Three types of amino-functionalized calixarenes, i.e. the diaminocalix[4]arenes 5,17-diaminomethyl-25,26,27,28-tetrapropoxycalix[4]arene, 25,27-diaminoethoxy-26,28-dihydroxycalix[4]arene and 5,11,17,23-tetra-tert-butyl-25,27-diaminoethoxy-26,28-dihydroxycalix[4]arene, were synthesized and incorporated as comonomers into the backbones of aromatic polyimides. As a first step, polyimide precursors (poly(amic acid)s) were prepared by condensation reaction of diamine with dianhydride at the stoichiometric ratio. The diamine component was composed of synthesized diaminocalix[4]arene and commercial 4,4 -oxydianiline combined in various molar ratios. The dianhydride used was 4,4 -oxydiphthalic anhydride. The poly(amic acid)s were characterized using intrinsic viscosity measurements and their chemical composition was determined using 1 H NMR spectroscopy. The precursors were then transformed into the polyimides using a thermal treatment. Thermal and dynamic mechanical behaviour, wide-angle X-ray diffraction and solubility of the resulting polyimide films in selected solvents were evaluated. The structure-property relationship of the novel types of synthesized polyimides is discussed in terms of the calixarene monomer used and the fraction of it incorporated into the polymer backbone.