Data di Pubblicazione:
2008
Citazione:
Spider-like oligothiophenes / T. Benincori, M. Capaccio, F. De Angelis, L. Falciola, M. Muccini, P. Mussini, A. Ponti, S. Toffanin, P. Traldi, F. Sannicolò. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 14:2(2008), pp. 459-471. [10.1002/chem.200701117]
Abstract:
Careful analysis and comparison
of optical and electrochemical
data available in recent literature for
multi-thiophene molecular assemblies
suggested a few basic rules for the
design of structurally simple and easily
accessible oligothiophenes endowed
with properties not far from those exhibited
by much more complex and
synthetically demanding architectures.
The synthesis and computational investigation
of three examples of a class of
oligothiophenes (spider-like) tailored
according to these indications are reported
together with their exhaustive
optical and electrochemical characterization.
The new compounds (T95, T146,
T197) are characterized by a thiophene,
a 2,2’-bithiophene and a 2,2’,5’,2’’-terthiophene
unit (the spider body) fully
substituted with 5-(2,2’-bithiophen)yl
pendants (the spider legs). Absorption
and electrochemical data are in good
agreement and point to a high p-conjugation
level, comparable to those displayed
by much larger assemblies.
Electrode potential cycling in proximity
of the first oxidation peak affords
fast and reproducible formation of conducting,
highly stable [TXn]m films,
mainly consisting of dimers (m=2).
Electrooxidation kinetic experiments
on deuterium-labelled T95, coupled to
laser-desorption-ionization mass spectroscopy
on the resulting dimer demonstrated
that the coupling process is extremely
regioselective in the a positions
of the more conjugated pentathiophene
chain. The optical and the
electrochemical properties of the films
are reported and discussed. A peculiar
feature is their impressive charge-trapping
ability. Spider-like oligothiophenes
are promising materials for applications
as active layers in multifunctional
organic devices.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Conducting materials; Dendrimers; Electrochemistry; Oligothiophenes UV/Vis spectroscopy
Elenco autori:
T. Benincori, M. Capaccio, F. De Angelis, L. Falciola, M. Muccini, P. Mussini, A. Ponti, S. Toffanin, P. Traldi, F. Sannicolò
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