Polymers of Intrinsic Microporosity with Dinaphthyl and Thianthrene Segments

Abstract

Novel intrinsically microporous homopolymers and copolymers derived from PIM-1 monomers (5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethylspirobisindane and 2,3,5,6-tetrafluoroterephthalonitrile) with two additional monomers—tetrahydroxydinaphthyl and tetrafluorotetraoxide thianthrene—are reported as potential materials for membrane-based gas separations. The resulting copolymers prevent efficient space packing of the stiff polymer chains and consequently exhibit analogous behavior to that of PIM-1, the most widely reported polymer in this class of materials. In addition, the copolymerization provides high molecular weight copolymers and low polydispersity if the polymerization reactions were conducted at elevated temperature for an extended period of time. Detailed structural characterization of the new monomers and polymers was determined by 1H and 19F nuclear magnetic resonance spectroscopy (NMR). The thermal properties were detected by differential scanning calorimetry (DSC) and thermogravimetric analysis ...