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Absolute Configurations of Topologically Chiral [2]Catenanes and the Acid/Base-Flippable Directions of Their Optical Rotations

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journal contribution
posted on 08.07.2019, 00:00 by Tzu-Yi Tai, Yi-Hung Liu, Chien-Chen Lai, Shie-Ming Peng, Sheng-Hsien Chiu
The absolute configurations of the two enantiomers of a topologically chiral [2]­catenane were determined unambiguously based on HPLC resolution and X-ray crystal analysis. Although structurally dissimilar to simple amino acids, the optical rotations of these separated [2]­catenanes share the Clough–Lutz–Jirgensons behavior of amino acids: the optical rotation flips direction in the presence of acid and base, the first example of such behavior for a mechanically interlocked topologically chiral catenane.