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Keywords:

  • conformational dynamics;
  • diphenylacetylene;
  • hydrogen bonding;
  • molecular switch;
  • pH dependence
Thumbnail image of graphical abstract

The conformational equilibrium of a pH-dependent switch based on an intramolecularly H-bonded diphenylacetylene can be predictably biased by using electron-donating or -withdrawing groups (see scheme). Furthermore, protonation of the electron-donating dimethylamino group converts it into an electron-withdrawing dimethylammonium cation with a concomitant switch in conformation.