The novel 4-(3-tert-butyl-4-hydroxyanisole)]phthalonitrile and its peripherally tetra substituted zinc phthalocyanine complex [2,9(10),16(17),23(24)-tetrakis(4-(3-tert-butyl-4-hydroxyanisole) phthalocyaninato]zinc(II) (ZnPc) were synthesized and characterized by elemental and spectroscopic analysis techniques. The inverse gas chromatography (IGC) method was used to obtain secondary transition, surface properties, and thermodynamic interaction parameters of the phthalocyanine glass. Phthalocyanine selectivity was investigated using the acetate and alcohol isomers by IGC method at temperatures between 313.2 and 423.2 K. The secondary transition temperature was obtained by IGC method and differential scanning calorimetry (DSC). The dispersive component of the surface free energy, gamma(D)(S), of adsorbent surface was calculated in the infinite dilution region. The specific enthalpy of adsorption, Delta H-A(S), the specific free energy of adsorption, Delta G(A)(S), and the specific entropy of adsorption, Delta S-A(S) of solvents on ZnPc were determined. The acidic K-A and the basic K-D parameters of the ZnPc surface were calculated. The values obtained for K-A and K-D parameters indicated that the ZnPc surface has a basic character. The specific retention volume, V-g(0) Flory-Huggins interaction parameter, chi(infinity)(12), equation-of-state interaction parameter, chi(12)*, weight fraction activity coefficient, Omega(infinity)(1), and effective exchange energy parameter, X-eff of ZnPc were determined. Then, the partial molar heat of sorption, Delta H-1,H-s and partial molar heat of mixing, Delta H-1(infinity), at infinite dilution were determined.