Preparation and characterization of meso-tetrakis(2,6-diaryloxyphenyl)porphyrins

A series of meso-tetrakis(2,6-diaryloxyphenyl)porphyrins was synthesized by the Lindsey method from pyrrole and 2,6-diaryloxybenzaldehydes, which were prepared by regioselective formylation of 1,3-diaryloxybenzenes. In CDCl 3 solution, 1 H NMR spectral analysis of ring current shifts arising from the porphyrin macrocycle and the attached phenyl rings indicated that meso-tetrakis(2,6-diphenoxyphenyl)porphyrin, the prototypical meso-tetrakis(2,6-diaryloxyphenyl)porphyrin, forms deep open well cavities above and below the porphyrin plane.