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Hindered Urea Bond: A Bilaterally Responsive Chemistry to Hydrogen Peroxide
Author(s) -
Ying Hanze,
Yang Yingfeng,
Cai Kaimin,
Cheng Jianjun
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801307
Subject(s) - chemistry , isocyanate , hydrogen peroxide , amine gas treating , moiety , covalent bond , hydrogen bond , peroxide , photochemistry , quenching (fluorescence) , combinatorial chemistry , polymer chemistry , organic chemistry , molecule , polyurethane , fluorescence , physics , quantum mechanics
As a type of safe, clean, and bio‐relevant oxidant, hydrogen peroxide has been widely used as a trigger in the design of stimuli‐responsive materials. Hindered urea bond (HUB) is a type of dynamic covalent bond which can reversibly dissociate into isocyanate and amine. Quenching of isocyanate or amine will shift the equilibrium and facilitate the degradation of HUB bond. Herein, we report that one of the HUB moiety – 1,1‐ tert ‐butylethylurea (TBEU) can react with hydrogen peroxide (H 2 O 2 ) resulting in two opposing outcomes. Perhydrolysis of isocyanate and oxidation of amine lead to the bond fracture, while formation of urethane product with an oxygen inserted into the original TBEU structure was also observed giving a stabilized form of linkage. More precise kinetic control of the two distinct pathways are expected to make hydrogen peroxide a trigger to either degrade or fix the HUB based polymeric materials.