# Systematic C–C Bond Cleavage in Oligomers via Diels–Alder Reaction on Au(111)

https://mdr.nims.go.jp/datasets/1f0c2aad-e791-43e9-a015-2a47b6e91acc

## File

- [systematic-c-c-bond-cleavage-in-oligomers-via-diels-alder-reaction-on-au(111).pdf](https://mdr.nims.go.jp/filesets/127b02bd-82dc-4216-98a3-602a5af88660/download) ([Detail](https://mdr.nims.go.jp/filesets/127b02bd-82dc-4216-98a3-602a5af88660.md))
- [nn5c12424_si_001.pdf](https://mdr.nims.go.jp/filesets/924006da-c661-4320-9a4a-93c64fc5fd46/download) ([Detail](https://mdr.nims.go.jp/filesets/924006da-c661-4320-9a4a-93c64fc5fd46.md))

## Id

1f0c2aad-e791-43e9-a015-2a47b6e91acc

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2025-10-15T01:07:44.457241Z

## Updated at

2025-10-21T07:06:44.177823Z

## Published at

2025-10-21T06:43:40.404062Z

## Doi



## First published url

https://doi.org/10.1021/acsnano.5c12424

## Date published

2025-10-14

## Recorded date published

2025-10-14

## Resource type

journal_article

## Manuscript type

vor

## Collection



## Title

- title: Systematic C–C Bond Cleavage in Oligomers via Diels–Alder Reaction on Au(111)
  title_type: original
  lang: en

## Description

- description: On-surface synthesis became a powerful strategy to synthesize extended
    nanocarbon materials, such as oligomers and graphene nanoribbons, via C–C bond
    formation between small precursor molecules. However, the reverse reaction, namely
    C–C bond cleavage, remains challenging due to the high activation barrier. Here,
    we present systematic fragmentation to individual units from tetra(9-anthryl)benzene
    oligomers, which were synthesized by the Ullmann-type homocoupling on Au(111).
    The detailed mechanism of the fragmentation was investigated with a combination
    of scanning tunneling microscopy and density functional theory calculations. We
    found that the Diels-Alder reaction between anthracene groups in the unit significantly
    lowers the activation barrier to cleave the C–C bond between the units in the
    oligomer. Our findings may offer an approach to disassemble oligomers in a controlled
    manner.
  description_type: abstract
  lang: und

## Creator

- name: Donglin Li
  role: author
  department: Center for Basic Research on Materials
- name: Tatsuhiko Ohto
  role: author
  orcid: https://orcid.org/0000-0001-8681-3800
  organization: Nagoya University
- name: Tomohiko Nishiuchi
  role: author
  orcid: https://orcid.org/0000-0002-2113-0731
  organization: Osaka University
- name: Shino Takeuchi
  role: author
  organization: Osaka University
- name: Yuki Nishide
  role: author
  organization: Nagoya University
- name: Hajime Kimizuka
  role: author
  orcid: https://orcid.org/0000-0002-4610-9760
  organization: Nagoya University
- name: Takashi Kubo
  role: author
  orcid: https://orcid.org/0000-0001-6809-7396
  organization: Osaka University
- name: Shigeki Kawai
  role: author
  orcid: https://orcid.org/0000-0003-2128-0120
  department: Center for Basic Research on Materials

## Contact agent



## Publisher

organization: American Chemical Society (ACS)

## Managing organization



## Keyword

- subject: on-surface synthesis
  schema: not_defined
- subject: fragmentation
  schema: not_defined
- subject: Diels-Alder reaction
  schema: not_defined
- subject: scanning tunneling microscopy
  schema: not_defined
- subject: density functional theory
  schema: not_defined
- subject: oligonomers
  schema: not_defined

## Rights

- identifier: https://creativecommons.org/licenses/by/4.0/

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo



## Journal

- title: ACS Nano
  issn: '19360851'
  volume: '19'
  issue: '40'
  start_page: 35825
  end_page: 35832

## Conference



## Related item



## Funding

- identifier: 24K01454
  funder_name: Japan Society for the Promotion of Science
- identifier: 24K21721
  funder_name: Japan Society for the Promotion of Science
- identifier: 24KF0269
  funder_name: Japan Society for the Promotion of Science
- identifier: 25H00422
  funder_name: Japan Society for the Promotion of Science
- funder_name: Eneos Tonegeneral research foundation

## Instrument



## Instrument operator



## Instrument managing organization



## Measurement method



## Specimen



## Chemical composition



## Structure for specimen



## Structural feature for specimen



## Specific property for specimen



## Process for specimen treatment



## Computational method



## Energy level/transition state



## Software



## Custom property



## Fileset

- id: 127b02bd-82dc-4216-98a3-602a5af88660
  filename: systematic-c-c-bond-cleavage-in-oligomers-via-diels-alder-reaction-on-au(111).pdf
  content_type: application/pdf
  size: 7793020
  md5: fc28f3a4c56c52ddaf7961351aef4f21
- id: 924006da-c661-4320-9a4a-93c64fc5fd46
  filename: nn5c12424_si_001.pdf
  content_type: application/pdf
  size: 1320133
  md5: 18a47069421dacf47fcd6278793b8d1f

## Thumbnail

fileset_id: 127b02bd-82dc-4216-98a3-602a5af88660
filename: systematic-c-c-bond-cleavage-in-oligomers-via-diels-alder-reaction-on-au(111).pdf