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

Ross S. Forgan, Jeremiah J. Gassensmith, David Bradford Cordes, Megan M. Boyle, Karel J. Hartlieb, Douglas C. Friedman, Alexandra Martha Zoya Slawin, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p-phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a pi-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a pi-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 center dot center dot center dot 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.

Original languageEnglish
Pages (from-to)17007-17010
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number41
DOIs
Publication statusPublished - 17 Oct 2012

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