Installation of a Ratchet Tooth and Pawl to Restrict Rotation in a Cyclodextrin Rotaxane

Hideki Onagi; Christopher J. Blake; Christopher J. Easton; Stephen F. Lincoln

doi:10.1002/chem.200305280

Installation of a Ratchet Tooth and Pawl to Restrict Rotation in a Cyclodextrin Rotaxane

Hideki Onagi, Christopher J. Blake, Christopher J. Easton^*, Stephen F. Lincoln

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

66 Citations (Scopus)

Abstract

Eight new [2]rotaxanes have been prepared, incorporating an α-cyclodextrin as the rotor, a stilbene as the axle, and trinitrophenyl substituents as capping groups. Strategies have been devised to elaborate these by linking the rotor to the axle, to produce two new [1]rotaxanes. Rotational motion in a selection of these rotaxanes has been investigated through the application of two-dimensional NMR spectroscopy by performing TOCSY, DQF-COSY, ROESY and HMQC experiments. This has shown that a methoxyl group incorporated on the stilbene and a succinamide joining the stilbene and the cyclodextrin behave analogously to a ratchet tooth and pawl, respectively, to restrict rotation.

Original language	English
Pages (from-to)	5978-5988
Number of pages	11
Journal	Chemistry - A European Journal
Volume	9
Issue number	24
DOIs	https://doi.org/10.1002/chem.200305280
Publication status	Published - 15 Dec 2003

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title = "Installation of a Ratchet Tooth and Pawl to Restrict Rotation in a Cyclodextrin Rotaxane",

abstract = "Eight new [2]rotaxanes have been prepared, incorporating an α-cyclodextrin as the rotor, a stilbene as the axle, and trinitrophenyl substituents as capping groups. Strategies have been devised to elaborate these by linking the rotor to the axle, to produce two new [1]rotaxanes. Rotational motion in a selection of these rotaxanes has been investigated through the application of two-dimensional NMR spectroscopy by performing TOCSY, DQF-COSY, ROESY and HMQC experiments. This has shown that a methoxyl group incorporated on the stilbene and a succinamide joining the stilbene and the cyclodextrin behave analogously to a ratchet tooth and pawl, respectively, to restrict rotation.",

keywords = "Cyclodextrins, Molecular devices, Molecular dynamics, NMR spectroscopy, Rotaxanes",

author = "Hideki Onagi and Blake, \{Christopher J.\} and Easton, \{Christopher J.\} and Lincoln, \{Stephen F.\}",

year = "2003",

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doi = "10.1002/chem.200305280",

language = "English",

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TY - JOUR

T1 - Installation of a Ratchet Tooth and Pawl to Restrict Rotation in a Cyclodextrin Rotaxane

AU - Onagi, Hideki

AU - Blake, Christopher J.

AU - Easton, Christopher J.

AU - Lincoln, Stephen F.

PY - 2003/12/15

Y1 - 2003/12/15

N2 - Eight new [2]rotaxanes have been prepared, incorporating an α-cyclodextrin as the rotor, a stilbene as the axle, and trinitrophenyl substituents as capping groups. Strategies have been devised to elaborate these by linking the rotor to the axle, to produce two new [1]rotaxanes. Rotational motion in a selection of these rotaxanes has been investigated through the application of two-dimensional NMR spectroscopy by performing TOCSY, DQF-COSY, ROESY and HMQC experiments. This has shown that a methoxyl group incorporated on the stilbene and a succinamide joining the stilbene and the cyclodextrin behave analogously to a ratchet tooth and pawl, respectively, to restrict rotation.

AB - Eight new [2]rotaxanes have been prepared, incorporating an α-cyclodextrin as the rotor, a stilbene as the axle, and trinitrophenyl substituents as capping groups. Strategies have been devised to elaborate these by linking the rotor to the axle, to produce two new [1]rotaxanes. Rotational motion in a selection of these rotaxanes has been investigated through the application of two-dimensional NMR spectroscopy by performing TOCSY, DQF-COSY, ROESY and HMQC experiments. This has shown that a methoxyl group incorporated on the stilbene and a succinamide joining the stilbene and the cyclodextrin behave analogously to a ratchet tooth and pawl, respectively, to restrict rotation.

KW - Cyclodextrins

KW - Molecular devices

KW - Molecular dynamics

KW - NMR spectroscopy

KW - Rotaxanes

UR - https://www.scopus.com/pages/publications/0346732166

U2 - 10.1002/chem.200305280

DO - 10.1002/chem.200305280

M3 - Article

SN - 0947-6539

VL - 9

SP - 5978

EP - 5988

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 24

ER -

Installation of a Ratchet Tooth and Pawl to Restrict Rotation in a Cyclodextrin Rotaxane

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