Supramolecular self-assembled nanowires by the aggregation of a protoporphyrin derivative in low-polarity solvents

The self-assembly of a simple tetraalkyl-substituted protoporphyrin derivative into fibril wire-like nanostructures from CHCl3/cyclohexane solvent mixes is explored. The protoporphyrin IX derivative is synthesised in two efficient steps by amidation of the two propylenic acid groups followed by a cross metathesis of the vinyl groups using Grubbs' second-generation catalyst. The self-assembly of the functionalised protoporphyrin is sensitive to solvent and under favourable conditions forms ‘nanowires’ of micrometre length. The nanowires were characterised by absorption and fluorescence spectroscopy, transmission electron microscopy and atomic force microscopy.