Design and Synthesis of Maleimide Group Containing Polymeric Materials via the Diels‐Alder/Retro Diels‐Alder Strategy

Aldehyde-functional copolymers based on poly(2-oxazoline) for post-polymerization modification

“…For example, post-polymerization modification allows for chemical transformation of commodity polyolefins into value-added materials [4], or to tailor poly(carbonate)s for specific biomedical applications [5][6][7]. A wide variety of chemoselective and/or orthogonal reactions, including thiol-ene addition [8], thiol exchange, Diels-Alder cycloaddition [9], Michael addition or reactions with active esters [10], epoxides, anhydrides, isocyanates, ketones and aldehydes, have been applied to modify functional polymer precursors [11,12].…”

Biobased and Aromatic Reversible Thermoset Networks from Condensed Tannins via the Diels−Alder Reaction

“…Several systems can be used to form reversible covalent bonds with temperature including urethane or ester bonds, nitroso or azlactone groups, ionene formation, and Diels−Alder reaction. The Diels−Alder (DA) [4 + 2] cycloaddition involves a diene and a dienophile reacting to yield a substituted cyclohexene, which can be broken by further increasing the temperature via the retro Diels−Alder reaction (rDA). , The furan−maleimide system exhibits relatively low reaction temperature for DA and rDA, around 60−70 and 110−120 °C, respectively, making it compatible with the thermal stability of most polymeric materials …”

“…27 Several systems can be used to form reversible covalent bonds with temperature including urethane or ester bonds, nitroso or azlactone groups, ionene formation yield a substituted cyclohexene, which can be broken by further increasing the temperature via the retro Diels−Alder reaction (rDA). 28,29 The furan−maleimide system exhibits relatively low reaction temperature for DA and rDA, around 60−70 and 110−120 °C, respectively, making it compatible with the thermal stability of most polymeric materials. 30 In this study, we first designed original furan-bearing tannins via the reaction of mimosa (Acacia mearnsii) tannins with furfuryl glycidyl ether in various ratios.…”

Post‐polymerization modification of aromatic polyimides via Diels‐Alder cycloaddition

“…For polyimides, the most common approach to D‐A post‐polymerization modification is the incorporation of the maleimide group 30 and the closely related nadimide group 31 . These groups can be placed at one 32 or both 33 ends of a polymer chain or as pendant side chains 30 and are used mainly for postprocessing modifications like crosslinking and molecular weight enhancement 34 . Alkyne moieties have only sparingly been investigated for post‐polymerization functionalization 29 .…”