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Development of Indigo Derivatives as Functional Molecules with Novel Photochemical Properties

Research Project

Project/Area Number 22K20522
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeMulti-year Fund
Review Section 0501:Physical chemistry, functional solid state chemistry, organic chemistry, polymers, organic materials, biomolecular chemistry, and related fields
Research InstitutionHokkaido University

Principal Investigator

Huang Chung-Yang  北海道大学, 化学反応創成研究拠点, 准教授 (90956153)

Project Period (FY) 2022-08-31 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2023: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2022: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsindigo / photoswitch / organic synthesis / metal catalyst / data science / photochemistry / metal catalysis
Outline of Research at the Start

Indigo is one of the most abundant dyes used in daily life, and their derivatives show interesting photochemical properties when irradiated with red light. This research project aims to develop efficient synthetic methods to functionalize indigo dye as red-light responsive molecules.

Outline of Final Research Achievements

In this project, we have made significant progress in promoting the use of indigo compounds as photoresponsive molecular tools. We first developed a new copper-catalyzed direct functionalization of indigo dye to build new red-light photoswitches. Computational studies and data science approaches have provided insight on reaction mechanism and structure-property relationships. We have also successfully implemented the first example of indigo photoswitches in thin films, which demonstrates its potential in material science. Additionally, we have prepared a review to summarize the history and perspectives of utilizing indigos as photoresponsive molecular tools. Overall, this project will yield three publications and has pointed out new directions for indigo chemistry.

Academic Significance and Societal Importance of the Research Achievements

Due to their red-light absorbance, indigo derivatives are expected to be useful in biomedicine and material science. This research has demonstrated their potential as photoresponsive molecular tools by developing new synthetic methods and building structure-property relationships.

Report

(3 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • Research Products

    (20 results)

All 2024 2023 2022 Other

All Int'l Joint Research (5 results) Journal Article (2 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 1 results,  Open Access: 1 results) Presentation (12 results) (of which Int'l Joint Research: 11 results,  Invited: 1 results) Remarks (1 results)

  • [Int'l Joint Research] Humboldt University of Berlin(ドイツ)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] Tampere University(フィンランド)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] Heinrich-Heine-University Dusseldorf(ドイツ)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] Tampere University(フィンランド)

    • Related Report
      2022 Research-status Report
  • [Int'l Joint Research] Humboldt University at Berlin(ドイツ)

    • Related Report
      2022 Research-status Report
  • [Journal Article] Accessing a Diverse Set of Functional Red-Light Photoswitches by Selective Copper-Catalyzed Indigo N-Arylation2024

    • Author(s)
      Jaiswal Amit K.、Saha Priya、Jiang Julong、Suzuki Kimichi、Jasny Anna、Schmidt Bernd M.、Maeda Satoshi、Hecht Stefan、Huang Chung-Yang (Dennis)
    • Journal Title

      ChemRxiv

      Volume: ー

    • DOI

      10.26434/chemrxiv-2024-62zmf

    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Journal Article] Red-light photoswitching of indigos in polymer thin films2023

    • Author(s)
      Kuntze Kim、Viljakka Jani、Virkki Matti、Huang Chung-Yang、Hecht Stefan、Priimagi Arri
    • Journal Title

      Chemical Science

      Volume: 14 Issue: 10 Pages: 2482-2488

    • DOI

      10.1039/d2sc06790k

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      Gordon Research Conference: Artificial Molecular Switches and Motors
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      International Conference on Photochemistry
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      ACS Fall National Meeting
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      14th Indian Scientists Association in Japan Annual Symposium
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      The 15th International Kyoto Conference on Organic Chemistry
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Red-Light Photoswitching of Indigos in Polymer Thin Films2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      6th ICReDD International Symposium
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      10th International Symposium on Photochromism
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Saha, Priya
    • Organizer
      CSE Summer School & ALP International Symposium
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Red-Light Photoswitches2023

    • Author(s)
      Saha, Priya
    • Organizer
      6th ICReDD International Symposium
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Red-Light Photoswitching of Indigos in Polymer Thin Films2023

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      4th ICReDD International Symposium
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of Indigos as Photo-responsive Molecular Tools2023

    • Author(s)
      Jaiswal, Amit Kumar
    • Organizer
      2023 Bowei Research Conference
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] Indigos as Red-Light Photoswitches2022

    • Author(s)
      Huang, Chung-Yang
    • Organizer
      8th Hokkaido University Cross-Departmental Symposium
    • Related Report
      2022 Research-status Report
  • [Remarks] ICReDD Research News

    • URL

      https://www.icredd.hokudai.ac.jp/research/8687

    • Related Report
      2022 Research-status Report

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Published: 2022-09-01   Modified: 2025-01-30  

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