On-Surface Formation of Cyano-Vinylene Linked Chains by Knoevenagel Condensation

Kwan Ho Au-Yeung, Tim Kühne, Daniel Becker, Marcus Richter, Dmitry A. Ryndyk, Gianaurelio Cuniberti, Thomas Heine, Xinliang Feng, Francesca Moresco

Research output: Contribution to journalArticlepeer-review

Abstract

The rapid development of on-surface synthesis provides a unique approach toward the formation of carbon-based nanostructures with designed properties. Herein, we present the on-surface formation of CN-substituted phenylene vinylene chains on the Au(111) surface, thermally induced by annealing the substrate stepwise at temperatures between 220 °C and 240 °C. The reaction is investigated by scanning tunneling microscopy and density functional theory. Supported by the calculated reaction pathway, we assign the observed chain formation to a Knoevenagel condensation between an aldehyde and a methylene nitrile substituent.

Original languageEnglish
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2021

Bibliographical note

Funding Information:
This work was funded by the German Research Foundation (DFG) Collaborative Research Centre (CRC) 1415 “Chemistry of Synthetic Two‐Dimensional Materials” (No. 417590517). Support by the DFG Project 43234550 and European Union Horizon 2020 FET open project “Mechanics with Molecules” (MEMO, grant 766864) is gratefully acknowledged. We thank the Center for Information Services and High Performance Computing (ZIH) at TU Dresden for computational resources. Open Access funding enabled and organized by Projekt DEAL.

Publisher Copyright:
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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