Self-assembly of a [2]Pseudorota[3]catenane in water

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)

Full text not currently available from Enlighten.

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
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Forgan, Dr 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

University Staff: Request a correction | Enlighten Editors: Update this record