Reversible covalent bonds play a significant role in achieving the high‐yielding synthesis of mechanically interlocked molecules. Still, only a handful of such bonds have been successfully employed in synthetic procedures. Herein, we introduce a novel approach for the fast and simple preparation of interlocked molecules, combining the dynamic bond character of bis(acyloxy)iodate(I) anions with macrocyclic bambusuril anion receptors. The proof of principle was demonstrated on rotaxane synthesis, with near‐quantitative yields observed in both the classical and “in situ” approach. The rotaxane formation was confirmed in the solid‐state and solution by the X‐ray and NMR studies. Our novel approach could be utilized in the fields of dynamic combinatorial chemistry, supramolecular polymers, or molecular machines, as well inspire further research on molecules that exhibit dynamic behavior, but owing to their high reactivity, have not been considered as constituents of more elaborate supramolecular structures.
Reversible covalent bonds play as ignificant role in achieving the high-yielding synthesis of mechanically interlocked molecules.Still, only ahandful of such bonds have been successfully employed in synthetic procedures.H erein, we introduce anovel approach for the fast and simple preparation of interlocked molecules,c ombining the dynamic bond character of bis(acyloxy)iodate(I) anions with macrocyclic bambusuril anion receptors.T he proof of principle was demonstrated on rotaxane synthesis,w ith near-quantitative yields observed in both the classical and "in situ" approach. The rotaxane formation was confirmed in the solid-state and solution by the X-raya nd NMR studies.O ur novel approach could be utilized in the fields of dynamic combinatorial chemistry,s upramolecular polymers,o rm olecular machines, as well inspire further researcho nm olecules that exhibit dynamic behavior,b ut owing to their high reactivity,h ave not been considered as constituents of more elaborate supramolecular structures.
Monofunctionalization of cucurbiturils is essential for transferring these potent supramolecular macrocyclic hosts into realworld application. Here, we present the synthesis of cucurbit[6] urils 1 and 2 in which one methylene bridge is modified by a single substituent containing a nitro or an ammonium group. We investigated host-guest properties in water and 0.2 M NaCl using 1 H NMR and isothermal titration calorimetry, particularly for 2. The macrocycle 2 self-associated into dimeric aggregates in pure water, but readily disassembled in the presence of NaCl or organic cations. Cucurbit[7]uril was able to encapsulate the ammonium substituent of 2 inside its cavity resulting in a complex of 1 : 1 stoichiometry with an association constant of 3.1 × 10 5 M À 1 . The presented host-guest properties together with further possible derivatization showcase the potential of cucurbiturils modified in the methylene position such as 1 and 2 for the development of advanced supramolecular systems.
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