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 (Ks′) of these complexes. The Ks′ values were calculated on the basis of the chemical shift changes of the protons in 2 on varying the 1/2 ratio. The Ks′ 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 |
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頁(從 - 到) | 1144-1150 |
頁數 | 7 |
期刊 | Journal of the American Chemical Society |
卷 | 112 |
發行號 | 3 |
DOIs | |
出版狀態 | 已發佈 - 1990 1月 |
對外發佈 | 是 |
ASJC Scopus subject areas
- 催化
- 化學 (全部)
- 生物化學
- 膠體和表面化學