Articolo in rivista, 2010, ENG, 10.1002/chem.201001489

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

L. Flamigni; B. Ventura; A. Barbieri; H. Langhals; F. Wetzel; K. Fuchs; A. Walter

1. CNR, Ist ISOF, I-40129 Bologna, Italy 2. LMU Univ Munich, Dept Chem, D-81377 Munich, Germany

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.

Chemistry - A European Journal 16 (45), pp. 13406–13416

Keywords

bisimides, charge separation, electron transfer, luminescence, supramolecular chemistry

CNR authors

Barbieri Andrea, Flamigni Lucia, Ventura Barbara

CNR institutes

ISOF – Istituto per la sintesi organica e la fotoreattività