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2016 Fiscal Year Annual Research Report

Development of near-IR responsible photoelectric systems using lithium encapsulated fullerene supramolecules

Research Project

Project/Area Number 26288037
Research InstitutionOsaka University

Principal Investigator

大久保 敬  大阪大学, 未来戦略機構, 招へい教授 (00379140)

Project Period (FY) 2014-04-01 – 2017-03-31
Keywords超分子 / クロリン / ポルフィリノイド / フラーレン / 金属内包フラーレン / 光電子移動
Outline of Annual Research Achievements

優れた電子アクセプターであるフラーレンと優れた光捕集機能を持つポルフィリンを組み合わせたドナー・アクセプター光誘起電荷分離系については数多くの報告があった。これまでフラーレンとポルフィリンの連結分子の合成や、超分子形成などが試みられているが、その多くは非極性溶媒中で主に行われていた。本年度は電子受容特性がC60よりも優れているリチウムイオン内包フラーレン(Li+@C60)がカチオンであることに着目し、アニオン性置換基を有するクロリン誘導体との間で極性溶媒中においても電子ドナー・アクセプター超分子系が形成することを見出した。またその超分子内での長寿命光電荷分離状態生成について検討を行った。
Li+@C60とアニオン性分子の亜鉛クロリンカルボキシレート (ZnCh-) をベンゾニトリル中で混合するとイオン間相互作用および π-π 相互作用によって超分子を形成し、Li+@C60/ ZnCh- と錯形成定数は1.9 × 104 M-1であった。三重項励起状態ZnCh-の酸化電位は-1.1 V vs SCEでありLi+@C60(Ered = 0.13 V)への電子供与が可能である。そこで、Li+@C60/ ZnCh- 錯体にレーザー光照射を行うと三重項励起状態ZnCh- からLi+@C60への超分子内電子移動が進行し、Li+@C60ラジカルアニオンとZnCh-ラジカルカチオン由来の吸収帯がそれぞれ790 nmと1035 nmに観測された。その電荷分離寿命は過渡吸収スペクトルの減衰より170 μs であることが分かった。この超分子錯体を用いて太陽電池を作製し、その光電変換特性の評価を行った結果、亜鉛クロリンに対し、フリーベースクロリンうを用いた超分子錯体の方が著しく良い光電変換効率を示すことが分かった。

Research Progress Status

28年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

28年度が最終年度であるため、記入しない。

Causes of Carryover

28年度が最終年度であるため、記入しない。

Expenditure Plan for Carryover Budget

28年度が最終年度であるため、記入しない。

  • Research Products

    (40 results)

All 2017 2016 Other

All Int'l Joint Research (3 results) Journal Article (26 results) (of which Int'l Joint Research: 26 results,  Peer Reviewed: 26 results,  Acknowledgement Compliant: 26 results,  Open Access: 15 results) Presentation (10 results) (of which Int'l Joint Research: 4 results,  Invited: 4 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] 梨花女子大学(韓国)

    • Country Name
      KOREA (REP. OF KOREA)
    • Counterpart Institution
      梨花女子大学
  • [Int'l Joint Research] ミゲルフェルナンデス大(スペイン)

    • Country Name
      SPAIN
    • Counterpart Institution
      ミゲルフェルナンデス大
  • [Int'l Joint Research] 国ヒューストン大/ロズウェル癌研/ジョンズホプキンス大(米国)

    • Country Name
      U.S.A.
    • Counterpart Institution
      国ヒューストン大/ロズウェル癌研/ジョンズホプキンス大
  • [Journal Article] Thermodynamics and Photodynamics of a Monoprotonated Porphyrin Directly Stabilized by Hydrogen Bonding with Polar Protic Solvents2017

    • Author(s)
      Suzuki, W.; Kotani, H.; Ishizuka, T.; Ohkubo, K.; Shiota, Y.; Yoshizawa, K.; Fukuzumi, S.; Kojima, T.
    • Journal Title

      Chem.-Eur. J.

      Volume: 23 Pages: 印刷中

    • DOI

      10.1002/chem.201606012

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Selective CO Production in Photoelectrochemical Reduction of CO2 with a Cobalt Chlorin Complex Adsorbed on Multi-walled Nanotubes in Water2017

    • Author(s)
      Aoi, S.; Mase, K.; Ohkubo, K.; Suenobu, T.; Fukuzumi, S.
    • Journal Title

      ACS Energy Lett.

