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

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 (1)H 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.