Syntheses and dynamics of donor-acceptor [2]catenanes in water

Abstract

A subset of mechanically interlocked molecules, namely, donor-acceptor [2]catenanes, have been produced in aqueous solutions in good yields from readily available precursors. The catenations are templated by strong hydrophobic and [π⋯π] stacking interactions, which serve to assemble the corresponding supramolecular precursors, prior to postassembly covalent modification. Dynamic 1H NMR spectroscopic investigations performed on one of these [2]catenanes reveal that the pirouetting motion of the butadiyne-triethylene glycol chain occurs with a dramatically lower activation enthalpy, yet with a much higher negative activation entropy in water, compared to organic solvents. The preparations of mechanically interlocked molecules in water constitute the basis for the future development of complex functional molecular machinery in aqueous environments. © 2011 American Chemical Society.