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Synthesis of polymers containing vicinal tricarbonyl moiety and construction of reversible crosslinking–decrosslinking polymer system
Author(s) -
Endo Takeshi,
Yonekawa Morio,
Sudo Atsushi
Publication year - 2021
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.6222
Subject(s) - nucleophile , vicinal , moiety , chemistry , electrophile , adduct , dissociation (chemistry) , molecule , polymer chemistry , polymer , organic chemistry , catalysis
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