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A Toggle Nanoswitch Alternately Controlling Two Catalytic Reactions
Author(s) -
De Soumen,
Pramanik Susnata,
Schmittel Michael
Publication year - 2014
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.201408457
Subject(s) - piperidine , catalysis , chemistry , diethyl malonate , copper , knoevenagel condensation , ion , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry
Abstract Reversible switching between two states of the triangular nanoswitch [Cu( 1 )] + was accomplished by alternate addition of 2‐ferrocenyl‐1,10‐phenanthroline ( 2 ) and copper(I) ions. The two switching states regulate the binding and release of two distinct catalysts, piperidine and [Cu( 2 )] + , in a fully interference‐free manner and allow alternating on/off switching of two orthogonal catalytic processes. In switching state I, piperidine is released from the nanoswitch and catalyzes a Knoevenagel addition between 4‐nitrobenzaldehyde and diethyl malonate (ON‐1 and OFF‐2), while in state II the released [Cu( 2 )] + catalyzes a click reaction between 4‐nitrophenylacetylene and benzylazide (OFF‐1 and ON‐2). Upon addition of one equivalent of 2 to the (OFF‐1 and ON‐2)‐state, both catalytically active processes are shut down (OFF‐1 and OFF‐2).