A molecular shuttle for driving a multilevel fluorescence switch

doi:10.1002/chem.200701105

CORC > 化学研究所 > 中国科学院化学研究所

	A molecular shuttle for driving a multilevel fluorescence switch
	Zhou, Weidong; Li, Junbo; He, Xiaorong; Li, Cuihong; Lv, Jing; Li, Yuliang; Wang, Shu; Liu, Huibiao; Zhu, Daoben
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2008
卷号	14 期号:2 页码:754-763
关键词	Fluorescence Molecular Devices Rotaxanes Supramolecular Chemistry Template Synthesis
ISSN号	0947-6539
DOI	10.1002/chem.200701105
英文摘要	A [2] rotaxane -based molecular shuttle comprised a macrocycle mechanically interlocked to a chemical "dumbbell" has been prepared in high yields by a thermodynamically controlled, template-induced clipping procedure. This molecular shuttle has two different recognition sites, namely, NH2+- and amide, separated by a phenyl unit. The macrocycle exhibits high selectivity for the -NH2+- recognition sites in the protonated form through noncovalent interactions, which include 1) N+-H...O. hydrogen bonds; 2) C-H...O interactions between the CH2NH2+CH2, protons on the thread and the oligo(ethylene glycol) unit in the macrocycle; 3) pi...pi. a stacking interaction between macrocycle and aromatic unit. Upon deprotonation of the [2]rotaxane the macrocycle glides to the amide recognition site due to the hydrogen bonds between the -CONH- group and the oligo(ethylene glycol) unit in the macrocycle. The deprotonation process requires about 10 equivalents of base (iPr(2),NEt) in polar acetone, while the amount of base is only 1.2 equivalents in apolar tetrachloroethane. Upon addition of Li+, the conformation of the [2]rotaxane was altered as a result of the collective interactions of 1) hydrogen bonds between pyridine nitrogen and amide hydrogen atoms; 2) coordination between the oligo(ethylene glycol) unit, amide oxygen atom and Li+ cation. Then, when Zn2+ ions are added, the macrocycle returns to the deprotonated -NH- recognition site owing to coordination of the macrocycle and -NH- from the axle with the Zn2+ ion. All the above-mentioned movement processes are reversible through the alternate addition of TFA/iPr(2)NEt, Li/[12]-crown-4 and Zn2+/ethylenediaminetetraacetate (EDTA), by virtue of hydrogen bonding and metalion complexation. Significantly, the three independent movement processes are all accompanied by fluorescent responses: 1) complete repression in the protonated form; 2) low-level expression in the deprotonated form; 3) medium-level expression following addition of Li+; 4) high-level expression on complexation with Zn2+.
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000252457600033
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/64247]
专题	中国科学院化学研究所
通讯作者	Li, Yuliang
作者单位	Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Key Lab Organ Solid, Beijing 100080, Peoples R China
推荐引用方式 GB/T 7714	Zhou, Weidong,Li, Junbo,He, Xiaorong,et al. A molecular shuttle for driving a multilevel fluorescence switch[J]. CHEMISTRY-A EUROPEAN JOURNAL,2008,14(2):754-763.
APA	Zhou, Weidong.,Li, Junbo.,He, Xiaorong.,Li, Cuihong.,Lv, Jing.,...&Zhu, Daoben.(2008).A molecular shuttle for driving a multilevel fluorescence switch.CHEMISTRY-A EUROPEAN JOURNAL,14(2),754-763.
MLA	Zhou, Weidong,et al."A molecular shuttle for driving a multilevel fluorescence switch".CHEMISTRY-A EUROPEAN JOURNAL 14.2(2008):754-763.