Symmetry breakdown of 4,4″-diamino-p-terphenyl on a Cu(111) surface by lattice mismatch

Qigang Zhong, Daniel Ebeling (), Jalmar Tschakert, Yixuan Gao, Deliang Bao, Shixuan Du (), Chen Li, Lifeng Chi () and André Schirmeisen
Additional contact information
Qigang Zhong: Soochow University
Daniel Ebeling: Justus-Liebig University
Jalmar Tschakert: Justus-Liebig University
Yixuan Gao: Institute of Physics & University of Chinese Academy of Sciences, Chinese Academy of Sciences
Deliang Bao: Institute of Physics & University of Chinese Academy of Sciences, Chinese Academy of Sciences
Shixuan Du: Institute of Physics & University of Chinese Academy of Sciences, Chinese Academy of Sciences
Chen Li: Dongguan University of Technology
Lifeng Chi: Soochow University
André Schirmeisen: Justus-Liebig University

Nature Communications, 2018, vol. 9, issue 1, 1-7

Abstract: Abstract Site-selective functionalization of only one of two identical chemical groups within one molecule is highly challenging, which hinders the production of complex organic macromolecules. Here we demonstrate that adsorption of 4,4″-diamino-p-terphenyl on a metal surface leads to a dissymmetric binding affinity. With low temperature atomic force microscopy, using CO-tip functionalization, we reveal the asymmetric adsorption geometries of 4,4″-diamino-p-terphenyl on Cu(111), while on Au(111) the symmetry is retained. This symmetry breaking on Cu(111) is caused by a lattice mismatch and interactions with the subsurface atomic layer. The dissymmetry results in a change of the binding affinity of one of the amine groups, leading to a non-stationary behavior under the influence of the scanning tip. Finally, we exploit this dissymmetric binding affinity for on-surface self-assembly with 4,4″-diamino-p-terphenyl for side-preferential attachment of 2-triphenylenecarbaldehyde. Our findings provide a new route towards surface-induced dissymmetric activation of a symmetric compound.

Date: 2018
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-018-05719-y Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05719-y

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-018-05719-y

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().