Realization of single wavelength excited multicolor photochromism using orthogonal pai-conjugation

• Project/Area Number: 18K05255
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 35030:Organic functional materials-related
• Research Institution: Yokohama National University
• Principal Investigator: Nakagawa Tetsuya 横浜国立大学, 大学院工学研究院, 助教 (30586128)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Project Status: Completed (Fiscal Year 2020)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: フォトクロミズム / 高効率フォトクロミック反応 / マルチカラー蛍光変調 / スピロジアリールエテン / 光化学 / 分子動力学計算 / ジアリールエテン / スピロ誘導体 / 直交π共役系 / 蛍光

Outline of Final Research Achievements

A series of novel diarylethene derivatives having a spiro moiety at the ethene moiety was designed and synthesized. These compounds exhibited relatively high photocyclization reaction quantum yields and multicolor fluorescence modulation. We also found that the size of the spiro ring affects the photocyclization quantum yield, and that the multicolor fluorescence modulation characteristics associated with photochromism can be controlled by changing the molecular structure.

Academic Significance and Societal Importance of the Research Achievements

光照射によって可逆的な光異性化が生じる光応答性分子材料は、次世代の有機エレクトロニクス分子材料として注目を集めており、さらなる機能化が待たれている。しかしながら、高効率フォトクロミック特性と高い分子拡張性を両立した光応答性分子を設計することは容易ではない。本研究では、スピロ誘導体の高い分子拡張性に着目した新しい分子設計指針を用いることで、高い光反応性とマルチカラー蛍光変調といった機能性を同時に発現する光応答性分子材料システムを見出した。本研究成果は、新しい有機エレクトロニクス材料のみならず、光化学、材料化学といった幅広い学術研究分野の発展に寄与するものと期待される。

Research Products

• [Journal Article] A thermoresponsive fluorophore based on a photochromic diarylethene having donor?acceptor moieties (2020)
  • Author(s): Takeuchi Sakiko、Nakagawa Tetsuya、Yokoyama Yasushi
  • Journal Title: Chemical Communications Volume: 56 Issue: 48 Pages: 6492-6494
  • DOI: 10.1039/d0cc02411b
  • Peer Reviewed
• [Presentation] Molecular switches based on spiro-functionalized diarylethenes (2019)
  • Author(s): Tetsuya Nakagawa
  • Organizer: International Conference on Energy, Materials and Photonics 2019 (EMP19)
  • Int'l Joint Research / Invited
• [Presentation] Photoresponsive materials based on spiro-functionalized diarylethenes (2019)
  • Author(s): Tetsuya Nakagawa
  • Organizer: The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
  • Int'l Joint Research
• [Presentation] Spiro-functionalized diarylethenes and their photoreactivities (2019)
  • Author(s): Tetsuya Nakagawa, Yosuke Miyasaka, Nagara Kato, Yasushi Yokoyam
  • Organizer: 9th International Symposium on Photochromism (ISOP2019)
  • Int'l Joint Research
• [Presentation] PHOTOCHROMIC AND FLUORESCENT PROPERTIES OF SPIRO-FUNCTIONALIZED DIARYLETHENES (2018)
  • Author(s): Tetsuya Nakagawa, Yosuke Miyasaka, Nagara Kato, Yutaro Otomo, Yasushi Yokoyama
  • Organizer: 27th IUPAC International Symposium on Photochemistry
  • Int'l Joint Research
• [Presentation] Photochromism of Spiro-functionalized Diarylethenes (2018)
  • Author(s): Tetsuya Nakagawa
  • Organizer: International Symposium on Advanced Molecular Sciences (ISAMS)
  • Int'l Joint Research / Invited
• [Presentation] Highly efficient photochromic system based on spiro-functionalized diarylethene (2018)
  • Author(s): Tetsuya Nakagawa
  • Organizer: International Congress on Pure & Applied Chemistry Langkawi (ICPAC Langkawi 2018)
  • Int'l Joint Research / Invited
• [Presentation] MULTI-COLOR FLUORESCENCE MODULATION BASED ON SPIRO-FUNCTIONALIZED DIARYLETHENES (2018)
  • Author(s): Tetsuya Nakagawa, Yosuke Miyasaka, Nagara Kato, Yasushi Yokoyama
  • Organizer: 10th Asian Photochemistry Conference
  • Int'l Joint Research
• [Presentation] Photon-quantitative photocyclization reaction of spiro-functionalized diarylethenes (2018)
  • Author(s): Yosuke Miyasaka, Nagara Kato, Yutaro Otomo, Yasushi Yokoyama, Tetsuya Nakagawa
  • Organizer: 2018年光化学討論会