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Formation and Out‐of‐Equilibrium, High/Low State Switching of a Nitroaldol Dynamer in Neutral Aqueous Media
Author(s) -
Karalius Antanas,
Zhang Yang,
Kravchenko Oleksandr,
Elofsson Ulla,
Szabó Zoltán,
Yan Mingdi,
Ramström Olof
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201911706
Subject(s) - nitromethane , nitroaldol reaction , aqueous solution , covalent bond , formaldehyde , aqueous medium , chemistry , dynamic covalent chemistry , pyridine , organic chemistry , catalysis , enantioselective synthesis , molecule , supramolecular chemistry
The nitroaldol reaction is demonstrated as an efficient dynamic covalent reaction in phosphate buffers at neutral pH. Rapid equilibration was recorded with pyridine‐based aldehydes, and dynamic oligomerization could be achieved, leading to nitroaldol dynamers of up to 17 repeating units. The dynamers were applied in a coherent stimuli‐responsive molecular system in which larger dynamers transiently existed out‐of‐equilibrium in a neutral aqueous system rich in formaldehyde, controlled by nitromethane.