Mechanical Fixation by Porphyrin Connection: Synthesis and Transport Studies of a Bicyclic Dimer

Patrick Zwick; Kevin J. Weiland; Juraj Malinčík; Davide Stefani; Daniel Häussinger; Herre S.J. Van Der Zant; Diana Dulić; Marcel Mayor

doi:10.1021/acs.joc.9b02327

Mechanical Fixation by Porphyrin Connection: Synthesis and Transport Studies of a Bicyclic Dimer

Patrick Zwick, Kevin J. Weiland, Juraj Malinčík, Davide Stefani, Daniel Häussinger, Herre S.J. Van Der Zant, Diana Dulić, Marcel Mayor

QN/van der Zant Lab

Research output: Contribution to journal › Article › Scientific › peer-review

2 Citations (Scopus)

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.

Original language	English
Number of pages	11
Journal	Journal of Organic Chemistry
DOIs	https://doi.org/10.1021/acs.joc.9b02327
Publication status	Published - 2019

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Zwick, P., Weiland, K. J., Malinčík, J., Stefani, D., Häussinger, D., Van Der Zant, H. S. J., Dulić, D., & Mayor, M. (2019). Mechanical Fixation by Porphyrin Connection: Synthesis and Transport Studies of a Bicyclic Dimer. Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.9b02327

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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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Mechanical Fixation by Porphyrin Connection : Synthesis and Transport Studies of a Bicyclic Dimer. / Zwick, Patrick; Weiland, Kevin J.; Malinčík, Juraj; Stefani, Davide; Häussinger, Daniel; Van Der Zant, Herre S.J.; Dulić, Diana; Mayor, Marcel.

In: Journal of Organic Chemistry, 2019.

Research output: Contribution to journal › Article › Scientific › peer-review

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T1 - Mechanical Fixation by Porphyrin Connection

T2 - Synthesis and Transport Studies of a Bicyclic Dimer

AU - Zwick, Patrick

AU - Weiland, Kevin J.

AU - Malinčík, Juraj

AU - Stefani, Davide

AU - Häussinger, Daniel

AU - Van Der Zant, Herre S.J.

AU - Dulić, Diana

AU - Mayor, Marcel

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AB - 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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