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2013 Fiscal Year Final Research Report

Development of caged compounds via photoinduced electron transfer reaction

Research Project

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Project/Area Number 23350075
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionUniversity of Tsukuba

Principal Investigator

ARAI TATSUO  筑波大学, 数理物質系, 教授 (50151139)

Project Period (FY) 2011-04-01 – 2014-03-31
Keywordsケージド化合物 / 光分解 / 電子移動 / 励起状態 / 増感剤 / 生理活性物質 / 三重項状態
Research Abstract

Caged compounds which control various functions of living cells by light irradiation have been synthesized and their photochemical cleavage reactions have been studied. Various kinds of pigments and aromatic systems were used for the light absorption part, and these parts and the electron accepting part were connected with the methylene chain. Furthermore, bioactive glutamic acid or acetic acid group was introduced at the electron accepting pyridinium moiety. As a result, release of acetic acid took place via electron transfer reaction from the aromatic dyes to the pyridinium part followed by cleavage reaction with light irradiation. In this case the quantum yield for this reaction attained very high value in the presence of sacrificial donors.

  • Research Products

    (33 results)

All 2014 2013 2012 2011 Other

All Journal Article (23 results) (of which Peer Reviewed: 23 results) Presentation (7 results) (of which Invited: 1 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] 14 Element Complexes of Dipyrrins Based on a Central Atom2014

    • Author(s)
      Red/Near-Infrared Luminescence Tuning of Group-M. Yamamura, M. Albrecht, M. Albrecht, Y. Nishimura, T. Arai and T. Nabeshima
    • Journal Title

      Inorg. Chem

      Volume: 53 Pages: 1355-1360

    • DOI

      10.1021/ic402116j

    • Peer Reviewed
  • [Journal Article] Evaluation of Dialkylaminofluorene-Based Hemicyanine Dyes for Second Harmonic Generation Imaging by the Direct Comparison Approach2013

    • Author(s)
      M. Nuriya, A. Momotake, Y. Kimura, M. Yasui, H. Kasai and T. Arai
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 86 Pages: 1190-1192

    • DOI

      10.1246/bcsj.20130094

    • Peer Reviewed
  • [Journal Article] Singlet Oxygen Generating Activity of an Electron Donor-Connecting Porphyrin Photosensitizer Can Be Controlled by DNA2013

    • Author(s)
      K. Hirakawa, Y. Nishimura, T. Arai and S. Okazaki
    • Journal Title

      J. Phys. Chem. B

      Volume: 117 Pages: 13490-13496

    • DOI

      10.1021/jp300142e

    • Peer Reviewed
  • [Journal Article] Photochemical Characteristics of Amphiphilic Stilbene Dendrimers Induced by Aggregate Formation at Very Low Concentration2013

    • Author(s)
      K. Kataoka and T. Arai
    • Journal Title

      Chem. Lett

      Volume: 42 Pages: 536-537

    • DOI

      10.1246/cl.130098

    • Peer Reviewed
  • [Journal Article] Photosensitized protein damage by dimethoxyphosphorus(V) tetraphenylporphyrin2013

    • Author(s)
      K. Hirakawa, N. Fukunaga, Y. Nishimura, T. Arai and S. Okazaki
    • Journal Title

      Bioorg Med Chem Lett

      Volume: 23 Pages: 2704-2707

    • DOI

      10.1016/j.bmcl.2013.02.081

    • Peer Reviewed
  • [Journal Article] Photochemistry of arylacetylenyl-substituted stilbenes2013

    • Author(s)
      M. Suzuki, A. Momotake, Y. Kanna, Y. Nishimura, K. Hirota, K. Morihashi and T. Arai
    • Journal Title

      J. Photochem. Photobiol. A : Chem

      Volume: 252 Pages: 203-210

    • DOI

      10.1016/j.jphotochem.2012.11.019

    • Peer Reviewed
  • [Journal Article] Hydrogen Bonding Induced Highly Selective Isomerization of an Olefin Having Heteroaromatic Rings2012

    • Author(s)
      T. Kobayashi and T. Arai
    • Journal Title

      Heterocyles

      Volume: 86 Pages: 1129-1134

    • Peer Reviewed
  • [Journal Article] Fluorescence Turn-On Sensing of Anions Based on Disassembly Process of Urea-Functionalized Poly(phenylenebutadiynylene) Aggregates2012

    • Author(s)
      R. Sakai, A. Nagai, Y. Tago, S. Sato, Y. Nishimura, T. Arai, T. Satoh and T. Kakuchi
    • Journal Title

