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Pyrazolino[60]fullerene–Oligophenylenevinylene Dumbbell‐Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self‐Assembly on Surfaces
Author(s) -
Langa Fernando,
GomezEscalonilla Maria J.,
Rueff JeanMichel,
Figueira Duarte Teresa M.,
Nierengarten JeanFrançois,
Palermo Vincenzo,
Samorì Paolo,
Rio Yannick,
Accorsi Gianluca,
Armaroli Nicola
Publication year - 2005
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.200500089
Subject(s) - fullerene , materials science , electron transfer , dumbbell , scanning tunneling microscope , photochemistry , nanotechnology , crystallography , chemistry , organic chemistry , medicine , physical therapy
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→C 60 singlet energy transfer. In its turn the fullerene singlet state is quenched by pyrazoline→C 60 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 CH 2 Cl 2 and in toluene at 298 K. Under these conditions the OPV→C 60 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.