Spider-like Oligothiophenes (Articolo in rivista)

  • Spider-like Oligothiophenes (Articolo in rivista) (literal)
  • 2008-01-01T00:00:00+01:00 (literal)
  • 10.1002/chem.200701117 (literal)
Alternative label
  • Benincori, T.; Capaccio, M.; De Angelis, F.; Falciola, L.; Muccini, M.; Mussini, P.; Ponti, A.; Toffanin, S.; Traldi, P.; Sannicolò F. (2008)
    Spider-like Oligothiophenes
    in Chemistry - A European Journal
  • Benincori, T.; Capaccio, M.; De Angelis, F.; Falciola, L.; Muccini, M.; Mussini, P.; Ponti, A.; Toffanin, S.; Traldi, P.; Sannicolò F. (literal)
Pagina inizio
  • 459 (literal)
Pagina fine
  • 471 (literal)
  • 14 (literal)
  • DOI: 10.1002/chem.200701117 (literal)
  • ISI Web of Science (WOS) (literal)
  • [a] Prof. F. Sannicolò Dipartimento di Chimica Organica e Industriale C.I.MA.I.NA, Università di Milano, ISTM, CNR, via Venezian 21 20133 Milano (Italy) Fax: (+39) 02-5031-4139 E-mail: francesco.sannicolo@unimi.it [b] Prof. T. Benincori Dipartimento di Scienze Chimiche ed Ambientali Universit7 dell'Insubria, via Valleggio 11 22100 Como (Italy) [c] Dr. M. Capaccio C.I.MA.I.NA., Universit7 di Milano, via Celoria 16 20133 Milano (Italy) [d] Dr. F. De Angelis ISTM-CNR, Via Elce di Sotto 8 06123 Perugia (Italy) [e] Dr. L. Falciola, Prof. P. Mussini Dipartimento di Chimica Fisica ed Elettrochimica C.I.MA.I.NA, Universit7 di Milano, via Golgi 19 20133 Milano (Italy) [f] Dr. M. Muccini, Dr. S. Toffanin ISMN--Istituto per lo Studio dei Materiali Nanostrutturati-CNR, Via P.Gobetti, 101 40129 Bologna (Italy) [g] Dr. A. Ponti ISTM--Istituto di Scienze e Tecnologie Molecolari--CNR via Golgi 19, 20133 Milano (Italy) [h] Dr. P. Traldi ISTM--Istituto di Scienze e Tecnologie Molecolari--CNR Dipartimento di Scienze Chimiche Università degli Studi di Padova, Via Marzolo 1 35131 Padova (Italy) (literal)
  • Spider-like Oligothiophenes (literal)
  • 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 (T9(5), T14(6), T19(7)) 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 pi-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 T9(5), coupled to laser-desorption-ionization mass spectroscopy on the resulting dimer demonstrated that the coupling process is extremely regioselective in the alpha positions of the more conjugated pentathiophene chain. ne 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. (literal)
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