      Macromolecules

      Volume: 45 Pages: 4122-4127

    • DOI

      10.1021/ma300481j

    • Peer Reviewed
  • [Journal Article] Kinetic analysis of photoinduced reactions in hydrogen-bonded complexes of anthracene-urea with anions2012

    • Author(s)
      H. Masai, S. Ikedu, Y. Nishimura and T. Arai
    • Journal Title

      J. Photochem. Photobiol. A : Chem

      Volume: 250 Pages: 1-5

    • DOI

      10.1016/j.jphotochem.2012.09.011

    • Peer Reviewed
  • [Journal Article] Self-assembly of poly(glutamate) dendrimer : solvent-dependent expression of molecular chirality and [2+2] photocrosslinking reaction2012

    • Author(s)
      M. Ikeda, A. Momotake, Y. Kanna, K. Shimotori and T. Arai
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 11 Pages: 1524-1527

    • DOI

      10.1039/C2PP25221J

    • Peer Reviewed
  • [Journal Article] Photoisomerization and energy transfer in naphthalene-terminated stilbene dendrimers2012

    • Author(s)
      S. Nakazato, T. Takizawa and T. Arai
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 11 Pages: 885-888

    • DOI

      10.1039/C2PP05328D

    • Peer Reviewed
  • [Journal Article] 2-(N-Acyl-N-carboxymethylamino) -1-nitrodibenzo[b, d]thiophene : A new class of caging group for environmental selective photorelease of carboxylic acid2012

    • Author(s)
      Y. Tanaka, A. Momotake and T. Arai
    • Journal Title

      Chem. Lett

      Volume: 41 Pages: 642-643

    • DOI

      10.1246/cl.2012.642

    • Peer Reviewed
  • [Journal Article] Polarity-dependent photophysical properties of hemicyanine dyes and their application in 2-photon microscopy biological imaging2012

    • Author(s)
      Y. Kimura, A. Momotake, N. Takahashi, H. Kasai and T. Arai
    • Journal Title

      Chem. Lett.

      Volume: 41 Pages: 528-530

    • DOI

      10.1246/cl.2012.528

    • Peer Reviewed
  • [Journal Article] Control of photoisomerization in water-soluble stilbene dendrimers by conformation of dendrons : How water-soluble dendrimer molecules are dissolved in water2012

    • Author(s)
      T. Takizawa and T. Arai
    • Journal Title

      Chem. Lett.

      Volume: 41 Pages: 415-417

    • DOI

      10.1246/cl/2012.415

    • Peer Reviewed
  • [Journal Article] Environmental polarity estimation in living cells by use of quinoxaline-based full-colored solvatochromic fluorophore PQX and its derivatives2012

    • Author(s)
      K. Kudo, A. Momotake, J. K. Tanaka, Y. Miwa and T. Arai
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 11 Pages: 674-678

    • DOI

      10.1039/C2PP05337C

    • Peer Reviewed
  • [Journal Article] Dynamics of singlet oxygen generation by DNA-binding photosensitizers2012

    • Author(s)
      K. Hirakawa, T. Hirano, Y. Nishimura, T. Arai and Y. Nosaka
    • Journal Title

      J. Phys. Chem. B

      Volume: 116 Pages: 3037-3044

    • DOI

      10.1021/jp300142e

    • Peer Reviewed
  • [Journal Article] N-Acyl-N-carboxymethyl-2- nitroaniline and its analogues : a new class of water-soluble photolabile precursor of carboxylic acids2012

    • Author(s)
      T. Honda, A. Momotake and T. Arai
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 11 Pages: 493-496

    • DOI

      10.1039/C2PP05322E

    • Peer Reviewed
  • [Journal Article] Extremely efficient photoisomerization of water-soluble diphenylbutadiene dendrimers2012

    • Author(s)
      Y. Miura. A. Momotake, Y. Kanna, Y. Nishimura, and T. Arai
    • Journal Title

      Dyes & Pigments

      Volume: 92 Pages: 802-806

    • DOI

      10.1016/j.dyepig.2011.05.002

    • Peer Reviewed
  • [Journal Article] Remote Controlled Intramolecular Exciplex Formation and Enhanced Photoisomerization in Stilbene-cored Poly(benzyl ether) Dendrimers with Alkoxycarbonyl Surface Functional Groups2011

    • Author(s)
      T. Takizawa and T. Arai
    • Journal Title

      Chem. Lett.

