Citation

Spruell JM, Dichtel WR, Heath JR, Stoddart JF. Chemistry (Weinheim) 2008; 14(14): 4168-4177.

Copyright

(Copyright © 2008, John Wiley and Sons)

DOI

10.1002/chem.200800067

PMID

unavailable

Abstract

A one-pot sequential CuI-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 AgI-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.