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meso-Tetrakis(pentafluorophenyl)porphyrin-derived chromene-annulated chlorins. | LitMetric

meso-Tetrakis(pentafluorophenyl)porphyrin-derived chromene-annulated chlorins.

J Org Chem

Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.

Published: April 2012

AI Article Synopsis

Article Abstract

The synthesis of mono- and bis-chromene-annulated meso-(pentafluorophenyl)chlorins from meso-tetrakis(pentafluorophenyl)porphyrins by an OsO(4)-mediated dihydroxylation reaction, followed by an intramolecular nucleophilic aromatic substitution reaction, is described. The reaction sequence is applicable to the free base systems as well as their Zn(II), Ni(II), Pd(II), and Pt(II) complexes. The optical properties (UV-vis and fluorescence spectra) of the (metallo)chlorin-like chromophores that possess slightly red-shifted optical spectra compared to the corresponding 2,3-dihydroxychlorins are reported. Molecular modeling and (1)H-(19)F-HOESY NMR spectroscopy provide indications for the conformation of the chromene-annulated chromophores. Using (1)H-(1)H COSY and (19)F-(19)F QF-COSY NMR spectra, we interpret the (1)H and (19)F NMR spectra of the porphyrins and chlorins, thus providing a refined reference point for the use of (19)F NMR spectroscopy as a diagnostic tool in the analysis of meso-pentafluorophenyl-substituted porphyrinoids.

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Source
http://dx.doi.org/10.1021/jo3001436DOI Listing

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