Functional Chiral Materials based on Propeller Chirality Dynamics

• Project/Area Number: 18K19077
• Research Category: Grant-in-Aid for Challenging Research (Exploratory)
• Allocation Type: Multi-year Fund
• Review Section: Medium-sized Section 33:Organic chemistry and related fields
• Research Institution: Osaka University
• Principal Investigator: Mori Tadashi 大阪大学, 工学研究科, 准教授 (70311769)
• Co-Investigator(Kenkyū-buntansha): 福原 学 東京工業大学, 理学院, 准教授 (30505996)
• Project Period (FY): 2018-06-29 – 2021-03-31
• Project Status: Completed (Fiscal Year 2020)
• Budget Amount: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000); Fiscal Year 2020: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2019: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: キラル発光材料 / 機能性材料 / ヘキサアリールベンゼン / トロイダル相互作用 / スイッチング機能 / 円二色性 / 異方性 / プロペラキラリティー

Outline of Final Research Achievements

This study revealed that the hexaarylbenzene derivatives are able to function as unique chiral materials due to their propeller chirality and the dynamic propeller-blade interactions. Success of our implication and the detailed experimental observations have been published in more than 30 research papers as well as invited international lectures and in other media. A review article related on this topic has been selected as a highly cited manuscript and the first book on this subject was appeared recently.

Academic Significance and Societal Importance of the Research Achievements

本研究では、有機小分子を用いるキラル発光材料の開発を行った。キラル発光はセキュリティ光通信技術、偽造防止用の紙幣印刷、キラリティを感知するバイオセンサーへの応用、三次元表示可能なディスプレイへの応用などが期待されている。このような材料には高い発光量子収率と異方性が必要不可欠であるが、さらに機能性を付与できればその応用可能性は計り知れない。本研究では、機能性のキラル発光材料開発の端緒となる基礎研究に位置づけられる。本成果によりヘキサアリールベンゼン誘導体が機能性を有するキラル発光材料となりうることが示された。この知見に基づき、今後さらに高性能な機能性キラル発光材料開発が進むことが期待される。

