Porphyrin networks. Synthesis and supramolecular self-assembly of 5,10,15-tri(4-hydroxyphenyl)-20-(2-quinolyl) metalloporphyrins

Abstract

The syntheses of a new asymmetrically functionalized porphyrin framework, the meso- 5,10,15-tri(4-hydroxyphenyl)-20-(2-quinolyl)porphyrin, and of its copper and aqua-zinc complexes are reported, along with a detailed structural characterization of the self-assembled architectures exhibited by the metalloporphyrin materials. Crystals of the two compounds consist of polymeric two-dimensional networks with similar connectivity features that are sustained by extensive hydrogen bonding, involving the three hydroxylic O-atoms as well as the quinolyl N-site. The layered assemblies have corrugated surfaces and pack in the form of intercalate structures, entrapping molecules of the nitrobenzene solvent within the interlayer voids. The results represent a relatively rare example of a successful formulation of extended multiporphyrin arrays based on asymmetric building blocks bearing different molecular recognition functions.