# On-Surface Synthesis of Azobenzene-Linked Porphyrin Derivatives

https://mdr.nims.go.jp/datasets/66a242e7-9bdf-4060-995e-dddd58e61914

## File

- [on-surface-synthesis-of-azobenzene-linked-porphyrin-derivatives.pdf](https://mdr.nims.go.jp/filesets/ab4f5373-7ee3-4964-9f98-ddad5a42e363/download) ([Detail](https://mdr.nims.go.jp/filesets/ab4f5373-7ee3-4964-9f98-ddad5a42e363.md))
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- [jz5c03174_si_003.cif](https://mdr.nims.go.jp/filesets/4d737399-14b2-4dbc-b506-4e8b4332c57b/download) ([Detail](https://mdr.nims.go.jp/filesets/4d737399-14b2-4dbc-b506-4e8b4332c57b.md))
- [jz5c03174_si_004.pdf](https://mdr.nims.go.jp/filesets/1109658c-6593-43dd-b7c7-caf63d0b45e4/download) ([Detail](https://mdr.nims.go.jp/filesets/1109658c-6593-43dd-b7c7-caf63d0b45e4.md))

## Id

66a242e7-9bdf-4060-995e-dddd58e61914

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2025-11-20T00:13:07.561954Z

## Updated at

2025-11-20T03:30:19.672054Z

## Published at

2025-11-20T03:24:30.743519Z

## Doi



## First published url

https://doi.org/10.1021/acs.jpclett.5c03174

## Date published

2025-11-13

## Recorded date published

2025-11-13

## Resource type

journal_article

## Manuscript type

vor

## Collection



## Title

- title: On-Surface Synthesis of Azobenzene-Linked Porphyrin Derivatives
  title_type: original
  lang: en

## Description

- description: On-surface synthesis has become an attractive strategy to obtain functionalized
    carbon nanostructures from small precursor molecules using a bottom-up approach.
    Although various on-surface reactions have been developed, it is still unclear
    how the chirality of self-assembled structures prior to reaction affects the coupling
    process. Here, we investigate homocoupling of nitro-phenyl groups in Pt-porphyrin
    derivatives on Au(111) surfaces using low-temperature scanning tunneling microscopy.
    Two different self-assembled structures composed either of linear oligomer of
    molecules of opposing chirality or of discrete trimers of molecules having the
    same chirality (i.e., homochiral) were respectively obtained by using differently
    substituted phenyl and 3,5-di-tert-butylphenyl groups porphyrin cores. A machine-learning-assisted
    protocol was used for large-scale statistical analysis revealing the distinct
    difference in reaction yields of azobenzene formation between two different self-assembled
    structures. Since the azobenzene (dimer) products are composed of two molecules
    with opposing chirality (i.e., they are heterochiral), the molecules in the homochiral
    assembly must first be disassembled, which is one of the reasons for the low reaction
    yield. This study highlights the significant role of porphyrin chirality in the
    azo coupling reaction process on surface.
  description_type: abstract
  lang: en

## Creator

- name: Yuji Isshiki
  role: author
  orcid: https://orcid.org/0009-0000-6254-8723
  organization: National Institute for Materials Science
- name: Donglin Li
  role: author
  orcid: https://orcid.org/0009-0001-6866-8715
  organization: National Institute for Materials Science
- name: Saranyan Vijayaraghavan
  role: author
  organization: CSIR-Central Electrochemical Research Institute
- name: Kewei Sun
  role: author
  orcid: https://orcid.org/0000-0002-1835-243X
  organization: National Institute for Materials Science
- name: Huynh Thien Ngo
  role: author
  organization: National Institute for Materials Science
- name: Luiza Buimaga-Iarinca
  role: author
  organization: National Institute for Research and Development of Isotopic and Molecular
    Technologies
- name: Yoshitaka Matsushita
  role: author
  orcid: https://orcid.org/0000-0002-4968-8905
  organization: National Institute for Materials Science
- name: Edward A. Neal
  role: author
  organization: National Institute for Materials Science
- name: Cristian Morari
  role: author
  organization: National Institute for Research and Development of Isotopic and Molecular
    Technologies
- name: Jonathan P. Hill
  role: author
  orcid: https://orcid.org/0000-0002-4229-5842
  organization: National Institute for Materials Science
- name: Shigeki Kawai
  role: author
  orcid: https://orcid.org/0000-0003-2128-0120
  organization: National Institute for Materials Science

## Contact agent



## Publisher

organization: American Chemical Society (ACS)

## Managing organization



## Keyword

- subject: On-surface synthesis
  schema: not_defined
- subject: scanning tunneling microscopy
  schema: not_defined
- subject: chirality
  schema: not_defined
- subject: porphyrin derivatives
  schema: not_defined
- subject: azobenzene
  schema: not_defined
- subject: molecular structure
  schema: not_defined
- subject: pyrroles
  schema: not_defined

## Rights

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

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo



## Journal

- title: The Journal of Physical Chemistry Letters
  issn: '19487185'
  volume: '16'
  issue: '45'
  start_page: 11833
  end_page: 11841

## Conference



## Related item



## Funding

- identifier: 24KF0269
  funder_name: Japan Society for the Promotion of Science
- identifier: 25H00422
  funder_name: Japan Society for the Promotion of Science
- identifier: PN23 24 01 04
  funder_name: Ministerul Cercetarii, Inovarii si Digitalizarii
- identifier: 24K21721
  funder_name: Japan Society for the Promotion of Science

## 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



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## Thumbnail

fileset_id: ab4f5373-7ee3-4964-9f98-ddad5a42e363
filename: on-surface-synthesis-of-azobenzene-linked-porphyrin-derivatives.pdf