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Mono‐ and Bis(pyrrolo)tetrathiafulvalene Derivatives Tethered to C 60 : Synthesis, Photophysical Studies, and Self‐Assembled Monolayers
Author(s) -
Solano Marta Vico,
Della Pia Eduardo Antonio,
Jevric Martyn,
Schubert Christina,
Wang Xintai,
van der Pol Cornelia,
Kadziola Anders,
Nørgaard Kasper,
Guldi Dirk M.,
Nielsen Mogens Brøndsted,
Jeppesen Jan O.
Publication year - 2014
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.201402623
Subject(s) - tetrathiafulvalene , moiety , chemistry , monolayer , cyclic voltammetry , supramolecular chemistry , triad (sociology) , photochemistry , absorption spectroscopy , molecule , stereochemistry , electrochemistry , organic chemistry , psychology , biochemistry , physics , electrode , quantum mechanics , psychoanalysis
Abstract A series of mono‐ (MPTTF) and bis(pyrrolo)tetrathiafulvalene (BPTTF) derivatives tethered to one or two C 60 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 C 60 . Electronic communication between the MPTTF/BPTTF units and the C 60 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 C 60 moieties. In addition, femtosecond and nanosecond transient absorption spectroscopy revealed, rather surprisingly, that no charge transfer from the MPTTF/BPTTF units to the C 60 moieties takes place on excitation of the fullerene moiety. Finally, it was shown that the MPTTF–C 60 and C 60 –BPTTF‐C 60 dyad and triad molecules formed self‐assembled monolayers on a Au(111) surface by anchoring to C 60 .