Self-assembly of porphyrin–azulene–porphyrin and porphyrin–azulene conjugates

Abstract

In this paper we report the synthesis and self-assembling behavior of new porphyrin-azulene-porphyrin and porphyrin-azulene conjugates. The porphyrin-azulene-porphyrin conjugate gelates a number of organic solvents, while the porphyrin-azulene conjugates form vesicles in a chloroform–methanol binary mixture. The structures of the organogels and vesicles have been characterized by SEM and AFM. Two porphyrin-naphthalene-porphyrin and porphyrin-naphthalene conjugates were also prepared. A comparison of their properties with those of the azulene analogues reveals that the intermolecular dipole–dipole interaction of the azulene units plays an important role in promoting the self-assembly of the porphyrin-azulene-porphyrin and porphyrin-azulene conjugates.