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A One‐Pot Synthesis of Constitutionally Unsymmetrical Rotaxanes Using Sequential Cu I ‐Catalyzed Azide–Alkyne Cycloadditions
Author(s) -
Spruell Jason M.,
Dichtel William R.,
Heath James R.,
Stoddart J. Fraser
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800067
Subject(s) - alkyne , cycloaddition , chemistry , azide , rotaxane , combinatorial chemistry , catalysis , amphiphile , silylation , organic chemistry , molecule , supramolecular chemistry , copolymer , polymer
A one‐pot sequential Cu I ‐catalyzed azide–alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat‐ p ‐phenylene)‐based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl‐protection and Ag I ‐catalyzed deprotection of a terminal alkyne. The methodology is highlighted by the synthesis of an amphiphilic branched [4]rotaxane. The methodology increases the ability to access ever more complicated mechanically interlocked compounds to serve in devices as sophisticated and functional molecular machinery.