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Breakthrough in Chiral Photochemistry based on the Excitation of Charge-Transfer Complex

Research Project

Project/Area Number 18H01964
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionOsaka University

Principal Investigator

Mori Tadashi  大阪大学, 工学研究科, 准教授 (70311769)

Co-Investigator(Kenkyū-buntansha) 西嶋 政樹  東北大学, 多元物質科学研究所, 助教 (70448017)
Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2021: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2020: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2019: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2018: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywords不斉光反応 / 電荷移動錯体 / エキシプレックス / エントロピー制御 / 分子キラリティー / 可視光励起 / キラルルイス酸 / 励起三重項 / 光不斉反応 / キラリティー / CT錯体
Outline of Final Research Achievements

This study examined the chiral photoreaction between naphthoquinone and alkene mediated by the chiral Lewis acid such as oxazaborolidine derivatives. Upon complexation, the substrate immediately forms 1:2 complex in the ground state, which is partially decomplexed in the excited state upon photoirradiation. Accordingly, high enantioselectivities were attained for the straight and crossed cycloaddition products. This study thus clearly demonstrated that the excited state decomplexation is an additional clue for the control of stereoeslective outcome in the chiral photoreaction involving weak interactions. The results were presented in the international conferences as well as are published in the international journals.

Academic Significance and Societal Importance of the Research Achievements

キラル光反応は、励起状態化学種の特異な反応性、立体選択性を活かした光反応に不斉情報を取り込み、高ひずみで複雑な構造を一気に構成する優れた方法論である。しかしながら、高反応性、短寿命などの制約により、効率的にキラル情報を伝達することは本質的に難しい。本研究では、ナフトキノンを基質とし、キラルルイス酸を配位させた環化付加光反応系を検討し、このような問題の解決を試みた。成果は医薬品などの新規合成法にも応用可能である。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (41 results)

All 2021 2020 2019 Other

All Int'l Joint Research (8 results) Journal Article (20 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 20 results,  Open Access: 7 results) Presentation (12 results) (of which Int'l Joint Research: 8 results,  Invited: 8 results) Book (1 results)

  • [Int'l Joint Research] ミュンヘン工科大学(ドイツ)

    • Related Report
      2021 Annual Research Report
  • [Int'l Joint Research] 四川大学(中国)

    • Related Report
      2021 Annual Research Report
  • [Int'l Joint Research] ミュンヘン工科大学(ドイツ)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] 四川大学(中国)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] ミュンヘン工科大学(ドイツ)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] 四川大学(中国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ミュンヘン工科大学(ドイツ)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] 四川大学(中国)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Cyclodextrins with Multiple Pyrenyl Groups: An Approach to Organic Molecules Exhibiting Bright Excimer Circularly Polarized Luminescence2021

    • Author(s)
      Shigemitsu Hajime、Kawakami Kosei、Nagata Yuuya、Kajiwara Rikuo、Yamada Shintaro、Mori Tadashi、Kida Toshiyuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 8

    • DOI

      10.1002/anie.202114700

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Overtemperature-protection intelligent molecular chiroptical photoswitches2021

    • Author(s)
      Yao Jiabin、Wu Wanhua、Xiao Chao、Su Dan、Zhong Zhihui、Mori Tadashi、Yang Cheng
    • Journal Title

      Nature Communications

      Volume: 12 Issue: 1 Pages: 2600-2600

    • DOI

      10.1038/s41467-021-22880-z

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis, Structure, and Chiroptical Properties of Indolo‐ and Pyridopyrrolo‐Carbazole‐Based C2‐Symmetric Azahelicenes2021

    • Author(s)
      T. Taniguchi, U. Nishii, T. Mori, K. Nakayama, M. Miura
    • Journal Title

      Chem. Eur. J.

      Volume: 27 Issue: 26 Pages: 1-7

    • DOI

      10.1002/chem.202100327

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A cyanine dye based supramolecular photosensitizer enabling visible-light-driven organic reaction in water2021

    • Author(s)
      Shigemitsu Hajime、Tamemoto Tomoe、Ohkubo Kei、Mori Tadashi、Osakada Yasuko、Fujitsuka Mamoru、Kida Toshiyuki
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 85 Pages: 11217-11220

    • DOI

      10.1039/d1cc04685c

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chiroptical Properties of Symmetric Double, Triple, and Multiple Helicenes2021

    • Author(s)
      Mori Tadashi
    • Journal Title

      Chemical Reviews

      Volume: 121 Issue: 4 Pages: 2373-2412

    • DOI

      10.1021/acs.chemrev.0c01017

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Irreverent Nature of Dissymmetry Factor and Quantum Yield in Circularly Polarized Luminescence of Small Organic Molecules2021

