Synthesis and characterization of novel fluorinated polyimides derived from 1,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic dianhydrides

A new structurally asymmetric diamine monomer containing flexible ether linkages and bulky trifluoromethyl substituents, namely 1,3-bis(4-amino-2-trifluoromethylphenoxy)naphthalene, was prepared from 1,3-dihydroxynaphthalene and 2-chloro-5-nitrobenzotrifluoride. New series of fluorinated polyimides were synthesized from the diamine with six commercially available aromatic tetracarboxylic dianhydrides using a conventional two-stage process with thermal or chemical imidization. The resulting polyimides were highly soluble in a variety of organic solvents and could afford transparent and tough films via solution casting. These polyimides exhibited moderately high glass-transition temperatures (by DSC) of 236–268 °C and softening temperatures (by thermomechanical analysis) of 231–250 °C, and they did not show significant decomposition before 500 °C under either nitrogen or air atmosphere. Also, they revealed low moisture absorptions (0.32–0.78%), low dielectric constants (2.81–3.24 at 10 kHz), and high optical transparency (ultraviolet–visible absorption cutoff wavelengths of 377–426 nm).