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

36 Scopus citations


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

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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