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Fullerene Derivatives Functionalized with Diethylamino‐Substituted Conjugated Oligomers: Synthesis and Photoinduced Electron Transfer
Author(s) -
Gégout Aline,
Nierengarten JeanFrançois,
DelavauxNicot Béatrice,
Duhayon Carine,
Saquet Alix,
Listorti Andrea,
Belbakra Abdelhalim,
Chiorboli Claudio,
Armaroli Nicola
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901216
Subject(s) - photoinduced electron transfer , photochemistry , benzonitrile , fullerene , ultrafast laser spectroscopy , quenching (fluorescence) , chemistry , electron transfer , electron acceptor , conjugated system , cyclic voltammetry , moiety , acceptor , electrochemistry , fluorescence , spectroscopy , organic chemistry , polymer , physics , quantum mechanics , electrode , condensed matter physics
Abstract Diethylamino‐substituted oligophenylenevinylene (OPV) building blocks have been prepared and used for the synthesis of two [60]fullerene–OPV dyads, F‐D1 and F‐D2 , which exhibit different conjugation length of the OPV fragments. The electrochemical properties of these acceptor–donor dyads have been studied by cyclic voltammetry. The first reduction is always assigned to the fullerene moiety and the first oxidation centered on the diethylaniline groups of the OPV rods, thus making these systems suitable candidates for photoinduced electron transfer. Both the OPV and the fullerene‐centered fluorescence bands are quenched in toluene and benzonitrile, which suggests the occurrence of photoinduced electron transfer from the amino‐substituted OPVs to the carbon sphere in the dyads in both solvents. By means of bimolecular quenching experiments, transient absorption spectral fingerprints of the radical cationic species are detected in the visible (670 nm) and near‐IR (1300–1500 nm) regions, along with the much weaker fullerene anion band at λ max =1030 nm. Definitive evidence for photoinduced electron transfer in F‐D1 and F‐D2 comes from transient absorption measurements. A charge‐separated state is formed within 100 ps and decays in less than 5 ns.