Development of new functional materials based on hydroquinone dimers

2021 Fiscal Year Final Research Report

• Project/Area Number: 17H03023
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Yamaguchi University
• Principal Investigator: KAMIMURA Akio 山口大学, 大学院創成科学研究科, 教授 (30194971)
• Co-Investigator(Kenkyū-buntansha): 川本 拓治 山口大学, 大学院創成科学研究科, 助教 (70756139)
• Project Period (FY): 2017-04-01 – 2021-03-31
• Keywords: 蛍光材料 / バイオイメージング / 水溶性 / ポリエチレングリコール / 大環状化合物

Outline of Final Research Achievements

Preparation of water-soluble 2-sulfanylhydroquinone dimer and derivatized it for a bio-imaging material. We succeeded to detect BSA protein as a model study using this derivative and showed it would be a potential photoluminescence compound for this purpose. We also developed selective demethylation reaction for its tetramethyl ether, and achieved one-step preparation of mono-methyl derivative. Its oxidation form, mono-quinone derivative, showed good photolumenscence when exposed to reductive conditions delivered by ascorbic acid, and found that it would be a potential compound serving as a new reagent for detection of reducing agents.
Several derivatives of deltaarene, a new macrocyclic compounds based on a 2-sulfanylhydroquinone dimer, were prepared and estimated their shape and size of the holes. We also examined several reactions towards their derivatization and chemical modification.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

本研究により我々が開発した新規蛍光染料である2-スルファニルヒドロキノン二量体がバイオイメージング材料として利用可能であることを明らかにした。この成果は生化学分野に新しい検出材を提供することが期待され、この分野の発展に寄与する成果である。また新規大環状化合物のデルタアレーンの化学の基礎的な研究を進め、この化合物群を新しい分子ホストとして活用できる足がかりを得た。この成果も生化学をはじめ材料開発にも新しい方法論をもたらすことが期待できる。