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1998 Fiscal Year Final Research Report Summary

Photochemical synthesis of new ionophores and their application

Research Project

Project/Area Number 08555226
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Synthetic chemistry
Research InstitutionGUNMA UNIVERSITY

Principal Investigator

NISHIMURA Jun  Department of Chem., Gunma Univ., prof., 工学部, 教授 (10107352)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Yosuke  Department of Chem., Gunma Univ., Instructor, 有機化学基礎研究センター, 助手 (60261864)
Project Period (FY) 1996 – 1998
Keywords[2+2]photocycloaddition / styrene derivertives / oligo(oxyethylene)linkage / crown compounds / crownophanes / lithiophilic ionophores / extraction / silver metal ion
Research Abstract

We have developed intramolecular [2+2] photocycloaddition of styrene derivatives, such as substituted styrene, vinylnaphthalene, vinyiphenanthrene, and so on. The photocyclization showed tether-length dependency ; i.e., the longer the tether becomes, the lower yield is obtained. If oligo(oxyethylene) linkage is used as the tether, however, the yield does not depend on the length and generally becomes quantitative. This tendency has been determined to be due to the flexible property of oligo(oxyethylene) chain.
We were prompted to use this efficient reaction to make a new type of crown compounds (so- called crownophanes) and succeeded in the cultivation of a new ionophore synthetic method.
The prototypical crownophanes showed relatively high Li^+ ion selectivity on the solid-liquid extraction, so we tried to improve the selectivity and found, after several trials, that simply and appropriately modified crownophanes having two cyclobutane linkages (crownopaddlanes) extracted the Li ion exclusively and quantitatively on the extraction experiment.
Next we tried to make crownophanes working efficiently for the extraction of heavy metal cations. We first made some precursors having two hydroxyl groups on the oligo(oxyethylene) linkage or the aromatic nuclei and then treated these functional groups with pyridylmethyl chloride. The modified crownophanes with two pyridine side arms showed high affinity toward Ag^+ ion on the liquid-liquid extraction. Especially, the compound having the side arms on the aromatic nuclei exhibited the excellent selectivity.

  • Research Products

    (47 results)

All Other

All Publications (47 results)

