# Synthesis of azahexabenzocoronenium salts through a formal [3 + 3] cycloaddition strategy

https://mdr.nims.go.jp/datasets/f9ea2e9f-c77f-4e80-befb-7fc7f9de18a1

## File

- [NATSYNTH-23090974_Manuscript.pdf](https://mdr.nims.go.jp/filesets/288146d3-823b-4b6f-9b14-aeb236859e71/download) ([Detail](https://mdr.nims.go.jp/filesets/288146d3-823b-4b6f-9b14-aeb236859e71.md))

## Id

f9ea2e9f-c77f-4e80-befb-7fc7f9de18a1

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2024-10-23T00:28:06.803580Z

## Updated at

2025-01-10T07:31:17.633577Z

## Published at

2025-01-10T07:31:17.715435Z

## Doi

https://doi.org/10.48505/nims.4884

## First published url

https://doi.org/10.1038/s44160-024-00595-5

## Date published

2024-07-10

## Recorded date published



## Resource type

journal_article

## Manuscript type

accepted_manuscript

## Collection



## Title

- title: Synthesis of azahexabenzocoronenium salts through a formal [3 + 3] cycloaddition
    strategy
  title_type: original
  lang: en

## Description

- description: Heteroatom-embedded hexa-peri-hexabenzocoronene (HBC) molecules exhibit
    interesting properties depending on the number and position of the introduced
    heteroatoms and are promising materials for applications in organic electronics
    and supramolecular chemistry. However, their synthesis is quite limited because
    of the difficulty in selectively introducing heteroatoms into the HBC core, which
    poses a challenge in organic synthesis. Here we report a strategy for the in-solution
    synthesis of 3a2-azahexa-peri-hexabenzocoronenium salts, which are cationic nitrogen-embedded
    HBC derivatives. The synthesis was enabled by the formal [3 + 3] cycloaddition
    of polycyclic aromatic azomethine ylides with cyclopropenes, as a three-atom dipolarophile,
    followed by mechanochemical intramolecular cyclization. Furthermore, on-surface
    polymerization of aza-HBC precursors was performed to synthesize aza-HBC-based
    chevron-like graphene nanoribbons. This study provides the possibility for the
    further use of nitrogen-embedded HBC derivatives in a variety of potential applications.
  description_type: abstract
  lang: en

## Creator

- name: Xinjiang Zhang
  role: author
  organization: Nanyang Technological University
  department: School of Chemistry, Chemical Engineering and Biotechnology
- name: Donglin Li
  role: author
  orcid: https://orcid.org/0009-0001-6866-8715
  organization: National Institute for Materials Science
  department: Center for Basic Research on Materials
  ror: https://ror.org/026v1ze26
- name: Cheryl Cai Hui Tan
  role: author
  department: School of Chemistry, Chemical Engineering and Biotechnology
- name: Fiona Hanindita
  role: author
  organization: Nanyang Technological University
  department: School of Chemistry, Chemical Engineering and Biotechnology
- name: Yosuke Hamamoto
  role: author
  organization: Nanyang Technological University
  department: School of Chemistry, Chemical Engineering and Biotechnology
- name: Adam S. Foster
  role: author
  organization: Aalto University
  department: Department of Applied Physics
- name: Shigeki Kawai
  role: author
  orcid: https://orcid.org/0000-0003-2128-0120
  organization: National Institute for Materials Science
  department: Center for Basic Research on Materials
  ror: https://ror.org/026v1ze26
- name: Shingo Ito
  role: author
  organization: Nanyang Technological University
  department: School of Chemistry, Chemical Engineering and Biotechnology

## Contact agent



## Publisher

organization: Springer Science and Business Media LLC

## Managing organization



## Keyword

- subject: Sureface spectroscopy
  schema: not_defined
- subject: Synthetic chemistry methodology
  schema: not_defined
- subject: Heteroatom-embedded hexa-peri-hexabenzocoronene
  schema: not_defined

## Rights

- identifier: http://rightsstatements.org/vocab/InC/1.0/

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo

start_date: 2024-07-10
end_date: 2025-01-10

## Journal

- title: Nature Synthesis
  issn: '27310582'
  volume: '3'
  start_page: 1283
  end_page: 1291

## Conference



## Related item



## Funding

- identifier: RG2/23
  funder_name: Ministry of Education - Singapore
- identifier: 22H00285
  funder_name: MEXT | Japan Society for the Promotion of Science

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## Fileset

- id: 288146d3-823b-4b6f-9b14-aeb236859e71
  filename: NATSYNTH-23090974_Manuscript.pdf
  content_type: application/pdf
  size: 1574452
  md5: edb5fb4a1807556a03194518ae70bfb8

## Thumbnail

fileset_id: 288146d3-823b-4b6f-9b14-aeb236859e71
filename: NATSYNTH-23090974_Manuscript.pdf