On-off switching of the perylene tetracarboxylic bisimide luminescence via substitution at the N position by electron rich mono-, di- and tri-methoxybenzenes (Articolo in rivista)

Type
Label
  • On-off switching of the perylene tetracarboxylic bisimide luminescence via substitution at the N position by electron rich mono-, di- and tri-methoxybenzenes (Articolo in rivista) (literal)
Anno
  • 2010-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.201001489 (literal)
Alternative label
  • L. Flamigni; B. Ventura; A. Barbieri; H. Langhals; F. Wetzel; K. Fuchs; A. Walter (2010)
    On-off switching of the perylene tetracarboxylic bisimide luminescence via substitution at the N position by electron rich mono-, di- and tri-methoxybenzenes
    in Chemistry - A European Journal
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • L. Flamigni; B. Ventura; A. Barbieri; H. Langhals; F. Wetzel; K. Fuchs; A. Walter (literal)
Pagina inizio
  • 13406 (literal)
Pagina fine
  • 13416 (literal)
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  • 16 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#note
  • DOI: 10.1002/chem.201001489 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 45 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • 1. CNR, Ist ISOF, I-40129 Bologna, Italy 2. LMU Univ Munich, Dept Chem, D-81377 Munich, Germany (literal)
Titolo
  • On-off switching of the perylene tetracarboxylic bisimide luminescence via substitution at the N position by electron rich mono-, di- and tri-methoxybenzenes (literal)
Abstract
  • A series of perylene tetracarboxylic bisimides, substituted at the N-position with methoxyphenyl groups, have been synthesized together with model compounds and their photophysical properties have been investigated by means of steady-state and time-resolved spectroscopic techniques. The luminescence properties of the examined compounds vary remarkably with the substitution pattern, with emission quantum yields ranging from 1 to 10-2–10-3. The observed quenching of the luminescence is assigned to a photoinduced electron transfer (PET) from the electron-rich methoxybenzene unit to the perylene bisimide moiety. The radical anion of perylene bisimide has been detected by transient-absorption spectroscopy. The results could satisfactorily be explained by taking into consideration the redox potentials of the partners and the electron-releasing ability of each methoxy group in relation to its position with respect to N. Quantum-chemical calculations were also performed. (literal)
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