Novel Organosoluble Poly(pyridine−imide) with Pendent Pyrene Group: Synthesis, Thermal, Optical, Electrochemical, Electrochromic, and Protonation Characterization

Abstract

A new diamine containing a pyridine heterocyclic group and a pyrene substituent, 4-(1-pyrene)-2,6-bis(4-aminophenyl)pyridine (PBAPP), was synthesized and used in a preparation of poly(pyridine−imide) by direct polycondensation with 4,4‘-hexafluoroisopropylidenediphathalic anhydride (6FDA) in N-methyl-2-pyrrolidinone (NMP). The poly(pyridine−imide) derived from diamine (PBAPP) was highly soluble in several solvents such as THF, NMP, DMAc, DMF, pyridine, DMSO, and cyclohexanone at room temperature or upon heating at 70 °C and exhibited good thermal stability both in nitrogen and air (Td10>520 °C) and a high dielectric constant of 4.32 at 1 kHz. The poly(pyridine−imide) could be cast into a flexible and tough film from DMAc solution. The poly(pyridine−imide) film had a tensile strength of 118 MPa and a tensile modulus of 2.2 GPa. The optical properties exhibited the UV−vis absorption bands at the region of 200−400 nm and possessed strong orange fluorescent (560 nm) after protonated with protic acid.