RIKEN Center for Emergent Matter Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
Photosciences and Photonics Section, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram, Kerala, 695 019, India.
Nat Commun. 2020 May 8;11(1):2311. doi: 10.1038/s41467-020-16127-6.
Since various helical supramolecular polymers became available, their application to molecular chirality recognition have been anticipated but not extensively studied. So far, only a few examples of chiral reactions have been reported, but none for chiral separation. Here, we report the application of a helical supramolecular polymer to the enantio-separation of chiral guest molecules. The monomer of this supramolecular polymer is the salt-pair of a dendritic carboxylic acid with an enantiopure amino alcohol. In an apolar solvent, this salt-pair stacks via hydrogen bonds to form a helical polymer. In conjunction with this carboxylic acid, various amino alcohols afford supramolecular polymers, whose helical handedness is determined by the stereochemistry of the amino alcohols. When two salts with the same chirality are mixed, they undergo copolymerization, while those with opposite chirality do not. Owing to this stereoselective copolymerizability, the helical supramolecular polymer could bias the enantiomeric composition of chiral amino alcohols.
自从各种螺旋超分子聚合物问世以来，人们一直期待它们能够应用于分子手性识别，但目前研究还不够广泛。到目前为止，只有少数手性反应的例子被报道，而没有手性分离的例子。在这里，我们报告了一种螺旋超分子聚合物在手性客体分子对映体分离中的应用。该超分子聚合物的单体是树枝状羧酸与对映纯氨基醇形成的盐对。在非极性溶剂中，通过氢键堆积形成螺旋聚合物。与这种羧酸结合，各种氨基醇提供超分子聚合物，其螺旋手性由氨基醇的立体化学决定。当两种具有相同手性的盐混合时，它们会发生共聚，而具有相反手性的盐则不会。由于这种立体选择性共聚性，螺旋超分子聚合物可以影响手性氨基醇的对映体组成。
