Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers

Marta Vico Solano; Eduardo Antonio Della Pia; Martyn Jevric; Christina Schubert; Xintai Wang; Cornelia van der Pol; Anders Kadziola; Kasper Nørgaard; Dirk M. Guldi; Mogens Brøndsted Nielsen; Jan Oskar Jeppesen

doi:10.1002/chem.201402623

Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers

Marta Vico Solano, Eduardo Antonio Della Pia, Martyn Jevric, Christina Schubert, Xintai Wang, Cornelia van der Pol, Anders Kadziola, Kasper Nørgaard, Dirk M. Guldi, Mogens Brøndsted Nielsen, Jan Oskar Jeppesen

Department of Chemistry

14 Citations (Scopus)

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.

Original language	English
Journal	Chemistry: A European Journal
Volume	20
Issue number	32
Pages (from-to)	9918-9929
Number of pages	12
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.201402623
Publication status	Published - 4 Aug 2014

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Vico Solano, M., Della Pia, E. A., Jevric, M., Schubert, C., Wang, X., van der Pol, C., Kadziola, A., Nørgaard, K., Guldi, D. M., Nielsen, M. B., & Jeppesen, J. O. (2014). Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers. Chemistry: A European Journal, 20(32), 9918-9929. https://doi.org/10.1002/chem.201402623

Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers. / Vico Solano, Marta; Della Pia, Eduardo Antonio; Jevric, Martyn et al.
In: Chemistry: A European Journal, Vol. 20, No. 32, 04.08.2014, p. 9918-9929.

Research output: Contribution to journal › Journal article › Research › peer-review

Vico Solano, M, Della Pia, EA, Jevric, M, Schubert, C, Wang, X, van der Pol, C, Kadziola, A, Nørgaard, K, Guldi, DM, Nielsen, MB & Jeppesen, JO 2014, 'Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers', Chemistry: A European Journal, vol. 20, no. 32, pp. 9918-9929. https://doi.org/10.1002/chem.201402623

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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 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.",

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AU - Jevric, Martyn

AU - Schubert, Christina

AU - Wang, Xintai

AU - van der Pol, Cornelia

AU - Kadziola, Anders

AU - Nørgaard, Kasper

AU - Guldi, Dirk M.

AU - Nielsen, Mogens Brøndsted

AU - Jeppesen, Jan Oskar

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AB - 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.

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DO - 10.1002/chem.201402623

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JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

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Mono- and bis(pyrrolo)tetrathiafulvalene derivatives tethered to C60: synthesis, photophysical studies, and self-assembled monolayers

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