SYNTHESIS AND CHARACTERIZATION OF POLYAMIDES BASED ON CUBANE-1,4-DICARBOXYLIC ACID

The direct polycondensations of cubane-1,4-dicarboxylic acid with 1,4- phenylenediamine (2a), 4,4'-oxydianiline (2b), 4,4'-sulfonyldianiline (2c), and 9,9'-bis(4-aminophenyl)florene (2d) were carried out in N-me thyl-2-pyrrolidone/pyridine containing triphenylphosphite and lithium chloride at 110 degrees C for 9 h. Polyamide 3a obtained from 2a was s carcely soluble in organic solvent even during heating, and was solubl e only in conc-H2SO4, whereas 3c and 3d derived from 2c and 2d, respec tively, were readily soluble in N-methyl-2-pyrrolidone, N,N-dimethylac etamide, N,N-dimethylformamide, and dimethylsulfoxide. After treating polyamide 3d with the rhodium complex catalyst in NMP, cubane units we re quantitatively converted into cyclooctatetraenes.