Synthesis of polymers containing vicinal tricarbonyl moiety and construction of reversible crosslinking–decrosslinking polymer system. Issue 9 (3rd April 2021)

• Record Type: Journal Article
• Authors: Endo, Takeshi; Yonekawa, Morio; Sudo, Atsushi
• Is Part Of: Polymer international. Volume 70:Issue 9(2021)
• Page Start: 1176
• Page End: 1181
• Publication Date: 2021-04-03
• Subjects: vicinal tricarbonyl -- crosslinking -- decrosslinking -- polymer recycling; Plastics -- Periodicals; Polymers -- Periodicals; Polymerization -- Periodicals; 547.7
• DOI: 10.1002/pi.6222
• Languages: English
• ISSNs: 0959-8103

Abstract

Abstract: Vicinal tricarbonyl compounds, in which three carbonyl groups are consecutively connected, are intriguing reactive molecules with a highly electrophilic nature. The center carbonyl group activated by two adjacent electron‐withdrawing carbonyl groups reacts efficiently with weak nucleophiles such as water, alcohols, thiols and aromatic amines to afford the corresponding adducts. In addition, because the reactions of the center carbonyl group with nucleophiles are intrinsically in equilibrium, the adducts undergo dissociation into the corresponding tricarbonyl compounds and nucleophiles under the appropriate conditions. Based on the reversible nature of vicinal tricarbonyl compounds with nucleophiles, a reversible crosslinking–decrosslinking system can be constructed where appropriately designed polymers and crosslinkers bearing vicinal tricarbonyl compounds are effectively used. © 2021 Society of Chemical Industry Abstract : Vicinal tricarbonyl compounds react with weak nucleophiles such as water, alcohols, thiols and aromatic amines. The resulting adducts connected by dynamic covalent bonds dissociate selectively under the appropriately selected conditions. Based on these unique reaction behaviors of vicinal tricarbonyl compounds, highly efficient cycles including crosslinking and decrosslinking steps have been developed.