A1 Journal article (refereed)
An aryl-fused redox-active tetrathiafulvalene with enhanced mixed-valence and radical-cation dimer stabilities (2018)

Schröder, H. V., Witte, F., Gaedke, M., Sobottka, S., Suntrup, L., Hupatz, H., Valkonen, A., Paulus, B., Rissanen, K., Sarkar, B., & Schalley, C. A. (2018). An aryl-fused redox-active tetrathiafulvalene with enhanced mixed-valence and radical-cation dimer stabilities. Organic and Biomolecular Chemistry, 16(15), 2741-2747. https://doi.org/10.1039/C8OB00415C

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Publication details

All authors or editors: Schröder, Hendrik V.; Witte, Felix; Gaedke, Marius; Sobottka, Sebastian; Suntrup, Lisa; Hupatz, Henrik; Valkonen, Arto; Paulus, Beate; Rissanen, Kari; Sarkar, Biprajit; et al.

Journal or series: Organic and Biomolecular Chemistry

ISSN: 1477-0520

eISSN: 1477-0539

Publication year: 2018

Volume: 16

Issue number: 15

Pages range: 2741-2747

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/C8OB00415C

Publication open access: Not open

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Molecular recognition of stable organic radicals is a relatively novel, but important structural binding motif in supramolecular chemistry. Here, we report on a redox-switchable veratrole-fused tetrathiafulvalene derivative VTTF which is ideally suited for this purpose and for the incorporation into stimuli-responsive systems. As revealed by electrochemistry, UV/Vis measurements, X-ray analysis, and electrocrystallisation, VTTF can be reversibly oxidised to the corresponding radical-cation or dication which shows optoelectronic and structural propterties similar to tetrathiafulvalene and tetrakis(methylthio)tetrathiafulvalene. However, theoretical calculations, variable temperature EPR, and NIR spectroscopy indicate that the dispersion-driven binding in the mixed-valence dimer (VTTF2)˙+ (KMV = 69 M−1 in CH2Cl2) and the radical-cation dimer (VTTF˙+)2 (KRC = 38 M−1 in CH3CN) is significantly enhanced by the additional veratrole π-surface in comparison to pristine tetrathiafulvalene.

Keywords: supramolecular chemistry

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Ministry reporting: Yes

Reporting Year: 2018

JUFO rating: 1

Last updated on 2021-18-06 at 18:50