Intramolecular C-H?F hydrogen bondinginduced 1,2,3-triazole-based foldamers

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	Intramolecular C-H?F hydrogen bondinginduced 1,2,3-triazole-based foldamers
	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
刊名	Org. Chem. Front.
	2014
卷号	1 页码:494-500
其他题名	分子内 C-H?F 氢键诱导的1,2,3-三氮唑折叠体
英文摘要	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.
学科主题	物理有机化学
原文出处	http://dx.doi.org/10.1039/c4qo00047a
语种	英语
内容类型	期刊论文
源URL	[http://ir.sioc.ac.cn/handle/331003/39148]
专题	上海有机化学研究所_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
推荐引用方式 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.