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2002 Fiscal Year Final Research Report Summary

Synthesis and Application of New Host Molecules derived from Macrocycles.

Research Project

Project/Area Number 11305063
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionGunma University

Principal Investigator

NISHIMURA Jun  Gunma University, Department of Chemistry, Professor, 工学部, 教授 (10107352)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Yousuke  Gunma Univ., Dept. of Chem., Associate Prof., 工学部, 助手 (60261864)
OKADA Yukihiro  Gunma Univ., Dept. of Chem., Associate Prof., 工学部, 助教授 (80211118)
Project Period (FY) 1999 – 2002
Keywordscrownether / cyclophane / catenane / fullerene / calixarene / receptor / ionophore / high selectivity
Research Abstract

1. Double armed crownophanes were successfully synthesized. They showed the high ion selectivity for silver ion. Crownophanes containing amino group were also synthesized with cyclodextrin in water by photocycloaddition. Catenanes including[2]- and [3] catenanes were successfully synthesized by using ion-dipole interaction with crownether.
2. The product distribution of [60]fullerene bisadducts was investigated by the different two methods. The benzyne method exclusively gave cis-1 form. All racemates (trans-2, trans-3, and cis-3) were successfully resolved into each enantiomer by using chiral HPLC column chromatography. Bisadducts attaching crownether moiety showed the unique ion selectivity for alkali metalions.
3. Calixarenes having some ethyl acetate units were successfully synthesized. They showed the good extractability for alkali metal ions. When the number of the ethylacetate unit decreased, the extractability for larger ions like Rb^+ and Cs^+ gradually decreased. They were successfully converted to dendrimer type molecules with amino alcohol.

  • Research Products

    (72 results)

All Other

All Publications (72 results)

