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Open AccessArticle

Self-Assembly of Covalently Linked Porphyrin Dimers at the Solid–Liquid Interface

1
Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
2
Institute of Physics, University of Rostock, Albert-Einstein-Straße 23, 18059 Rostock, Germany
3
Department Life, Light & Matter—University of Rostock, 18051 Rostock, Germany
*
Author to whom correspondence should be addressed.
These authors contributed equally.
Academic Editors: Nathalie Solladié and Regis Rein
Molecules 2019, 24(16), 3018; https://doi.org/10.3390/molecules24163018
Received: 31 July 2019 / Revised: 12 August 2019 / Accepted: 17 August 2019 / Published: 20 August 2019
(This article belongs to the Special Issue Spatial Organization of Multi-Porphyrins for Pre-Defined Properties)
The synthesis and surface self-assembly behavior of two types of metal-porphyrin dimers is described. The first dimer type consists of two porphyrins linked via a rigid conjugated spacer, and the second type has an alkyne linker, which allows rotation of the porphyrin moieties with respect to each other. The conjugated dimers were equipped with two copper or two manganese centers, while the flexible dimers allowed a modular built-up that also made the incorporation of two different metal centers possible. The self-assembly of the new porphyrin dimers at a solid–liquid interface was investigated at the single-molecule scale using scanning tunneling microscopy (STM). All dimers formed monolayers, of which the stability and the internal degree of ordering of the molecules depended on the metal centers in the porphyrins. While in all monolayers the dimers were oriented coplanar with respect to the underlying surface (‘face-on’), the flexible dimer containing a manganese and a copper center could be induced, via the application of a voltage pulse in the STM setup, to self-assemble into monolayers in which the porphyrin dimers adopted a non-common perpendicular (‘edge-on’) geometry with respect to the surface. View Full-Text
Keywords: porphyrins; self-assembly; scanning tunneling microscopy; surfaces porphyrins; self-assembly; scanning tunneling microscopy; surfaces
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MDPI and ACS Style

Habets, T.; Lensen, D.; Speller, S.; Elemans, J.A. Self-Assembly of Covalently Linked Porphyrin Dimers at the Solid–Liquid Interface. Molecules 2019, 24, 3018.

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