One-pot reaction of aminoarenes and porphyrin – A fused amino acid-tetraphyrin(1.1.1.1) hybrid

Abstract

Tetraphyrins(1.1.1.1) (Porphyrins) were merged with amino acids forming a direct bond between a meso-position of macrocycle and a nitrogen available in the side chain of the amino acid. The following intramolecular fusion observed for a free base porphyrin forms a structure with extended [Formula: see text]-delocalisation on the additional carbocyclic fragment, that substantially modifies the observed absorption and emission. A further modulation of electron behaviour has been observed for a deprotonated form of the fused system. A nitrogen atom introduced into the system can be treated as a switching factor that controls the delocalisation significantly influencing the emission by shifting between the available amine and imine tautomeric forms.