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

Authors :
Zwick, Patrick
Weiland, Kevin J.
Malinčík, Juraj
Stefani, Davide
Häussinger, Daniel
van der Zant, Herre S. J.
Dulić, Diana
Mayor, Marcel
Source :
The Journal of Organic Chemistry; January 2020, Vol. 85 Issue: 1 p118-128, 11p
Publication Year :
2020

Abstract

The bowl-shaped, 3-fold interlinked porphyrin dimer 2was 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 1with 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.

Details

Language :
English
ISSN :
00223263
Volume :
85
Issue :
1
Database :
Supplemental Index
Journal :
The Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs51456375
Full Text :
https://doi.org/10.1021/acs.joc.9b02327