安装棘轮齿和棘爪以限制环糊精轮烷中的旋转。

Installation of a ratchet tooth and pawl to restrict rotation in a cyclodextrin rotaxane.

作者信息

Onagi Hideki, Blake Christopher J, Easton Christopher J, Lincoln Stephen F

机构信息

Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra ACT 0200, Australia.

出版信息

Chemistry. 2003 Dec 15;9(24):5978-88. doi: 10.1002/chem.200305280.

DOI:10.1002/chem.200305280

PMID:14679510

Abstract

Eight new [2]rotaxanes have been prepared, incorporating an alpha-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.

摘要

已制备出八种新型[2]轮烷，其中包含α-环糊精作为转子、芪作为轴以及三硝基苯基取代基作为封端基团。已设计出通过将转子与轴相连来对这些进行精细加工的策略，以制备出两种新型[1]轮烷。通过进行TOCSY、DQF-COSY、ROESY和HMQC实验，应用二维核磁共振光谱对这些轮烷中的一部分的旋转运动进行了研究。结果表明，芪上引入的甲氧基以及连接芪和环糊精的琥珀酰胺分别类似于棘齿和棘爪，起到限制旋转的作用。