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Synthesis and Photophysical Properties of a Pyrazolino[60]fullerene with Dimethylaniline Connected by an Acetylene Linkage
Author(s) -
Gouloumis Andreas,
Oswald Frédéric,
ElKhouly Mohamed E.,
Langa Fernando,
Araki Yasuyuki,
Ito Osamu
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500903
Subject(s) - chemistry , moiety , dimethylaniline , photochemistry , sonogashira coupling , fullerene , radical ion , conjugated system , ultrafast laser spectroscopy , excited state , photoinduced charge separation , fluorescence , chromophore , singlet state , spectroscopy , ion , stereochemistry , organic chemistry , photocatalysis , palladium , polymer , physics , quantum mechanics , nuclear physics , artificial photosynthesis , catalysis
A new triad based on pyrazolino[60]fullerene and a conjugated dimethylaniline group has been synthesized by a copper‐free Sonogashira cross‐coupling reaction using microwave irradiation as the source of energy. The electrochemical and photophysical properties of the triad were systematically investigated by techniques such as time‐resolved fluorescence and transient absorption spectroscopy. Charge separation via the excited singlet state of the C 60 moiety was confirmed in polar and nonpolar solvents and competes with triplet formation of the C 60 moiety. The charge‐separated state persisted for 91 ns. Such long lifetimes are characteristic of long distances between the radical anion of the pyrazolino[60]fullerene derivative and the radical cation of the dimethylaniline moiety. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)