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Window[1]resorcin[3]arenes: A Novel Macrocycle Able to Self-Assemble to a Catalytically Active Hexameric Cage
JACS Au ( IF 8.5 ) Pub Date : 2024-05-03 , DOI: 10.1021/jacsau.4c00097
Tian-Ren Li 1 , Chintu Das 2 , Ivan Cornu 1 , Alessandro Prescimone 1 , GiovanniMaria Piccini 2 , Konrad Tiefenbacher 1, 3
Affiliation  

The hexameric resorcin[4]arene capsule has been utilized as one of the most versatile supramolecular capsule catalysts. Enlarging its size would enable expansion of the substrate size scope. However, no larger catalytically active versions have been reported. Herein, we introduce a novel class of macrocycles, named window[1]resorcin[3]arene (wRS), that assemble to a cage-like hexameric host. The new host was studied by NMR, encapsulation experiments, and molecular dynamics simulations. The cage is able to bind tetraalkylammonium ions that are too large for encapsulation inside the hexameric resorcin[4]arene capsule. Most importantly, it retained its catalytic activity, and the accelerated conversion of a large substrate that does not fit the closed hexameric resorcin[4]arene capsule was observed. Thus, it will help to expand the limited substrate size scope of the closed hexameric resorcin[4]arene capsule.

中文翻译:


Window[1]间苯二酚[3]芳烃:一种能够自组装成催化活性六聚笼的新型大环化合物



六聚间苯二酚[4]芳烃胶囊已被用作最通用的超分子胶囊催化剂之一。增大其尺寸可以扩大基板尺寸范围。然而,尚未报道更大的催化活性版本。在这里,我们引入了一类新型大环化合物,名为窗口[1]间苯二酚[3]芳烃(wRS),它组装成笼状六聚体宿主。通过核磁共振、封装实验和分子动力学模拟对新主体进行了研究。该笼能够结合太大而无法封装在六聚间苯二酚[4]芳烃胶囊内的四烷基铵离子。最重要的是,它保留了其催化活性,并且观察到不适合封闭的六聚间苯二酚[4]芳烃胶囊的大底物的加速转化。因此,这将有助于扩大封闭六聚间苯二酚[4]芳烃胶囊的有限底物尺寸范围。
更新日期:2024-05-03
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