New aromatic polyazomethines were synthesized by polycondensation reaction of a diamine containing 1,3,4-oxadiazole ring, namely, 4,4′-diamino-4″-[2-(4-phenoxy)-5-(4-dimethylaminophenyl)-1,3,4-oxadiazole)]triphenylmethane, with terephthalic aldehyde or bis(4-formylphenoxyphenyl)fluorene, by using N-methyl-2-pyrrolidinone (NMP) as solvent. The polymers were easily soluble in polar solvents, such as NMP, N,N-dimethylacetamide, or chloroform, and showed high thermal stability with the initial decomposition temperature above 415°C and the temperature of 10% weight loss in the range of 450–460°C. They exhibited high char yield at 800°C in the range of 52–56%. Optical properties were studied by absorption and photoluminescence spectra. In solution, the polymers presented two absorption maxima in the ranges 273–278 and 330–346 nm and emitted violet-blue light in the range of 413–468 nm, depending on the solvent polarity. The Stokes shift and emission quantum yield values depend on the polymer structure and solvent polarity. The emission intensity in NMP solution was enhanced upon increasing the HCl concentration, while the absorption spectral profile was slightly influenced.
MorganPWKwolekSLPletcherTC. Aromatic azomethine polymers and fibers. Macromolecules1987; 20: 729–739.
2.
IwanASekD. Processible polyazomethines and polyketanils: from aerospace to light-emitting diodes and other advanced applications. Prog Polym Sci2008; 33: 289–345.
3.
ZaltariovMFCazacuMShovaS. A silicon-containing polyazomethine and derived metal complexes: synthesis, characterization, and evaluation of the properties. Des Monomers Polym2014; 17: 668–683.
4.
JeevadasonAWMurugavelKKNeelakantanMA. Review on Schiff bases and their metal complexes as organic photovoltaic materials. Renew Sustain Energ Rev2014; 36: 220–227.
5.
MarinLCozanVBrumaM. Synthesis and thermal behaviour of new poly(azomethine-ether). Eur Polym J2006; 42: 1173–1182.
6.
IwanAPalewiczMSikoraA. Aliphatic-aromatic poly(azomethine)s with ester groups as thermotropic materials for opto(electronic) applications. Synth Met2010; 160: 1856–1867.
7.
IwanA. An overview of LC polyazomethines with aliphatic-aromatic moieties: thermal, optical, electrical and photovoltaic properties. Renew Sustain Energ Rev2015; 52: 65–79.
8.
IwanAPalewiczMChuchmałaA. Opto(electrical) properties of new aromatic polyazomethines with fluorine moieties in the main chain for polymeric photovoltaic devices. Synth Met2012; 162: 143–153.
9.
NiuHCaiJZhaoP. Simple approach to regulate the spectra of novel kinds of polyazomethines containing bulky triphenylamine: electrochemistry, electrochromism and photophysical responsive to environment. Dyes Pigments2013; 96: 158–169.
10.
IwanABalcerzakESKoronaKP. Investigation of optical and electrical properties of new aromatic polyazomethine with thiophene and cardo moieties toward application in organic solar cells. Synth Met2013; 185–186: 17–24.
11.
OlingaTInganasOAnderssonMR. Synthesis and properties of a soluble conjugated poly(azomethine) with high molecular weight. Macromolecules1998; 31: 2676–2678.
12.
MishraMDasDPadhiKB. Synthesis and characterization of a novel heterocyclic poly(Schiff base sulfide) polymer: polymerization of N,N′-bis(p-chlorobenzylidine)-2,6-diaminopyridine with sodium sulfide. J Macromol Sci Part A: Pure Appl Chem1998; 35: 867–873.
BenerjeeSGutchPKSaxenaC. Poly-Schiff bases—IV. Synthesis and characterization of poly(etherazomethine)s. Des Monomers Polym1999; 2: 135–142.
15.
SchulzBBrumaMBrehmerL. Aromatic poly(1,3,4-oxadiazole)s as advanced materials. Adv Mater1997; 9: 601–613.
16.
HamciucCIpateAMHamciucE. Thermal degradation kinetics of some aromatic poly(1,3,4-oxadiazole-ether)s. High Perform Polym2008; 20: 296–310.
17.
MarinLPerjuEDamaceanuMD. Designing thermotropic liquid crystalline polyazomethines based on fluorine and/or oxadiazole chromophores. Eur Polym J2011; 47: 1284–1299.
18.
LisaGIpateAMHamciucC. Thermal and thermo-oxidative degradation of some heterocyclic aromatic polyethers containing phenylquinoxaline and/or 1,3,4-oxadiazole rings. J Anal Appl Pyrol2015; 112: 37–47.
19.
ChochosCLGovarisGKKakaliF. Synthesis, optical and morphological characterization of soluble main chain 1,3,4-oxadiazole copolyarylethers—potential candidates for solar cells applications as electron acceptors. Polymer2005; 46: 4654–4663.
20.
SeguraJL. The chemistry of electroluminescent organic materials. Acta Polym1998; 49: 319–344.
HamciucEHamciucCCazacuM. Poly(1,3,4-oxadiazole-ether-imide)s and their polydimethylsiloxane-containing copolymers. Eur Polym J2007; 43: 4739–4749.
27.
HamciucCHamciucESerbezeanuD. Thermal and optical properties of some phosphorus-containing poly(1,3,4-oxadiazole-ester-imide)s. Polym Adv Technol2011; 22: 2458–2468.
28.
IpateAMHomocianuMHamciucC. Photophysical behavior of some aromatic poly(1,3,4-oxadiazole-ether)s derivatives. Spectrochim Acta Part A: Mol Biomol Spectrosc2014; 123: 167–175.
29.
HamciucCHamciucEHomocianuM. Blue light-emitting polyamide and poly(amide-imide)s containing 1,3,4-oxadiazole ring in the side chain. Dyes Pigments2015; 114: 110–123.
30.
ParkKHTaniTKakimotoM. Synthesis and characterization of new diphenylfluorene-based aromatic polyazomethines. Macromol Chem Phys1998; 199: 1029–1033.
31.
CorreiaFCSantosTCFGarciaJR. Synthesis and characterization of a new semiconductor oligomer having quinoline and fluorene units. J Braz Chem Soc2015; 26: 84–91.
32.
SekDIwanAJarzabekB. Hole transport triphenylamine-azomethine conjugated system: synthesis and optical, photoluminescence, and electrochemical properties. Macromolecules2008; 41: 6653–6663.
33.
JonesBAFacchettiAWasilewskiMR. Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport. J Am Chem Soc2007; 129: 15259–15278.
WuCSLeeYTChenY. Organometallic polymers based on fluorene-bridged bis-benzimidazolylidene via direct ligand–metal coordination: synthesis, characterization and optical properties. Polym Chem2012; 3: 2776–2784.
