Syntheses of Special Structure Polymers Using Characteristic Reactivity of Phenol Residue and Elucidation of Their Specific Characters

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1. 2, 6-Dihydroxynaphthalene underwent the oxidative coupling polymerization in basic water, producing poly(2, 6-dihydroxy-1, 5-naphthylene).2. Thermal polycondensation took place for the tyrosine derivative, whose phenolic moiety was 3, 5-dihydroxymethylated, and for tetra-hydroxymethylated bisphenols in the solid sate as well as in the solution.3. The copper-catalyzed oxidative coupling polymerization of the crown ether possessing a phenol moiety in the ring gave unique poly (phenylene oxide), whose side chains of crown ether arranged perpendicularly on the main chain. The p-brominated monomer was found to give no homopolymer for halogen displacement polymerization but to produce the copolymer with 2, 6-dimethy1-4-bromophenol.4. The crown ether tube oligomer was synthesized by the stepwise Williamson-type condensation of the crown ether containing two phenol residues. The obtained dimer was found to make an inclusion complex with ammonium salt.5. Tetra-p-chloromethylated thiacalix [4] arene was polymerized by using the Williamson-type condensation. The soluble polymers were successfully obtained under appropriate reaction conditions.6. Tri-p-brominated homooxacalix [3] arene underwent the halogen displacement polymerization in the presence of base, producing the tubular poly (phenylene oxide), however, not perfect.7. The oxidative coupling polymerization of thiacalix [4] arene did not take place, while that of the di-O-methylated or-bezoylated derivative was found to produce the poly (phenylene oxide).8. Di-O-bezoylated calix [4] arene was di-p-brominated at the unprotected phenoilc moieties and then underwent the halogen displacement polymerization; the degree of the reaction was found to be 60%.