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Hydrogen-Bond-Driven Controlled Molecular Marriage in Covalent Cages

机译：共价笼中氢键驱动的分子婚姻

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摘要

A supramolecular approach that uses hydrogenbonding interaction as a driving force to accomplish exceptional self-sorting in the formation of imine-based covalent organic cages is discussed. Utilizing the dynamic covalent chemistry approach from three geometrically similar dialdehydes (A, B, and D) and the flexible triamine tris(2-aminoethyl) amine (X), three new [3+2] self-assembled nanoscopic organic cages have been synthesized and fully characterized by various techniques. When a complex mixture of the dialdehydes and triamine X was subjected to reaction, it was found that only dialdehyde B (which has OH groups for Hbonding) reacted to form the corresponding cage B_3X_2 selectively. Surprisingly, the same reaction in the absence of aldehyde B yielded a mixture of products. Theoretical and experimental investigations are in complete agreement that the presence of the hydroxyl moiety adjacent to the aldehyde functionality in B is responsible for the selective formation of cage B_3X_2 from a complex reaction mixture. This spectacular selection was further analyzed by transforming a nonpreferred (non-hydroxy) cage into a preferred (hydroxy) cage B_3X_2 by treating the former with aldehyde B. The role of the H-bond in partner selection in a mixture of two dialdehydes and two amines has also been established. Moreover, an example of unconventional imine bond metathesis in organic cage-to-cage transformation is reported.
机译：讨论了一种超分子方法，该方法利用氢键相互作用作为驱动力来完成基于亚胺的共价有机笼形成中的出色自分选。利用三个几何相似的二醛（A，B和D）和柔性三胺三（2-氨基乙基）胺（X）的动态共价化学方法，合成了三个新的[3 + 2]自组装纳米有机笼并以各种技术为特色。当使二醛和三胺X的复杂混合物进行反应时，发现仅二醛B（其具有用于氢键键合的OH基）反应以选择性地形成相应的笼B_3X_2。令人惊讶地，在没有醛B的情况下的相同反应产生了产物的混合物。理论和实验研究完全一致，认为B中与醛官能团相邻的羟基部分的存在是由复杂的反应混合物选择性形成笼型B_3X_2的原因。通过用醛B处理前者，将非优选（非羟基）笼转化为优选（羟基）笼B_3X_2，进一步分析了这一出色的选择。在两种二醛和两种二醛的混合物中，H键在配偶选择中的作用胺也已经建立。此外，还报道了有机笼到笼转化中非常规亚胺键复分解的例子。

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