    • Author(s)
      Nagata Yuya、Mori Tadashi
    • Journal Title

      Frontiers in Chemistry

      Volume: 8 Pages: 448-448

    • DOI

      10.3389/fchem.2020.00448

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Relevance of the Entropy Factor in Stereoselectivity Control of Asymmetric Photoreactions2021

    • Author(s)
      Mori Tadashi
    • Journal Title

      Synlett

      Volume: 31 Issue: 13 Pages: 1259-1267

    • DOI

      10.1055/s-0040-1707962

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiodifferentiating Photodimerization of a 2,6-Disubstituted Anthracene Assisted by Supramolecular Double-Helix Formation with Chiral Amines2020

    • Author(s)
      A. Urushima, D. Taura, M. Tanaka, N. Horimoto, J. Tanabe, N. Ousaka, T. Mori, E. Yashima
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 59 Issue: 19 Pages: 7478-7486

    • DOI

      10.1002/anie.201916103

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Combined Experimental and Theoretical Studies on Planar Chirality of Partially Overlapped C2-Symmetric [3.3](3,9)Dicarbazolophanes2020

    • Author(s)
      Tani Keita、Imafuku Risa、Miyanaga Kanae、Masaki Miyuki Eiraku、Kato Haruka、Hori Kazushige、Kubono Koji、Taneda Masatsugu、Harada Takunori、Goto Kenta、Tani Fumito、Mori Tadashi
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 124 Issue: 10 Pages: 2057-2063

    • DOI

      10.1021/acs.jpca.0c00286

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aggregation-induced photocatalytic activity and efficient photocatalytic hydrogen evolution of amphiphilic rhodamines in water2020

    • Author(s)
      Shigemitsu Hajime、Tani Youhei、Tamemoto Tomoe、Mori Tadashi、Li Xinxi、Osakada Yasuko、Fujitsuka Mamoru、Kida Toshiyuki
    • Journal Title

      Chemical Science

      Volume: 11 Issue: 43 Pages: 11843-11848

    • DOI

      10.1039/d0sc04285d

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enhancing Photostability of a Coumarin Dye by Self‐inclusion into a Cyclodextrin Cavity in Aqueous Solution and Living Cells2020

    • Author(s)
      Shigemitsu Hajime、Matsuda Keigo、Mori Tadashi、Nakatsuji Hirotaka、Matsusaki Michiya、Kida Toshiyuki
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 9 Issue: 12 Pages: 2112-2115

    • DOI

      10.1002/ajoc.202000365

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions2020

    • Author(s)
      Pecho Franziska、Zou You‐Quan、Gram?ller Johannes、Mori Tadashi、Huber Stefan M.、Bauer Andreas、Gschwind Ruth M.、Bach Thorsten
    • Journal Title

      Chemistry - A European Journal

      Volume: 26 Issue: 23 Pages: 5190-5194

    • DOI

      10.1002/chem.202000720

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Figure‐eight Octaphyrin Bis‐Ge(IV) Complexes: Synthesis, Structures, Aromaticity, and Chiroptical Properties2020

    • Author(s)
      M. Izawa, T. Suito, S.-i. Ishida, D. Shimizu, T. Tanaka, T. Mori, A. Osuka
    • Journal Title

      Chem. Asian J.

      Volume: N/A Issue: 9 Pages: 1440-1448

    • DOI

      10.1002/asia.202000159

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Ultimate Stereocontrol in Supramolecular Photochirogenesis: Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Sulfur-Linked β-Cyclodextrin Dimers2019

    • Author(s)
      Ji Jiecheng、Wu Wanhua、Liang Wenting、Cheng Guo、Matsushita Ryohei、Yan Zhiqiang、Wei Xueqin、Rao Ming、Yuan De-Qi、Fukuhara Gaku、Mori Tadashi、Inoue Yoshihisa、Yang Cheng
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 23 Pages: 9225-9238

    • DOI

      10.1021/jacs.9b01993

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Diastereoselective photocycloaddition reaction of vinyl ether tethered to 1,4-naphthoquinone2019

    • Author(s)
      Hiroki Ishikawa, Tim Chung, Gaku Fukuhara, Hajime Shigemitsu, Toshiyuki Kida, Thorsten Bach, Tadashi
    • Journal Title

      ChemPhotoChem

      Volume: 印刷中 Issue: 5 Pages: 243-250

    • DOI

      10.1002/cptc.201900022

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 3.Transient Circular Dichroism Measurement of The Excited Triplet State of Pristine Hexahelicene in Solution at Room Temperature2019

    • Author(s)
      Makoto Kuronuma , Takehito Sato , Yasuyuki Araki ,* Tadashi Mori , Seiji Sakamoto, Yoshihisa Inoue , Osamu Ito , and Takehiko Wada
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 4 Pages: 357-360

