José I. Urgel¹, Julian Bock^2,3, Marco Di Giovannantonio¹, Pascal Ruffieux¹, Carlo A. Pignedoli^1*, Milan Kivala^2,3, Roman Fasel^1,4*

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), https://doi.org/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.

Materials Cloud sections using this data

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ReadMe.yaml MD5md5:344bcf00348acb163b1db2bbbf618c68	16.9 KiB	ReadMe file in yaml format detailing the content of the archive
data.tgz MD5md5:daf41e765112835a9530542776355d5f	17.0 MiB	Compressed tar archive containing the files of the record
bandstructure-non-magnetic.aiida MD5md5:de9f406aa7267dffdcaddda1eeda8c8a Open this AiiDA archive on renkulab.io (https://renkulab.io/)	127.5 MiB	Archive file containing AiiDA nodes to reproduce bandstructure (non magnetic) calculations
bandstructure.aiida MD5md5:d1f48a9916e266a57e2b77fbbea411ff Open this AiiDA archive on renkulab.io (https://renkulab.io/)	253.4 MiB	Archive file containing AiiDA nodes to reproduce bandstructure (magnetic) calculations
geo_opt.aiida MD5md5:4337c71723bd7d9a5f470d447d40dfd7 Open this AiiDA archive on renkulab.io (https://renkulab.io/)	117.2 MiB	Archive file containing AiiDA nodes to reproduce calculations on the Au substrate

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External references

Keywords

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