Expanding the porphyrin pi-system by fusion with anthracene.
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).
Davis
Nicola K S
NK
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK.
Pawlicki
Miłosz
M
Anderson
Harry L
HL