Research Products

• [Int'l Joint Research] ミュンヘン工科大学(ドイツ)
• [Int'l Joint Research] 四川大学(中国)
• [Int'l Joint Research] ミュンヘン工科大学(ドイツ)
• [Int'l Joint Research] 四川大学(中国)
• [Int'l Joint Research] ミュンヘン工科大学(ドイツ)
• [Int'l Joint Research] 四川大学(中国)
• [Journal Article] Enantiodifferentiating Photodimerization of a 2,6-Disubstituted Anthracene Assisted by Supramolecular Double-Helix Formation with Chiral Amines (2020)
  • 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
  • Peer Reviewed
• [Journal Article] Combined Experimental and Theoretical Studies on Planar Chirality of Partially Overlapped C2-Symmetric [3.3](3,9)Dicarbazolophanes (2020)
  • 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
  • Peer Reviewed
• [Journal Article] Aggregation-induced photocatalytic activity and efficient photocatalytic hydrogen evolution of amphiphilic rhodamines in water (2020)
  • 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
  • Peer Reviewed / Open Access
• [Journal Article] Enhancing Photostability of a Coumarin Dye by Self‐inclusion into a Cyclodextrin Cavity in Aqueous Solution and Living Cells (2020)
  • 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
  • Peer Reviewed
• [Journal Article] A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions (2020)
  • 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
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Figure‐eight Octaphyrin Bis‐Ge(IV) Complexes: Synthesis, Structures, Aromaticity, and Chiroptical Properties (2020)
  • 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
  • Peer Reviewed
• [Journal Article] An Ultimate Stereocontrol in Supramolecular Photochirogenesis: Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Sulfur-Linked β-Cyclodextrin Dimers (2019)
  • 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
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Diastereoselective photocycloaddition reaction of vinyl ether tethered to 1,4-naphthoquinone (2019)
  • 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
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Selective Formation of Helical Tetrapyrrin‐fused Porphyrins by Oxidation of beta‐to‐beta Linked meso‐Aminoporphyrin Dimers (2019)
  • 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
  • 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 Hexane (2019)
  • 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
  • Peer Reviewed
• [Journal Article] 3.Transient Circular Dichroism Measurement of The Excited Triplet State of Pristine Hexahelicene in Solution at Room Temperature (2019)
  • 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
  • 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 Scaffold (2019)
  • 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
  • Peer Reviewed
• [Journal Article] Propeller Chirality (2019)
  • Author(s): Mori Tadashi
  • Journal Title: Kokagaku Volume: 49 Pages: 163-166
  • NAID: 40021760386
  • Peer Reviewed
• [Journal Article] Supramolecular Photochirogenesis Driven by Higher-Order Complexation: Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate to Slipped Cyclodimers via a 2:2 Complex with β-Cyclodextrin (2018)
  • Author(s): Wei, X.#; Wu, W.#; Matsushita, R.#; Yan, Z.#; Zhou, D.; Chruma, J. J.; Nishijima, M.; Fukuhara, G.; Mori, T.; Inoue, Y.*; Yang, C.* (# Equal contributions)
  • Journal Title: J. Am. Chem. Soc. Volume: 140 Issue: 11 Pages: 3959-3974
  • DOI: 10.1021/jacs.7b12085
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Circular Dichroisms of Mono- and Dibromo[2.2]paracyclophanes: A Combined Experimental and Theoretical Study (2018)
  • Author(s): Toda Mitsunobu、Inoue Yoshihisa、Mori Tadashi
  • Journal Title: ACS Omega Volume: 3 Issue: 1 Pages: 22-29
  • DOI: 10.1021/acsomega.7b01642
  • Peer Reviewed / Open Access
• [Journal Article] Combined Experimental and Theoretical Study on Circular Dichroism and Circularly Polarized Luminescence of Configurationally Robust D3-Symmetric Triple Pentahelicene (2018)
  • Author(s): Tanaka Hiroki、Kato Yuka、Fujiki Michiya、Inoue Yoshihisa、Mori Tadashi
  • Journal Title: The Journal of Physical Chemistry A Volume: 122 Issue: 37 Pages: 7378-7384
  • DOI: 10.1021/acs.jpca.8b05247
  • Peer Reviewed
• [Journal Article] Cover Feature: Circularly Polarized Luminescence and Circular Dichroisms in Small Organic Molecules: Correlation between Excitation and Emission Dissymmetry Factors (ChemPhotoChem 5/2018) (2018)
  • Author(s): Tanaka Hiroki、Inoue Yoshihisa、Mori Tadashi
  • Journal Title: ChemPhotoChem Volume: 2 Issue: 5 Pages: 383-383
  • DOI: 10.1002/cptc.201800093
  • Peer Reviewed
• [Journal Article] Circularly Polarized Luminescence and Circular Dichroisms in Small Organic Molecules: Correlation between Excitation and Emission Dissymmetry Factors (2018)
  • Author(s): Tanaka Hiroki、Inoue Yoshihisa、Mori Tadashi
  • Journal Title: ChemPhotoChem Volume: 2 Issue: 5 Pages: 386-402
  • DOI: 10.1002/cptc.201800015
  • Peer Reviewed
• [Journal Article] Symmetry-based rational design for boosting chiroptical responses (2018)
  • Author(s): Tanaka Hiroki、Ikenosako Mina、Kato Yuka、Fujiki Michiya、Inoue Yoshihisa、Mori Tadashi
  • Journal Title: Communications Chemistry Volume: 1 Issue: 1 Pages: 38-38
  • DOI: 10.1038/s42004-018-0035-x
  • Peer Reviewed / Open Access
• [Journal Article] Spiroborate-Based Double-Stranded Helicates: Meso-to-Racemo Isomerization and Ion-Triggered Springlike Motion of the Racemo-Helicate (2018)
  • Author(s): Ousaka Naoki、Shimizu Kaori、Suzuki Yoshimasa、Iwata Takuya、Itakura Manabu、Taura Daisuke、Iida Hiroki、Furusho Yoshio、Mori Tadashi、Yashima Eiji
  • Journal Title: Journal of the American Chemical Society Volume: 140 Issue: 49 Pages: 17027-17039
