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Metal Ion‐Driven Constitutional Adaptation in Dynamic Covalent C=C/C=N Organo‐Metathesis
Author(s) -
Gu Ruirui,
Lehn JeanMarie
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202001001
Subject(s) - chemistry , trifluoromethanesulfonate , metathesis , knoevenagel condensation , covalent bond , ligand (biochemistry) , metal , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , polymerization , polymer , biochemistry , receptor
Abstract Knoevenagel barbiturate derivatives and imines are able to undergo efficient component recombination through dynamic covalent C=C/C=N organo‐metathesis in absence of a catalyst. A [2×2] dynamic covalent library (DCL) containing two Knoevenagel derivatives Kn1 and Kn2 and two imines A1 and A2 has been established and its adaptive features in response to the addition of metal cations have been investigated. Addition of Cu(I) triflate as an effector, induces fast and remarkable constitutional selection of the DCL towards amplification of the Cu(I)‐ A2 complex and its agonist Kn1 . This adaptation process could be reversed by addition of neocuproine as a competitive Cu(I) ligand. Furthermore, separate addition of five other metal cations as input agents, i. e. Ag(I), Fe(II), Zn(II), Cu(II) and Li(I), led to the generation of cation‐specific distribution patterns as outputs, showing the ability of the present DCL to recognize different effectors.