On-Surface Synthesis and Characterization of Acene-Based Nanoribbons Incorporating Four-Membered Rings

Carlos Sánchez-Sánchez, Thomas Dienel, Adrien Nicolaï, Neerav Kharche, Liangbo Liang, Colin Daniels, Vincent Meunier, Junzhi Liu, Xinliang Feng, Klaus Müllen, Juan Ramón Sánchez-Valencia, Oliver Gröning, Pascal Ruffieux, Roman Fasel

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

A bottom up method for the synthesis of unique tetracene-based nanoribbons, which incorporate cyclobutadiene moieties as linkers between the acene segments, is reported. These structures were achieved through the formal [2+2] cycloaddition reaction of ortho-functionalized tetracene precursor monomers. The formation mechanism and the electronic and magnetic properties of these nanoribbons were comprehensively studied by means of a multitechnique approach. Ultra-high vacuum scanning tunneling microscopy showed the occurrence of metal-coordinated nanostructures at room temperature and their evolution into nanoribbons through formal [2+2] cycloaddition at 475 K. Frequency-shift non-contact atomic force microscopy images clearly proved the presence of bridging cyclobutadiene moieties upon covalent coupling of activated tetracene molecules. Insight into the electronic and vibrational properties of the so-formed ribbons was obtained by scanning tunneling microscopy, Raman spectroscopy, and theoretical calculations. Magnetic properties were addressed from a computational point of view, allowing us to propose promising candidates to magnetic acene-based ribbons incorporating four-membered rings. The reported findings will increase the understanding and availability of new graphene-based nanoribbons with high potential in future spintronics.

Original languageEnglish
Pages (from-to)12074-12082
Number of pages9
JournalChemistry - A European Journal
Volume25
Issue number52
DOIs
StatePublished - Sep 18 2019

Funding

We are grateful for financial support from the Swiss National Science Foundation, the Office of Naval Research BRC program, and the European Union’s Horizon 2020 Research and Innovation programme under grant agreement GrapheneCore2 785219. C.S.S. acknowledges Ministerio de Economía y Com-petitividad for financial support through the Juan de la Cierva Incorporación grant (IJCI-2014-19291). We are grateful for financial support from the Swiss National Science Foundation, the Office of Naval Research BRC program, and the European Union's Horizon 2020 Research and Innovation programme under grant agreement GrapheneCore2 785219. C.S.S. acknowledges Ministerio de Econom?a y Competitividad for financial support through the Juan de la Cierva Incorporaci?n grant (IJCI-2014-19291).

Keywords

  • acene
  • cycloaddition
  • nanoribbons
  • on-surface chemistry
  • zigzag

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