Abstract
Towards the morphology control of oriented porphyrin aggregates by added saccharides, three amphiphilic porphyrins bearing boronic acid groups were synthesised. Among them, an amphiphilic tetraphenylporphyrin ( 4) bearing two octadecyl groups at 5,10-positions and two boronic acid groups (acting as saccharide-binding sites) at 15,20-positions has been found to act as a membrane-forming amphiphile in an aqueous system. Spectroscopic (UV–Vis and CD), light-scattering, DSC and electron micrographic studies have established that in aqueous media 4 forms stable fibrous aggregates only in the presence of saccharides, which are chirally twisted by the absolute configuration of the added saccharides. This is a novel method to control the aggregate morphology by saccharides and well imitates the morphological functions of certain cell membranes, the surfaces of which are covered by saccharides.
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