Abstract
A study was done on the synthesis of a new poly(arylene ether) and poly(arylene sulfide) with rigid benzoxazole pendants using nucleophilic aromatic substitution reaction. 1,4-Bis(2-benzoxazolyl-2,5-dibromobenzene (I) was synthesized in two steps starting from 2,5-dibromo-p-xylene. A model reaction of aryl dibromide (I) with two equivalent of thiophenol or m-cresol in a typical ether condensation and Ullmann ether reaction condition, respectively, gave very high yield (>93%) of substitution product, suggesting the feasibility of polymer formation in these systems. Monomer (I) was polymerized with 4,4′-thiobisbenzenethiol in 1-methyl-2-pyrrolidone (NMP) using NaOH or K2CO3 as base. Also the same monomer was polymerized with 4,4′-dihydroxydiphenyl ether in an Ullmann ether reaction. The molecular weight of the resulting polymers, however, seemed relatively low according to solution viscosity (ηinh=0.1—0.14 dL g-1). The benzoxazole-substituted poly(phenylene sulfide) polymer was only soluble in strong acids like sulfuric acid and trifluoroacetic acid. The poly(phenylene oxide) analog was soluble in several common organic solvents including chloroform, pyridine and N,N′-dimethylformamide. The polymers were stable up to 450°C as determined by the temperature that weight loss began to appear on TGA. Finally preliminary results on the photoluminacence property in solution were presented.
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Kim, JH., Bang, S. Synthesis of Poly(phenylene oxide) and Poly(phenylene sulfide) Bilaterally Substituted with a Rigid Benzoxazole Group. Polym J 32, 118–121 (2000). https://doi.org/10.1295/polymj.32.118
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DOI: https://doi.org/10.1295/polymj.32.118