Tetraaryltetraanthra[2,3]porphyrins: synthesis, structure, and optical properties

J Org Chem. 2012 Dec 21;77(24):11119-31. doi: 10.1021/jo302135q. Epub 2012 Dec 12.

Abstract

A synthetic route to symmetrical tetraaryltetraanthra[2,3]porphyrins (Ar(4)TAPs) was developed. Ar(4)TAPs bearing various substituents in meso-phenyls and anthracene residues were prepared from the corresponding pyrrolic precursors. The synthesized porphyrins possess high solubility and exhibit remarkably strong absorption bands in the near-infrared region (790-950 nm). The scope of the method, selection of the peripheral substituents, choice of the metal, and their influence on the optical properties are discussed together with the first X-ray crystallographic data for anthraporphyrin.