Augsburg University, Institute of Physics, Chair of Solid State and Material Science, Universitaetsstrasse 1, D-86159 Augsburg, Germany
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Ruhr University Bochum, Chair of Inorganic Chemistry 2, Organometallics and Materials Chemistry, Universitaetsstrasse 150, D-44780 Bochum, Germany
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Dalton Trans., 2012,41, 5995-6002
16 Dec 2011,
21 Mar 2012
First published online
22 Mar 2012
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 = 14550 ± 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.
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