# Ring-Size Effect on Molecular Assembly Structures and Optical Properties of <i>C</i><sub>3</sub>-Symmetrical Dehydrobenzoannulene Derivatives

https://mdr.nims.go.jp/datasets/8ef1b2b0-0a5b-4679-9671-33629254c04c

## File

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## Id

8ef1b2b0-0a5b-4679-9671-33629254c04c

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2025-08-22T06:27:01.133350Z

## Updated at

2026-02-14T13:09:53.491570Z

## Published at

2026-08-04T23:28:55.116597Z

## Doi

https://doi.org/10.48505/nims.5663

## First published url

https://doi.org/10.1021/acs.jpcb.5c04027

## Date published

2025-08-21

## Recorded date published

2025-8-21

## Resource type

journal_article

## Manuscript type

accepted_manuscript

## Collection



## Title

- title: Ring-Size Effect on Molecular Assembly Structures and Optical Properties
    of <i>C</i><sub>3</sub>-Symmetrical Dehydrobenzoannulene Derivatives
  title_type: original
  lang: en

## Description

- description: We reported that C8[12]DBA, a C3-symmetric hexadecahydrotribenzo[12]annulene
    ([12]DBA) with a pore surrounded by three −C≡C− bonds, forms a stable molecular
    glass during cooling from the liquid state when an octylbenzoate group was introduced
    at the molecular terminal. In this study, to understand the influence of the molecular
    structure of C3-symmetric DBA derivatives on molecular assembly structures and
    optical properties, we newly synthesized C8[18]DBA, which has a pore surrounded
    by more elongated −C≡C−C≡C− bonds. Furthermore, a comparison was made with an
    octylbenzoate-substituted triphenylene derivative (C8Trip) that has C3 symmetry
    and no pore at the molecular center. The strength of intermolecular interactions
    decreased in the order C8[18]DBA > C8Trip > C8[12]DBA. C8[18]DBA formed π-dimers
    and gave crystalline molecular assemblies, whereas in C8[12]DBA, the suppression
    of π-π interactions stabilized the glass state. C8[18]DBA did not exhibit dielectric
    anomalies, whereas C8Trip and C8[12]DBA showed dielectric relaxation associated
    with the thermal motion of the octyl ester chains. Furthermore, while C8[12]DBA
    exhibited similar fluorescence spectra in solution and solid states, both C8[18]DBA
    and C8Trip exhibited aggregation-induced quenching with a significant decrease
    in fluorescence intensity in the solid state.
  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: Hayato Anetai
  role: author
  orcid: https://orcid.org/0000-0001-7469-8489
- 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: Molecular assembly structures
  schema: not_defined
- subject: Molecular glass
  schema: not_defined
- subject: Dielectric properties
  schema: not_defined
- subject: Optical properties
  schema: not_defined
- subject: Ring-size effect
  schema: not_defined

## Rights

- description: This document is the Accepted Manuscript version of a Published Work
    that appeared in final form in The Journal of Physical Chemistry B, copyright
    © 2025 American Chemical Society after peer review and technical editing by the
    publisher. To access the final edited and published work see https://doi.org/10.1021/acs.jpcb.5c04027.
  identifier: http://rightsstatements.org/vocab/InC/1.0/

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo

start_date: 2025-08-05
end_date: 2026-08-05

## Journal

- title: The Journal of Physical Chemistry B
  issn: '15205207'
  volume: '129'
  issue: '33'
  start_page: 8603
  end_page: 8614

## Conference



## Related item



## Funding

- identifier: JPMJAX23DF
  funder_name: Japan Science and Technology Corporation
- identifier: JPMJFS2102
  funder_name: Japan Science and Technology Corporation
- funder_name: Izumi Science and Technology Foundation
- identifier: JPMJSP2114
  funder_name: Support for Pioneering Research Initiated by the Next Generation
- identifier: JP20H05865
  funder_name: Japan Society for the Promotion of Science
- identifier: JP23K13715
  funder_name: Japan Society for the Promotion of Science
- identifier: JP24K01475
  funder_name: Japan Society for the Promotion of Science
- funder_name: Ministry of Education, Culture, Sports, Science and Technology
- identifier: JP24H01727
  funder_name: Japan Society for the Promotion of Science
- identifier: JP24K01452
  funder_name: Japan Society for the Promotion of Science
- identifier: JP24K01468
  funder_name: Japan Society for the Promotion of Science

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## Specimen



## Chemical composition



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- id: be90c12c-5a60-470e-bc88-a841d2d481dd
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## Thumbnail

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filename: MS 20250724.pdf