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Development of New Molecular Materials Based on Visible Light Responsive p-Single Bonded species

Research Project

Project/Area Number 21H01921
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 InstitutionHiroshima University

Principal Investigator

Abe Manabu  広島大学, 先進理工系科学研究科(理), 教授 (30273577)

Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2023: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2022: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2021: ¥7,930,000 (Direct Cost: ¥6,100,000、Indirect Cost: ¥1,830,000)
Keywordsπ単結合 / 可視吸収 / 酸化還元活性 / 一重項ジラジカル / スピン制御 / ジラジカル / マルチラジカル / 脱窒素 / 置換基効果 / 粘性効果 / 脱窒素反応
Outline of Research at the Start

本研究では,独自に見出してきたπ単結合化合物を,置換基,分子骨格,並びに媒質効果によって長寿命化/単離し,光物性測定,光電子分光,核磁気共鳴測定,さらには,X線構造解析を行い,その電子構造と分子構造の全貌を明らかにする.その基盤研究に加えて,可視光応答性の新物質・π単結合化合物の光応答性,酸化還元活性,多光子吸収活性に関する機能を検証し,太陽電池,発光材料,非線形光学材料などの光に応答する分子素材の開発研究へと展開する.このことにより,未開拓な結合様式を持つ新規な化合物群の物性・機能を明らかにし,秀逸な新しい機能性物質群を世界に提供する.

Outline of Final Research Achievements

The functionality of molecules and materials arises from their electronic structure and three-dimensional shape. In this study, we have investigated π-conjugated compounds that we independently discovered. By substituting functional groups, modifying molecular skeletons, and considering solvent effects, we extended their lifetimes and isolated them. We conducted optical property measurements, photoelectron spectroscopy, nuclear magnetic resonance measurements, and even X-ray crystallography to reveal the complete picture of their electronic and molecular structures. These efforts have led to the development of molecular materials that respond to light, such as solar cells, luminescent materials, and nonlinear optical materials.

Academic Significance and Societal Importance of the Research Achievements

分子・物質の機能は,その電子構造と3次元的な形に由来する.本研究では,平面4配位炭素をもつπ単結合(C-π-C)の創製と,その新奇なπ結合様式 が小さなπ電子系にも関わらず,可視-近赤外領域に強い光吸収機能を示すことを明らかにした.本研究では,独自に見出してきたπ単結合化合物を,置換基,分子骨格,並びに媒質効果によって長寿命化/単離し,光物性測定,光電子分光,核磁気共鳴測定,さらには,X線構造解析を行い,その電子構造と分子構 造の全貌を明らかにすることができた

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (34 results)

All 2024 2023 2022 2021 Other

All Int'l Joint Research (6 results) Journal Article (24 results) (of which Int'l Joint Research: 9 results,  Peer Reviewed: 24 results,  Open Access: 10 results) Remarks (3 results) Funded Workshop (1 results)

  • [Int'l Joint Research] Universit de Reims Champagne-Ardenne(フランス)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] Institut Ruder Boskovic(クロアチア)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] University of Cincinnati(米国)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] University of Algarve UAlg(ポルトガル)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] University of Cincinnati(米国)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] National Central University(台湾)

    • Related Report
      2022 Annual Research Report
  • [Journal Article] Bidirectional Neuronal Actuation by Uncaging with Violet and Green Light2024

    • Author(s)
      Sansalone Lorenzo、Zhao Jun、Nguyen Linh T. B.、Gupta Swati、Benson Deanna L.、Abe Manabu、Ellis‐Davies Graham C. R.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 63 Issue: 13

    • DOI

      10.1002/anie.202315726

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Formation of Sterically Congested C-N Bonds by Electrochemical Reductive Coupling of Amines and α‐Bromocarboxamides2024

    • Author(s)
      Ghosh Titli、Kaizawa Hazuki、Funato Shohei、Rahman M. Azadur、Sasaki Norihiko、Nokami Toshiki、Abe Manabu、Nishikata Takashi
    • Journal Title

      ChemElectroChem

      Volume: 11 Issue: 5

    • DOI

      10.1002/celc.202300636

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Substituent Effects on the Electronic Ground State (Singlet versus Triplet) of Indenyl Cations: DFT and CASPT2 Studies2024

    • Author(s)
      Takano Ma‐aya、Antol Ivana、Abe Manabu
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 27 Issue: 7

    • DOI

      10.1002/ejoc.202301226

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Photoexcitation of (diarylmethylene)amino benziodoxolones for alkylamination of styrene derivatives with carboxylic acids2024

    • Author(s)
      Okumatsu Daichi、Kiyokawa Kensuke、Bao Nguyen Linh Tran、Abe Manabu、Minakata Satoshi
    • Journal Title

