Mechanical Fixation by Porphyrin Connection

Synthesis and Transport Studies of a Bicyclic Dimer

Journal Article (2019)
Author(s)

Patrick Zwick (University of Basel)

Kevin J. Weiland (University of Basel)

Juraj Malinčík (University of Basel)

Davide Stefani (TU Delft - QN/van der Zant Lab, Kavli institute of nanoscience Delft)

Daniel Häussinger (University of Basel)

Herre S.J. Van Der Zant (Kavli institute of nanoscience Delft, TU Delft - QN/van der Zant Lab)

Diana Dulić (Universidad de Chile)

Marcel Mayor (University of Basel, Sun Yat-sen University, Karlsruhe Institut für Technologie)

Research Group
QN/van der Zant Lab
DOI related publication
https://doi.org/10.1021/acs.joc.9b02327 Final published version
More Info
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Publication Year
2019
Language
English
Research Group
QN/van der Zant Lab
Bibliographical Note
Green Open Access added to TU Delft Institutional Repository ‘You share, we take care!’ – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.
Journal title
Journal of Organic Chemistry
Issue number
1
Volume number
85
Pages (from-to)
118-128
Downloads counter
262
Collections
Institutional Repository
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Abstract

The bowl-shaped, 3-fold interlinked porphyrin dimer 2 was obtained in respectable yields during macrocyclization attempts. Its bicyclic structure, consisting of a macrocycle made of a pair of acetylene interlinked tetraphenylporphyrins which are additionally linked by a C-C bond interlinking two pyrrole subunits, has been confirmed spectroscopically (2D-NMR, UV/vis, HR-MALDI-ToF MS). Late-stage functionalization provided the structural analogue 1 with acetyl-protected terminal thiol anchor groups enabling single molecule transport investigations in a mechanically controlled break junction experiment. The formation of single-molecule junctions was observed, displaying large variations in the observed conductance values pointing at a rich diversity in the molecular junctions.

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