Related Experiment Video
Updated: Apr 27, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Silicone boronates reversibly crosslink using Lewis acid-Lewis base amine complexes
Laura Dodge1, Yunqing Chen, Michael A Brook
1Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St. W., Hamilton ON, L8S 4M1 (Canada).
Researchers developed recyclable silicone elastomers using reversible amine-boronate chemistry. This approach allows for dynamic B-N bond reformation, enabling material disassembly and reformation for sustainable applications in silicone materials.
Area of Science:
- Polymer Chemistry
- Materials Science
- Supramolecular Chemistry
Background:
- Traditional silicone elastomers are thermosets, limiting their recyclability and repurposing.
- Existing thermoplastic silicones rely on less robust reversible covalent or non-covalent interactions.
- Developing sustainable alternatives for silicone materials is crucial.
Purpose of the Study:
- To introduce a novel method for creating reversible crosslinked silicone elastomers.
- To explore the use of amine-boronate complex formation for dynamic silicone networks.
- To demonstrate the recyclability and reformability of these novel silicone materials.
Main Methods:
- Synthesized silicone elastomers functionalized with amine and boronate groups.
- Characterized network structures using Shore-hardness, swelling, and rheological analyses.
- Investigated dynamic bond reformation via B-N interactions at elevated temperatures (60°C).
Main Results:
- Successfully created reversible crosslinked silicone networks through amine-boronate complexation.
- Demonstrated that compressive stress can be relieved via dynamic B-N bond reformation at 60°C.
- Showcased full material disassembly with n-butylamine and successful reformation upon its removal.
Conclusions:
- Amine-boronate complexation offers a straightforward and adaptable route to recyclable silicone elastomers.
- The dynamic nature of B-N bonds allows for stress relaxation, disassembly, and reformation.
- This method provides a promising pathway towards sustainable silicone materials with enhanced end-of-life options.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Lewis Acids and Bases
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
Lewis Acids and Bases
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...