Photo-Switchable Self-Assemblies Based on Thymine-Containing Bolaamphiphiles.

The photoswitching of photosensitive bolaamphiphiles based on thymine was investigated. Topochemical principles were applied to create light-responsive supra-amphiphiles by the utilisation of dynamic covalent bonds created by the photo-dimerisation of a DNA base, thymine. In order to induce the photo-dimerisation of thymine, two bolaamphiphilic molecules were designed and synthesised to meet the required [2 π+2 π] photo-cycloaddition conditions. The amphiphiles were synthesised with different spacers and their photo-reversibility and morphologies were studied by using UV/Vis, NMR and infrared spectroscopy, rheometry, dynamic light scattering and transmission electron microscopy.