  • [Publications] Y.Nakamura 他7名: "Photophysical Properties of Various Regioisomers of [60]Fullerene-ο-Quinodimethane Bisadducts" J.Chem.Soc., Perkin Trans.2. 127-131 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada 他3名: "New Ionophores Derived from a Rigid Calixarene Regioisomer" Tetrahedron Lett.in press. (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他3名: "Effects of Oligooxyethylene Linkage on Intramolecular[2+2]Photocycloaddition of Styrene Derivatives" J.Phys.Org.Chem.11. 79-8〓 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada 他3名: "A New Intermolecular Photochemical Approach of Calix[4]arene Synthesis" Synlett. 269-270 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma, K.Kimura, and J.Nishimura: "Photochemical Synthesis of Diazacryptophane" Chem.Lett.287-288 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma 他4名: "Efficient and Selective Synthesis of Crownopaddlanes Possessing Two Cyclobutane Rings : Exclusive Li+Ion Complexation" J.Org.Chem.63・17. 5791-5796 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Taki 他4名: "[60]Fullerene(A1, D1)-Bisadducts : CD Spectra and Diastereospecific Synthesis" Enantiomer. 3. 231-239 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada, M.Mizutani, and J.Nishimura: "Highly selective Li+ion transport by calix[4]arenes" Tetrahedron Lett.39. 8467-8470 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada 他4名: "Characterization of New Rigid Calixarenes Capping Crown Ethers" Tetrahedron Lett.39. 8461-8464 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Taki 他6名: "Selective Functionalization on[60]Fullerene Governed by Tether Length" J.Am.Chem.Soc.109. 926-932 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他3名: "Synthesis of Paddlanes Possessing Cyclophane Shaft and Cyclobutane Blades" Tetrahedron. 53・13. 4593-4600 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他3名: "Synthesis of 1, 8-Naphthylene-Bridged syn-Cyclophanes by Efficient Intramolecular[2+2]Photocycloaddition" Tetrahedron Lett.38・11. 1983-1986 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Yamaji 他3名: "Laser Flash Photolysis Studies on Dynamic Behaviors of Triplet Naphthalenophanes Sensitized by Triplet Benzophenone" J.Chem.Soc., Faraday Trans.93・6. 1065-1070 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他4名: "Interaction between Benzene and Naphthalenophane : In Gas Phase and Crystalline Lattice" Ann./Recueil. 1769-1776 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Taki 他4名: "Synthesis of Polyesters Containing[60]Fullerene Moiety in the Main Chain by Mild Surface Condensation Method" Polym.J.29. 1020-1022 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada 他3名: "A New Class of Chiral Calix[4]arenes as Receptors Having a Plane of Chirality" Tetrahedron Lett.38・52. 9013-9016 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma 他4名: "Ag^+-Selective Bisaminimides Possessing Oligo(oxyethylene)Linkages" Chem.Lett.123-124 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他6名: "Synthesis, Structure, and Electronic Properties of syn-[2.2]Phenan-threnophanes : First Observation of Their Excimer Fluorescence at High Temperature" J.Am.Chem.Soc.118. 1006-1012 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他5名: "Relaxation Processes in the Exited State of C60-ο-quinodimethane Adducts" J.Chem.Soc., Faraday Trans.92. 377-382 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura 他6名: "Inclusion Crystals from Naphtharenophanes in Aromatic Solvents," Mol.Cryst.Liq.Cryst.276. 105-112 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada, K.Endoh, and J.Nishimura: "A New Molecular Cleft for Organic Diols by Using a Rigid Calixarene Analog" J.Soc.Photogr.Sci.Technol.Jpn.59. 471-474 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura, T.Mita, and J.Nishimura: "Synthesis and Properties of [2.2](3,3')Biphenylo(3,6)-phenanthrenophane" Tetrahedron Lett.37・22. 3877-3880 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.-R.Gao, S.Inokuma, and J.Nishimura: "Selective Ion Clefts Based on a Three-Bridged[43]Cyclophane" J.Inclusion Phenomena. 23・4. 329-341 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中村洋介, 西村 淳(分担): "季刊化学総説「炭素第三の同素体フラーレンの化学」" 日本化学会編, 学会出版センター, 東京, 印刷中 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura, M.Taki, S.Tobita, H.Shizuka, H.Yokoi, K.Ishiguro, Y.Sawaki, and J.Nishimura: "Photophysical Properties of Various Regioisomers of[60]Fullerene-o-Quinodimethane Bisadducts" J.Chem.Soc., Perkin Trans. 2. 