Related Experiment Video
Updated: Sep 21, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Productive Exchange of Thiols and Thioesters to Form Dynamic Polythioester-Based Polymers
Chen Wang1, Sudheendran Mavila1, Brady T Worrell1
1Department of Chemical and Biological Engineering, University of Colorado, UCB 596, Boulder, Colorado 80309, United States.
Abstract:
Polymers that possess dynamic covalent bonds activated at ambient conditions are ideal platforms for smart, responsive materials. Herein, a class of dynamic covalent polymerizations is developed based on the thiol-thioester exchange, that is, transthioesterification, reaction. Shifts in the equilibrium extent of the exchange reactions are deliberately utilized to drive the formation of oligomers and polymers. In particular, a series of AB and A2-B2 monomers, including amino acid derivatives, were polymerized rapidly by catalytic amounts of mild bases in various organic solvents under ambient conditions. Thioester backbone oligopeptides, including cysteine and glycine, were obtained with an average repeating unit of four and a PDI of 1.8. Further, structurally dynamic hydrogels were obtained by such reactions between four-armed poly(ethylene glycol)-10000 based monomers in neutral water. These hydrogels showed dynamic, frequency-dependent flow behavior between sol and gel states.
More Related Videos
Related Concept Videos
Preparation and Reactions of Thiols
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
Preparation and Reactions of Sulfides
Types of Step-Growth Polymers: Polyesters
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the...
Ion Exchange
Polymers

