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921930-28-1

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3
Homo- and Hetero-[3]Rotaxanes with Two -Systems Clasped in a Single
Macrocycle

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1. Homo- and Hetero-[3]Rotaxanes with Two -Systems Clasped in a Single Macrocycle

By: Klotz, Eric J. F.; Claridge, Tim D. W.; Anderson, Harry L.
Source: Journal of the American Chemical
ISSN: 0002-7863, DOI: 10.1021/ja0665139

Society,

Volume: 128, Issue: 48, Pages: 15374-15375, Journal, 2006, CODEN: JACSAT,

Company/Organization: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK, OX1 3TA
Accession Number: 2006:1194689, CAN 146:122210, CAPLUS
Publisher: American Chemical Society
Language: English

Abstract
Here we present the first synthesis of a [3]rotaxane with two dumbbell components threaded through a single cyclodextrin macrocycle. This synthesis is carried out in two steps: first one dumbbell is synthesized threaded through
the macrocycle to give a [2]rotaxane, then a second dumbbell is synthesized through the remaining cavity of the
[2]rotaxane. We have synthesized a hetero-[3]rotaxane with one stilbene and one cyanine dye threaded through cyclodextrin, which exhibits quant. energy transfer between the two encapsulated dyes. The stilbene [2]rotaxane
intermediate in this synthesis has a remarkably high affinity for suitably shaped hydrophobic guests in aq. soln.,
facilitating the synthesis of [3]rotaxanes and suggesting possible applications in sensors.

Indexing
Carbohydrates (Section 33-4)
Section cross-reference(s):22, 25, 41
Concepts
Oligosaccharides
cyclic; prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle
Formation, unclassified; Properties; Synthetic preparation; Formation, nonpreparative; Preparation
Dyes
Energy transfer
Sensors
prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle

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Rotaxanes
prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle
Formation, unclassified; Properties; Reactant; Synthetic preparation; Formation, nonpreparative; Preparation; Reactant
or reagent
Inclusion compounds
prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle
Formation, unclassified; Properties; Synthetic preparation; Formation, nonpreparative; Preparation
Substances
918410-57-8P
prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle
Properties; Synthetic preparation; Preparation
563-80-4 Isopropylmethyl ketone
14047-29-1
17878-23-8
20766-56-7
73183-34-3
338793-56-9
prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle
Reactant; Reactant or reagent
540-37-4P
13116-27-3P
918410-53-4P
918410-55-6P
918410-59-0P
918410-60-3P
918410-61-4P
918410-62-5P
918410-63-6P
918410-64-7P
921930-28-1P

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prepn. of homo- and hetero-rotaxane inclusion compds. with cyclodextrins with two -systems clasped in single
macrocycle
Reactant; Synthetic preparation; Preparation; Reactant or reagent
Supplementary Terms
rotaxane macrocycle cyclodextrin inclusion prepn stilbene cyanine dye sensor
Citations
1)Arunkumar, E; Eur J Org Chem 2005, 4051
2)Craig, M; Angew Chem, Int Ed 2001, 40, 1072
3)Stanier, C; Chem Commun 2001, 493
4)Wenz, G; Chem Rev 2006, 106, 782
5)Harada, A; Acc Chem Res 2001, 34, 456
6)Sauvage, J; Molecular Catenanes, Rotaxanes and Knots:A Journey through the World of Molecular Topology 1999
7)Ueno, A; J Chem Soc, Chem Commun 1980, 921
8)Herrmann, W; Chem Commun 1997, 1709
9)Herrmann, W; Angew Chem, Int Ed Engl 1997, 36, 2511
10)Roa, K; J Org Chem 1999, 64, 8098
11)Kim, J; J Am Chem Soc 2000, 122, 540
12)Kim, H; Angew Chem, Int Ed 2001, 40, 1526
13)Amirsakis, D; Angew Chem, Int Ed 2001, 40, 4256
14)Lin, C; J Org Chem 2002, 67, 7761
15)Murphy, S; J Org Chem 1995, 60, 2411
16)Hamer, F; J Org Chem 1995, 60, 2411
17)Ishiyama, T; Tetrahedron 2001, 57, 9813
18)Hwang, T; J Am Chem Soc 2001, 57, 9813
19)Melthuish, W; J Phys Chem 1961, 65, 229
20)Magde, D; J Phys Chem 1979, 83, 696
21)Bourson, J; J Phys Chem 1989, 93, 3871
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