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

doi:10.1002/chem.202103094

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

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 language	English
Pages (from-to)	17336-17340
Number of pages	5
Journal	Chemistry - A European Journal
Volume	27
Issue number	69
DOIs	https://doi.org/10.1002/chem.202103094
Publication status	Published - 2021 Dec 9

Bibliographical note

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

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.202103094

Cite this

@article{62b49a0f3d8a410982e1552859fe2d6c,

title = "On-Surface Formation of Cyano-Vinylene Linked Chains by Knoevenagel Condensation",

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.",

author = "Au-Yeung, {Kwan Ho} and Tim K{\"u}hne and Daniel Becker and Marcus Richter and Ryndyk, {Dmitry A.} and Gianaurelio Cuniberti and Thomas Heine and Xinliang Feng and Francesca Moresco",

note = "Publisher Copyright: {\textcopyright} 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH",

year = "2021",

month = dec,

day = "9",

doi = "10.1002/chem.202103094",

language = "English",

volume = "27",

pages = "17336--17340",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "69",

}

TY - JOUR

T1 - On-Surface Formation of Cyano-Vinylene Linked Chains by Knoevenagel Condensation

AU - Au-Yeung, Kwan Ho

AU - Kühne, Tim

AU - Becker, Daniel

AU - Richter, Marcus

AU - Ryndyk, Dmitry A.

AU - Cuniberti, Gianaurelio

AU - Heine, Thomas

AU - Feng, Xinliang

AU - Moresco, Francesca

PY - 2021/12/9

Y1 - 2021/12/9

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85117413444&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85117413444&partnerID=8YFLogxK

U2 - 10.1002/chem.202103094

DO - 10.1002/chem.202103094

M3 - Article

C2 - 34652042

AN - SCOPUS:85117413444

SN - 0947-6539

VL - 27

SP - 17336

EP - 17340

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 69

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this