Ruijuan Ye

Persistently Folded Circular Aromatic Amide Pentamers Containing Modularly Tunable Cation-Binding Cavities with High Ion Selectivity

In this work, we illustrated a novel design strategy that allows systematically tunable interior properties (effective cavity size, steric crowdedness, and hydrophobicity) contained within a novel class of shape-persistent aromatic pentamers to take place on a scale below 3 A. Such finely tunable structural features are complimented by experimentally observable functional variations in ion-binding potential. Results of the selective, differential binding affinities of three circular pentamers for Li(+), Na(+), K(+), Rb(+), and Cs(+), substantiated by metal-containing crystal structures and computational modeling, are detailed.

One-Pot Synthesis of Hybrid Macrocyclic Pentamers with Variable Functionalizations around the Periphery

Rather than four- or six-residue macrocylces, one-pot macrocyclization allows for the highly selective formation of five-residue macrocycles rigidified by intramolecular hydrogen bonds. Variable functionalizations around the pentameric periphery were achieved by reacting monomers with higher oligomers bearing different exterior side chains. The formation of these hybrid pentamers suggests a chain-growth mechanism for the one-pot macrocyclization where the successive addition of monomers onto higher oligomers is faster than those between two monomers or two higher oligomers.

CCDC 746518: Experimental Crystal Structure Determination

Related Article: Yan Yan, Bo Qin, Changliang Ren, Xiuying Chen, Yeow Kwan Yip, Ruijuan Ye, Dawei Zhang, Haibin Su, Huaqiang Zeng|2010|J.Am.Chem.Soc.|132|5869|doi:10.1021/ja100579z