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On-surface synthesis of π-conjugated ladder-type polymers comprising nonbenzenoid moieties

José I. Urgel1, Julian Bock2,3, Marco Di Giovannantonio1, Pascal Ruffieux1, Carlo A. Pignedoli1*, Milan Kivala2,3, Roman Fasel1,4*

1 Empa - Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland

2 Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

3 Centre for Advanced Materials, Ruprecht-Karls-University Heidelberg, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany

4 Department of Chemistry and Biochemistry, University of Bern, 3012 Bern, Switzerland

* Corresponding authors emails: carlo.pignedoli@empa.ch, roman.fasel@empa.ch
DOI10.24435/materialscloud:a6-2z [version v1]

Publication date: Oct 26, 2021

How to cite this record

José I. Urgel, Julian Bock, Marco Di Giovannantonio, Pascal Ruffieux, Carlo A. Pignedoli, Milan Kivala, Roman Fasel, On-surface synthesis of π-conjugated ladder-type polymers comprising nonbenzenoid moieties, Materials Cloud Archive 2021.170 (2021), doi: 10.24435/materialscloud:a6-2z.

Description

In this record we provide data to support our recent findings related to the fabrication of π-conjugated ladder-type polymers comprising nonbenzenoid moieties. On-surface synthesis provides a powerful approach toward the atomically precise fabrication of π-conjugated ladder polymers (CLPs). In the manuscript we report the surface-assisted synthesis of nonbenzenoid CLPs from cyclopenta-annulated anthracene monomers on Au(111) under ultrahigh vacuum conditions. Successive thermal annealing steps reveal the dehalogenative homocoupling to yield an intermediate 1D polymer and the subsequent cyclodehydrogenation to form the fully conjugated ladder polymer. Notably, neighbouring monomers may fuse in two different ways, resulting in six- and five-membered rings, respectively. The structure and electronic properties of the reaction products have been investigated via low-temperature scanning tunneling microscopy and spectroscopy, complemented by density-functional theory calculations. Our results provide perspectives for the on-surface synthesis of nonbenzenoid CLPs with the potential to be used for organic electronic devices.

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Files and data are licensed under the terms of the following license: Creative Commons Attribution 4.0 International.
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External references

Journal reference (Manuscript where the results are discussed)
J. I. Urgel, J. Bock, M. Di Giovannantonio, P. Ruffieux, C. A. Pignedoli, M. Kivala, R. Fasel RSC Adv. 11, 23437 (2021). doi:10.1039/D1RA03253D

Keywords

polymers nonbenzenoid ab initio on surface synthesis MARVEL/DD3 CSCS SNSF Horizon 2020

Version history:

2021.170 (version v1) [This version] Oct 26, 2021 DOI10.24435/materialscloud:a6-2z