Control of Intramolecular Hydrogen Bonding in a Conformation-Switchable Helical-Spring Polymer by Solvent and Temperature

Angew Chem Int Ed Engl. 2020 Jan 27;59(5):1837-1844. doi: 10.1002/anie.201910269. Epub 2019 Dec 16.

Abstract

A substituted poly(phenylacetylene) derivative (PPAHB ) with two hydroxymethyl groups at the meta position of the side phenyl ring was examined as a conformation-switchable helical spring polymer that responds to solvent and heat stimuli in a precisely controlled manner. Intramolecular hydrogen bonds, which cause the helical structure of the polymer, were broken and re-formed by adjusting the hydrogen-bonding strength values (pKHB ) of various combinations of solvents or by varying the temperature. In this process, a reversible conformational change from cis-cisoid to cis-transoid, accompanied by a phase transition in the form of a helix-coil transformation occurred, with the polymer exhibiting critical changes of color fading and recovery in specific environments. These results demonstrate that PPAHB can be used as either a pKHB indicator or a thermometer. The color changes of the polymer solution are described in detail based on spectroscopic analyses and thermodynamic considerations.

Keywords: conformational change; helical spring; hydrogen bonding; phase transitions; poly(phenylacetylene).

Publication types

  • Research Support, Non-U.S. Gov't