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Solvophobically-driven oligo(ethylene glycol) helical foldamers. Synthesis, characterization, and complexation with ethane-1,2-diaminium
其他题名疏溶剂作用驱动的寡聚乙二醇螺旋体:合成、鉴定及对乙二铵络合作用
Hou JL(侯军利); Jiang XK(蒋锡夔); Li ZT(黎占亭); Jia MX(贾木欣); Chen GJ(陈光巨)
2004
发表期刊J. Org. Chem.
ISSN0022-3263
卷号69期号:19页码:6228-6237
摘要Oligo(ethylene glycols) la-h, which are incorporated with one to eight 2,3-naphthylene units, respectively, have been synthesized and characterized. The conformational changes of the new oligomers have been investigated in chloroform- acetonitrile binary solvents by the LTV-vis, H-1 NMR, and fluorescent spectroscopy. It has been revealed that the naphthalene units in hexamer 1f, heptamer 1g, and octamer 1h are driven by solvophobic interaction to stack in polar solvents. As a result, compact helical conformations are formed that give rise to a cavity similar to that of 18-crown-6. Shorter oligomers 1b-e exhibit weaker folding tendency. H-1 NMR studies reveal that 1f-h are able to complex ammonium or ethane-1,2-diaminium 19, but not secondary ammonium compounds. The association constants of complexes 1f(.)19, 1g(.)19, and 1h(.)19 in acetonitrile are determined to be 3.5(+/-0.4) x 10(3), 1.0(+/-0.12) x 10(4), and 2.5(+/-0.4) x 10(4) M-1, respectively, with the H-1 NMR titration method. For comparison, hexamer 22, which incorporates six 1,5-naphthylene units, is also prepared. The LTV-vis and fluorescent investigations show that 22 is also able to fold in polar solvents, but no helical structure can be produced due to mismatch of the stacking naphthalene units and consequently there is no obvious complexation between 22 with ethane-1,2-diaminium ion. The structures of the longest foldamer 1h and its complex with 19 have been studied with molecular mechanics calculations. This work represents a new approach to building folding conformations from flexible linear molecules.
学科领域物理有机化学
部门归属中国科学院上海有机化学研究所物理有机化学研究室; 北京师范大学
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收录类别SCI
语种英语
WOS记录号WOS:000223897700008
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被引频次:34[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/12654
专题物理有机化学研究室
通讯作者Li ZT(黎占亭); Chen GJ(陈光巨)
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GB/T 7714
Hou JL,Jiang XK,Li ZT,et al. Solvophobically-driven oligo(ethylene glycol) helical foldamers. Synthesis, characterization, and complexation with ethane-1,2-diaminium[J]. J. Org. Chem.,2004,69(19):6228-6237.
APA 侯军利,蒋锡夔,黎占亭,贾木欣,&陈光巨.(2004).Solvophobically-driven oligo(ethylene glycol) helical foldamers. Synthesis, characterization, and complexation with ethane-1,2-diaminium.J. Org. Chem.,69(19),6228-6237.
MLA 侯军利,et al."Solvophobically-driven oligo(ethylene glycol) helical foldamers. Synthesis, characterization, and complexation with ethane-1,2-diaminium".J. Org. Chem. 69.19(2004):6228-6237.
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