Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy

Jack Hellerstedt, Aleš Cahlík, Oleksander Stetsovych, Martin Švec, Tomoko Shimizu, Pingo Mutombo, Jiří Klívar, Irena G. Stará, Pavel Jelínek, Ivo Starý

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Chemical transformation of 9-azidophenanthrene on the Ag(111) surface was studied by nc-AFM in UHV. High-resolution imaging supported by first-principle calculations revealed the structure of the final products that originated from a common and elusive 9-phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ- and π-bonds between their transformation products on a solid surface was demonstrated at a single-molecule level.

Original languageEnglish
Pages (from-to)2266-2271
Number of pages6
JournalAngewandte Chemie - International Edition
Volume58
Issue number8
DOIs
Publication statusPublished - 2019 Feb 18
Externally publishedYes

Fingerprint

Scanning probe microscopy
Azides
Dimerization
Hydrogenation
Imaging techniques
Molecules

Keywords

  • azides
  • density functional calculations
  • on-surface chemistry
  • scanning probe microscopy
  • silver surface

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy. / Hellerstedt, Jack; Cahlík, Aleš; Stetsovych, Oleksander; Švec, Martin; Shimizu, Tomoko; Mutombo, Pingo; Klívar, Jiří; Stará, Irena G.; Jelínek, Pavel; Starý, Ivo.

In: Angewandte Chemie - International Edition, Vol. 58, No. 8, 18.02.2019, p. 2266-2271.

Research output: Contribution to journalArticle

Hellerstedt, J, Cahlík, A, Stetsovych, O, Švec, M, Shimizu, T, Mutombo, P, Klívar, J, Stará, IG, Jelínek, P & Starý, I 2019, 'Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy', Angewandte Chemie - International Edition, vol. 58, no. 8, pp. 2266-2271. https://doi.org/10.1002/anie.201812334
Hellerstedt, Jack ; Cahlík, Aleš ; Stetsovych, Oleksander ; Švec, Martin ; Shimizu, Tomoko ; Mutombo, Pingo ; Klívar, Jiří ; Stará, Irena G. ; Jelínek, Pavel ; Starý, Ivo. / Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy. In: Angewandte Chemie - International Edition. 2019 ; Vol. 58, No. 8. pp. 2266-2271.
@article{5f07f635862a43b5b809f61870bd91d5,
title = "Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy",
abstract = "Chemical transformation of 9-azidophenanthrene on the Ag(111) surface was studied by nc-AFM in UHV. High-resolution imaging supported by first-principle calculations revealed the structure of the final products that originated from a common and elusive 9-phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ- and π-bonds between their transformation products on a solid surface was demonstrated at a single-molecule level.",
keywords = "azides, density functional calculations, on-surface chemistry, scanning probe microscopy, silver surface",
author = "Jack Hellerstedt and Aleš Cahl{\'i}k and Oleksander Stetsovych and Martin Švec and Tomoko Shimizu and Pingo Mutombo and Jiř{\'i} Kl{\'i}var and Star{\'a}, {Irena G.} and Pavel Jel{\'i}nek and Ivo Star{\'y}",
year = "2019",
month = "2",
day = "18",
doi = "10.1002/anie.201812334",
language = "English",
volume = "58",
pages = "2266--2271",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "8",

}

TY - JOUR

T1 - Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy

AU - Hellerstedt, Jack

AU - Cahlík, Aleš

AU - Stetsovych, Oleksander

AU - Švec, Martin

AU - Shimizu, Tomoko

AU - Mutombo, Pingo

AU - Klívar, Jiří

AU - Stará, Irena G.

AU - Jelínek, Pavel

AU - Starý, Ivo

PY - 2019/2/18

Y1 - 2019/2/18

N2 - Chemical transformation of 9-azidophenanthrene on the Ag(111) surface was studied by nc-AFM in UHV. High-resolution imaging supported by first-principle calculations revealed the structure of the final products that originated from a common and elusive 9-phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ- and π-bonds between their transformation products on a solid surface was demonstrated at a single-molecule level.

AB - Chemical transformation of 9-azidophenanthrene on the Ag(111) surface was studied by nc-AFM in UHV. High-resolution imaging supported by first-principle calculations revealed the structure of the final products that originated from a common and elusive 9-phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ- and π-bonds between their transformation products on a solid surface was demonstrated at a single-molecule level.

KW - azides

KW - density functional calculations

KW - on-surface chemistry

KW - scanning probe microscopy

KW - silver surface

UR - http://www.scopus.com/inward/record.url?scp=85060345331&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85060345331&partnerID=8YFLogxK

U2 - 10.1002/anie.201812334

DO - 10.1002/anie.201812334

M3 - Article

C2 - 30600888

AN - SCOPUS:85060345331

VL - 58

SP - 2266

EP - 2271

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 8

ER -