Issue 48, 2014

A novel photo-responsive azobenzene-containing nanoring host for fullerene-guest facile encapsulation and release

Abstract

Azobenzenes in particular have been proved to have a robust photo-response, in which their configuration can transform between the trans- and cis-form upon UV-visible irradiation. Accordingly, azobenzene-containing molecules are frequently applied in the design of the guests, involving so-called host–guest chemistry. In this paper, a novel photo-responsive nanoring host molecule ([4]AB) has been designed by introducing four azobenzene groups onto the ring, and interactions between the designed nanoring host and fullerenes C60 and C70 guests were investigated at both the M06-L/MIDI! as well as M06-2X/6-31G(d) level of theory. By analyzing the geometric characteristics and host–guest binding energies, it is revealed that the designed [4]AB with diameter ca. 13.4 Å is an ideal host molecule for the encapsulation of guests C60 and C70 fullerene. Meanwhile, inferred from UV-vis-NIR spectroscopy, the guest C60 and C70 could be facilely released from the cavity of the [4]AB via configuration transformation between trans- and cis-form of the host under 474 and 506 nm photo-irradiation, respectively. Frontier orbital features, weak interaction regions, infrared spectroscopy and 1H NMR spectra have also been theoretically simulated. The present work would provide a new strategy for facile reversible encapsulation and release of fullerene guest by a novel nanoring host.

Graphical abstract: A novel photo-responsive azobenzene-containing nanoring host for fullerene-guest facile encapsulation and release

Supplementary files

Article information

Article type
Paper
Submitted
18 Aug 2014
Accepted
21 Oct 2014
First published
28 Oct 2014

Phys. Chem. Chem. Phys., 2014,16, 27053-27064

A novel photo-responsive azobenzene-containing nanoring host for fullerene-guest facile encapsulation and release

K. Yuan, Y. Guo and X. Zhao, Phys. Chem. Chem. Phys., 2014, 16, 27053 DOI: 10.1039/C4CP03687E

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