      Volume: 2 Pages: 印刷中

    • DOI

      10.1021/acsenergylett.6b00630

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Dihydroxylation of Styrene by Sodium Chlorite with Scandium Triflate2017

    • Author(s)
      Ohkubo, K.; Hirose, K.; Shibata, T.; Takamori, K.; Fukuzumi, S.
    • Journal Title

      J. Phys. Org. Chem

      Volume: 30 Pages: 印刷中

    • DOI

      10.1002/poc.3619

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Exfoliation and Supramolecular Functionalization of Graphene with an Electron Donor Perylenediimide Derivative2017

    • Author(s)
      Martin-Gomis, L.; Karousis, N.; Fernandez-Lazaro, F.; Petsalakis, I. D.; Ohkubo, K.; Fukuzumi, S.; Tagmatarchis N. Sastre-Santos, A;.
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 16 Pages: 印刷中

    • DOI

      10.1039/C6PP00351F

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photoinduced Electron Transfer in 9-Substituted 10-Methylacridinium Ions2016

    • Author(s)
      Tsudaka, T.; Kotani, H.; Ohkubo, K.; Nakagawa, T.; Tkachenko, N. V.; Lemmetyinen, H.; Fukuzumi, S.
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Pages: 1306-1317

    • DOI

      10.1002/chem.201605199

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Synthetic Control over Intra- and Intermolecular Charge Transfer Can Turn on the Fluorescence Emission of Non-emissive Coumarin2016

    • Author(s)
      Jhun, B. H.; Ohkubo, K.; Fukuzumi, S.; You, Y.
    • Journal Title

      J. Mater. Chem. C

      Volume: 4 Pages: 4556-4567

    • DOI

      10.1039/C6TC00639F

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photooxygenation of Alkanes by Dioxygen with p-Benzoquinone Derivatives with High Quantum Yields2016

    • Author(s)
      Ohkubo, K.; Hirose, K.; Fukuzumi, S.
    • Journal Title

      Photochem. Photobiol. Sci

      Volume: 8 Pages: 731-734

    • DOI

      10.1039/C6PP00102E

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Two-Phase Photocatalytic Oxidation of Toluene Derivatives by Dioxygen with 3-Cyano-1-decylquinolinium Ion2016

    • Author(s)
      Ohkubo, K.; Hirose, K.; Fukuzumi, S.
    • Journal Title

      RSC Adv

      Volume: 6 Pages: 41011-41014

    • DOI

      10.1039/C6RA05993G

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Catalytic Reduction of Proton, Oxygen and Carbon Dioxide with Cobalt Macrocyclic Complexes2016

    • Author(s)
      Mase, K.; Aoi, S.; Ohkubo, K.; Fukuzumi, S.
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 20 Pages: 935-949

    • DOI

      10.1142/S1088424616300111

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Catalytic Hydroxylation of Benzene to Phenol by Dioxygen with an NADH Analog2016

    • Author(s)
      Hirose, K.; Ohkubo, K.; Fukuzumi, S.
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Pages: 12904-12909

    • DOI

      10.1002/chem.201602856

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation2016

    • Author(s)
      Rotas, G.; Martin-Gomis, L.; Ohkubo, K.; Fernandez-Lazaro, F.; Fukuzumi, S.; Tagmatarchis, N.; Sastre-Santos, A.
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Pages: 15137-15143

    • DOI

      10.1002/chem.201603065

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Reactivity of 2,2-Diphenyl-1-picrylhydrzyl Solubilized in Water by β-Cyclodextrin and Its Methylated Derivative2016

    • Author(s)
      Nakanishi, I.; Ohkubo, K.; Kamibayashi, M.; Ogawa, Y.; Ozawa, T.; Matsumoto, K.; Fukuzumi, S.
    • Journal Title

      Chem. Select

      Volume: 1 Pages: 3367-3370

    • DOI

      10.1002/slct.201600745

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Controllable Threshold Voltage in Organic Complementary Logic Circuits with an Electron-Trapping Polymer and Photoactive Gate Dielectric Layer2016

    • Author(s)
      Dao, T. T.; Sakai, H.; Nguyen, H. T.; Ohkubo, K.; Fukuzumi, S.; Murata, H.
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 8 Pages: 18249-18255

    • DOI

      10.1021/acsami.6b03183

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Synthetically Tuneable Biomimetic Artificial Photosynthetic Reaction Centres That Closely Resemble the Natural System in Purple Bacteria2016

    • Author(s)
      Lee, S.-H.; Blake, I. M.; Larsen, A. G.; McDonald, J. A.; Ohkubo, K.; Fukuzumi, S.; Reimers, J. R.; Crossley, M. J.
    • Journal Title

      Chem. Sci.

