A photocontrolled, interconvertible supramolecular 2D-nanosheet/1D-nanotube system was constructed through the supramolecular assembly of adamantanyl-modified diphenylalanine with azobenzene-bridged bis(β-cyclodextrin). The nanosheet exhibited a greater fluorescence enhancement effect than the nanotube. Significantly, these nanosheets and nanotubes could interconvert via the photocontrolled trans/cis isomerization of azobenzene linkers in bis(β-cyclodextrin), and this photo-switchable one-dimensional/two-dimensional morphological interconversion was reversible and recyclable. This enables convenient routes to highly ordered nanostructures with various morphologies and dimensions that can be controlled by external stimuli.

A linear supramolecular architecture was successfully constructed by the inclusion complexation of α-cyclodextrin with azobenzene and the host-stabilized charge-transfer interaction of naphthalene and a bispyridinium guest with cucurbit[8]uril in water, which was comprehensively characterized by (1)H NMR spectroscopy, UV/Vis absorption, fluorescence, circular dichroism spectroscopy, dynamic laser scattering, and microscopic observations. Significantly, because it benefits from the photoinduced isomerization of the azophenyl group and the chemical reduction of bispyridinium moiety with noncovalent connections, the assembly/disassembly process of this supramolecular nanostructure can be efficiently modulated by external stimuli, including temperature, UV and visible-light irradiation, and chemical redox.

An amphiphilic compound, 5-(4'-dodecyloxyphenyl)-10,15,20-tri(permethyl-β-CD)-modified Zn(II)-porphyrin (1; β-CD = β-cyclodextrin), was synthesized by means of the click reaction of an alkylated Zn-porphyrin derivative with 6-deoxy-6-azidopermethyl-β-CD. The complexation between 1 and tetrasodium tetraphenylporphyrintetrasulfonate (5) with different molar ratios led to the formation of two distinctly different nanoarchitectures, which were proven to be vesicle and network aggregates, respectively, by using dynamic light scattering, scanning electron microscopy, transmission electron microscopy, and atomic force microscopy. On the basis of the results of the time-dependent TEM studies, fluorescence, and NMR spectroscopic measurements, we have determined that the mechanism of the morphology transition from vesicles to networks is controlled by the stepwise complexation of 1 with 5. Furthermore, these supramolecular nanoarchitectures show the controlled- release property of doxorubicin as potential candidates for drug delivery.