Synthesis of perillyl-containing meroterpenoids and their supramolecular self-assembly with pillar[5]arene

The S-perillyl alcohol derivatives containing pyridinium and imidazolium fragments were synthesized. The 2: 1 host—guest complex with model pillar[5]arene characterized by logK_ass = 6.13 was synthesized from perillyl-bearing meroterpenoid. The composition and structure of the synthesized complex were confirmed by ¹H and 2D ¹H—¹H NOESY NMR spectroscopy. The properties of associates formed by the meroterpenoid—pillar[5]-arene complexes were evaluated by dynamic light scattering, Doppler microelectrophoresis, and transmission electron microscopy. The studied systems are characterized by average hydrodynamic diameters of 191–345 nm and polydispersity indices of 0.18–0.32.