Dynamic [2]catenanes based on a hydrogen bonding-mediated bis-zinc porphyrin foldamer tweezer: A case study

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	Dynamic [2]catenanes based on a hydrogen bonding-mediated bis-zinc porphyrin foldamer tweezer: A case study
	Wu J(邬静) ; Hou JL(侯军利) ; Li C(李闯) ; Wu ZQ(吴宗铨) ; Jiang XK(蒋锡夔) ; Li ZT(黎占亭) ; Yu YH(余亦华)
刊名	J. Org. Chem.
	2007
卷号	72 期号:8 页码:2897-2905
ISSN号	0022-3263
其他题名	基于氢键介质的双锌卟啉折叠体分子镊的动态[2]索烃组装：一个案例研究
通讯作者	黎占亭 ; 余亦华
英文摘要	This paper describes the self-assembly of a new class of three-component dynamic [2]catenanes, which are driven or stabilized by intramolecular hydrogen bonding, coordination, and electrostatic interaction. One of the component molecules 2, consisting of an aromatic oligoamide spacer and two peripheral zinc porphyrin units, was designed to adopt a folded preorganized conformation, which is stabilized by consecutive intramolecular three-centered hydrogen bonds. Component molecule 3 is a linear secondary ammonium bearing two peripheral pyridine units, which was designed to form a 1:1 complex with 24-crown-8 (5). The H-1 NMR and UV-vis experiments in CDCl3-CD3CN (4:1 v/v) revealed that, due to the preorganized U-shaped feature, 2 could efficiently bind 3 through the cooperative zinc-pyridine coordination to generate highly stable 1:1 complex 2 center dot 3. Adding 5 to the 1:1 solution of 2 and 3 led to the formation of dynamic three-component [2]catenane 2 center dot 3 center dot 5 as a result of the threading of 3 through 5. H-1 NMR studies indicated that in the 1:1:1 solution (3 mM) [2]catenane 2 center dot 3 center dot 5 was generated in 55% yield at 25 degrees C. The yield was increased with the reduction of the temperature and [2]catenane could be produced quantitatively in a 1:1:2 solution ([2] = 3 mM) at -13 degrees C. Replacing 3 with 1,2-bis(4,4'-bipyridinium)ethane (4) in the three-component solution could also give rise to similar dynamic [2]catenane 2 center dot 4 center dot 5 albeit in slightly lower yield.
学科主题	物理有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo062523g
语种	英语
WOS记录号	WOS:000245510600022
公开日期	2013-01-16
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/12704]
专题	上海有机化学研究所_物理有机化学研究室
推荐引用方式 GB/T 7714	Wu J,Hou JL,Li C,et al. Dynamic [2]catenanes based on a hydrogen bonding-mediated bis-zinc porphyrin foldamer tweezer: A case study[J]. J. Org. Chem.,2007,72(8):2897-2905.
APA	邬静.,侯军利.,李闯.,吴宗铨.,蒋锡夔.,...&余亦华.(2007).Dynamic [2]catenanes based on a hydrogen bonding-mediated bis-zinc porphyrin foldamer tweezer: A case study.J. Org. Chem.,72(8),2897-2905.
MLA	邬静,et al."Dynamic [2]catenanes based on a hydrogen bonding-mediated bis-zinc porphyrin foldamer tweezer: A case study".J. Org. Chem. 72.8(2007):2897-2905.