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

Kemisk Institut

14 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Chemistry: A European Journal
Vol/bind	20
Udgave nummer	32
Sider (fra-til)	9918-9929
Antal sider	12
ISSN	0947-6539
DOI	https://doi.org/10.1002/chem.201402623
Status	Udgivet - 4 aug. 2014

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10.1002/chem.201402623

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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

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, bind 20, nr. 32, s. 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.",

author = "{Vico Solano}, Marta and {Della Pia}, {Eduardo Antonio} and Martyn Jevric and Christina Schubert and Xintai Wang and {van der Pol}, Cornelia and Anders Kadziola and Kasper N{\o}rgaard and Guldi, {Dirk M.} and Nielsen, {Mogens Br{\o}ndsted} and Jeppesen, {Jan Oskar}",

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AU - Vico Solano, Marta

AU - Della Pia, Eduardo Antonio

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

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