It is herein reported that a facile application of N-acyl dibenzazepine (ADBA) photochemistry for preparing photoreversible ADBA based thiol-ene networks. Crosslinking of the ADBA thiol-ene networks is successfully achieved by UV induced dimerization of ADBA groups at wavelengths above 300 nm while a subsequent deep UV exposure (λ = 250 nm) results in a well-defined cleavage of the crosslinks. The photochemical bonding and cleavage of the process has been determined and studied in detail by spectroscopic measurements.
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http://dx.doi.org/10.1002/marc.202000369 | DOI Listing |
RSC Adv
January 2025
Dept. of Chemical Engineering, McGill University 3610 Rue Universite Montreal QC H3A 0C5 Canada
Compositions of ethylene glycol dicyclopentenyl ether methacrylate (EGDEMA), a vegetable oil based alkyl methacrylate (C13MA), and furfuryl methacrylate (FMA) were terpolymerized for dual-crosslinked networks with tailored mechanical and thermal properties. Specifically, initiators for continuous activator regeneration (ICAR) atom transfer radical polymerization (ATRP) afforded materials with tailored glass transition temperature ( ) and incorporation of furan and norbornene functionalities within a single chain. The terpolymer with high furan and norbornene functionality (Ter2: = 0.
View Article and Find Full Text PDFMacromol Biosci
December 2024
INM - Leibniz Institute for New Materials, 66123, Saarbrücken, Germany.
Photocrosslinkable formulations based on the radical thiol-ene reaction are considered better alternatives than methacrylated counterparts for light-based fabrication processes. This study quantifies differences between thiol-ene and methacrylated crosslinked hydrogels in terms of precursors stability, the control of the crosslinking process, and the resolution of printed features particularized for hyaluronic acid (HA) inks at concentrations relevant for bioprinting. First, the synthesis of HA functionalized with norbornene, allyl ether, or methacrylate groups with the same molecular weight and comparable degrees of functionalization is presented.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Polymer Chemistry Research group, Centre of Macromolecular Chemistry (CMaC) and Laboratory of Organic Synthesis, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan, 281-S4, Ghent, 9000, Belgium.
Recycling thermosetting materials presents itself as a major challenge in achieving sustainable material use. Dynamic covalent cross-linking of polymers has emerged as a viable solution that can combine the structural integrity of thermosetting materials with the (re-)processability of thermoplastics. Thioether linkages between polymer chains are quite common, and their use dates back to the vulcanization of rubbers.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2025
Technical University of MunichTUM School of Natural Sciences, Department of Chemistry, WACKER-Chair of Macromolecular Chemistry, Lichtenbergstraße 485748 Garching, Germany.
Biomacromolecules
January 2025
Polymer Chemistry and Biomaterials (PBM) Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281, Building S4, Ghent 9000, Belgium.
Hydroxyapatite (HAP) and amorphous calcium phosphate (ACP) nanoparticles were incorporated into a thiol-ene clickable gelatin network to elucidate to what extent osteogenic differentiation of human dental pulp- and adipose-derived stem cells (HDPSCs/HASCs) could be further boosted. ACP nanoparticles increased the specific surface area by 23% and reduced the density by 13% while maintaining a comparable particle size (ACP: 25 ± 3 nm; HAP: 27 ± 3 nm). Overall, the incorporation of ceramic nanoparticles did not significantly alter the mechanical properties of the ceramic-containing composites compared to the unsubstituted thiol-ene network.
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