Synthesis and Selective Molecular Recognition of a Macrotricyclic Receptor Having Crown Ether and Cyclophane Subunits as Binding Sites

Kazuhiko Saigo, Nobuhiro Kihara, Yukihiko Hashimoto, Ru-Jang Lin, Hiroshi Fujimura, Yoshihiro Suzuki, Masaki Hasegawa

研究成果: 雜誌貢獻文章同行評審

33 引文 斯高帕斯(Scopus)

摘要

The synthesis and selective molecular recognition of a new type of cylindrical, macrotricyclic receptor (1) having crown ether and cyclophane subunits as binding sites and a large hydrophobic cavity are described. Receptor 1 was synthesized by the stepwise construction of three individually prepared subunits: bis(p-toIuenesulfonamido)dibenzo-18-crown-6 (6); diaminocyclophane (7); ethyl 4′-(bromomethyl)biphenyl-4-carboxylate (8). The interaction of 1 and various (ω-phenylalkyl) ammonium picrates 2, for which the number of methylene units varies from 3 to 9, was examined, and they were found to form 1/1 complexes. The selectivity of 1 for 2 was evaluated by comparing the stability constants (K s ′) of these complexes. The K s ′ values were calculated on the basis of the chemical shift changes of the protons in 2 on varying the 1/2 ratio. The K s ′ values of the complexes with (5-phenylpentyl)ammonium (2c) and (6-phenylhexyl)ammonium picrates (2d) were more than 3 times as large as those of the other complexes; i.e., 1 showed selective molecular recognition for 2. The selectivity could result from a cooperative phenomenon involving the electrostatic and hydrophobic interactions between the crown ether subunit and the ammonium group and between the cyclophane subunit and the phenyl group, respectively.

原文英語
頁(從 - 到)1144-1150
頁數7
期刊Journal of the American Chemical Society
112
發行號3
DOIs
出版狀態已發佈 - 1990 一月 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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