Thesis (M.Sc.)--Chulalongkorn University, 2000

4-Tolyldiphenylamine (TDPA) and N,N'-diphenyl-N,N'-bis(4-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD) monomers were synthesized via Tosoho method. The condensation polymerization of both monomers with benzaldehyde (BzA) was carried out to yield linear polymers using chlorobenzene as a solvent and p-toluenesulfonic acid as a catalyst. TDPA was polymerized with BzA at various conditions. It was found that the polymer with higher molecular weight (Mw) could be obtained when the amount of catalyst, the monomer ratio and the reaction temperature increased. In this research, two types of dopant, i.e., ionic compounds and oxidants were preliminarily doped with poly(vinylcarbazole) (PVK), a commercially common polymer in photoconductive field. Three ionic compounds, i.e., lithium perchlorate, tetraethyl perchlorate and tetrabutyl perchlorate agglomerated and separated from PVK while 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) performed the most effectiveresults. Both polymers were thus reacted with DDQ at various amount in tetrahydrofuran at room temperature. 1H-NMR spectra indicated that all methine protons of the polymers could be completely oxidized at the mole ratio of repeating unit:DDQ of 2:1 with the reaction time longer than 24 hours. Mw and glass transition temperature of the oxidized polymers were not significantly changed, which indicated that no crosslinking reaction occurred during the oxidation. FT-IR spectra indicated that neither residual DDQ nor its reduced form contaminated in the oxidized polymers. Both oxidized polymers performed the new UV-VIS absorbances around 700 nm due to the extended conjugation and radical cations on the polymer chains. ESR spectroscopy of both completely oxidized polymers clearly confirmed the existence of the radical on the polymer chains. Both completely oxidation potentials as the starting polymers. DC conductivity of both completely oxidized polymers was in the range of 10 -11 S/cm, which was over 2 magnitudes higher than the starting polymers.