Temperature-Responsive Chiral (A)6B Supramolecular Cages Based on Conformational Preferences

Chem Asian J. 2016 Feb 18;11(4):465-9. doi: 10.1002/asia.201501090. Epub 2015 Nov 25.

Abstract

Two chiral (A)6B-typed supramolecular cages were constructed from hydrogen-bonded C6 -symmetric zinc porphyrin hexamers and chiral C3-symmetric pyridyl hexadentates with a core of 1,3,5-triphenylbenzene. Circular dichroism and molecular simulations revealed that the symmetry of the supramolecular cages switched from pseudo-C3v to C3 with the rotational confinement of the biphenyl backbones at low temperatures, which generated conformationally chiral transfer and amplification. This unique phenomenon suggests a new strategy to develop smart materials with high sensitivity and excellent reversibility.

Keywords: chiral transfer; conformational chirality; conformational preference; supramolecular cages; temperature-responsive.