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A novel fluorinated pyridine-containing aromatic diamine monomer, 4-phenyl-2,6-bis[2-(4-amino-2-trifluoromethyphenoxy)phenyl]pyridine (o, p-6FPAPP), was prepared in a three-step synthetic route. This aromatic diamine was then employed to synthesize a series of fluorinated pyridine-containing polyimides (PIs) by polycondensation with various aromatic dianhydrides via the conventional two-step method. The inherent viscosities of the resulting poly(amic acid)s (PAAs) and PIs were in the range of 0.71–0.89 and 0.62–0.84 dL/g; all the PIs obtained by chemical imidization were readily soluble in common organic solvents such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), dimethyl sulfoxide (DMSO), tetrahydrofuran (THF) and so on. Meanwhile, transparent, strong and flexible PI films were obtained, which had good thermal stability, with the glass transition temperature (Tg) of 195.2°C–232.7°C, the temperature at 10% weight loss of 530.2°C–546.0°C in nitrogen atmosphere, and good optical transparency with the cutoff wavelengths of 354–382 nm, as well as outstanding mechanical properties with tensile strengths of 96.4–105.8 MPa, tensile modulus of 1.57–1.88 GPa and elongations at break of 9.5%–13.4%. The PI films were also found to possess low water uptake of 0.52%–0.67%. [ABSTRACT FROM PUBLISHER]