NDLI: Intramolecular C–H⋯F hydrogen bonding-induced 1,2,3-triazole-based foldamers

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Intramolecular C–H⋯F hydrogen bonding-induced 1,2,3-triazole-based foldamers

Content Provider	Semantic Scholar
Author	Liu, Yan-Hua Zhang, Liang Xu, Xiao-Na Li, Zhiming Zhang, Dan-Wei Zhao, Xin Li, Zhan-Ting
Copyright Year	2014
Abstract	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.
Starting Page	494
Ending Page	500
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1039/C4QO00047A
Alternate Webpage(s)	https://pubs.rsc.org/en/content/getauthorversionpdf/C4QO00047A
Alternate Webpage(s)	https://doi.org/10.1039/C4QO00047A
Volume Number	1
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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