for C60 fullerene

    S. Henne, B. Bredenkötter, A. A. Dehghan Baghi, R. Schmid and D. Volkmer, Dalton Trans., 2012, 41, 5995
    DOI: 10.1039/C2DT12435A

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