      Volume: 40 Pages: 1124-1126

    • DOI

      10.1246/cl.2011.1124

    • Peer Reviewed
  • [Journal Article] Kinetics of Hydrogen Bonding between Anthracene Urea Derivatives and Anions in the Excited State2011

    • Author(s)
      S. Ikedu, Y. Nishimura and T. Arai
    • Journal Title

      J. Phys. Chem. A

      Volume: 115 Pages: 8227-8233

    • DOI

      10.1021/jp2022693

    • Peer Reviewed
  • [Journal Article] Kinetic studies of emissive guanine derivatives bearing anthracene moiety2011

    • Author(s)
      Y. Nishimura, K. Shimamura, Y. Ohmori, Y. Shinohara and T. Arai
    • Journal Title

      J. Photochem. Photobiol. A : Chem.

      Volume: 218 Pages: 69-75

    • DOI

      10.1016/j.jphotochem.2010.12.005

    • Peer Reviewed
  • [Journal Article] Unusually efficient trans-to-cis photoisomerization of diphenylbutadiene dendrimers in water2011

    • Author(s)
      Y. Miura, A. Momotake, Y. Kanna, Y. Nishimura and T. Arai
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 10 Pages: 1524-1526

    • DOI

      10.1039/C1PP05212H

    • Peer Reviewed
  • [Journal Article] Extremely Efficient and Long Lifetime Fluorescence of cis-Stilbene Contained in a Rigid Dendrimer2011

    • Author(s)
      M. Tabuchi, A. Momotake, Y. Kanna, Y. Nishimura and T. Arai
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 10 Pages: 1521-1523

    • DOI

      10.1039/C1PP05126A

    • Peer Reviewed
  • [Presentation] Dendrimer photochemistry : Photoisomerization and energy transfer2013

    • Author(s)
      Tatsuo Arai
    • Organizer
      2013 Korea-Japan Symposium on Frontier Photoscience
    • Place of Presentation
      Seoul National University, Korea
    • Year and Date
      20131124-27
    • Invited
  • [Presentation] Control of photocleavage reaction of caged compounds by utilizing excited state intramorecular proton transfer reaction2013

    • Author(s)
      Takuya Honda・ Tatsuo Arai
    • Organizer
      2013 Korea-Japan Symposium on Frontier Photoscience
    • Place of Presentation
      Seoul National University, Korea
    • Year and Date
      20131124-27
  • [Presentation] 光誘起生理活性物質放出を目指した機能性ケージド化合物の合成とその光化学2013

    • Author(s)
      本田拓也・ 百武篤也・ 新井達郎
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛大学
    • Year and Date
      20130911-13
  • [Presentation] Photoisomerization and energy transfer in stilbene dendrimers and related compounds2013

    • Author(s)
      Tatsuo Arai
    • Organizer
      8Th International Dendrimer Symposium
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      20130623-27
  • [Presentation] 光誘起電子移動経由でカルボン酸を放出するケージド化合物の研究2012

    • Author(s)
      森山晴加・ 百武篤也・ 新井達郎
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京工業大学
    • Year and Date
      20120912-14
  • [Presentation] ニトロベンゼン骨格を活用したケージド化合物合成への展開2012

    • Author(s)
      高橋洋平・ 百武篤也・ 新井達郎
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京工業大学
    • Year and Date
      20120912-14
  • [Presentation] 光誘起電子移動反応を利用したケージドグルタミン酸の高性能化に関する研究2011

    • Author(s)
      森山晴加・ 百武篤也・ 西村賢宣・ 新井達郎
    • Organizer
      2011年光化学討論会
    • Place of Presentation
      宮崎市河畔コンベンションエリア
    • Year and Date
      20110906-08
  • [Book] Photochromism of organic compounds undergoing isomerization around the C=C double bond and/or intramolecular hydrogen atom transfer : Small and large structural change, New Frontiers in Photochromism2013

    • Author(s)
      K. Kataoka, T. Kobayashi and T. Arai
    • Total Pages
      248-271
    • Publisher
      Springer
  • [Remarks]

    • URL

      http://www.chem.tsukuba.ac.jp/arai/

  • [Patent(Industrial Property Rights)] 光第二高調波発生化合物, 光第二高調波発生色素組成物及び細胞検査方法2013

    • Inventor(s)
      塗谷睦生, 安井正人, 新井達郎, 百武篤也, 福嶋瞬
    • Industrial Property Rights Holder
      塗谷睦生, 安井正人, 新井達郎, 百武篤也, 福嶋瞬
    • Industrial Property Rights Type
      特許特願 2013-1-9179
    • Industrial Property Number
      特願 2013-1-9179
    • Filing Date
      2013-05-23

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Published: 2015-06-25  

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