Mono‐ and Bis(pyrrolo)tetrathiafulvalene Derivatives Tethered to C60: Synthesis,Photophysical Studies,and Self‐Assembled Monolayers |
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| Authors: | Dr. Marta Vico Solano Dr. Eduardo Antonio Della Pia Dr. Martyn Jevric Christina Schubert Xintai Wang Dr. Cornelia van der Pol Prof. Dr. Anders Kadziola Prof. Dr. Kasper Nørgaard Prof. Dr. Dirk M. Guldi Prof. Dr. Mogens Brøndsted Nielsen Prof. Dr. Jan O. Jeppesen |
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| Affiliation: | 1. Department of Physics, Chemistry, and Pharmacy, University of Southern Denmark, Campusvej 55, 5230, Odense M (Denmark), Fax: (+45)?6615‐8780;2. Department of Chemistry & Center for Exploitation of Solar Energy & Nano‐Science Center, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen ? (Denmark), Fax: (+45)?3532‐0212;3. Department of Chemistry and Pharmacy and Interdisciplinary Center for Molecular Materials, Lehrstuhl für Physikalische Chemie I, Friedrich‐Alexander‐Universit?t Erlangen‐Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany), Fax: (+49)?9131‐8528309 |
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| 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. |
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| Keywords: | cycloaddition donor– acceptor systems fullerenes monolayers tetrathiafulvalenes |
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