Copolymerization of a bisanthracene compound with bismaleimides by Diels–Alder cycloaddition

Abstract

Four new polymers have been synthesized via succesive Diels±Alder cycloadditions of a bisdiene compound bearing two anthracene groups and four bisdienophiles, all containing bismaleimide functions. The polycondensation reaction was performed in N,N-dimethylacetamide at 120°C leading to polymers soluble in polar solvents having molecular weights lower than 6000 g mol À1 .

Synthesis and thermal behavior of some anthracene‐based copolymers obtained by Diels–Alder cycloaddition reactions

“…Bis[(9‐anthryl)‐ N , N ‐dimethylene]azometine monomer ( 1 ) and bis[(9‐anthryl)‐ N , N ‐three‐methylene]azometine monomer ( 2 ) were synthesized using a reported method11 by a coupling reaction between 9‐anthrylcarboxaldehyde and 1,2‐diaminoethane, or 1,3‐diaminopropane, respectively. The monomers were twice recrystallized from methanol as yellow needles.…”

“…The Diels–Alder reaction involves a 2 + 4 cycloaddition between a diene and a dienophile compound. The application of Diels–Alder chemistry to polymer synthesis,2–13 modification14–17 and (reversible) crosslinking,18–23 or polyphenylene and ribbon‐like (two‐dimensional) conducting polymers24 has been reported. However, the lack of success in using at large scale of this method is limited by thermal reversibility of the cycloaddition and low molecular weight of the products.…”

Reversible cross-linking polymer-based self-healing materials

“…That is why healable polymeric materials containing DA adducts can undergo multiple healing cycles at the same damaged site. Although many dienes such as cyclopentadiene [64], fulvene [65], pyrone [66,67], and anthracene [68][69][70] can be utilized in preparing healable polymeric materials through DA reaction with maleimide, much of the research on healable polymeric materials has focused on DA reaction between furan and maleimide, due to the higher reactivity without catalyst and mild conditions of its retro-DA reaction [53]. In this section, we will mainly review the cross-linked healable polymeric materials from DA reaction between furan and maleimide.…”

High service temperature, self-mendable thermosets networked by isocyanurate rings

“…11 More recently, anthracene has been used as a substituent for furan in the DA reaction to achieve a higher cleavage temperature thus expanding the application space of these polymer materials. 14,15 Due to the high cleaving temperature of >250°C, 16,17 the use of thermal cleaving to assist in healing is limited when the cleaving temperature of A-M DA adducts is beyond the decomposition temperature of the polymers. For this reason, self-healing polymers based on thermally induced retro-DA reaction between A and M have not been reported yet.…”