Solvent-resolved self-assemblies of cholesteryl–cyanostilbene conjugates with photo- and thermo-responsiveness

Abstract

It remains challenging to construct multifunctional chiral stimulus-responsive molecules and to modulate their morphology at the nanoscale. In this paper, we synthesized a novel chiral molecule with both photoactive and potentially bioactive properties and found that the morphological changes of its self-assembly were influenced by solvent polarity and light exposure. This work enabled the synthesized molecule to undergo Z–E isomerization efficiently under light irradiation by introducing highly oriented hydrogen bonds into the cyanostilbene part. The photoisomerization of the cyanostilbene part from Z- to E-type was further exploited, leading to morphological changes from nanohelices to vesicles with chiroptical evolution. The light-modulated supramolecular chirality and nanostructure provide a green and efficient method for the design of responsive chiral materials.