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Boroxines, (R-BO)3, which can be easily synthesized via a dehydration reaction of boronic acids, R–B(OH)2, selectively self-assemble in toluene into nanofibers, nanorods, nanotapes, and nanotubes, depending on the aromatic substituent (R). Spectroscopic measurements show that the nanotube consists of a J-aggregate of the boroxine. Humidification converts the morphology from the nanotube to a sheet as a result of the hydrolysis of the boroxine components and subsequent molecular-packing rearrangement from the J-aggregate to an H-aggregate. Such a transformation leads to the compulsive release of guest molecules encapsulated in the hollow cylinder of the nanotube. The hydrolysis and the molecular-packing rearrangement described above are suppressed by coordination of pyridine to the boron atom, with the resulting moiety acting as a Lewis acid of the boroxine component. The pyridine-coordinated nanotube is transformed into a helical coil by humidification. Guest release during the nanotube-to-helical-coil transformation is much slower than during the nanotube-to-sheet transformation, but faster than from a nanotube that did not undergo morphological transformation. The storage and release of guest molecules from the boroxine nanotubes can be precisely controlled by adjusting the moisture level and the concentration of Lewis bases, such as amines.

Simple glycolipid N-alkaroyl-β-D-glucopyranosylamine 1(n) selectively self-assembles into sheets in water, nanotubes in alcohols, and helical nanocoils in toluene. All self-assemblies consist of bilayer membranes in which 1(n) packed in an interdigitated fashion. The outer surface of the sheet is covered with the hydrophilic glucose headgroup of 1(n), whereas those of the nanotube and helical nanocoil are covered with the hydrophobic alkyl-chain tail of 1(n). Heat treatment of the nanotube in the presence of water induces a rearrangement of the molecular packing of the outermost surface that allows the nanotube to become an effective nanocontainer for the dispersion of fullerene (C60) in water, a result of the ability of the hydrophilic outer surface of the nanotube and the hydrophobic nanochannel to encapsulate C60. The nanotube also exhibits photothermal characteristics after being hybridized with Au nanoparticles (AuNPs). The photothermal effect of the AuNPs allows the nanotube to unfold its tubular morphology and leads to compulsive release of the encapsulated C60 to the bulk water. Application of other nanotubes with similar photostimulated transformation ability should facilitate control of the dispersion/aggregation of other carbon nanomaterials, functional aromatic compounds, and drugs with low solubility in water.