5 years ago

C–I···π Halogen Bonding Driven Supramolecular Helix of Bilateral N-Amidothioureas Bearing β-Turns

C–I···π Halogen Bonding Driven Supramolecular Helix of Bilateral N-Amidothioureas Bearing β-Turns
Zhao Li, Jinlian Cao, Wenbin He, Maili Liu, Xiaosheng Yan, Yirong Mo, Yun-Bao Jiang, Xiaorui Li
We report the first example of C–I···π halogen bonding driven supramolecular helix in highly dilute solution of micromolar concentration, using alanine based bilateral I-substituted N-amidothioureas that contain helical fragments, the β-turn structures. The halogen bonding interactions afford head-to-tail linkages that help to propagate the helicity of the helical fragments. In support of this action of the halogen bonding, chiral amplification was observed in the supramolecular helix formed in acetonitrile solution. The present finding provides alternative tools in the design of self-assembling macromolecules.

Publisher URL: http://dx.doi.org/10.1021/jacs.6b13171

DOI: 10.1021/jacs.6b13171

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