• poly(naphthylimide-amide);
  • N[BOND]N bond;
  • micellar structure;
  • light emission;
  • hydrophobic;
  • n-doping


This work reports the synthesis and characterization of novel six-membered poly(imide-amide)s based on a naphthalene-N,N′-bis(imido-amine) and various dicarboxylic acids containing flexible units such as ether, hexafluoroisopropylidene and diphenylsilane. A new design is proposed for aromatic poly(imide-amide)s, in which the imide and amide units are directly connected through a N[BOND]N bond. These highly thermostable polymers were successfully synthesized using Yamazaki–Higashi reaction conditions. The poly(imide-amide)s were processed into thin hydrophobic films having self-assembled micellar structures. The presence of aggregates in solutions with concentrations below 1% was evidenced and is discussed in relation to the chemical structure. The photoluminescence properties of polymer solutions and films showed their ability to produce white and blue light emission. The lowest unoccupied molecular orbital energy level was calculated using cyclic voltammetry data, showing good electron injection and transport characteristics. The properties of these polymers make them attractive for applications in advanced optoelectronics and related fields. © 2014 Society of Chemical Industry