Abstract
The use of di(2‐pyridyl)ketone in subcomponent self‐assembly is introduced. When combined with a flexible triamine and zinc bis(trifluoromethanesulfonyl)imide, this ketone formed a new Zn4L4 tetrahedron 1 bearing twelve uncoordinated pyridyl units around its metal‐ion vertices. The acid stability of 1 was found to be greater than that of the analogous tetrahedron 2 built from 2‐formylpyridine. Intriguingly, the peripheral presence of additional pyridine rings in 1 resulted in distinct guest binding behavior from that of 2, affecting guest scope as well as binding affinities. The different stabilities and guest affinities of capsules 1 and 2 enabled the design of systems whereby different cargoes could be moved between cages using acid and base as chemical stimuli.
Highlights
We introduce the use of di(2-pyridyl)ketone in subcomponent self-assembly
Cargo delivery from the cavity of one molecular container to another would imitate the sequential transformations in the synthesis of natural products,[14] whereby the intermediate product from one enzymatic transformation becomes the substrate of another enzyme
We hypothesized that di(2-pyridyl)ketone might be employed in place of 2-formylpyridine during the construction of cages by subcomponent self-assembly.[12]
Summary
We introduce the use of di(2-pyridyl)ketone in subcomponent self-assembly. When combined with a flexible triamine and zinc bis(trifluoromethylsulfon)imide, this ketone formed a new Zn4L4 tetrahedron 1 bearing twelve uncoordinated pyridyl units around its metal-ion vertices. Addition of hydrogen bis(trifluoromethane)sulfonimide (triflimidic acid, HNTf2) to an acetonitrile solution of tetrahedron 2 led to the progressive disappearance of the cage peaks along with the appearance of new signals corresponding to free 2formylpyridine (Figures S63 and S64), indicating the disassembly of cage 2 upon acid addition.
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