Mechanism of Pyrrolyl Oxidation in Star-Shaped Compounds

Mechanism of Pyrrolyl Oxidation in Star-Shaped Compounds

The oxidation products in acetonitrile of hexapyrrolylbenzene (HPyB) and hexakis(3-octylpyrrolyl)benzene (HOPyB), two star-shaped compounds consisting of 6-fold N-pyrrolyl-substituted benzenes, were characterized by MALDI-TOF. These products result from intramolecular coupling of pyrrolyl residues w...

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Veröffentlicht in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2003-06, Vol.107 (25), p.5042-5048
Hauptverfasser: Lazerges, M, Jouini, M, Hapiot, P, Guiriec, P, Lacaze, P.-C
Format: Artikel
Sprache:eng
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Zusammenfassung:The oxidation products in acetonitrile of hexapyrrolylbenzene (HPyB) and hexakis(3-octylpyrrolyl)benzene (HOPyB), two star-shaped compounds consisting of 6-fold N-pyrrolyl-substituted benzenes, were characterized by MALDI-TOF. These products result from intramolecular coupling of pyrrolyl residues without dimer or polymer products. Transient electrochemical and flash photolysis experiments on HPyB indicate that this intramolecular coupling occurs via a radical cation/substrate mechanism and not by a radical cation/radical cation mechanism, as usually observed in intermolecular coupling that occurs during the polymerization of pyrrole derivatives.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp034417d