Eva 20

The solubilization experiments were performed by adding an excess of crystalline substrate (ibuprofen, naproxen, dodecanoic and ursodeoxycholic acid) to the aqueous or deuterium oxide solutions of calixresorcinarenes. The solutions were mixed at 20 1C for 4 h at a rate of 360 rpm. Then they were centrifuged (rate 6 krpm, 10 min, centrifuge Eva-20 (Hettich Zentrifugen, Germany)) to separate non-solubilized substrates and used in the next measurements. The determination of the amount of solubilized substrates was performed using 1 H NMR (D 2 O transparent solutions) by comparing the integral intensities of acid signals and macrocycle signals and by pH titration of macrocycle-substrate solutions with 0.1 H HCl until the formation of substrate precipitates (Tables S1 andS2, ESI †). pH-Values of aqueous solutions were measured using an Orion 2-Star Benchtop pH-Meter (Thermo Fisher Scientific, USA) using a pH-electrode H1 1093 (Hanna instruments, USA). The weight percentage of substrates (naproxen, ibuprofen and ursodeoxycholic acid) in associates with macrocycles was estimated by the equation C S /(C M + C S )Á100%, where C S is the concentration of substrates (mg mL À1 ) and C M is the concentration of macrocycles (mg mL À1 ).

The solubilization experiments were performed by adding an excess of the crystalline dye methyl yellow (MY) to aqueous solutions of CR (2.86 mM), CPC (1 mM), CR-CPC 4/1 (C(CPC) = 0.976 mM, C(CR) = 0.244 mM), and CPC/CR 1/4 (C(CPC) = 0.714 mM, C(CR) = 2.86 mM) mixtures. The solutions were mixed at 20 1C for 4 h at a rate of 360 rpm. They were then centrifuged (rate 6 krpm, 10 min, centrifuge Eva-20 (Hettich Zentrifugen, Germany)) to separate non-solubilized MY. The UV Vis spectra of the obtained solutions were registered on a Lambda 35 UV-Vis Spectrometer (Perkin-Elmer Instruments, USA) using quartz cells with an optical path of 0.1 cm.
The study of stoichiometry of CPC/CR by UV/Vis method A number of CPC/CR solutions with constant concentrations of CPC (0.1 and 0.5 mM) and different CR/CPC molar ratios (from 10/1 to 1/8) were prepared. The absorbance at 500 nm was measured with a Lambda 35 UV-Vis Spectrometer (Perkin-Elmer Instruments, USA) using quartz cells with an optical path of 0.2 cm.