Photoinduced processes in fullerenopyrrolidine and fullerenopyrazoline derivatives substituted with an oligophenylenevinylene moietyElectronic supplementary information (ESI) available: synthetic procedures and full characterization of all new compounds. See http://www.rsc.org/suppdata/jm/b2/b200432a/

Abstract

Photoinduced processes in fullerenopyrrolidine and fullerenopyrazoline derivatives substituted with an oligophenylenevinylene moiety Armaroli, N.; Accorsi, G.; Gisselbrecht, J.P.; Gross, M.; Krasnikov, V.V.; Tsamouras, D.; Hadziioannou, G; Gomez-Escalonilla, M.J.; Langa, F.; Eckert, J.F.

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

“…[ 19] The second oxidation wave in the two bis-hydrazones must be attributed to the hydrazone moiety; [53] an additional wave is observed in F-3 PV and F-5 PV at around + 0.6 V, assigned to the oxidation of the aldehyde group.…”

“…[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. The performance of these devices strongly depends on the interplay between electronic structure and arrangement at the supramolecular level.…”

“…Compounds F 1 and F 2 were prepared as previously reported. [19,53] The OPV derivatives 3 PV and 5 PV were obtained by LiAlH 4 reduction of the corresponding bis-aldehydes 5 and 11, respectively.…”

“…[12] Moreover the pyrazoline-C 60 unit was found to act as a charge-separation module for the construction of photoactive and tunable devices. [19] To take advantage of their original electronic properties, C 60 and its derivatives have been linked to a variety of organic conjugated oligomers, [20] such as oligophenylenevinylenes (OPV), [19,[21][22][23][24][25][26] oligophenyleneethynylene (OPE), [27] oligothiophenes (OTP), [28][29][30][31] and others. [25,[32][33][34][35][36] These dyad and triad systems exhibit interesting intramolecular photoprocesses between the conjugated linear backbone and the carbon sphere, that is, electron or energy transfer.…”

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

“…A plethora of C 60 -oPPV conjugates has been reported, including examples in which the length and the number of oPPVs were altered systematically in order to establish the relationship between electron-transfer rates and electron donor-acceptor distances. 29,[32][33][34][35][36][37] Attenuation factors as small as 0.01 Å −1 were derived from the measured distance dependences of electron transfer for both charge separation and recombination processes. The reorganization energies for electron transfer in these C 60 -oPPVs and, more importantly, their distance dependence have never been investigated in detail.…”