Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent

Abstract

Abstract A molecular tweezer having two bidentate pentafluorophenyl (C6F5) groups was synthesized, and the π–π stacking ability of the C6F5 groups toward benzene derivatives in a polar organic solvent was evaluated. The structure of the molecular tweezer was revealed to be dimeric in the crystalline state by X-ray analysis. Association constants (Ka) between the molecular tweezer and aromatic guests in THF were found to be roughly correlated with the quadrupole moment (Qzz) of the guests, suggesting that the quadrupole–quadrupole contribution plays a significant role in the π–π interaction even in a polar organic solvent.