Expanding the porphyrin pi-system by fusion with anthracene

Org Lett. 2008 Sep 18;10(18):3945-7. doi: 10.1021/ol801500b. Epub 2008 Aug 23.

Abstract

Synthesis of beta,meso,beta-anthracene triply fused and beta,meso-anthracene doubly fused porphyrins has been achieved via oxidative intramolecular ring closure of meso-(9-anthryl)porphyrins and meso-(1-anthryl)porphyrins, respectively. Fusion was only possible when the anthracene carried electron-donating alkoxy substituents. The fused porphyrins exhibit strongly red-shifted UV-vis absorption spectra and reduced electrochemical HOMO-LUMO gaps (relative to the unfused tetraaryl porphyrin precursor).