For the first time, the effectiveness of triazolinedione (TAD) click chemistry onto aliphatic polycarbonates (APC) is demonstrated. Statistic copolymers carrying click-reactive conjugated diene (in a ratio of 10%) are synthesized via organocatalyzed ring-opening polymerization. The highly efficient click reaction of TADs carrying simple butyl and phenyl functions are confirmed by H-NMR and DSC. Network formation using a bivalent TAD is also performed and simply characterized by DSC. This post-polymerization functionalization of biocompatible and biodegradable APC pave the way to easy and versatile "on-demand" materials design.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/marc.201800743 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A New Class of Mechano-Responsive Polyurethane Via Anthracene -TAD Diels-Alder (DA) Click Chemistry.
Small
November 2024
Rubber Technology Centre, Indian Institute of Technology, Kharagpur, 721302, India.
Article Synopsis
- Smart or stimuli-responsive polymers can react to various external factors like pH, temperature, and mechanical force, with mechanophoric polymers transforming stress into fluorescent signals for damage detection.
- A new mechanophoric polyurethane (PU) adduct was developed using Diels-Alder click chemistry, which initially deactivates the fluorescent properties of anthracene when linked with bis-TAD, making the material harder.
- This material can revert to its fluorescent state under mechanical stress and exhibits self-healing capabilities, indicating its potential for advanced applications in responsive materials.
Dynamic Recyclable High-Performance Epoxy Resins via Triazolinedione-Indole Click Reaction and Cation-π Interaction Synergistic Crosslinking.
Polymers (Basel)
July 2024
Research Center of Laser Fusion, China Academy of Engineering Physics, Mianyang 621900, China.
Thermosetting plastics exhibit remarkable mechanical properties and high corrosion resistance, yet the permanent covalent crosslinked network renders these materials challenging for reshaping and recycling. In this study, a high-performance polymer film (EI-TAD-Mg) was synthesized by combining click chemistry and cation-π interactions. The internal network of the material was selectively constructed through flexible triazolinedione (TAD) and indole via a click reaction.
View Article and Find Full Text PDFForce-reversible chemical reaction at ambient temperature for designing toughened dynamic covalent polymer networks.
Nat Commun
June 2022
State Key Laboratory of Environment-friendly Energy Materials & School of Materials and Chemistry, Southwest University of Science and Technology, Mianyang, 621010, P. R. China.
Force-reversible C-N bonds, resulting from the click chemistry reaction between triazolinedione (TAD) and indole derivatives, offer exciting opportunities for molecular-level engineering to design materials that respond to mechanical loads. Here, we displayed that TAD-indole adducts, acting as crosslink points in dry-state covalently crosslinked polymers, enable materials to display reversible stress-responsiveness in real time already at ambient temperature. Whereas the exergonic TAD-indole reaction results in the formation of bench-stable adducts, they were shown to dissociate at ambient temperature when embedded in a polymer network and subjected to a stretching force to recover the original products.
View Article and Find Full Text PDFTriazolinedione protein modification: from an overlooked off-target effect to a tryptophan-based bioconjugation strategy.
Chem Sci
May 2022
Department of Organic and Macromolecular Chemistry, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium
Labelling of tyrosine residues in peptides and proteins has been reported to selectively occur a 'tyrosine-click' reaction with triazolinedione reagents (TAD). However, we here demonstrate that TAD reagents are actually not selective for tyrosine and that tryptophan residues are in fact also labelled with these reagents. This off-target labelling remained under the radar as it is challenging to detect these physiologically stable but thermally labile modifications with the commonly used HCD and CID MS/MS techniques.
View Article and Find Full Text PDFSystematic position of the Clicking Frog (Kassinula Laurent, 1940), the problem of chimeric sequences and the revised classification of the family Hyperoliidae.
Mol Phylogenet Evol
September 2022
Institute of Vertebrate Biology of the Czech Academy of Sciences, Brno, Czech Republic; National Museum, Department of Zoology, Prague, Czech Republic. Electronic address:
The systematics of the African frog family Hyperoliidae has undergone turbulent changes in last decades. Representatives of several genera have not been genetically investigated or with only limited data, and their phylogenetic positions are thus still not reliably known. This is the case of the De Witte's Clicking Frog (Kassinula wittei) which belongs to a monotypic genus.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!