Abstract
Xenon binding has attracted interest due to the potential for xenon separation and emerging applications in magnetic resonance imaging. Compared to their covalent counterparts, assembled hosts that are able to effectively bind xenon are rare. Here, we report a tight yet soft chiral macrocycle dimeric capsule for efficient and adaptive xenon binding in both crystal form and solution. The chiral bisurea-bisthiourea macrocycle can be easily synthesized in multi-gram scale. Through assembly, the flexible macrocycles are locked in a bowl-shaped conformation and buckled to each other, wrapping up a tight, completely sealed yet adjustable cavity suitable for xenon, with a very high affinity for an assembled host. A slow-exchange process and drastic spectral changes are observed in both 1H and 129Xe NMR. With the easy synthesis, modification and reversible characteristics, we believe the robust yet adaptive assembly system may find applications in xenon sequestration and magnetic resonance imaging-based biosensing.
Highlights
Xenon binding has attracted interest due to the potential for xenon separation and emerging applications in magnetic resonance imaging
Cryptophanes are shown to be outstanding in terms of high affinity and competence for biosensing applications[8,9,13,41,42], though, tedious synthesis and sometimes chiral resolution of the intrinsic enantiomers are required for chirality-sensitive detection[43,44,45]
On the other hand, assembled hosts have the advantages of reversible formation and easy modular accessibility, they are barely explored for xenon binding
Summary
Shi-Xin Nie[1,2,3], Hao Guo[1,2,3], Teng-Yu Huang[1,2], Yu-Fei Ao1, De-Xian Wang 1,2 & Qi-Qiang Wang 1,2✉. Xenon binding has attracted interest due to the potential for xenon separation and emerging applications in magnetic resonance imaging Compared to their covalent counterparts, assembled hosts that are able to effectively bind xenon are rare. We report a tight yet soft chiral macrocycle dimeric capsule for efficient and adaptive xenon binding in both crystal form and solution. Modification and reversible characteristics, we believe the robust yet adaptive assembly system may find applications in xenon sequestration and magnetic resonance imaging-based biosensing. As an inert spherical monoatomic gas, xenon lacks an apparent binding site; van der Waals interaction, London dispersion force, is thought to be the main driving force. The adaptive-binding dynamics due to induced fit of the surrounding macrocyclic skeletons is revealed in crystal form, and in solution through the unique spectral features of the dimeric assembly
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