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On‐surface synthesis of cumulene‐containing polymers via two‐step dehalogenative homocoupling of dibromomethylene-functionalized tribenzoazulene

José I. Urgel1, Marco Di Giovannantonio1, Kristjan Eimre1, Thorsten G. Lohr2, Junzhi Liu2, Shantanu Mishra1, Qiang Sun1, Amogh Kinikar1, Roland Widmer1, Samuel Stolz1, Max Bommert1, Reinhard Berger2, Pascal Ruffieux1, Carlo A. Pignedoli1*, Klaus Müllen3, Xinliang Feng2, Roman Fasel1,4*

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

* Corresponding authors emails: carlo.pignedoli@empa.ch, roman.fasel@empa.ch
DOI10.24435/materialscloud:tx-ht [version v1]

Publication date: Oct 26, 2020

How to cite this record

José I. Urgel, Marco Di Giovannantonio, Kristjan Eimre, Thorsten G. Lohr, Junzhi Liu, Shantanu Mishra, Qiang Sun, Amogh Kinikar, Roland Widmer, Samuel Stolz, Max Bommert, Reinhard Berger, Pascal Ruffieux, Carlo A. Pignedoli, Klaus Müllen, Xinliang Feng, Roman Fasel, On‐surface synthesis of cumulene‐containing polymers via two‐step dehalogenative homocoupling of dibromomethylene-functionalized tribenzoazulene, Materials Cloud Archive 2020.131 (2020), doi: 10.24435/materialscloud:tx-ht.

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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Keywords

MARVEL/DD3 SNSF ERC CSCS DFG polymers cumulene on surface synthesis ab initio

Version history:

2020.131 (version v1) [This version] Oct 26, 2020 DOI10.24435/materialscloud:tx-ht