# Supramolecular Polymorphism of the Hydrogen-Bonded <i>C</i><sub>3</sub>-Symmetrical Hexadehydrotribenzo[12]annulene Derivative

https://mdr.nims.go.jp/datasets/64004d77-32af-4daa-9865-c80c2af12c7a

## File

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## Id

64004d77-32af-4daa-9865-c80c2af12c7a

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2025-06-16T01:09:38.888926Z

## Updated at

2025-06-16T03:30:39.322768Z

## Published at

2025-06-16T03:23:41.659115Z

## Doi



## First published url

https://doi.org/10.1021/jacs.5c02529

## Date published

2025-06-04

## Recorded date published

2025-6-4

## Resource type

journal_article

## Manuscript type

vor

## Collection



## Title

- title: Supramolecular Polymorphism of the Hydrogen-Bonded <i>C</i><sub>3</sub>-Symmetrical
    Hexadehydrotribenzo[12]annulene Derivative
  title_type: original
  lang: en

## Description

- description: "C3-symmetric hexadehydrotribenzo[12]annulene ([12]DBA) derivative
    with three tetradecylamide chains capable of hydrogen-bonding interaction formed
    either a two-dimensional lamellar (LM) or a one-dimensional (1D) nanofiber (NF)
    molecular assemblies, depending on the association state of the amide hydrogen
    bonds in\r\nsolution phase. The intermolecular amide hydrogen-bonding modes in
    the LM and NF structures were different from each other. The NF structure was
    metastable less stable than the LM structure, and was obtained through organogel
    formation. In chloroform, the [12]DBA derivative exhibited 1D association behavior
    following the isodesmic model due to intermolecular amide hydrogen bonds, whereas
    the presence of acetonitrile inhibited this association state. The NF structure
    had larger amplitude dynamics about the polar amide group than that of the LM
    structure, undergoing a phase transition from the NF to the LM structures upon
    heating. The absorption spectra of the NF and the solid state LM were different
    from each other, exhibiting a different optical properties. The coexistence of
    intermolecular amide hydrogen bonds and van der Waals interactions among the C3-symmetric
    molecules resulted in polymorphic phenomena, where energetically similar molecular
    assemblies were expressed."
  description_type: abstract
  lang: und

## Creator

- name: Yotaro Kasahara
  role: author
- name: Takashi Takeda
  role: author
  orcid: https://orcid.org/0000-0002-5254-2819
- name: Shun Dekura
  role: author
  orcid: https://orcid.org/0000-0003-2498-6428
- name: Yoshiki Ishii
  role: author
  orcid: https://orcid.org/0000-0003-0102-9326
- name: Hayato Anetai
  role: author
- name: Atsuro Takai
  role: author
  orcid: https://orcid.org/0000-0003-3457-3352
- name: Ichiro Hisaki
  role: author
  orcid: https://orcid.org/0000-0002-8170-5605
- name: Masayuki Takeuchi
  role: author
  orcid: https://orcid.org/0000-0002-0207-0665
- name: Tomoyuki Akutagawa
  role: author
  orcid: https://orcid.org/0000-0003-3040-1078

## Contact agent



## Publisher

organization: American Chemical Society (ACS)

## Managing organization



## Keyword

- subject: Polymorphism
  schema: not_defined
- subject: Supramolecular Assembly
  schema: not_defined

## Rights

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

## Other identifier(s)



## Data origin



## Embargo



## Journal

- title: Journal of the American Chemical Society
  issn: '00027863'
  volume: '147'
  issue: '22'
  start_page: 18783
  end_page: 18795

## Conference



## Related item



## Funding

- identifier: JPMJFS2102
  funder_name: University Fellowship Creation Project for Creating Scientific and
    Technological Innovation
- identifier: JPMJAX23D3
  funder_name: ACT-X
- identifier: JPMJAX23DF
  funder_name: ACT-X
- identifier: JP20H05865
  funder_name: Japan Society for the Promotion of Science
- identifier: JP23K13715
  funder_name: Japan Society for the Promotion of Science
- identifier: JP24H01727
  funder_name: Japan Society for the Promotion of Science
- identifier: JP24K01452
  funder_name: Japan Society for the Promotion of Science
- identifier: JPMJSP2114
  funder_name: Support for Pioneering Research Initiated by the Next Generation
- funder_name: Izumi Science and Technology Foundation

## Instrument



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## Specimen



## Chemical composition



## Structure for specimen



## Structural feature for specimen



## Specific property for specimen



## Process for specimen treatment



## Computational method



## Energy level/transition state



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## Fileset

- id: 67b2f60b-dd21-4df9-92fe-2cd3db9c3f24
  filename: JACS,2025,147,18783.pdf
  content_type: application/pdf
  size: 6197879
  md5: af7c9e32442b6feb56d892ffe565b5ac

## Thumbnail

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filename: JACS,2025,147,18783.pdf