title: Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers.
abstract: A series of mono- (MPTTF) and bis(pyrrolo)tetrathiafulvalene (BPTTF) derivatives tethered to one or two C60 moieties was synthesized and characterized. The synthetic strategy for these dumbbell-shaped compounds was based on a 1,3-dipolar cycloaddition reaction between aldehyde-functionalized MPTTF/BPTTF derivatives, two different tailor-made amino acids, and C60. Electronic communication between the MPTTF/BPTTF units and the C60 moieties was studied by a variety of techniques including cyclic voltammetry and absorption spectroscopy. These solution-based studies indicated no observable electronic communication between the MPTTF/BPTTF units and the C60 moieties. In addition, femtosecond and nanosecond transient absorption spectroscopy revealed, rather surprisingly, that no charge transfer from the MPTTF/BPTTF units to the C60 moieties takes place on excitation of the fullerene moiety. Finally, it was shown that the MPTTF-C60 and C60-BPTTF-C60 dyad and triad molecules formed self-assembled monolayers on a Au(111) surface by anchoring to C60.
authors.affiliation: Department of Physics, Chemistry, and Pharmacy, University of Southern Denmark, Campusvej 55, 5230, Odense M (Denmark), Fax: (+45) 6615-8780; Department of Chemistry & Center for Exploitation of Solar Energy & Nano-Science Center, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø (Denmark), Fax: (+45) 3532-0212.
authors.forename: Marta Vico
authors.initials: MV
authors.lastname: Solano
authors.forename: Eduardo Antonio
authors.initials: EA
authors.lastname: Della Pia
authors.forename: Martyn
authors.initials: M
authors.lastname: Jevric
authors.forename: Christina
authors.initials: C
authors.lastname: Schubert
authors.forename: Xintai
authors.initials: X
authors.lastname: Wang
authors.forename: Cornelia
authors.initials: C
authors.lastname: van der Pol
authors.forename: Anders
authors.initials: A
authors.lastname: Kadziola
authors.forename: Kasper
authors.initials: K
authors.lastname: Nørgaard
authors.forename: Dirk M
authors.initials: DM
authors.lastname: Guldi
authors.forename: Mogens Brøndsted
authors.initials: MB
authors.lastname: Nielsen
authors.forename: Jan O
authors.initials: JO
authors.lastname: Jeppesen
keywords: cycloaddition; donor-acceptor systems; fullerenes; monolayers; tetrathiafulvalenes