Solvent-Modulated Chiral Self-Assembly: Selective Formation of Helical Nanotubes, Nanotwists, and Energy Transfer

As the medium for self-assembly processes, solvents strongly influence the supramolecular assemblies via specific solute-solvent interactions, which may result in effective modulation of properties, self-assembled nanostructures, and functions through varying the solvent. Here, two kinds of pyridine-cyanostilbene functionalized chiral amphiphiles (l/d-PyPhG and l-PyG) were designed, and their self-assembly behaviors in different solvents were investigated. It was found that both amphiphiles formed gels in dimethyl sulfoxide (DMSO) and self-assembled into right-handed nanotwists, while they formed suspensions in ethanol consisting of left-handed nanotubes. Although the molecular chirality in the compounds remained unchanged in the two solvents, the nanoassemblies showed opposite handedness at the nanoscale together with opposite circular dichroism (CD) and circularly polarized luminescence (CPL) signals. Furthermore, when the amphiphiles were co-assembled with an achiral dye, it was found that efficient energy transfer took place in the systems composed of nanotubes rather than those composed of nanotwists. Therefore, by assembling molecules with the same molecular chirality in different solvents, a selective formation of helical nanotubes or nanotwists and the regulation of handedness as well as energy transfer efficiency were achieved.