Published October 26, 2020 | Version v1
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On‐surface synthesis of cumulene‐containing polymers via two‐step dehalogenative homocoupling of dibromomethylene-functionalized tribenzoazulene

  • 1. Empa – Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
  • 2. Center for Advancing Electronics and Department of Chemistry and Food Chemistry, Technical University of Dresden, 01062 Dresden, Germany
  • 3. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
  • 4. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland

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Description

The record contains data that support our recent findings in the fabrication of cumulene containing polymers. Cumulene compounds are notoriously difficult to prepare and study because their reactivity increases dramatically with the increasing number of consecutive double bonds. In this respect, the emerging field of on‐surface synthesis provides exceptional opportunities because it relies on reactions on clean metal substrates under well‐controlled ultrahigh‐vacuum conditions. In the work we report the on‐surface synthesis of a polymer linked by cumulene‐like bonds on a Au(111) surface via sequential thermally activated dehalogenative C−C coupling of a tribenzoazulene precursor equipped with two dibromomethylene groups. The structure and electronic properties of the resulting polymer with cumulene‐like pentagon–pentagon and heptagon–heptagon connections have been investigated by means of scanning probe microscopy and spectroscopy methods and X‐ray photoelectron spectroscopy, complemented by density functional theory calculations.

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References

Journal reference (Manuscript where the results are discussed)
J. I. Urgel, M. Di Giovannantonio, K. Eimre, T. G. Lohr, J. Liu, S. Mishra, Q. Sun, A. Kinikar, R. Widmer, S. Stolz, M. Bommert, R. Berger, P. Ruffieux, C. A. Pignedoli, K. Müllen, X. Feng, R. Fasel, Angew. Chem. Int. Ed. 59, 13281 - 13287 (2020), doi: 10.1002/anie.202001939

Journal reference (Manuscript where the results are discussed)
J. I. Urgel, M. Di Giovannantonio, K. Eimre, T. G. Lohr, J. Liu, S. Mishra, Q. Sun, A. Kinikar, R. Widmer, S. Stolz, M. Bommert, R. Berger, P. Ruffieux, C. A. Pignedoli, K. Müllen, X. Feng, R. Fasel, Angew. Chem. Int. Ed. 59, 13281 - 13287 (2020)