# Redox‐Activated Near Infrared/Shortwave Infrared Emissive Chromophores: Synthesis of Triphenylamine‐Appended Pyrazinacenes

https://mdr.nims.go.jp/datasets/cd46c0a3-d643-4dd6-8be3-d4c44825170e

## File

- [Angew Chem Int Ed - 2025 - Richards - Redox‐Activated Near Infrared Shortwave Infrared Emissive Chromophores  Synthesis of.pdf](https://mdr.nims.go.jp/filesets/b048a00b-1fae-494e-b2a4-4bd889896e1a/download) ([Detail](https://mdr.nims.go.jp/filesets/b048a00b-1fae-494e-b2a4-4bd889896e1a.md))

## Id

cd46c0a3-d643-4dd6-8be3-d4c44825170e

## Local identifier



## Visibility

open_to_public

## State

published

## Created at

2025-10-29T01:41:22.769864Z

## Updated at

2025-10-31T03:30:10.328714Z

## Published at

2025-10-31T03:24:38.276081Z

## Doi



## First published url

https://doi.org/10.1002/anie.202504564

## Date published

2025-03-20

## Recorded date published

2025-5

## Resource type

journal_article

## Manuscript type

vor

## Collection



## Title

- title: 'Redox‐Activated Near Infrared/Shortwave Infrared Emissive Chromophores:
    Synthesis of Triphenylamine‐Appended Pyrazinacenes'
  title_type: original
  lang: en

## Description

- description: Organic dyes showing absorbance and fluorescence in the near infrared
    and short-wave infrared regions are attractive for a variety of applications.
    Redox-coupled reversible switching of absorbance or fluorescence implies enhanced
    functionality of such dyes, especially where large changes in photophysical properties
    across the redox process can be realized. Here, the synthesis of two new pyrazinacenes
    containing four and five fused pyrazine units, appended with electron-donor triphenylamine
    groups, and redox-coupled switching of their photophysical properties is reported.
    In their reduced state, the compounds show absorbance and fluorescence in the
    visible region. Reversible shifts in absorbance and fluorescence from the visible
    to the near infrared or even short-wave infrared regions are observed upon chemical
    and electrochemical oxidations. Such large redox-coupled shifts in photophysical
    properties are unprecedented for a redox process that affects only a single, six-membered
    ring in which both reduced and oxidized states consist of neutral, closed-shell
    species. The compounds show high fluorescence quantum yields in their reduced
    states, and oxidized species show fluorescence quantum yields that compare well
    with existing near infrared and short-wave infrared active fluorescent dyes.
  description_type: abstract
  lang: und

## Creator

- name: Gary J. Richards
  role: author
- name: Kazushi Nakada
  role: author
- name: Keita Aoki
  role: author
- name: Tomoki Jitsukata
  role: author
- name: Kana Hashimoto
  role: author
- name: Toshiki Tajima
  role: author
- name: Ryusuke Mizoguchi
  role: author
- name: Ayumi Ishii
  role: author
- name: Jonathan P. Hill
  role: author
  orcid: https://orcid.org/0000-0002-4229-5842
  organization: National Institute for Materials Science
- name: Akiko Hori
  role: author

## Contact agent



## Publisher

organization: Wiley

## Managing organization



## Keyword

- subject: Pyrazinacene
  schema: not_defined
- subject: Acene
  schema: not_defined
- subject: N-heteroacene
  schema: not_defined
- subject: Redox-active
  schema: not_defined

## Rights

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

## Other identifier(s)



## Data origin

- data_origin_type: other

## Embargo



## Journal

- title: Angewandte Chemie International Edition
  issn: '00448249'
  volume: '64'
  issue: '19'
  article_number: e202504564

## Conference



## Related item



## Funding

- funder_name: Ministry of Education, Culture, Sports, Science and Technology
- identifier: 21H01955
  funder_name: Japan Society for the Promotion of Science London

## 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



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## Fileset

- id: b048a00b-1fae-494e-b2a4-4bd889896e1a
  filename: Angew Chem Int Ed - 2025 - Richards - Redox‐Activated Near Infrared Shortwave
    Infrared Emissive Chromophores  Synthesis of.pdf
  content_type: application/pdf
  size: 2259128
  md5: 41582415c7ce87e9d9014c7c1112e7ab

## Thumbnail

fileset_id: b048a00b-1fae-494e-b2a4-4bd889896e1a
filename: Angew Chem Int Ed - 2025 - Richards - Redox‐Activated Near Infrared Shortwave
  Infrared Emissive Chromophores  Synthesis of.pdf