Solid state deposition of chiral amphiphilic porphyrin derivatives on glass surface

Abstract

Herein, we present a straightforward method to achieve optically active films based on porphyrin derivatives. The introduction of an aminoacid functionality on the porphyrin platform confers to the macrocycle both the amphiphilic and chiral character exploited for its solvent-promoted self-aggregation leading to the formation of chiral supramolecular architectures. These ordered suprastructures have the propensity to spontaneously layer as solid films on glass surfaces. The deposited material has been characterized by means of UV-visible, fluorescence emission, circular dichroism spectroscopy and AFM. The reported studies show once more how the stereochemical information stored on a single porphyrin framework can induce the formation of supramolecular chiral architectures, in solution, as well as in solid state. Furthermore, slight modifications on the porphyrin skeleton can influence the aggregation process and the structural features of the final assemblies, leading to solid surfaces featuring different morphologies. These combined aspects can be of great importance for the achievement of solid state chemical sensors with stereoselective properties.