Related Experiment Video
Updated: Mar 11, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Thiol-Ene Step-Growth as a Versatile Route to Functional Polymers.
Joel M Sarapas1, Gregory N Tew1
1Department of Polymer Science and Engineering, University of Massachusetts Amherst, Amherst, MA, 01002, USA.
A novel thiol-ene reaction creates functional, redox-tunable polymers. This versatile method allows for diverse functional groups, leading to new redox-active polymer materials.
Area of Science:
- Polymer Chemistry
- Materials Science
Background:
- The thiol-ene reaction is a versatile click chemistry method.
- Developing functional and redox-tunable polymers is crucial for advanced materials.
Purpose of the Study:
- To demonstrate a new application of the thiol-ene reaction for creating functional, redox-tunable polymers.
- To showcase the versatility of this polymerization approach with various monomers.
Main Methods:
- Polymerization of divinyl ether monomers with triethylene glycol dithiol.
- Polymerization of dithioerythritol with triethylene glycol divinyl ether.
- Oxidation of resulting thioether polymers to sulfoxides and sulfones.
Main Results:
- Successfully synthesized polymers with carbonate or phosphocholine backbones.
- Created polymers with pendant diols by varying monomer combinations.
- Demonstrated selective and quantitative oxidation of thioether linkages to sulfoxides/sulfones.
Conclusions:
- The thiol-ene reaction is a broad and effective method for synthesizing novel redox-active polymers.
- This approach allows for the incorporation of diverse and dense functional groups into polymer structures.
- The resulting polymers exhibit tunable redox properties based on oxidation state.
More Related Videos
11:17Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
Published on: January 19, 2016
15:33Microwave-assisted Functionalization of Polyethylene glycol and On-resin Peptides for Use in Chain Polymerizations and Hydrogel Formation
Published on: October 29, 2013
Related Concept Videos
Step-Growth Polymerization: Overview
Many natural and synthetic polymers are produced by...
Radical Chain-Growth Polymerization: Overview
Molecular Weight of Step-Growth Polymers
As the step-growth polymerization involves step-wise condensation of monomers, the molecular weight also builds up eventually. Consequently, high molecular weight polymers are obtained at the late stages of the polymerization, where 99% of monomers have been consumed.
The extent of the...
Anionic Chain-Growth Polymerization: Mechanism
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 polymer...
Cationic Chain-Growth Polymerization: Mechanism