Synthesis and characterization of calix[4]arene‐containing polyimides

Abstract

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.

Recent progress to construct calixarene-based polymers using covalent bonds: synthesis and applications

“…The thermal and dynamic mechanical behavior, wide-angle Xray diffraction and solubility of the resulting polyimide lms in selected solvents were examined. 63 The application of dental composites for tooth restoration is limited by the bonding strength of composite and dentin. These bonding strengths are affected by the shrinkage during polymerization and the mechanical behavior of the composite.…”

A Novel Calix[4]Crown-Based 1,3,4-Oxadiazole as a Fluorescent Chemosensor for Copper(II) Ion Detection

“…Thus, the compound 1 might work as a new type of switchable off-on fluorescent chemosensor. ,arene 2 and 5, 17dibromo-25,27-dihydroxy-26,28-dipropoxycalix[4]arene 3 were synthesized according to the literature procedures (Hobzova, 2010). Dichloromethane and acetonitrile used for photophysical studies were of spectrometric grade.…”

Preparation of Calixarene-PI Nanofibers and Application as a Selective Adsorbent for Heavy Metal Ions

“…They are cyclic oligomers composed of phenol units. Calixarenes can be modified chemically on either the upper or the lower rim to obtain a wide range of various calixarene derivatives containing selected functional groups at desirable locations on the calixarene skeleton [14]. Due to unlimited derivative possibilities induced by their unique three-dimensional structure and their ability to form complexes with metal ions and neutral molecules, calixarenes are widely utilized in host-guest chemistry.…”