Fullerene Derivatives Functionalized with Diethylamino‐Substituted Conjugated Oligomers: Synthesis and Photoinduced Electron Transfer
- 1 September 2009
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 15 (35), 8825-8833
- https://doi.org/10.1002/chem.200901216
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 λmax=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.This publication has 56 references indexed in Scilit:
- Synthesis of Oligophenylenevinylene Heptamers Substituted with Fullerene MoietiesEuropean Journal of Organic Chemistry, 2008
- Fullerene Derivatives Substituted with Differently Branched Phenyleneethynylene Dendrons: Synthesis, Electronic and Excited State PropertiesEuropean Journal of Organic Chemistry, 2007
- Synthesis of Dendritic Branches with Peripheral Fullerene SubunitsEuropean Journal of Organic Chemistry, 2005
- Ultrafast Processes in Bimetallic Dyads with Extended Aromatic Bridges. Energy and Electron Transfer Pathways in Tetrapyridophenazine-Bridged ComplexesJournal of the American Chemical Society, 2002
- Photoinduced Electron Transfer between C60-Pendant Calixarene and Captured Electron Donor: Improvement of Electron-Transfer Efficiency by Applying Host−Guest ChemistryThe Journal of Physical Chemistry A, 2002
- Fullerene–porphyrin architectures; photosynthetic antenna and reaction center modelsChemical Society Reviews, 2001
- Photoinduced Electron-Transfer from Mono-/Oligo-1,4-phenylenevinylenes Containing Aromatic Amines to C60/C70 and Electron-Mediating Process to Viologen Dication in Polar SolutionThe Journal of Physical Chemistry A, 2001
- Photoinduced electron transfer between fullerenes (C60/C70) and disubstituted naphthalenes using laser flash photolysisJournal of Photochemistry and Photobiology A: Chemistry, 2001
- Competition between photosensitization and charge transfer in soluble oligo(naphthylenevinylene)–fullerene dyadsChemical Communications, 2000
- Measurement of photoluminescence quantum yields. ReviewThe Journal of Physical Chemistry, 1971