Synthesis of [1]rotaxane via covalent bond formation and its unique fluorescent response by energy transfer in the presence of lithium ion

被引:135
作者
Hiratani, K
Kaneyama, M
Nagawa, Y
Koyama, E
Kanesato, M
机构
[1] Utsunomiya Univ, Dept Appl Chem, Utsunomiya, Tochigi 3218585, Japan
[2] Natl Inst Adv Ind Sci & Technol, Nanoarchitecton Res Ctr, Tsukuba, Ibaraki 3058562, Japan
关键词
D O I
10.1021/ja046929r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Although there have been a lot of reports on the synthesis and properties of [n]rotaxanes (mainly n = 2), only a few reports on the synthesis of [1]rotaxane has been published by Vögtle's group and others (see ref 5). Generally speaking, [1]rotaxane might be expected to exhibit properties different from other rotaxanes, because the rotor and the axle in the [1]rotaxane is bound covalently and closely. We report on a novel method to make [1]rotaxanes via covalent bond formation from a macrocyclic compound. That is, we first prepared a bicyclic compound from macrocycle and then proceeded to [1]rotaxane by aminolysis. This is the first synthetic example of preparation of [1]rotaxane via covalent bond formation, not utilizing weak interactions such as hydrogen bonding, charge transfer, via metal complexation, etc. This method might provide a powerful and new tool for construction of [1]rotaxane as a new supramolecular system. In addition, we investigated energy transfer from rotor to axle using [1]rotaxane that we prepared. Energy transfer occurred perfectly from the naphthalene ring of the rotor to the anthracene ring of the axle. We found also that only lithium ion among alkali ions can drastically enhance the fluorescence intensity. This finding could be applicable to ion-sensing systems, switching devices, and so on. Copyright © 2004 American Chemical Society.
引用
收藏
页码:13568 / 13569
页数:2
相关论文
共 16 条
[1]   Simple mechanical molecular and supramolecular machines: Photochemical and electrochemical control of switching processes [J].
Ashton, PR ;
Ballardini, R ;
Balzani, V ;
Boyd, SE ;
Credi, A ;
Gandolfi, MT ;
GomezLopez, M ;
Iqbal, S ;
Philp, D ;
Preece, JA ;
Prodi, L ;
Ricketts, HG ;
Stoddart, JF ;
Tolley, MS ;
Venturi, M ;
White, AJP ;
Williams, DJ .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (01) :152-170
[2]   A built-in route leading to a self-inclusion complex of 6(A),6(B)-(bis-O-p-allyloxyphenyl)hexakis(2,3-di-O-methyl)-alpha-cylodextrin [J].
Chen, Z ;
Bradshaw, JS ;
Habata, Y ;
Lee, ML .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (03) :983-987
[3]   SYNTHESIS OF MACROCYCLIC POLYETHER COMPOUNDS DERIVED FROM 1,10-PHENANTHROLINE 2,9-DIPHENYL [J].
DIETRICHBUCHECKER, CO ;
SAUVAGE, JP .
TETRAHEDRON LETTERS, 1983, 24 (46) :5091-5094
[4]   Synthesis and characterization of the first pair of an unlocked and a locked self-inclusion complex from a permethylated α-cyclodextrin derivative [J].
Fukuhara, G ;
Fujimoto, T ;
Kaneda, T .
CHEMISTRY LETTERS, 2003, 32 (06) :536-537
[5]   A new synthetic method for rotaxanes via tandem Claisen rearrangement, diesterification, and aminolysis [J].
Hiratani, K ;
Suga, J ;
Nagawa, Y ;
Houjou, H ;
Tokuhisa, H ;
Numata, M ;
Watanabe, K .
TETRAHEDRON LETTERS, 2002, 43 (33) :5747-5750
[6]   Tandem claisen rearrangement: A novel, one-step synthesis of calixarene analogues from macrocyclic polyethers [J].
Hiratani, K ;
Kasuga, K ;
Goto, M ;
Uzawa, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12677-12678
[7]   SYNTHESIS AND STRUCTURE ELUCIDATION OF A NEW [2]-CATENANE [J].
HUNTER, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5303-5311
[8]  
Ishow E, 1999, CHEM-EUR J, V5, P984, DOI 10.1002/(SICI)1521-3765(19990301)5:3<984::AID-CHEM984>3.0.CO
[9]  
2-T
[10]  
Jager R, 1996, LIEBIGS ANN, P1201