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 - http://www.scopus.com/inward/record.url?scp=0346732166&partnerID=8YFLogxK
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 -