High yielding synthesis of 2,2 '-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes
File(s)
Published version
Author(s)
Type
Journal Article
Abstract
We present an operationally simple approach to 2,2′-bipyridine macrocycles. Our method uses simple starting materials to produce these previously hard to access rotaxane precursors in remarkable yields (typically >65%) across a range of scales (0.1–5 mmol). All of the macrocycles reported are efficiently converted (>90%) to rotaxanes under AT-CuAAC conditions. With the requisite macrocycles finally available in sufficient quantities, we further demonstrate their long term utility through the first gram-scale synthesis of an AT-CuAAC [2]rotaxane and extend this powerful methodology to produce novel Sauvage-type molecular shuttles.
Date Issued
2016-01-27
Date Acceptance
2016-01-26
Citation
Chemical Science, 2016, 7 (5), pp.3154-3161
ISSN
2041-6520
Publisher
Royal Society of Chemistry
Start Page
3154
End Page
3161
Journal / Book Title
Chemical Science
Volume
7
Issue
5
Copyright Statement
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
ACTIVE-TEMPLATE SYNTHESIS
SWITCHABLE MOLECULAR SHUTTLES
PHOTOPHYSICAL PROPERTIES
ARYL HALIDES
POLYAMINE MACROCYCLES
DIRECTED SYNTHESIS
CRYSTAL-STRUCTURE
TERMINAL ALKYNES
EFFICIENT METHOD
LIGANDS
Publication Status
Published