Self-Assembly of a [2]Pseudorota[3]catenane in Water

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-ric...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-10, Vol.134 (41), p.17007-17010
Main Authors: Forgan, Ross S, Gassensmith, Jeremiah J, Cordes, David B, Boyle, Megan M, Hartlieb, Karel J, Friedman, Douglas C, Slawin, Alexandra M. Z, Stoddart, J. Fraser
Format: Article
Language:English
Subjects:
Anthracenes - chemistry
Models, Molecular
Water - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3085115