  • DOI: 10.1021/jacs.8b08268
  • Peer Reviewed
• [Journal Article] Entropy-Driven Diastereoselectivity Improvement in the Paterno-Buchi Reaction of 1-Naphthyl Aryl Ethenes with a Chiral Cyanobenzoate through Remote Alkylation (2018)
  • Author(s): Nagasaki Keisuke、Inoue Yoshihisa、Mori Tadashi
  • Journal Title: Angewandte Chemie International Edition Volume: 57 Issue: 18 Pages: 4880-4885
  • DOI: 10.1002/anie.201801330
  • Peer Reviewed
• [Journal Article] Solvent and Temperature Effects on Dynamics and Chiroptical Properties of Propeller Chirality and Toroidal Interaction of Hexaarylbenzenes (2018)
  • Author(s): Kosaka Tomoyo、Iwai Satono、Inoue Yoshihisa、Moriuchi Toshiyuki、Mori Tadashi
  • Journal Title: The Journal of Physical Chemistry A Volume: 122 Issue: 37 Pages: 7455-7463
  • DOI: 10.1021/acs.jpca.8b06535
  • Peer Reviewed
• [Journal Article] 1,8-Diphenyl-9,10-Bis(arylethynyl)phenanthrenes: Synthesis, Distorted Structure, and Optical Properties (2018)
  • Author(s): Konishi Akihito、Morinaga Atsushi、Fukuhara Gaku、Nishijima Masaki、Mori Tadashi、Kida Toshiyuki、Yasuda Makoto
  • Journal Title: Chemistry A European Journal Volume: 印刷中 Issue: 25 Pages: 6625-6631
  • DOI: 10.1002/chem.201800150
  • Peer Reviewed / Open Access
• [Journal Article] A BODIPY-based near infrared fluorescent probe for Fe3+ in water (2018)
  • Author(s): Ji Jiecheng、Chereddy Syama Sundar、Ren Yi、Chen Xingming、Su Dan、Zhong Zhihui、Mori Tadashi、Inoue Yoshihisa、Wu Wanhua、Yang Cheng
  • Journal Title: Journal of Photochemistry and Photobiology A: Chemistry Volume: 355 Pages: 78-83
  • DOI: 10.1016/j.jphotochem.2017.10.043
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Significant Enhancement of Absorption and Luminescence Dissymmetry Factors in the Far-Red Region: A Zinc(II) Homoleptic Helicate Formed by a Pair of Achiral Dipyrromethene Ligands (2018)
  • Author(s): Ito Hiroaki、Sakai Hayato、Okayasu Yoshinori、Yuasa Junpei、Mori Tadashi、Hasobe Taku
  • Journal Title: Chemistry - A European Journal Volume: 24 Issue: 63 Pages: 16889-16894
  • DOI: 10.1002/chem.201804171
  • Peer Reviewed
• [Journal Article] Synthesis, Structures, and Optical Properties of Azahelicene Derivatives and Unexpected Formation of Azahepta[8]circulenes (2018)
  • Author(s): Fengkun Chen, Takayuki Tanaka, Tadashi Mori, and Atsuhiro Osuka
  • Journal Title: Chemistry A European Journal, Volume: N/A Issue: 29 Pages: 7489-7497
  • DOI: 10.1002/chem.201800617
  • Peer Reviewed / Open Access
• [Journal Article] Preface for special issue on photosynergetics (2018)
  • Author(s): Biju Vasudevanpillai、Mori Tadashi、Asahi Tsuyoshi、Miyasaka Hiroshi
  • Journal Title: Journal of Photochemistry and Photobiology C: Photochemistry Reviews Volume: 34 Pages: 1-1
  • DOI: 10.1016/j.jphotochemrev.2018.02.003
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Porphyrin-Based Air-Stable Helical Radicals (2017)
  • Author(s): Kato Kenichi、Furukawa Ko、Mori Tadashi、Osuka Atsuhiro
  • Journal Title: Chem. Eur. J. Volume: 24 Issue: 3 Pages: 572-575
  • DOI: 10.1002/chem.201705291
  • Peer Reviewed / Open Access
• [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
• [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
• [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
• [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
• [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
  • Int'l Joint Research / Invited
• [Presentation] Non-Conventional Control of Organic Photoreactions (2019)
  • Author(s): Tadashi Mori
  • Organizer: ICoPP 2019. International Conference on Photocatalysis and Photoenergy 2019
  • Int'l Joint Research / Invited
• [Presentation] Effectual Photon Upconversion through the Toroidal Interaction (2019)
  • Author(s): Tadashi Mori
  • Organizer: Final International Symposium on Photosynergetics, Grant-in-Aid for Scientific Research on Innovative Areas (2014-2018), MEXT, Japan
  • Int'l Joint Research / Invited
• [Presentation] Control of Circular Dichroisms and Circularly Polarized Luminescence Responses in Small Organic Molecules (2019)
  • Author(s): Tadashi Mori
  • Organizer: Green 2019. The 5th Global Research Efforts On Energy And Nanomaterials
  • Int'l Joint Research / Invited
• [Presentation] Ring Inversion Kinetics of Photoexcited Chiral [4n]Annulene Derivatives: Energetic Impact of Baird Aromaticity (2018)
  • Author(s): Yoshimitsu Itoh, Michihisa Ueda, Kjell Jorner, Young Mo Sung, Tadashi Mori, Qi Xiao1, Dongho Kim, Henrik Ottosson, Takuzo Aida
  • Organizer: ICPOC24. IUPAC International Conference on Physical Organic Chemistry
  • Int'l Joint Research
• [Presentation] Nontrivial Supramolecular Control of Organic Photoreactions (2018)
  • Author(s): Tadashi Mori
  • Organizer: Lecture Conference on Photochemistry
  • Int'l Joint Research / Invited
• [Presentation] Chiral Hexaarylbenzenes for Rathore Memorial (2018)
  • Author(s): Tadashi Mori
  • Organizer: Rathore Memorial Symposium
  • Int'l Joint Research / Invited
• [Presentation] Chirality and Weak Interactions (2018)
  • Author(s): Tadashi Mori
  • Organizer: Department Seminar at Technische Universitaet Muenchen
  • Int'l Joint Research / Invited
• [Presentation] Exploitation of Chiral Photochemistry Utilizing Charge-Transfer Interaction (2018)
  • Author(s): Tadashi Mori
  • Organizer: 2018年光化学討論会
  • Invited
• [Book] Circularly Polarized Luminescence of Isolated Small Organic Molecules (2020)
  • Author(s): Mori, Tadashi
  • Total Pages: 342
  • Publisher: Springer
  • ISBN: 9789811523090
• [Book] 光化学フロンティア (2018)
  • Author(s): 森 直（編集：水野 一彦、宮坂 博、池田 浩）
  • Total Pages: 17
  • Publisher: 化学同人
  • ISBN: 9784759814194