# Ethynylene-Bridged Pentacene Trimer and Tetramer Prepared Through Unexpected Oligomerization and Their Subsequent Thermal Conversions

https://mdr.nims.go.jp/datasets/d222b2f6-bbfb-435c-8301-ada6c07b2588

## File

- [Accepted_MS_MDR.pdf](https://mdr.nims.go.jp/filesets/231ac681-ee9a-4a26-aee7-0a6e2f419594/download) ([Detail](https://mdr.nims.go.jp/filesets/231ac681-ee9a-4a26-aee7-0a6e2f419594.md))

## Id

d222b2f6-bbfb-435c-8301-ada6c07b2588

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2024-11-29T13:07:08.096838Z

## Updated at

2025-08-12T23:30:36.858892Z

## Published at

2025-08-12T23:17:13.280148Z

## Doi

https://doi.org/10.48505/nims.5063

## First published url

https://doi.org/10.1002/ejoc.202400770

## Date published

2024-12-09

## Recorded date published

2024-12-9

## Resource type

journal_article

## Manuscript type

accepted_manuscript

## Collection



## Title

- title: Ethynylene-Bridged Pentacene Trimer and Tetramer Prepared Through Unexpected
    Oligomerization and Their Subsequent Thermal Conversions
  title_type: original
  lang: en

## Description

- description: 'Ethynylene-bridged acenes, which are pi-conjugated triple bond-containing
    systems, have attracted increasing interest as promising organic semiconductor
    materials due to their delocalized pi-electrons. In this study, ethynylene-bridged
    pentacene precursor oligomers were not only synthesized through multiple-organic
    reactions but also were unexpectedly obtained in one-pot by using a conventional
    reaction with lithium silylacetylide and quinone. In the case of one-pot synthesis,
    the formation of oligomers, including pentamer, was evidently confirmed by matrix-assisted-laser-desorption/ionization
    time-of-flight mass spectrometry. Single crystal X-ray analysis visualized the
    ethynylene-bridged structure of the dimer which was one of the major products
    in the one-pot reaction. It was found that the reaction time for the lithiation
    was the key factor in controlling oligomer formation. Finally, the thermal conversion
    from pentacene precursors to the corresponding pentacene oligomers was achieved
    via retro-Diels–Alder reaction. These results would open an access to synthesize
    a wide range of pi-conjugated systems. '
  description_type: abstract
  lang: eng

## Creator

- name: Hironobu Hayashi
  role: author
  orcid: https://orcid.org/0000-0002-7872-3052
  organization: National Institute for Materials Science
  department: Center for Basic Research on Materials/Advanced Materials Characterization
    Field/Nanoprobe Group
  ror: https://ror.org/026v1ze26
- name: Juanjuan Zhu
  role: author
  organization: NAIST
- name: Naoto Minamino
  role: author
  organization: NAIST
- name: Yuya Murakami
  role: author
  organization: NAIST
- name: Shoma Kasahara
  role: author
  organization: Institute for Chemical Research
- name: Kyohei Matsuo
  role: author
  organization: Institute for Chemical Research
- name: Naoki Aratani
  role: author
  organization: NAIST
- name: Hiroko Yamada
  role: author
  organization: Institute for Chemical Research

## Contact agent



## Publisher

organization: Wiley-Blackwell

## Managing organization



## Keyword

- subject: pentacene
  schema: not_defined
- subject: oligomer
  schema: not_defined
- subject: thermal conversion
  schema: not_defined
- subject: single crystal
  schema: not_defined
- subject: precursor approach
  schema: not_defined

## Rights

- description: 'This is the peer reviewed version of the following article: Ethynylene-Bridged
    Pentacene Trimer and Tetramer Prepared Through Unexpected Oligomerization and
    Their Subsequent Thermal Conversions, which has been published in final form at
    https://doi.org/10.1002/ejoc.202400770. This article may be used for non-commercial
    purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived
    Versions. This article may not be enhanced, enriched or otherwise transformed
    into a derivative work, without express permission from Wiley or by statutory
    rights under applicable legislation. Copyright notices must not be removed, obscured
    or modified. The article must be linked to Wiley’s version of record on Wiley
    Online Library and any embedding, framing or otherwise making available the article
    or pages thereof by third parties from platforms, services and websites other
    than Wiley Online Library must be prohibited.'
  identifier: http://rightsstatements.org/vocab/InC/1.0/

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo

start_date: 2024-08-13
end_date: 2025-08-13

## Journal

- title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  issn: '10990690'
  article_number: e202400770

## Conference



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## Fileset

- id: 231ac681-ee9a-4a26-aee7-0a6e2f419594
  filename: Accepted_MS_MDR.pdf
  content_type: application/pdf
  size: 986706
  md5: dc31c26a3ea5222d44ea326940318e36

## Thumbnail

fileset_id: 231ac681-ee9a-4a26-aee7-0a6e2f419594
filename: Accepted_MS_MDR.pdf