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

含手性空腔的四氮杂[14]轮烯配合物的合成与分子识别

基本信息

批准号：
14540517
负责人：
SAKATA Kazunori
金额：
$ 2.3万
依托单位：
Kyushu Institute of Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2002
资助国家：
日本
起止时间：
2002 至 2003
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-14540517/
关键词：
Tetraaza[14]annulene Template reaction Nickel(II) complexes Strapped types Cavities Chiral Molecular recognition amino acids 取り込み旋光度 DCC

项目摘要

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.

1)钳型四氮杂[14]环烯及其镍（II）配合物（3-L, 3-Ni）的合成——四氮杂[14]环烯或其镍（II）配合物与对硝基苯甲酰氯反应，在含三乙胺的回流甲苯中生成相应的7,16-二苯甲酰化化合物（1- l,1 -ni）。由化合物（1-L, 1-Ni）还原得到含有氨基（2-L, 2-Ni）的化合物。化合物（2-L, 2-Ni）与氨基酸反应得到钳型化合物（3-L, 3-Ni）。2)带链四氮杂[14]环烯及其含手性空腔（4-L, 4-Ni）镍（II）配合物的合成——化合物（3-L, 3-Ni）与2,6-吡啶-羧基氯化物反应生成相应的带链四氮杂[14]环烯及其含手性空腔（4-L, 4-Ni）镍（II）配合物。钳型四氮环烯及其镍(H)配合物的络合（3- l, 3- ni）与金属离子（锌，银，铜）的处理。等)提供了相应的配合物（5-L, 5-Ni）。4)带链四氮杂环烯及其含手性空腔的镍（II）配合物的分子识别。化合物（4- l, 4- ni）具有含一些氨基酸的手性空腔。这些空腔需要酰胺基团，因为化合物（4-L, 4-Ni）和氨基酸之间氢键的形成对最终包合化合物的稳定性非常重要。化合物（4-L, 4-Ni）对d -和l -氨基酸的分子识别存在差异。4-L、4-Ni与具有手性空腔的氨基酸之间的分子识别研究。红外光谱和核磁共振光谱结果表明，化合物（4-L、4-Ni）与具有氢键的氨基酸之间存在明显的相互作用。