Synthesis and Transport Studies of a Cofacial Porphyrin Cyclophane

Patrick Zwick; Chunwei Hsu; Maria El Abbassi; Olaf Fuhr; Dieter Fenske; Diana Dulić; Herre S J van der Zant; Marcel Mayor

doi:10.1021/acs.joc.0c01957

Synthesis and Transport Studies of a Cofacial Porphyrin Cyclophane

J Org Chem. 2020 Dec 4;85(23):15072-15081. doi: 10.1021/acs.joc.0c01957. Epub 2020 Nov 9.

Authors

Patrick Zwick¹, Chunwei Hsu², Maria El Abbassi², Olaf Fuhr^{3

4}, Dieter Fenske^{3

4}, Diana Dulić⁵, Herre S J van der Zant², Marcel Mayor^{1

3

6}

Affiliations

¹ Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
² Kavli Institute of Nanoscience, Delft University of Technology, 2600 GA Delft, The Netherlands.
³ Institute for Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), P.O. Box 3640, 76021 Karlsruhe, Germany.
⁴ Karlsruhe Nano Micro Facility (KNMF), Karlsruhe Institute of Technology (KIT), P.O. Box 3640, 76021 Karlsruhe, Germany.
⁵ Department of Physics and Department of Electrical Engineering, Faculty of Physical and Mathematical Sciences, University of Chile, Avenida Blanco Encalada 2008, 8330015 Santiago, Chile.
⁶ Lehn Institute of Functional Materials (LIFM), School of Chemistry, Sun Yat-Sen University (SYSU), 510275 Guangzhou, China.

PMID: 33166468
DOI: 10.1021/acs.joc.0c01957

Abstract

Porphyrin cyclophane 1, consisting of two rigidly fixed but still movable cofacial porphyrins and exposing acetate-masked thiols in opposed directions of the macrocycle, is designed, synthesized, and characterized. The functional cyclophane 1, as pioneer of mechanosensitive 3D materials, forms stable single-molecule junctions in a mechanically controlled break-junction setup. Its reliable integration in a single-molecule junction is a fundamental prerequisite to explore the potential of these structures as mechanically triggered functional units and devices.