      Volume: 7 Pages: 6534-6550

    • DOI

      10.1039/C6SC01076H

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photocatalytic Oxidation of Iron(II) Complexes by Dioxygen with 9-Mesityl-10-methylacridinium Ion2016

    • Author(s)
      Tsudaka, T.; Ohkubo, K.; Fukuzumi, S.
    • Journal Title

      Chem. Commun.

      Volume: 52 Pages: 6178-6180

    • DOI

      10.1039/C6CC00359A

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photoinduced Electron Transfer in Porous Organic Salt Crystals Impregnated with Fullerenes2016

    • Author(s)
      Hasegawa, T.; Ohkubo, K.; Hisaki, I.; Miyata, M.; Tohnai, N.; Fukuzumi, S.
    • Journal Title

      Chem. Commun.

      Volume: 52 Pages: 7928-7931

    • DOI

      10.1039/C6CC02377K

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Aluminium Ion-Promoted Radical-Scavenging Reaction of Methylated Hydroquinone Derivatives2016

    • Author(s)
      Nakanishi, I.; Ohkubo, K.; Ogawa, Y.; Matsumoto, K.; Ozawa, T.; Fukuzumi, S.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Pages: 7956-7961

    • DOI

      10.1039/C6OB01470D

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Electrochemical Reduction of Cationic Li+@C60 to Neutral Li+@C60.- Isolation and Characterisation of Endohedral [60]Fulleride2016

    • Author(s)
      Ueno, H.; Aoyagi, S.; Yamazaki, Y.; Ohkubo, K.; Ikuma, N.; Okada, H.; Kato, T.; Matsuo, Y.; Fukuzumi, S.; Kokubo, K.
    • Journal Title

      Chem. Sci

      Volume: 7 Pages: 5770-5774

    • DOI

      10.1039/C6SC01209D

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A Profluorescent Nitroxide Probe for Ascorbic Acid Detection and Its Application to Quantitative Analysis of Diabetic Rat Plasma2016

    • Author(s)
      Matsuoka, Y.; Ohkubo, K.; Yamasaki, T.; Yamato, M.; Ohtabu, H.; Shirouzu, T.; Fukuzumi, S.; Yamada, K.
    • Journal Title

      RSC. Adv.

      Volume: 6 Pages: 60907-60915

    • DOI

      10.1039/C6RA07693A

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photocatalytic Reduction of CO2 and H2O to CO and H2 with a Cobalt Chlorin Complex Adsorbed on Multi-Walled Carbon Nanotubes2016

    • Author(s)
      Aoi, S.; Mase, K.; Ohkubo, K.; Fukuzumi, S.
    • Journal Title

      Catal. Sci. Technol.

      Volume: 6 Pages: 4077-4080

    • DOI

      10.1039/C6CY00376A

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible Light Irradiation2016

    • Author(s)
      Ohkubo, K.; Fujimoto, A.; Fukuzumi, S.
    • Journal Title

      Chem. Asian J.

      Volume: 11 Pages: 996-999

    • DOI

      10.1002/asia.201600083

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photocatalytic Oxygenation of Substrates by Dioxygen with Protonated Manganese(III) Corrolazine2016

    • Author(s)
      Jung, J.; Neu, H. M.; Leeladee, P.; Siegler, M. A.; Ohkubo, K.; Goldberg, D. P.; Fukuzumi, S.
    • Journal Title

      Inorg. Chem

      Volume: 55 Pages: 3218-3228

    • DOI

      10.1021/acs.inorgchem.5b02019

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Much Enhanced Electron-Transfer Reactivity of a Nonheme Iron(IV)-Imido Complex as Compared to the Iron(IV)-Oxo Analog2016

    • Author(s)
      Vardhaman, A. K.; Lee, Y.-M.; Jung, J.; Ohkubo, K.; Nam, W.; Fukuzumi, S.
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 55 Pages: 3709-3713

    • DOI

      10.1002/anie.201600287

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Photoinduced Processes of Supramolecular Nanoarrays Composed of Porphyrin and Benzo[ghi]perylenetriimide Units through Triple Hydrogen Bonds with One-Dimensional Columnar Phases2016

    • Author(s)
      Sakai, H.; Ohkubo, K.; Fukuzumi, S.; Hasobe, T.
    • Journal Title

      Chem. Asian J.

