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.
Original language | English |
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Pages (from-to) | 3154-3161 |
Number of pages | 8 |
Journal | Chemical Science |
Volume | 7 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2016 |
Bibliographical note
Funding Information:We thank Fluorochem for the gift of reagents, the EPSRC National Mass Spectrometry Service for HRMS analysis and the EPSRC (EP/L016621/1), Queen Mary, University of London and the University of Southampton for funding. JEML is a European Commission Marie Sklodowska-Curie Fellow. SMG is a Royal Society Research Fellow. This project has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement No 660731.
Publisher Copyright:
© 2016 The Royal Society of Chemistry.
ASJC Scopus subject areas
- General Chemistry