127-131 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Okada, M.Mizutani, F.Ishii, and J.Nishimura: "New Ionophores Derived from a Rigid Calixarene Regioisomer" Tetrahedron Lett.in press. (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, T.Fujii, S.Inokuma, and J.Nishimura: "Effects of Oligooxyethylene Linkage on Intramolecular [2+2] Photocycloaddition of Styrene Derivatives" J.Phys.Org.Chem.11. 79-83 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Okada, M.Hagiwara, M.Mineo, and J.Nishimura: "A New Intermolecular Photochemical Approach of Calix[4]arene Synthesis" Synlett. 269-270 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Inokuma, K.Kimura, and J.Nishimura: "Photochemical Synthesis of Diazacryptophane" Chem.Lett.287-288 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Inokuma, M.Takezawa, H.Katoh, Y.Nakamura, and J.Nishimura: "Efficient and Selective Synthesis of Crownopaddlanes Possessing Two Cyclobutane Rings : Exclusive Li^+ Ion Complexation" J.Org.Chem.63(17). 5791-5796 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Taki, Y.Nakamura, H.Uehara, M.Sato, and J.Nishimura: "[60]Fullerene(A_1D_1)-Bisadducts : CD Spectra and Diastereospecific Synthesis" Enantiomer. 3. 231-239 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Okada, M.Mizutani, and J.Nishimura: "Highly selective Li^+ ion transport by calix[4]arenes" Tetrahedron Lett.39. 8467-8470 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Okada, M.Mizutani, F.Ishii, and J.Nishimura: "A Synthesis and Characterization of New Rigid Calixarenes Capping Crown Ethers" Tetrahedron Lett.39. 8461-8464 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Taki, S.Sugita, Y.Nakamura, E.Kasashima, E.Yashima, Y.Okamoto, and J.Nishimura: "Selective Functionalization on [60]Fullerene Governed by Tether Length" J.Am.Chem.Soc.109. 926-932 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, Y.Hayashida, Y.Wada, and J.Nishimura: "Synthesis of Paddlanes Possessing Cyclophane SHaft and Cyclobutane Blades" Tetrahedron. 53(13). 4593-4600 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, M.Matsumoto, Y.Hayashida, and J.Nishimura: "Synthesis of 1,8-Naphthylene-Bridged syn-Cyclophanes by Efficient Intramolecular[2+2] Photocycloaddition" Tetrahedron Lett.38(11). 1983-1986 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Yamaji, K.Shima, J.Nishimura and H.Shizuka: "Laser Flash Photolysis Studies on Dynamic Behaviors of Triplet Naphthalenophanes Sensitized by Triplet Benzophenone" J.Chem.Soc.Faraday Trans. 93(6). 1065-1070 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, H.Suzuki, Y.Hayashida, T.Kudo, and J.Nishimura: "Interaction between Benzene and Naphthalenophane : In Gas Phase and Crystalline Lattice" Ann./Recueil. 1769-1776 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Taki, S.Takigami, Y.Watanabe, Y.Nakamura, and J.Nishimura: "Synthesis of Polyesters Containing [60]Fullerene Moiety in the Main Chain by Mild Surface Condensation Method" Polym.J.29. 1020-1022 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Okada, M.Mizutani, F.Ishii, and J.Nishimura: "A New Class of Chiral Calix[4]arenes as Receptors Having a Plane of Chirality" Tetrahedron Lett.38(52). 9013-9016 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Inokuma, H.Satoh, T.Yasuda, S.Nishioka, and J.Nishimura: "Ag^+-Selective Bisaminimides Possessing Oligo(oxyethylene)Linkages" Chem Lett.123-124 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, T.Tsuihiji, T.Mita, T.Minowa, S.Tobita, H.Shizuka, and J.Nishimura: "Synthesis, Structure, and Electronic Properties of syn-[2.2]Phenanthrenophanes : First Observation of Their Excimer Fluorescence at High Temperature" J.Am.Chem.Soc.118. 1006-1012 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, T.Minowa, Y.Hayashida, S.Tobita, H.Shizuka, and J.Nishimura: "Relaxation Processes in the Exited State of C60-o-quinodimethane Adducts" J.Chem.Soc.Faraday Trans.92. 377-382 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, T.Kitada, T.Kushima, T.Kudo, J.Nishimura, N.Tatsuta, and O.Yamashita: "Inclusion Crystals from Naphtharenophanes in Aromatic Solvents" Mol.Cryst.Liq.Cryst.276. 105-112 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Okada, K.Endoh, and J.Nishimura: "A New Molecular Cleft for Organic Diols by Using a Rigid Calixarene Analog" J.Soc.Photogr.Sci.Technol.Jpn.59. 471-474 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nakamura, T.Mita, and J.Nishimura: "Synthesis and Properties of [2,2](3,3')Biphenylo(3,6)phenanthrenophane" Tetrahedron Lett.37(22). 3877-3880 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.-R.Gao, S.Inokuma, and J.Nishimura: "Selective Ion Clefts Based on a Three-Bridged[4_3]Cyclophane" J.Inclusion Phenomena. 23(4). 329-341 (1996)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-12-08  

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