Synthesis\nand Characterization of Functionalized <i>meso</i>-Triaryltetrabenzocorroles

Abstract

5,10,15-Triaryltetrabenzocorroles\nfunctionalized with different\nelectron-withdrawing groups on the <i>β</i>,<i>β</i>′-fused rings have been prepared by a cross-coupling\nHeck procedure between octabrominated copper corrole and a terminal\nalkene bearing electron-withdrawing moieties. The spectroscopic characterization\nof these complexes showed red-shifted UV–vis absorption bands\ncharacterized by a significant band broadening. The same feature was\nobserved in the case of NMR spectra, where low-resolution groups of\nsignals were observed. This behavior derives from a strong tendency\nof these macrocycles to aggregate in solution, as has been demonstrated\nby an ¹H NMR study performed on one of these tetrabenzocorroles.\nThe influence of the substituents on the fused benzene ring on the\nproperties of the tetrabenzocorroles was investigated by electrochemistry\nand spectroelectrochemistry, and comparisons were made between properties\nof the newly synthesized compounds and those of the tetrabenzocorroles\nreported earlier in the literature.