  • [Publications] Y.Okada: "Synthesis and Characterization of Chiral Calixarene Analogs Locked in the Cone Conformation by the Photocycloaddition"Synlett. (in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 岡田行弘: "キラルカリックス[4]アレーン"有機合成化学協会誌. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 岡田行弘: "コーン型配座"有機合成化学協会誌. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Inokuma: "A Pseudo Thiacrown Compound Formed by Hydrophobic Interaction of Its Lipophilic Parts in Water : Ag^+-Selective Fluorophore in Water"Heterocycles. 60. 145-150 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "Behavior of [2.n] metacyclophane-fused cyclobutane rings in bromination"Tetrahedron Lett.. 43. 5821-5824 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "A Synthesis and Characterization of New Chiral Calix[4]arenes"Enantiomer. 7. 93-106 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Synthesis and Properties of Triply-Bridged syn-Carbazolophanes"J.Org.Chem.. 67. 8706-8709 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Regioselective Synthesis and Properties of Novel [60]Fullerene Bisadducts Containing a Dibenzocrown Ether Moiety"J.Am.Chem.Soc.. 124. 4329-4335 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Photochemical Synthesis, Conformational Analysis, and Transformation of [60] Fullerene-ο-quinodimethane Adducts Bearing a Hydroxy Group"J.Org.Chem.. 67. 1247-1252 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma: "Synthesis and Complexing Properties of Thiacrownophanes"Heterocycles. 55. 1635-1639 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma: "Synthesis of Crownophane possessing Pyridine Moieties on the Aromatic Nuclei(Pyridine-Lariat Crownophane) : A Crownophane Exhibiting Perfect Selectivity Toward Ag^+"Heterocycles. 55. 447-451 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma: "Synthesis and Complexing Ability of Azacrownophanes : The Cyclodextrin Catalysis of the Photochemical Cyclization Reaction"J.Incl.Phenom.. 39. 35-40 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Synthesis and Fluorescence Emission Behavior of anti-[2.3](3,10)Phenanthrenophane : Overlap between Phenanthrene Rings Required for Excimer Formation"Chem.Lett.. 970-971 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "First Isolation and Characterization of Eight Regioisomers for [60]Fullerene-Benzyne Bisadducts"Org.Lett.. 3. 1193-1196 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Inokuma: "Synthesis of Pyridinocrownophanes Exhibiting High Ag^+-Affinity"Heterocycles. 54. 123-130 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "The Formylation of syn-[2.n] Metacyclophanes and Application to Multi-bridged Cyclophane Synthesis"Tetrahedron Lett.. 42. 1919-1921 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "Synthesis and Characterization of Calixarene Analogs Locked in the Cone Conformation by the Dimerization of syn-Dihydroxymetacyclophanes as a Building Block"Tetrahedron. 57. 1219-1227 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "Chloromethylation of syn-[2.n]Metacyclophanes and Application toward Multi-bridged Cyclophane Synthesis"Tetrahedron Lett.. 42. 25-27 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] J.Nishimura: "Stereocontrol in Cyclophane Synthesis : Photochemical Method to Overlap Aromatic Rings"Acc.Chem.Res.. 33. 679-686 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Separation and characterization of [60]fullerene bisadducts modified by 4,5-dimethoxy-ο-quinodimethane"Tetrahedron. 56. 5429-5434 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Langmuir and LB Films of Amphiphilic [60]Fullerene Derivatives"Bull.Chem.Soc.Jpn.. 73. 1615-1619 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.O-kawa: "Facile modification of [60]fullerene by photochemically generated hydroxy-ο-quinodimethane derivatives"Tetrahedron Lett.. 41. 3103-3106 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 林田喜任: "極性置換基を有する[2.n]ナフタレノファンの合成とその包接挙動"日本化学会誌. 247-255 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Regioselective synthesis and complexation behavior of novel [60]fullerene bisadducts containing dibenzo-18-crown-6 moiety"Tetrahedron Lett.. 41. 2193-2197 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Synthesis and fluorescence emission behavior of novel anti-[2.n] (3,9)phenanthrenophanes"Tetrahedron Lett.. 41. 1419-1423 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "New Caixcrown-type Ionophores Derived from All Possible Regioisomers of Rigid Calix[4]arene"Synlett. 41-44 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Okada: "New Ionophores Derived from a Rigid Calixarenes Regioisomer"Tetrahedron Lett.. 40. 1353-1356 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Excimer Fluorescence from anti-[2.3](2,7)Phenanthrenophane"Chem.Lett.. 1039-1040 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Hayashida: "Synthesis and Structure of Novel [2.n](4,4')Binaphthylophanes : A New Family in Cyclophane Chemistry"Tetrahedron Lett.. 40. 6435-6438 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Synthesis and Photophysical Properties of syn-and anti-[2.n] (3,9) Carbazolophanes"Tetrahedron Lett.. 40. 4693-4696 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Synthesis of [2.n]Thiophenophanes by Intramolecular [2+2] Photocycloaddition"Heterocycles. 51. 1059-1065 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Photophysical Properties of Various Regioisomers of [60] Fullerene-ο-Quinodimethane Bisadducts"J.Chem.Soc., Perkin Trans.2. 127-130 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 猪熊精一: "分子内[2+2]光付加環化反応によるクラウノファン類の合成と錯形成能"日本化学会誌. 305-316 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Inokuma: "Crownophanes : Photochemical Preparation and Unique Complexing Ability"Cyclophane Chemistry for the 21^<th> Century, Research Signpost. (in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] J.Nishimura: "Photochemical Synthesis of Cyclophane"Handbook of Organic Photochemistry. (in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakamura: "Homocalixarenes"Calixarene 2001, (ed.by Z.Asfari, and J.Vicens, V.Bohmer)(Kluwer Academic Publishers). 219-234 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S. Inokuma: "Crownophanes : Photochemical Preparation and Unique Complexing Ability"Cyclophane Chemistry for the 21^<th> Century Research Signpost. in press.