Related Experiment Video
Updated: Jun 30, 2025

Light-mediated Formation and Patterning of Hydrogels for Cell Culture Applications
Published on: September 29, 2016
Using Stereochemistry to Control Mechanical Properties in Thiol-Yne Click-Hydrogels
Laura J Macdougall1, Maria M Pérez-Madrigal2, Joshua E Shaw3
1Department of Chemistry University of Warwick Coventry CV4 7AL UK.
Abstract:
The stereochemistry of polymers has a profound impact on their mechanical properties. While this has been observed in thermoplastics, studies on how stereochemistry affects the bulk properties of swollen networks, such as hydrogels, are limited. Typically, changing the stiffness of a hydrogel is achieved at the cost of changing another parameter, that in turn affects the physical properties of the material and ultimately influences the cellular response. Herein, we report that by manipulating the stereochemistry of a double bond, formed in situ during gelation, materials with diverse mechanical properties but comparable physical properties can be obtained. Click-hydrogels that possess a high % trans content are stiffer than their high % cis analogues by almost a factor of 3. Human mesenchymal stem cells acted as a substrate stiffness cell reporter demonstrating the potential of these platforms to study mechanotransduction without the influence of other external factors.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Polymer Classification: Stereospecificity
Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation and Reactions of Thiols

