Photoinduced energy transfer in a fullerene–oligophenylenevinylene conjugate

Armaroli, Nicola; Barigelletti, Francesco; Ceroni, Paola; Eckert, Jean‐François; Nicoud, Jean‐François; Nierengarten, Jean‐François

doi:10.1039/b000564i

Cited by 95 publications

(74 citation statements)

References 15 publications

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“…Both F 1 and F 2 exhibit virtually identical absorption spectra, but F 2 is a stronger emitter with a fluorescence quantum yield of 5.0 10 À4 in CH 2 Cl 2 (Table 3). This value is quite similar to that of fulleropyrrolidines, [38] which are among the strongest emitters within the family of monosubstituted fullerenes.…”

Section: Photophysical Propertiessupporting

confidence: 63%

“…[21,27,37] In the OPV-C 60 arrays described so far, the desired OPV!C 60 electron-transfer process undergoes competition from an efficient OPV!C 60 singlet-singlet energy transfer. [21,22,24,38,39] Practically, in solution, the OPV unit acts as a light collecting (i.e., antenna) module, whilst electron transfer, the extent of which can be modulated by solvent polarity, occurs only from the lowest electronic singlet state of the C 60 moiety. [19,40] The exploitation of the fullerene-based molecular systems for the fabrication of optoelectronic devices requires the processing of the molecular architecture in thin films.…”

Section: Introductionmentioning

confidence: 99%

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Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces

Langa

Gómez‐Escalonilla

Rueff

et al. 2005

Chemistry A European J

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Symmetrically substituted oligophenylenevinylene (OPV) derivatives bearing terminal p-nitrophenylhydrazone groups have been prepared and used for the synthesis of dumbbell-shaped bis(pyrazolino[60]fullerene)-OPV systems. In these triad arrays, the OPV-type fluorescence is dramatically quenched as a consequence of ultrafast OPV-->C60 singlet energy transfer. In its turn the fullerene singlet state is quenched by pyrazoline-->C60 electron transfer, in line with the behavior of the corresponding reference fullerene molecule. The occurrence of electron transfer in the multicomponent arrays is evidenced by recovery of fullerene fluorescence at 77 K in CH2Cl2 and in toluene at 298 K. Under these conditions the OPV-->C60 energy transfer is unaffected. The rate of this process turns out to be higher for the OPV trimer than for the corresponding pentameric OPV arrays, in agreement with energy-transfer theory expectations. Scanning tunneling microscopy (STM) and scanning force microscopy (SFM) revealed that the bis(pyrazolino[60]fullerene)-OPV can self-assemble into ordered layered crystalline architectures on the basal plane of highly oriented pyrolitic graphite.

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Section: Photophysical Propertiessupporting

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces

Langa

Gómez‐Escalonilla

Rueff

et al. 2005

Chemistry A European J

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“…17,18,26,27 Long-lived charge-separated states were identified in C 60 -oPPV-ZnPs as products of the rapid deactivation of the ZnP singlet excited state. 28,29 In C 60 -oPPV-ZnPs, the electron-transfer rates for fast charge separation and slow charge recombination are close to the top and inverted region of the Marcus parabola, respectively. A key factor for such a parabolic Marcus relationship is the total reorganization energy, which stems from both the electron donors and the electron acceptors.…”

Section: Introductionmentioning

confidence: 96%

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

et al. 2015

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Oligo(p-phenylenevinylene) (oPPV) wires of various lengths featuring pyridyls at one terminal and C 60 moieties at the other, have been used as molecular building blocks in combination with porphyrins to construct a novel class of electron donor-acceptor architectures. These architectures, which are based on non-covalent, directional interactions between the zinc centers of the porphyrins and the pyridyls, have been characterized by nuclear magnetic resonance spectroscopy and mass spectrometry. Complementary physico-chemical assays focused on the interactions between electron donors and acceptors in the ground and excited states. No appreciable electron interactions were noted in the ground state, which was being probed by electrochemistry, absorption spectroscopy, etc.; the electron acceptors are sufficiently decoupled from the electron donors. In the excited state, a different picture evolved. In particular, steady-state and time-resolved fluorescence and transient absorption measurements revealed substantial electron donor-acceptor interactions. These led, upon photoexcitation of the porphyrins, to tunable intramolecular electron-transfer processes, that is, the oxidation of porphyrin and the reduction of C 60 . In this regard, the largest impact stems from a rather strong distance dependence of the total reorganization energy in stark contrast to the distance independence seen for covalently linked conjugates.

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“…[12] However, the application of such molecular structures to organic photovoltaics requires consideration and optimisation of their behaviour in solid films. Several studies have addressed the photovoltaic performance of organic thin films fabricated from C 60 -OPV (fullerene-oligo(phenylenevinylene)) [13][14][15][16][17][18][19][20] and C 60 -OPE (fullerene-oligo-(phenyleneethynylene)) [21,22] conjugates and double cables. However, only very modest device efficiencies were achieved that were attributed to excessive charge-recombination losses.…”

Section: Introductionmentioning

confidence: 99%

Solid Film versus Solution‐Phase Charge‐Recombination Dynamics of exTTF–Bridge–C₆₀ Dyads

Handa

Giacalone

Haque

et al. 2005

Chemistry A European J

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The charge-recombination dynamics of two exTTF-C60 dyads (exTTF = 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene), observed after photoinduced charge separation, are compared in solution and in the solid state. The dyads differ only in the degree of conjugation of the bridge between the donor (exTTF) and the acceptor (C60) moieties. In solution, photoexcitation of the nonconjugated dyad C60-BN-exTTF (1) (BN = 1,1'-binaphthyl) shows slower charge-recombination dynamics compared with the conjugated dyad C60-TVB-exTTF (2) (TVB = bisthienylvinylenebenzene) (lifetimes of 24 and 0.6 micros, respectively), consistent with the expected stronger electronic coupling in the conjugated dyad. However, in solid films, the dynamics are remarkably different, with dyad 2 showing slower recombination dynamics than 1. For dyad 1, recombination dynamics for the solid films are observed to be tenfold faster than in solution, with this acceleration attributed to enhanced electronic coupling between the geminate radical pair in the solid film. In contrast, for dyad 2, the recombination dynamics in the solid film exhibit a lifetime of 7 micros, tenfold slower than that observed for this dyad in solution. These slow recombination dynamics are assigned to the dissociation of the initially formed geminate radical pair to free carriers. Subsequent trapping of the free carriers at film defects results in the observed slow recombination dynamics. It is thus apparent that consideration of solution-phase recombination data is of only limited value in predicting the solid-film behaviour. These results are discussed with reference to the development of organic solar cells based upon molecular donor-acceptor structures.

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Photoinduced energy transfer in a fullerene–oligophenylenevinylene conjugate

Cited by 95 publications

References 15 publications

Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces

Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

Solid Film versus Solution‐Phase Charge‐Recombination Dynamics of exTTF–Bridge–C₆₀ Dyads

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Photoinduced energy transfer in a fullerene–oligophenylenevinylene conjugate

Cited by 95 publications

References 15 publications

Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces

Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

Solid Film versus Solution‐Phase Charge‐Recombination Dynamics of exTTF–Bridge–C60 Dyads

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Solid Film versus Solution‐Phase Charge‐Recombination Dynamics of exTTF–Bridge–C₆₀ Dyads