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J. Nishimura: "Photochemical Synthesis of Cyclophane"Handbook of Organic Photochemistry. in press.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "Synthesis and Characterization of Chiral Calixarene Analogs Locked in the Cone Conformation by the Photocycloaddition"Synlett. in press.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "Chiral Calix[4]arene"J. Synth. Org. Chem. Jpn. in press.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "Cone Conformation"J. Synth. Org. Chem. Jpn. in press.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inokuma: "A Pseudo Thiacrown Compound Formed by Hydrophobic Interaction of Its Lipophilic Parts in Water : Ag^+-Selective Fluorophore in Water"Heterocycles. 60. 145-150 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "Behavior of [2.n]metacyclophane-fused cyclobutane rings in bromination"Tetrahedron Lett.. 43. 5821-5824 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "A Synthesis and Characterization of New Chiral Calix[4]arenes"Enantiomer. 7. 93-106 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Synthesis and Properties of Triply-Bridged syn- Carbazolophanes"J. Org. Chem.. 67. 8706-8709 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Regioselective Synthesis and Properties of Novel [60]Fullerene Bisadducts Containing a Dibenzocrown Ether Moiety"J. Am. Chem. Soc.. 124. 4329-4335 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Photochemical Synthesis, Conformational Analysis, and Transformation of [60]Fullerene-o-quinodimethane Adducts Bearing a Hydroxy Group"J. Org. Chem.. 67. 1247-1252 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inokuma: "Synthesis and Complexing Properties of Thiacrownophanes"Heterocycles. 55. 1635-1639 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inokuma: "Synthesis of Crownophane possessing Pyridine Moieties on the Aromatic Nuclei (Pyridine-Lariat Crownophane) : A Crownophane Exhibiting Perfect Selectivity Toward Ag^+"Heterocycles. 55. 447-451 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inokuma: "Synthesis and Complexing Ability of Azacrownophanes ; The Cyclodextrin Catalysis of the Photochemical Cyclization Reaction"J. Incl. Phenom.. 39. 35-40 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Synthesis and Fluorescence Emission Behavior of anti-[2.3](3,10)Phenanthrenophane : Overlap between Phenanthrene Rings Required for Excimer Formation"Chem. Lett.. 970-971 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "First Isolation and Characterization of Eight Regioisomers for [60]Fullerene-Benzyne Bisadducts"Org. Lett.. 3. 1193-1196 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inokuma: "Synthesis of Pyridinocrownophanes Exhibiting High Ag^+- Affinity"Heterocycles. 54. 123-130 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "The Formylation of syn-[2.n]Metacyclophanes and Application to Multi-bridged Cyclophane Synthesis"Tetrahedron Lett.. 42. 1919-1921 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "Synthesis and Characterization of Calixarene Analogs Locked in the Cone Conformation by the Dimerization of syn-Dihydroxymetacyclophanes as a Building Block"Tetrahedron. 57. 1219-1227 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "Chloromethylation of syn-[2.n]Metacyclophanes and Application toward Multi-bridged Cyclophane Synthesis"Tetrahedron Lett.. 42. 25-27 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J. Nishimura: "Stereocontrol in Cyclophane Synthesis : Photochemical Method to Overlap Aromatic Rings"Acc. Chem. Res.. 33. 679-686 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Separation and characterization of [60]fullerene bisadducts modified by 4,5-dimethoxy-o-quinodimethane"Tetrahedron. 56. 5429-5434 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Langmuir and LB Films of Amphiphilic [60]Fullerene Derivatives"Bull. Chem. Soc. Jpn.. 73. 1615-1619 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. O-kawa: "Facile modification of [60]fullerene by photochemically generated hydroxy-o-quinodimethane derivatives"Tetrahedron Lett.. 41. 3103-3106 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Hayashida: "Synthesis and Inclusion Behavior of [2.n]Naphthalenophanes Possessing Polar Groups"Nippon Kagaku Kaishi. 247-255 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Regioselective synthesis and complexation behavior of novel [60]fullerene bisadducts containing dibenzo-18-crown-6 moiety"Tetrahedron Lett.. 41. 2193-2197 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Synthesis and fluorescence emission behavior of novel anti-[2.n](3,9)phenanthrenophanes"Tetrahedron Lett.. 41. 1419-1423 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "New Caixcrown-type Ionophores Derived from All Possible Regioisomers of Rigid Calix[4]arene"Synlett. 41-44 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Okada: "New Ionophores Derived from a Rigid Calixarenes Regioisomer"Tetrahedron Lett.. 40. 1353-1356 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Excimer Fluorescence from anti-[2.3](2,7)Phenanthrenophane"Chem. Lett.. 1039-1040 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Hayashida: "Synthesis and Structure of Novel [2.n](4,4')Binaphthylophanes : A New Family in Cyclophane Chemistry"Tetrahedron Lett.. 40. 6435-6438 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Synthesis and Photophysical Properties of syn-and anti-[2.n](3,9)Carbazolophanes"Tetrahedron Lett.. 40. 4693-4696 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Synthesis of [2.n]Thiophenophanes by Intramolecular [2+2] Photocycloaddition"Heterocycles. 51. 1059-1065 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura: "Photophysical Properties of Various Regioisomers of [60]Fullerene-o-Quinodimethane Bisadducts"J. Chem. Soc. Perkin Trans.. 2. 127-130 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Inokuma: "Synthesis of Crownophanes by Means of Intramolecular [2+2] Photocycloaddition of Styrene Derivatives and Their Complexing Ability"Nippon Kagaku Kaishi. 305-316 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakamura , ed. by Z. Asfari, J. Vice and V. Bohmer: "Homocalixarenes Calixarene 2001"Kluwer Academy Publishers. Ch. 11 219-234 (2001)

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

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Published: 2004-04-14  

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