申请人:United States of America as represented by the Secretary of the Air Force
公开号:US05081256A1
公开(公告)日:1992-01-14
2-Benzimidazole terephthalic acid, 4,4'-dicarboxy-2,2'-bisbenzimidazole benyl and 4,4"-dicarboxy-2'-phenyl-3'-[2-(4-phenylbenzthiazole)]-6'-[2-(3-phenylbenz imidazole]-p-terphenyl are provided. Also provided are methods for preparing these dicarboxylic acids. 2-benzimidazole terephthalic acid is prepared by reacting trimellitic anhydride with o-phenylenediamine in a suitable solvent. 4,4'-dicarboxy-2,2'-bisbenzimidazole biphenyl is prepared by diazotizing 2-amino-5-bromobenzoic acid to prepare 4,4'-dibromodiphenic acid, reacting the 4,4'-dibromodiphenic acid with o-phenylenediamine in trimethylsilyl polyphosphate solution to prepare 4,4'-dibromo-2,2'-bisbenzimidazolyl biphenyl, reacting the 4,4'-dibromo-2,2'-bisbenzimidazolyl biphenyl with cuprous cyanide to prepare the corresponding dicyano compound, and hydrolyzing the dicyano compound. 4,4"-Dicarboxy-2'-phenyl-3'-[2-(4-phenylbenzthiazole)]-6'-[2-(3-phenylbenz imidazole)]-p-terphenyl is prepared by reacting a 4-benzazole benzil with 1,3-bis(p-bromophenyl)-2-propanone to prepare 2,5-bis(p-bromophenyl)-3-phenyl-4-(2-phenylbenzazole) cyclopentadienone, reacting the cyclopentadienone with 2-(3-ethynylphenyl) benzimidazole to prepare the corresponding dibromo terphenyl compound, reacting the dibromo terphenyl compound with cuprous cyanide to prepare the corresponding dicyano terphenyl compound, and hydrolyzing the dicyano compound.
提供2-苯并咪唑对苯二甲酸,4,4'-二羧基-2,2'-双苯并咪唑苯基和4,4"-二羧基-2'-苯基-3'-[2-(4-苯基苯并噻唑)]-6'-[2-(3-苯基苯并咪唑)]-对联苯。还提供了制备这些二羧酸的方法。2-苯并咪唑对苯二甲酸通过将三羧基异构酸酐与邻苯二胺在适当的溶剂中反应制备而成。4,4'-二羧基-2,2'-双苯并咪唑联苯通过重氮化2-氨基-5-溴苯甲酸制备4,4'-二溴联苯甲酸,将4,4'-二溴联苯甲酸与邻苯二胺在三甲基硅基聚磷酸酯溶液中反应制备4,4'-二溴-2,2'-双苯并咪唑基联苯,将4,4'-二溴-2,2'-双苯并咪唑基联苯与氰化亚铜反应制备相应的二氰化合物,并水解二氰化合物制备而成。4,4"-二羧基-2'-苯基-3'-[2-(4-苯基苯并噻唑)]-6'-[2-(3-苯基苯并咪唑)]-对联苯通过将4-苯并咪唑苯甲酮与1,3-双(对溴苯基)-2-丙酮反应制备2,5-双(对溴苯基)-3-苯基-4-(2-苯基苯并咪唑)环戊二烯酮,将环戊二烯酮与2-(3-乙炔基苯基)苯并咪唑反应制备相应的二溴联苯化合物,将二溴联苯化合物与氰化亚铜反应制备相应的二氰联苯化合物,并水解二氰化合物制备而成。