Neutral molecule receptor systems using ferrocene's ''atomic ball bearing'' character as the flexible element

被引:65
作者
Li, CS
Medina, JC
Maguire, GEM
Abel, E
Atwood, JL
Gokel, GW
机构
[1] UNIV MISSOURI, DEPT CHEM, COLUMBIA, MO 65211 USA
[2] UNIV MIAMI, DEPT CHEM, CORAL GABLES, FL 33124 USA
[3] WASHINGTON UNIV, SCH MED, BIOORGAN CHEM PROGRAM, ST LOUIS, MO 63110 USA
[4] WASHINGTON UNIV, SCH MED, DEPT MOL BIOL & PHARMACOL, ST LOUIS, MO 63110 USA
关键词
D O I
10.1021/ja9600284
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Fourteen novel ferrocene derivatives have been designed to serve as receptors for low molecular weight diamines. The compounds that have been prepared and fully characterized possess two ferrocenedicarboxylic acid residues bridged by amide formation in their respective 1'-positions by 4,4'-benzidinyl (15), 3,3'-dimethoxy-4,4'-benzidinyl (16), 2,7-fluorenyl (17), 3-methoxy-2,7-fluorenyl (18), 4-N-piperazinoanilinyl (19), N,N-4,4'-bipiperdinyl (20), and 4,13-diaza-18-crown-6 (21). In two cases, ferrocenecarboxylic acid was bridged by spacers attached using l-methylene groups. The bridges in these cases were 4,13-diaza-18-crown-6 (22) and 1,5-diaminoanthraquinone (24). In a single case, ferrocenecarboxylic acid was bridged by 1,5-dicarbonylnaphthalene (25). In one additional case, the bridge was created by formation of an imine followed by hydrogenation, but both compounds (26, 27) proved to be relatively unstable. Attempts to increase solubility afforded the N-ethylated derivative 28 of 15 and the derivative 29 of 27 having carboxamides in the 1'-positions. A solid state structure of the diethyl ester of 20 confirms the design criteria. Complexation constants were determined in THF-d(8) or CDCl3 for combinations of receptors 18, 19, and 20 with 4-aminopyridine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetramethylpropylenediamine, DABCO, 3-propyladenine, and benzimidazole and were in the range 10(2)-10(4). The anticipated complexation mechanism for 20 with N,N,N',N'-tetramethylpropylenediamine was confirmed by observation of an NOE between host and guest.
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页码:1609 / 1618
页数:10
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