Overcoming steric hindrance in aryl-aryl homocoupling via on-surface copolymerization

Authors: José I. Urgel1, Marco Di Giovannantonio1, Guido Gandus1, Qiang Chen2, Xunshan Liu3, Hironobu Hayashi4, Pascal Ruffieux1, Silvio Decurtins 3, Akimitsu Narita 5, Daniele Passerone1, Hiroko Yamada4, Shi‐Xia Liu 3, Klaus Müllen 6, Carlo A. Pignedoli 1*, Roman Fasel1*

  1. nanotech@surfaces Laboratory, Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600, Dübendorf, Switzerland
  2. Max Planck Institute for Polymer Research, 55128, Mainz, Germany
  3. Department of Chemistry and Biochemistry, University of Bern, 3012, Bern, Switzerland
  4. Division of Materials Science, Graduate School of Science and Technology Nara Institute of Science and Technology (NAIST) 8916-5 Takayama-cho, Ikoma, 630-0192, Japan
  5. Max Planck Institute for Polymer Research, 55128, Mainz, Germany and Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University 1919-1 Tancha, Onna-son, Kunigami, Okinawa, 904-0495, Japan
  6. Max Planck Institute for Polymer Research, 55128, Mainz, Germany and Institute of Physical Chemistry, Johannes Gutenberg-Universität Mainz, 55128, Mainz, Germay
  • Corresponding authors emails: carlo.pignedoli@empa.ch, roman.fasel@empa.ch

DOI10.24435/materialscloud:2019.0056/v1 (version v1, submitted on 10 October 2019)

How to cite this entry

José I. Urgel, Marco Di Giovannantonio, Guido Gandus, Qiang Chen, Xunshan Liu, Hironobu Hayashi, Pascal Ruffieux, Silvio Decurtins , Akimitsu Narita , Daniele Passerone, Hiroko Yamada, Shi‐Xia Liu , Klaus Müllen , Carlo A. Pignedoli , Roman Fasel, Overcoming steric hindrance in aryl-aryl homocoupling via on-surface copolymerization, Materials Cloud Archive (2019), doi: 10.24435/materialscloud:2019.0056/v1.

Description

On‐surface synthesis is a unique tool for growing low‐dimensional carbon nanomaterials with precise structural control down to the atomic level.
One of the most applied reactions to covalently interlink molecular precursors is dehalogenative aryl‐aryl coupling.
Failures in this process are often related to the steric hindrance between reactants, which may arise due to their coplanarity upon adsorption on a surface. In a recent work we proposed a copolymerization approach to overcome the limitations that prevent intermolecular homocoupling. We used suitable linkers as additional reactants to demonstrate formation of fully conjugated polycyclic nanowires incorporating non‐benzenoid rings. This record contains data to support the experimental and theoretical evidences discussed in the manuscript.

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External references

Journal reference (Manuscript in which the results are presented)
ChemPhysChem 20, 2360 - 2366, (2019) doi:10.1002/cphc.201900283

Keywords

MARVEL/DD3 MARVEL ab initio scanning probe microscopy on surface synthesis nanomaterials

Version history

10 October 2019 [This version]