A novel diamine monomer 4-(4-diethylaminophenyl)-2,6-bis(4-aminophenyl)pyridine (APAP) was successfullysynthesized, and then a series of poly(pyridine imide)s was prepared from APAP with five commercial dianhydrides:pyromellitic dianhydride (PMDA), 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA), 4,4′-oxydiphthalic anhydride(ODPA), 3,3′,4,4′-benzophenone tetracarboxylic dianhydride (BTDA), and 4,4′-(hexafluoroisopropylidene)diphthalicanhydride (6FDA) via a two-step solution polycondensation method. The structure of APAP was characterized by FT-IR,NMR, and MS. The resulting polymers have good solubility in polar solvents, such as NMP, DMF, and DMSO. Furthermore,they exhibited outstanding thermal stability. The glass transition temperature (Tg) of polymers range from 326 to 346 oC, andthe temperature at 5 % and 10 % weight loss in the range of 527 oC to 570 oC and 550 oC to 601 oC, respectively. Moreover,they also presented excellent hydrophobicity with contact angels in the range of 88.4 o to 94.0 o.