      Chemical Science

      Volume: 15 Issue: 3 Pages: 1068-1076

    • DOI

      10.1039/d3sc06090j

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Substituted effects on bonding characteristics of cyclopentane‐1,3‐diyl diradicals monitored by time‐resolved infrared spectroscopy2023

    • Author(s)
      Masato Kondoh, Shunsuke Kuboki, Hidetaka Kume, Eriku Oda, Manabu Abe*, and Taka-aki Ishibashi*
    • Journal Title

      Journal of Physical Organic Chemistry

      Volume: 37 Issue: 2

    • DOI

      10.1002/poc.4575

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Energetically More Stable Singlet Cyclopentane-1,3-diyl Diradical with π-Single Bonding Character than the Corresponding σ-Single Bonded Compound2023

    • Author(s)
      Liu Qian、Onishi Keita、Miyazawa Yuki、Wang Zhe、Hatano Sayaka、Abe Manabu
    • Journal Title

      Journal of the American Chemical Society

      Volume: 145 Issue: 49 Pages: 27089-27094

    • DOI

      10.1021/jacs.3c10971

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced α‐Aminoalkylation of Sulfonylarenes with Alkylamines2023

    • Author(s)
      Yonekura Kyohei、Aoki Kohei、Nishida Tomoya、Ikeda Yuko、Oyama Ryoko、Hatano Sayaka、Abe Manabu、Shirakawa Eiji
    • Journal Title

      Chemistry -A European Journal

      Volume: 29 Issue: 68

    • DOI

      10.1002/chem.202302658

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photochemically Induced Hydrogen Atom Transfer and Intramolecular Radical Cyclization Reactions with Oxazolones2023

    • Author(s)
      Latrache Mohammed、Lefebvre Corentin、Abe Manabu、Hoffmann Norbert
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 88 Issue: 23 Pages: 16435-16455

    • DOI

      10.1021/acs.joc.3c01951

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Development of Photoremovable Protecting Groups Responsive to Near-Infrared Two-Photon Excitation and Their Application to Drug Delivery Research2023

    • Author(s)
      Nguyen Linh Tran Bao、Abe Manabu
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 96 Issue: 9 Pages: 899-906

    • DOI

      10.1246/bcsj.20230140

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Molecular and Crystal Structure, Spectroscopy, and Photochemistry of a Dispiro Compound Bearing the Tetraoxane Pharmacophore2023

    • Author(s)
      Amado Patrcia S. M.、Lopes Susy、Brs Elisa M.、Paixo JosA.、Takano Ma‐aya、Abe Manabu、Fausto Rui、Cristiano Maria L. S.
    • Journal Title

      Chemistry - A European Journal

      Volume: 29 Issue: 48

    • DOI

      10.1002/chem.202301315

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Generation and Characterization of a Tetraradical Embedded in a Curved Cyclic Paraphenylene Unit2023

    • Author(s)
      Miyazawa Yuki、Wang Zhe、Hatano Sayaka、Takagi Ryukichi、Matsuoka Hideto、Amamizu Naoka、Kitagawa Yasutaka、Kayahara Eiichi、Yamago Shigeru、Abe Manabu
    • Journal Title

      Chemistry A European Journal

      Volume: - Issue: 42

    • DOI

      10.1002/chem.202301009

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Light-Mediated Synthesis of 2-(4-Methoxyphenyl)-1-pyrroline via Intramolecular Reductive Cyclization of a Triplet Alkylnitrene2023

    • Author(s)
      George Sobiya、Govorov Dmitrii、Gatlin DeVonna M.、Merugu Rajkumar、Wasson Fiona J.、Shields Dylan J.、Allen Yasmine、Muthukrishnan Sivaramakrishnan、Krause Jeanette A.、Abe Manabu、Gudmundsdottir Anna D.
    • Journal Title

      Organic Letters

      Volume: 25 Issue: 23 Pages: 4345-4349

    • DOI

      10.1021/acs.orglett.3c01476

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Manipulation of an electron by photoirradiation in the electron-catalyzed cross-coupling reaction2023

    • Author(s)
      Shirakawa Eiji、Ota Yuki、Yonekura Kyohei、Okura Keisho、Mizusawa Sahiro、Sarkar Sujan Kumar、Abe Manabu
    • Journal Title

      Science Advances

      Volume: 9 Issue: 22

    • DOI

      10.1126/sciadv.adh3544

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] DMPO Spin Trapping Study of the Photolysis of 2-(4-Nitrophenyl)-1H-indolyl-3-methyl Derivatives2023

    • Author(s)
      Oyama Ryoko、Hayashi Ryuei、Abe Manabu
    • Journal Title

      Chemistry Letters

      Volume: 52 Issue: 1 Pages: 10-12

    • DOI

      10.1246/cl.220462

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Excited-State Intramolecular Proton Transfer in Salicylidene-α-Hydroxy Carboxylate Derivatives: Direct Detection of the Triplet Excited State of the cis-Keto Tautomer2023

