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Synthesis and molecular recognition of tetraaza[14]annulene complexes containing chiral cavities

Research Project

Project/Area Number 14540517
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Inorganic chemistry
Research InstitutionKyushu Institute of Technology

Principal Investigator

SAKATA Kazunori  Kyushu Institute Of Technology, Faculty of Engineering, Professor, 工学部, 教授 (50037991)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 2002: ¥2,800,000 (Direct Cost: ¥2,800,000)
KeywordsTetraaza[14]annulene / Template reaction / Nickel(II) complexes / Strapped types / Cavities / Chiral / Molecular recognition / amino acids / 取り込み / 旋光度 / DCC
Research Abstract

1)Syntheses of pincers-type tetraaza[ 14]annulenes and theirr nickel(II) complexes (3-L, 3-Ni) -The reaction of tetraaza[14]annulenes or their nickel(II) complexes with p-nitrobenzoyl chloride led to the corresponding 7,16-dibenzoylated compounds (1-L, 1-Ni) in refluxing toluene containing triethylamine. The compounds with amino groups (2-L, 2-Ni) were obtained in reduction of the compounds (1-L, 1-Ni). The reaction between the compounds (2-L, 2-Ni) and amino acids gave pincers-type compounds (3-L, 3-Ni).
2)Syntheses of strapped tetraaza[14]anulenes and their nickel(II) complexes containing chiral cavities (4-L, 4-Ni) -The reaction of the compounds (3-L, 3-Ni) with 2,6-pyridinedi-carboxylchlorides yielded the corresponding strapped tetraaza[14]anulenes and their nickel(II) complexes containing chiral cavities (4-L, 4-Ni).
3)Complexation of pincers-type tetraaza[14]annulenes and their nickel(H) complexes The treatment of the compounds (3-L, 3-Ni) with metal ions (zinc, silver, copper. etc.) offered the corresponding complexes (5-L, 5-Ni).
4)Molecular recognition of strapped tetraaza[14]anulenes and their nickel(II) complexes containing chiral cavities The compounds (4-L, 4-Ni) have-the chiral cavities which include some amino acids. The cavities need the amide groups in them because the formation of hydrogen bonds between the compounds (4-L, 4-Ni) and amino acids is very important for the stability of resulting inclusion compounds. The compounds (4-L, 4-Ni) exhibit the difference in the molecular recognition of D-and L-amino acids by ORD spectra.
5)Discussion on molecular recognition strapped tetraaza[14]anulenes and their nickel(II) complexes containing chirall cavities The results of IR and NMR spectra show week interaction between the compounds (4-L, 4-Ni) and amino acids with hydrogen bonds.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] Yasuhiro Tanoue: "A facile synthesis of naturally occurring binahthoquinones : efficient oxidative dimerization of 4-alkoxy-1-napthols using silver(II) oxide-40% nitric acid"Tetrahedron. 58(1). 99-104 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Akihiko Tsuge: "Preparation and molecular arrangement of novel pyrenophanes"Chem.Lett.. 2002(3). 384-385 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "Synthesis and reaction of novel (tetraaza[14]annulene)nickel(II) complexes with amino groups in their side chains"J.Coord.Chem.. 55(2). 225-239 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Syntheses and characterization of di-and mono-thiocyanato germanium(IV) complexes with 5,14-dihydro-6,8,15,17-tetra-methyldibenzo[b, i][1,4,8,11]tetraazacyclotetradecine"Polyhedron. 21(5). 969-973 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "Preparation spectroscopic properties and characterization of oxo-vanadium(IV) isothiocyanatomanganese(III),cyanocobalt(III),and cobalt(II) complexes with a bis-crown ether tetraaza[14]annulene"J.Coord.Chem.. 55(11). 1283-1291 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "Synthesis and spectral properties off frond(II),copper(I),silver(I),and palladium(II) of a bidentate diisonitrile"Synth.React.Inorg.Met.-Org.Chem.. 33(1). 11-22 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Syntheses, characterization and crystal structures of diamine-bridged dinuclear 5,14-dihydro-6,8,15,17-tetramethyldibenzo[b, i][1,4,8,11]tetraazacyclotetradecinatozinc(II) complexes"Polyhedron. 22(4). 529-534 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Akihiko Tsuge: "Preparation and structural properties of novel fluorenophanes"Chem.Lett.. 32(8). 776-777 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Crystal Structure of a dinuclear 1,2-bis(diphenylphosphinooxide)-ethanebridged(6,8,15,17-tetramethyldibenzo[b, i][1,4,8,11,]tetra-azacycloteradecinatozinc(II)complex"Anal.Sci.. 19(11). x49-x50 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuhiro Tanoue: "Synthesis of 7,10,20,23-tetramethoxy-1,5,14,18-tetraoxa [5,5]-(1,4)naphthaienophane and its structure"ITE Lett.Batt.Tech.Med.. 4(6). 802-805 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Synthesis, characterization, and crystal structures of two trans six-coordinate germanium(IV) complexes of H_2 tmtaa(5,14-dihydro-6,8,15,17-tetramethyldibenzo[b, i][1,4,8,11,]tetraazacyclotetradecine)"Synth.React.Inorg.Met.-Org.Chem.. 34(2). 