Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 41, Pages 17007-17010Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3085115
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Funding
- U.S. by the National Science Foundation [CHE-0924620]
- U.K. by the Engineering and Physical Sciences Research Council [EP/H003517/1]
- Engineering and Physical Sciences Research Council [EP/H003517/1] Funding Source: researchfish
- EPSRC [EP/H003517/1] Funding Source: UKRI
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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.
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