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Almost Enclosed Buckyball Joints: Synthesis, Complex Formation, and Computational Simulations of Pentypticene‐Extended Tribenzotriquinacene
Author(s) -
Henne Stefan,
Bredenkötter Björn,
Alaghemandi Mohammad,
Bureekaew Sareeya,
Schmid Rochus,
Volkmer Dirk
Publication year - 2014
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201402475
Subject(s) - molecular dynamics , chemistry , chemical physics , molecular machine , computational chemistry , molecular physics , materials science , nanotechnology
We report the synthesis of a tribenzotriquinacene‐based (TBTQ) receptor ( 3 ) for C 60 fullerene, which is extended by pentiptycene moieties to provide an almost enclosed concave ball bearing. The system serves as a model for a self‐assembling molecular rotor with a flexible and adapting stator. Unexpectedly, nuclear magnetic resonance spectroscopic investigations reveal a surprisingly low complex stability constant of K 1 =213±37 M −1 for [C 60 ⊂ 3 ], seemingly inconsistent with the previously reported TBTQ systems. Molecular dynamics (MD) simulations have been conducted for three different [C 60 ⊂TBTQ] complexes to resolve this. Because of the dominating dispersive interactions, the binding energies increase with the contact area between guest and host, however, only for rigid host structures. By means of free‐energy calculations with an explicit solvent model it can be shown that the novel flexible TBTQ receptor 3 binds weakly because of hampering entropic contributions.