Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C 60: Synthesis, photophysical studies, and self-assembled monolayers

Solano MV, Della Pia EA, Jevric M, Schubert C, Wang X, Van Der Pol C, Kadziola A, Norgaard K, Guldi DM, Nielsen MB, Jeppesen JO (2014)

Publication Type: Journal article

Publication year: 2014

Journal

Chemistry - A European Journal Wiley

Book Volume: 20

Pages Range: 9918-9929

Journal Issue: 32

DOI: 10.1002/chem.201402623

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 C 60. 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-C 60 and C60-BPTTF-C60 dyad and triad molecules formed self-assembled monolayers on a Au(111) surface by anchoring to C 60. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Authors with CRIS profile

Christina Schubert Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

University of Southern Denmark / Syddansk Universitet DK Denmark (DK) University of Copenhagen DK Denmark (DK)

How to cite

APA:

Solano, M.V., Della Pia, E.A., Jevric, M., Schubert, C., Wang, X., Van Der Pol, C.,... Jeppesen, J.O. (2014). Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C 60: Synthesis, photophysical studies, and self-assembled monolayers. Chemistry - A European Journal, 20(32), 9918-9929. https://doi.org/10.1002/chem.201402623

MLA:

Solano, Marta Vico, et al. "Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C 60: Synthesis, photophysical studies, and self-assembled monolayers." Chemistry - A European Journal 20.32 (2014): 9918-9929.

BibTeX: Download