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Intramolecular C-H?F hydrogen bondinginduced 1,2,3-triazole-based foldamers
其他题名分子内 C-H?F 氢键诱导的1,2,3-三氮唑折叠体
Liu YH(刘艳华)1; Zhang L(张亮)1; Xu XN(徐晓娜)1; Li ZM(李志明)1; Zhang DW(张丹维)1; Zhao X(赵新)1; Li ZT(黎占亭)1
2014
发表期刊Org. Chem. Front.
卷号1页码:494-500
摘要This paper reports the first series of artificial secondary structures that are induced by intermolecular C–H?F hydrogen bonding. Oligomers that contain two, four, six, and eight 1,2,3-triazole units have been designed and prepared by connecting the neighbouring 1,2,3-triazole units with 4,6-difluoro-m-phenylene linker(s). Two triphenylmethyl groups are appended at the ends of the backbones to suppress the stacking of the backbones and provide solubility. X-Ray analysis and 1H NMR and two-dimensional 1H–19F heteronuclear Overhauser enhancement spectroscopic (HOESY) experiments support that the 1,2,3-triazole backbones adopt folded or helical conformations due to the formation of continuous three-centred C–H?F hydrogen bonding. Quantum chemical calculations reveal that the longest 8-mer foldamer can form a one-turn helical cavity with a diameter of ca. 1.7 nm. Halide anion competition experiments show that the intramolecular C–H?F hydrogen bonding is more stable than the well-established intermolecular C–H?X? (X = Cl and I) hydrogen bonding.
学科领域物理有机化学
DOI10.1039/c4qo00047a
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语种英语
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被引频次:15[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/331003/39148
专题物理有机化学研究室
作者单位1.中科院上海有机化学研究所
2.复旦大学
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GB/T 7714
Liu YH,Zhang L,Xu XN,et al. Intramolecular C-H?F hydrogen bondinginduced 1,2,3-triazole-based foldamers[J]. Org. Chem. Front.,2014,1:494-500.
APA 刘艳华.,张亮.,徐晓娜.,李志明.,张丹维.,...&黎占亭.(2014).Intramolecular C-H?F hydrogen bondinginduced 1,2,3-triazole-based foldamers.Org. Chem. Front.,1,494-500.
MLA 刘艳华,et al."Intramolecular C-H?F hydrogen bondinginduced 1,2,3-triazole-based foldamers".Org. Chem. Front. 1(2014):494-500.
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