Non-classical ethylene-bridged oligoureas represent a new class of dynamic foldamers having a continuous network of hydrogen bonds, each urea in the foldamer is conformationally mobile and forms hydrogen bonds with directly adjacent ureas in the chain. The hydrogen bond network is dynamic and directional with all the urea carbonyls pointing in the same direction. Complete control of directionality was achieved by applying electronic bias at one terminus of the chain. The polarity of foldamers was switched reversibly in response to pH, and by using interactions with ligands such as acetate, phosphate, chloride. The binding of a ligand (input) at one end of the foldamer induced a global conformational switch of the hydrogen bond network causing a change of fluorescence properties (output) of a probe located at the other extremity of the foldamer. Conformationally flexible oligourea communicate information down the chain to a remote site, behaving as synthetic analogues of proteins involved in signal transduction.

Ligand induced polarity switch of dynamic ethylene-bridged non classical oligoureas

2019 Fall National Meeting

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