Published October 26, 2021 | Version v1
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On-surface synthesis of π-conjugated ladder-type polymers comprising nonbenzenoid moieties

  • 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

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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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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