title: OsO4-mediated dihydroxylation of meso-tetraphenylporphyrin N-oxide and transformation of the resulting diolchlorin N-oxide regioisomers.
abstract: The OsO(4)-mediated dihydroxylation of meso-tetraphenylporphyrin N-oxide yields two regioisomeric chlorin N-oxides. These chlorin N-oxides can be manipulated to provide pairs of regioisomers of pyrrole-modified porphyrin N-oxides. The UV-vis absorption and fluorescence emission spectra of the neutral and protonated regioisomers are distinct from each other, and generally different from the parent chromophore. The outcome of diol oxidation reactions of some N-oxide diolchlorins varies from the corresponding reactions of the parent diolchlorins. The crystal structure of a free base porpholactone N-oxide carrying the N-oxide on the oxazolone moiety is reported.
authors.affiliation: Department of Chemistry, University of Connecticut, Unit 3060, Storrs, Connecticut 06269-3060, USA.
authors.forename: Subhadeep
authors.initials: S
authors.lastname: Banerjee
authors.forename: Matthias
authors.initials: M
authors.lastname: Zeller
authors.forename: Christian
authors.initials: C
authors.lastname: Brückner
mesh_terms: D003198:Computer Simulation; D018360:Crystallography, X-Ray; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D009993:Osmium Tetroxide / Q000737:chemistry*; D010081:Oxazolone / Q000737:chemistry*; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003497:Cyclic N-Oxides; D006843:Hydrocarbons, Chlorinated; D010087:Oxides; D011166:Porphyrins; C409084:tetraphenylporphyrin; D010081:Oxazolone; D009993:Osmium Tetroxide