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El Aziz, Youssef; Taylor, Peter G.; Bassindale, Alan R.; Coles, Simon J. and Pitak, Mateusz B.
(2016).
DOI: https://doi.org/10.1021/acs.organomet.6b00565
Abstract
The novel coordinate compounds T8[(CH2)n-EWG]8F−-18-crown-6-M+ were prepared by reaction of EWG-(CH2)n-Si(OEt)3 (where n = 1−3 and the electron-withdrawing group, EWG, contains an Si−C(sp3) bond) with an 18-crown-6-M+F− complex (where M+ is K+, Cs+, and Rb+) in the presence of a limited amount of water. The EWG facilitates the formation and encapsulation of the fluoride anion in a silsesquioxane cage. The reaction takes place by complexing an alkali metal in the crown ether, catalyzing silsesquioxane cage formation, and concomitant encapsulation of a fluoride ion within the final T8 cage. The reaction is simple and takes place in a single step with excellent yields of 81−95%. These novel materials have been studied by 19F and 29Si NMR spectroscopy and X-ray crystallography as well as by MALDI-TOF and ESI mass spectrometry. The T8[(CH2)n-EWG]8F−-18-crown-6-M+ compounds can be also synthesized by a facile reaction of 18-crown-6-M+F− with the corresponding T8[(CH2)n-EWG]8 cage in nearly quantitative yield. Surprisingly, the single-crystal X-ray diffraction analysis has revealed the presence of 1D and 3D polymeric complexes of T8[(CH2)n-EWG]8F−-18-crown-6-M+. To the best of our knowledge, this represents the first dual-encapsulation host−octasilsesquioxane system. The results from thermostability experiments monitored by 19F NMR and 1H NMR and DSC suggest that compound T8[CH2CH2(CF2)3CF3]8F−-18-crown-6-K+ is a potential ionic liquid (IL).
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About
- Item ORO ID
- 48419
- Item Type
- Journal Item
- ISSN
- 1520-6041
- Academic Unit or School
-
Faculty of Science, Technology, Engineering and Mathematics (STEM) > Life, Health and Chemical Sciences
Faculty of Science, Technology, Engineering and Mathematics (STEM)
Other Departments > Vice-Chancellor's Office
Other Departments - Copyright Holders
- © 2016 American Chemical Society
- Depositing User
- Peter Taylor