    • Author(s)
      Weragoda Geethika K.、Abdelaziz Nayera M.、Govorov Dmitrii、Merugu Rajkumar、Patton Leanna J.、Grabo Jennifer E.、Ranaweera R. A. A. Upul、Ratliff Anna C.、Mendis W. Dinindu、Ahmed Noha、Vilinsky Katrin H.、Abe Manabu、Baldwin Michael J.、Gudmundsdottir Anna D.
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 127 Issue: 12 Pages: 2765-2778

    • DOI

      10.1021/acs.jpca.3c00543

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Tris(4′-Nitrobiphenyl)amine─An Octupolar Chromophore with High Two-Photon Absorption Cross-Section and Its Application for Uncaging of Calcium Ions in the Near-Infrared Region2022

    • Author(s)
      Nguyen Linh Tran Bao、Wu Cheng-Lin、Lin Tzu-Chau、Abe Manabu
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 23 Pages: 15888-15898

    • DOI

      10.1021/acs.joc.2c01987

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Pyrrolo[2,1-a]isoquinolines as multitasking organophotocatalysts in chemical synthesis2022

    • Author(s)
      Liu Yuliang、Li Haoyu、Tan Eugene Yew Kun、Santiko Erik Budi、Chitose Youhei、Abe Manabu、Chiba Shunsuke
    • Journal Title

      Chem Catalysis

      Volume: 2 Issue: 10 Pages: 2726-2749

    • DOI

      10.1016/j.checat.2022.08.013

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Thermal Reaction Behavior of Triphenylimidazolyl Radical with a Bulky Substituent2022

    • Author(s)
      Okamoto Kazunori、Hatano Sayaka、Abe Manabu
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 10 Pages: 6877-6885

    • DOI

      10.1021/acs.joc.2c00672

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoreaction of 4-(Bromomethyl)-7-(diethylamino)coumarin: Generation of a Radical and Cation Triplet Diradical during the C-Br Bond Cleavage2022

    • Author(s)
      Takano Ma-aya、Abe Manabu
    • Journal Title

      Organic Letters

      Volume: 24 Issue: 15 Pages: 2804-2808

    • DOI

      10.1021/acs.orglett.2c00694

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 2-(4-Nitrophenyl)-1-indolyl-3-methyl Chromophore: A Versatile Photocage that Responds to Visible-light One-photon and Near-infrared-light Two-photon Excitations2022

    • Author(s)
      Lin Qianghua、Guo Runzhao、Hamao Kozue、Takagi Ryukichi、Abe Manabu
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 2 Pages: 153-156

    • DOI

      10.1246/cl.210668

    • NAID

      130008161616

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Impacts of Solvent and Alkyl Chain Length on the Lifetime of Singlet Cyclopentane-1,3-diyl Diradicaloids with π-Single Bonding2022

    • Author(s)
      Liu Qian、Wang Zhe、Abe Manabu
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 3 Pages: 1858-1866

    • DOI

      10.1021/acs.joc.1c02895

    • Related Report
      2022 Annual Research Report 2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] SOMO?HOMO Conversion in Triplet Cyclopentane-1,3-diyl Diradicals2021

    • Author(s)
      Wang Zhe、Murata Ryo、Abe Manabu
    • Journal Title

      ACS Omega

      Volume: 6 Issue: 35 Pages: 22773-22779

    • DOI

      10.1021/acsomega.1c03125

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Direct Detection of Singlet Cyclopentane-1,3-diyl Diradicals By Infrared and Ultraviolet?Visible Spectroscopy at Cryogenic Temperature and Their Photoreactivity2021

    • Author(s)
      Sarkar Sujan K.、Abe Manabu
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 86 Issue: 17 Pages: 12046-12053

    • DOI

      10.1021/acs.joc.1c01410

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Long-lived localised singlet diradicaloids with carbon-carbon π-single bonding (C-π-C)2021

    • Author(s)
      Wang Zhe、Yadav Pinky、Abe Manabu
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 86 Pages: 11301-11309

    • DOI

      10.1039/d1cc04581d

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Remarks] 広島大学 反応有機化学研究室

    • URL

      https://hiu-roc.webnode.jp/

    • Related Report
      2023 Annual Research Report
  • [Remarks] Research Group of Reaction Organic Chemistry

    • URL

      https://www.hiu-roc.com

    • Related Report
      2022 Annual Research Report
  • [Remarks] The Research Group of Professor Dr. Manabu Abe

    • URL

      https://www.hiu-roc.com/

    • Related Report
      2021 Annual Research Report
  • [Funded Workshop] ICPOC-252022

    • Related Report
      2022 Annual Research Report

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Published: 2021-04-28   Modified: 2025-01-30  

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