Novel thermally stable poly(amine hydrazide)s and poly(amine‐1,3,4‐oxadiazole)s for luminescent and electrochromic materials

Abstract

We describe the preparation, characterization, and luminescence of four novel electrochromic aromatic poly(amine hydrazide)s containing main‐chain triphenylamine units with or without a para‐substituted N,N‐diphenylamino group on the pendent phenyl ring. These polymers were prepared from either 4,4′‐dicarboxy‐4″‐N,N‐diphenylaminotriphenylamine or 4,4′‐dicarboxytriphenylamine and the respective aromatic dihydrazide monomers via a direct phosphorylation polycondensation reaction. All the poly(amine hydrazide)s were amorphous and readily soluble in many common organic solvents and could be solution‐cast into transparent and flexible films with good mechanical properties. These poly(amine hydrazide)s exhibited strong ultraviolet–visible absorption bands at 346–348 nm in N‐methyl‐2‐pyrrolidone (NMP) solutions. Their photoluminescence spectra in NMP solutions or as cast films showed maximum bands around 508–544 and 448–487 nm in the green and blue region for the two series of polymers. The hole‐transporting and electrochromic properties were examined by electrochemical and spectroelectrochemical methods. All obtained poly(amine hydrazide)s and poly(amine‐1,3,4‐oxadiazole)s exhibited two reversible oxidation redox couples at 0.8 and 1.24 V vs. Ag/AgCl in acetonitrile solution and revealed excellent stability of electrochromic characteristics, changing color from original pale yellow to green and then to blue at electrode potentials of 0.87 and 1.24 V, respectively. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 3245–3256, 2005

Synthesis and evaluation of photoluminescent and electrochemical properties of new aromatic polyamides and polyimides with a kink 1,2‐phenylenediamine moiety

“…Recently, we reported the synthesis of soluble aromatic polyamides and polyimides bearing TPA units in the main chain based on N,N ′‐bis(4‐aminophenyl)‐ N,N ′‐diphenyl‐1,4‐phenylenediamine,41, 42 N,N ‐bis(4‐aminophenyl)‐ N ′, N ′‐diphenyl‐1,4‐phenylenediamine 43, 44. and N,N ‐bis(4‐carboxyphenyl)‐ N ′, N ′‐diphenyl‐1,4‐phenylenediamine 45, 46. Because of the incorporation of bulky, three‐dimensional propeller‐shaped TPA units along the polymer backbone, all the polymers were amorphous, had good solubility in many aprotic solvents and good film‐forming capability, and exhibited high thermal stability.…”

Synthesis, spectral properties and application of novel disazo disperse dyes derived from polyester waste

“…As an attempt towards fruitful chemical recycling, pure terephthalic dihydrazide 3 was prepared in good yield by aminolysis of PET bottle waste using hydrazine hydrate under reflux conditions (Scheme 1). Terephthalic dihydrazide is a crystalline solid which has been used for the synthesis of thermally stable aromatic polyamines that have electron‐transport properties [28], and for synthesis of some potent analogues of bis‐1,3,4‐oxadiazole, bis‐1,2,4‐triazole and 4‐thiazolidinone derivatives which are found to show anti‐bacterial activity [29].…”

Multielectrochromic property of N-phenylnaphthalen-2-amine and N-(4-(1H-pyrrol-1-yl)phenyl)-N-phenylnaphthalen-2-amine

“…Arylamine-based polymers are widely used as the hole-transport layer in electroluminescent diodes, but they also show interesting electrochromic behaviors. Electron-rich arylamines are known to be easily oxidized, and the oxidation process is always associated with a noticeable change of the coloration [8][9][10][11][12][13]. N-phenylnaphthalen-2-amine (BNA) and its polymer (PBNA) are excellent light-emitting materials, and the polymer can be synthesized electrochemically [14].…”