      Volume: 11 Pages: 613-624

    • DOI

      10.1002/asia.201501367

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] The Effect of Metallation on Porphyrin-Based Bifunctional Agents in Tumor-Imaging and Photodynamic Therapy2016

    • Author(s)
      Patel, N. J.; Chen, Y.; Joshi, P.; Pera, P.; Baumann, H.; Missert, J. R.; Ohkubo, K.; Fukuzumi, S.; Nani, R. R.; Schnermann, M. J.; Chen, P.; Zhu, J.; Kadish, K. M.; Pandey, R. K.
    • Journal Title

      Bioconjugate Chem.

      Volume: 27 Pages: 667-680

    • DOI

      10.1021/acs.bioconjchem.5b00656

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] An Amphoretic Reactivity of a Mixed-Valent Bis(μ-oxo)dimanganese(III,IV) Complex Acting as an Electrophile and a Nucleophile2016

    • Author(s)
      Sankaralingam, M.; Jeon, S. H.; Lee, Y.-L.; Seo, M. S.; Ohkubo, K.; Fukuzumi, S.; Nam, W.
    • Journal Title

      Dalton Trans.

      Volume: 45 Pages: 376-383

    • DOI

      10.1039/C5DT04292E

    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] 二酸化塩素ラジカルを用いた光酸素化反応2017

    • Author(s)
      大久保敬
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      慶応大
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] 超高難易度酸化反応を可能にする光触媒2016

    • Author(s)
      大久保敬
    • Organizer
      有機光化学研究会
    • Place of Presentation
      あわら市
    • Year and Date
      2016-12-01 – 2016-12-02
  • [Presentation] 亜塩素酸ナトリウムを用いたスチレンの水酸化反応2016

    • Author(s)
      大久保敬
    • Organizer
      第49回酸化反応討論会
    • Place of Presentation
      徳島大
    • Year and Date
      2016-11-12 – 2016-11-13
  • [Presentation] One-step Aerobic Oxygenation of Hydrocarbons by Electron Transfer2016

    • Author(s)
      Ohkubo, Kei
    • Organizer
      PRiME2016
    • Place of Presentation
      ホノルル
    • Year and Date
      2016-10-02 – 2016-10-06
    • Int'l Joint Research / Invited
  • [Presentation] リチウムイオン内包フラーレンとペプチドポルフィリンの超分子内光電荷分離2016

    • Author(s)
      大久保敬
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学
    • Year and Date
      2016-09-06 – 2016-09-08
  • [Presentation] ベンゾキノンの光励起状態を用いたアルカンの酸素酸化反応2016

    • Author(s)
      大久保敬
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島
    • Year and Date
      2016-09-01 – 2016-09-03
  • [Presentation] Supramolecular Electron-Transfer Chemistry of Li+@C60 with Porphyrinoids2016

    • Author(s)
      Ohkubo, Kei
    • Organizer
      International Conference on Porphyrins andPhthalocyanines
    • Place of Presentation
      南京
    • Year and Date
      2016-07-03 – 2016-07-08
    • Int'l Joint Research / Invited
  • [Presentation] ベンゾキノンの光励起状態を用いたアルカンの酸化反応2016

    • Author(s)
      大久保敬
    • Organizer
      第40回有機電子移動化学討論会
    • Place of Presentation
      新潟大学
    • Year and Date
      2016-06-23 – 2016-06-24
  • [Presentation] Multiple photosynthetic reaction centers of porphyrinic polypeptide-Li+@C60supramolecular complexes2016

    • Author(s)
      Ohkubo, Kei
    • Organizer
      229th ECS MEETING - ECS - The Electrochemical Society
    • Place of Presentation
      サンディエゴ
    • Year and Date
      2016-05-31 – 2016-06-04
    • Int'l Joint Research / Invited
  • [Presentation] ONE-STEP OXYGENATION OF ALKANES PHOTOSENSITIZED BY BENZOQUINONE DERIVATIVES2016

    • Author(s)
      Ohkubo, Kei
    • Organizer
      The 26th IUPAC Symposium on Photochemistry
    • Place of Presentation
      大阪
    • Year and Date
      2016-04-03 – 2016-04-08
    • Int'l Joint Research / Invited
  • [Patent(Industrial Property Rights)] ポリマー成形体2016

    • Inventor(s)
      大久保敬・井上豪・高森清人
    • Industrial Property Rights Holder
      大阪大学・株式会社エースネット
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      特願 2016-244690
    • Filing Date
      2016-12-16

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Published: 2018-01-16   Modified: 2022-02-16  

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