Expanding the Porphyrin π-System by Fusion with Anthracene

Synthesis of β,meso,β-anthracene triply fused and β,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 a...

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Bibliographic Details
Published in:Organic letters 2008-09, Vol.10 (18), p.3945-3947
Main Authors: Davis, Nicola K. S, Pawlicki, Miłosz, Anderson, Harry L
Format: Article
Language:English
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Summary:Synthesis of β,meso,β-anthracene triply fused and β,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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801500b