Synthesis and properties of poly(amine-amide)s and poly(amine-imide)s based on 4,4′-diamino-4″-fluorotriphenylamine

• A new fluorine-containing, triphenylamine-based diamine monomer was synthesized.
• New redox-active polyamides and polyimides with fluorotriphenylamine units were prepared.
• The polymers could afford flexible and tough films with moderately high thermal stability.
• The polymers are potential anodically coloring green or blue electrochromes.

Novel electroactive aromatic poly(amine-amide)s and poly(amine-imide)s with 4-fluorotriphenylamine units in the backbone were prepared from a newly synthesized diamine monomer, 4,4′-diamino-4″-fluorotriphenylamine, with aromatic dicarboxylic acids and tetracarboxylic dianhydrides via the phosphorylation technique and conventional two-step polycondensation technique, respectively. All the synthesized polymers could afford flexible and tough films with moderately high thermal stability. Cyclic voltammograms of the poly(amine-amide) and poly(amine-imide) films on the indium-tin oxide (ITO)-coated glass substrate exhibited a pair of reversible oxidation waves with oxidation half-wave potentials (E1/2) of 0.91–0.99 V and 1.19–1.23 V (vs. Ag/AgCl), respectively, in an electrolyte/acetonitrile solution. They also exhibited obvious electrochromic behavior between their neutral and oxidized states changing from pale yellow to green or blue.

A new fluorine-containing, triphenylamine-based diamine monomer, 4,4′-diamino-4″-fluorotriphenylamine, was synthesized and led to a series of redox-active and electrochromic aromatic polyamides and polyimides.Figure optionsDownload as PowerPoint slide