207-218 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuhiro Tanoue: "A facile synthesis of naturally occurring binaphthoquinones : Efficierit oxidative dimerization of 4-alkoxy-1-naphthols using silver(II) oxide-40% nitric acid"Tetrahedron. 58(1). 99-104 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Akihiko Tsuge: "Preparation and molecular arrangment of navel pyrenophanes"Chem.Lett.. 2002(3). 384-385 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "Synthesis and reaction of novel (tetraaza[14]annulene)nickel(II) complexes with amino groups in their side chains"J.Coord.Chem.. 55(2). 225-239 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Syntheses and characterization of di-and mono-thiocyanato gernianium(IV) complexes with 5,14-dihydro-6,8,15,17-tetramethyldibenzo-[b, i][1,4,8,11]tetraazacyclotetradecine"Polyhedron. 21(5). 969-973 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "PreParation, spectroscopic properties and chaiacterization of oxovanadium(IV), isothiocyanatomanganese(III), cyanocobalt(III) and cobalt(II), complexes with a bis-crown ether tetraaza[14]annulene"J.Coord.Chem.. 55(11). 1283-1291 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "Synthesis and spectral properties of iron(II), copper(I), silver(I), and palladium(II) complexes of a bidentate diisonitrile"Synth.React.Inorg.Met.-Org.Chem.. 33(1). 11-22 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Syntheses, characterization and crystal structures of diamine-bridged dinuclear 5,14-dihydro-6,8,15, 17-teramethyldibenzo[b, i][1,4,8,11]tetraazacyclotetradecinatozinc(II) complexes"Polyhedron. 22(4). 529-534 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Akihiko Tsuge: "Preparation and structural properties of novel fluorenophanes"Chem.Lett.. 32(8). 776-777 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Crystal structure of a dinuclear 1,2-bis(diphenylphosphinooxide)ethane-bridged (6,8,15,17-tetramethyldibenzo[b, i][1,4,8,11]tetra-azacyclotetradecinatozinc(II) complex"Anal.Sci.. 19(11). x49-x50 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Yasuhiro Tanou: "Synthesis of 7,10,20,23-tetramethoxy-1,5,14,18-tetraoxa[5,5](1,4)-napththalenophane and its structure"ITL Lett.Batt.Tech.Med.. 4(6). 802-805 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Xuan Shen: "Syntheses, characterization, and crystal structures of two trans six-coordinate gerrnanium(IV) complexes of.H2tmtaa (5,14-dihydro-6,8,15,17-tetramethyldibenzo[b, i] [1,4,8,11]tetraazacyclotetradecine)"Synth.React.Inorg.Met.-Org.Chem.. 34(2). 207-218 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Kazunori Sakata: "Synthesis and spectral properties of iron(II), copper(I), silver(I), and palladium(II) of a bidentate diisonitrile"Synth.React.Inorg.Met.-Org.Chem.. 33(1). 11-22 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Xuan Shen: "Syntheses, characterization and crystal structures of diamine-bridged dinuclear 5,14-dihydro-6,8,15,17-tetramethyldibnezo[b,i][1,4,8,11]tetraazacyclotetradeinatozinc(II) complexes"Polyhedron. 22(4). 529-534 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Akihiko Tsuge: "Preparation and structural properties of novel fluorenophanes"Chem.Lett.. 32(8). 776-777 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Xuan Shen: "Crystal structure of a dinuclear 1,2-bis(diphenylphosphinooxide)ethanebridged (6,8,15,17-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato)zinc(II) Complex"Anal.Sci.. 19(11). x49-x50 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasuhiro Tanoue: "Synthesis of 7,10,20,23-tetramethoxy-1,5,14,18-tetraoxa[5,5](1,4)-naphthalenophane and its structure"ITE Lett.Batt.Tech.Med.. 4(6). 802-805 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Xuan Shen: "Synthese, characterization, and crystal structures of two trans six-coordinate germanium(IV) complexes of H_2tmtaa (5,14-dihydro-6,8,15,17-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecine)"Synth.React.Inorg.Met.-Org.Chem.. 34(2). 207-218 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasuhiro Tanoue: "A facile synthesis of naturally occurring binaphthoquinones : efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver(II) oxide-40% nitric acid"Tetrahedron. 58(1). 99-104 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Akihiko Tsuge: "Preparation and molecular arrangement of novel pyrenophanes"Chemistry Letters. 2002(3). 384-385 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kazunori Sakata: "Synthesis and reaction of novel (tetraaza[14]annulene)nickel(II) complexes with amino groups in their side chains"J. Coord. Chem.. 55(2). 225-239 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Xuan Shen: "Syntheses and characterization of di-and mono-thiocyanato germanium(IV) complexes with 5,14-dihydro-6,8,15,17-tetramethtyl-dibenzo[b, i][1,4,8,11] tetraazacyclotetradecine"Polyhedron. 21(5). 969-973 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kazunori Sakata: "Preparation, spectroscopic properties and characterization of oxo-vanadium(IV), isothiocyanatomanganese(III), cyanocobalt(III) and cobalt(II) complexes with a bis-crown ether tetraaza[14]annulene"J. Coord. Chem.. 55(11). 1283-1291 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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