    • DOI

      10.1246/cl.190012

    • NAID

      130007624434

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Sign Control of Circularly Polarized Luminescence Based on Geometric Arrangement of Fluorescent Pyrene Units in a Binaphthyl Scaffold2019

    • Author(s)
      Kaji Daiki、Ikeda Shintaro、Takamura Kenya、Tajima Nobuo、Shizuma Motohiro、Mori Tadashi、Miyasaka Makoto、Imai Yoshitane
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 8 Pages: 874-876

    • DOI

      10.1246/cl.190246

    • NAID

      130007687741

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Propeller Chirality2019

    • Author(s)
      Mori Tadashi
    • Journal Title

      Kokagaku

      Volume: 49 Pages: 163-166

    • NAID

      40021760386

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Formation of Helical Tetrapyrrin‐fused Porphyrins by Oxidation of beta‐to‐beta Linked meso‐Aminoporphyrin Dimers2019

    • Author(s)
      Osuka Atsuhiro、Fujimoto Keisuke、Shimizu Daiki、Mori Tadashi、Li Yuanyuan、Zhou Mingbo、Song Jianxin
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 7 Pages: 1711-1715

    • DOI

      10.1002/chem.201805659

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Hydrostatic Pressure on Toroidal Interaction and Propeller Chirality of Hexaarylbenzenes: Explicit Solvent Effects on Differential Volumes in Methylcyclohexane and Hexane2019

    • Author(s)
      Kosaka, T.; Iwai, S.; Fukuhara, G.; Imai, Y.; Mori, T.
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 8 Pages: 2011-2018

    • DOI

      10.1002/chem.201804688

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] Organic Asymmetric Photoreactions Controlled by Weak Molecular Interactions2021

    • Author(s)
      Tadashi Mori
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Supramolecular Asymmetric Photochirogenesis (SMAP) of 2-Anthracene Carboxylate and 2,6-Anthracene Dicarboxylate mediated by Serum Albumin as Chiral Reaction Nanoreactor2021

    • Author(s)
      Masaki Nishijima, Nagisa Kawa, Misaki Kawai, Sota Toyooka, Yuta Fujishiro, Tadashi Mori, Yasuyuki Araki, Yoshihisa Inoue, Takehiko Wada
    • Organizer
      Materials Research Meeting 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Rational Design for Small Molecule Circular Dichroisms and Circularly Polarized Luminescence2021

    • Author(s)
      Tadashi Mori
    • Organizer
      Materials Research Meeting 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Organic Photoreactions Controlled by Weak Molecular Interactions2021

    • Author(s)
      Tadashi Mori
    • Organizer
      APC2021. 11th Asian Photochemistry Conference
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] キラルルイス酸を用いた1,4-ナフトキノンとアルケンの分子内光環化付加反応2020

    • Author(s)
      清水菜生・森 直
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 多環式芳香族化合物を修飾したシクロデキストリン誘導体の円偏光発光特性2020

    • Author(s)
      山田慎太郎・重光孟・川上晃聖・森 直・木田敏之
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] シクロデキストリン環上でのピレンエキシマー形成による円偏光発光特性の発現2020

    • Author(s)
      川上晃聖・重光孟・梶原陸生・森 直・木田敏之
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ヒト血清アルブミンをキラル反応場に用いたアントラセン誘導体の触媒的超分子不斉光反応系の構築2020

    • Author(s)
      西嶋政樹・河合美咲・豊岡壮太・藤城祐也・森 直・荒木保幸・井上佳久・和田健彦
    • Organizer
      第14回バイオ関連化学シンポジウム2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] Is There Any Meaningful Correlation between Emission and Absorption Dissymmetry Factor Values?2019

    • Author(s)
      Tadashi Mori
    • Organizer
      Chirality 2019. 31th International Symposium on Chirality
    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Non-Conventional Control of Organic Photoreactions2019

    • Author(s)
      Tadashi Mori
    • Organizer
      ICoPP 2019. International Conference on Photocatalysis and Photoenergy 2019
    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Effectual Photon Upconversion through the Toroidal Interaction2019

    • Author(s)
      Tadashi Mori
    • Organizer
      Final International Symposium on Photosynergetics, Grant-in-Aid for Scientific Research on Innovative Areas (2014-2018), MEXT, Japan
    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Control of Circular Dichroisms and Circularly Polarized Luminescence Responses in Small Organic Molecules2019

    • Author(s)
      Tadashi Mori
    • Organizer
      Green 2019. The 5th Global Research Efforts On Energy And Nanomaterials
    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Book] Circularly Polarized Luminescence of Isolated Small Organic Molecules2020

    • Author(s)
      Mori, Tadashi
    • Total Pages
      342
    • Publisher
      Springer
    • ISBN
      9789811523090
    • Related Report
      2020 Annual Research Report

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Published: 2018-04-23   Modified: 2023-01-30  

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