Issue 19, 2008

Computational characterization and modeling of buckyball tweezers: density functional study of concave–convex π⋯π interactions

Abstract

The geometries and binding energies of a recent buckyball tweezers (C60H28) and its supramolecular complexes are investigated using recently developed density functionals (M06-L and M06-2X) that include an accurate treatment of medium-range correlation energy. The pincer part of the tweezers, corannulene, has a strong attractive interaction with C60. However, due to the entropy penalty, the calculated gas-phase free energy of association of the C60@corannulene supramolecule is positive 3.5 kcal mol−1; and this entropy penalty explains why it is difficult to observe C60@corannulene supramolecule experimentally. By using a π-extended tetrathiafulvalene (TTF), in particular 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (TTFAQ or C20H10S4), as the pincer part, we modeled a new buckyball tweezers. The geometries and binding energies of the new buckyball tweezers and its supramolecular complexes are also calculated. Due to fact that the attractive interaction between TTFAQ and C60 is weaker than that between corannulene and C60, the gas-phase binding free energy in the C60@C60H 32S8 supramolecular complex is smaller than that in the C60@C60H28 supramolecule. We also discuss solvent effects.

Graphical abstract: Computational characterization and modeling of buckyball tweezers: density functional study of concave–convex π⋯π interactions

Supplementary files

Article information

Article type
Paper
Submitted
16 Nov 2007
Accepted
14 Jan 2008
First published
18 Feb 2008

Phys. Chem. Chem. Phys., 2008,10, 2813-2818

Computational characterization and modeling of buckyball tweezers: density functional study of concave–convex π⋯π interactions

Y. Zhao and D. G. Truhlar, Phys. Chem. Chem. Phys., 2008, 10, 2813 DOI: 10.1039/B717744E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements