Forgan, R. S. , Gassensmith, J. J., Cordes, D. B., Boyle, M. M., Hartlieb, K. J., Friedman, D. C., Slawin, A. M.Z. and Stoddart, J. F. (2012) Self-assembly of a [2]Pseudorota[3]catenane in water. Journal of the American Chemical Society, 134(41), pp. 17007-17010. (doi: 10.1021/ja3085115)
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Abstract
A donor–acceptor [3]catenane incorporating two cyclobis(paraquat-p-phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C–H···O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.
Item Type: | Articles |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Forgan, Professor Ross |
Authors: | Forgan, R. S., Gassensmith, J. J., Cordes, D. B., Boyle, M. M., Hartlieb, K. J., Friedman, D. C., Slawin, A. M.Z., and Stoddart, J. F. |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | Journal of the American Chemical Society |
Publisher: | American Chemical Society |
ISSN: | 0002-7863 |
ISSN (Online): | 1520-5126 |
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