A new diether-diamine monomer, 1,1-bis [4-(4-aminophenoxy)-3-methylphenyl]cyclopentane (BAMPC), containing a cardo cyclopentane unit and a pendant methyl substituent, was synthesized through a multistep procedure. The structure of the methyl-substituted diether-diamine monomer was confirmed using FT-IR, 1H NMR, 13C NMR, and mass spectrometry. Polycondensation of BAMPC with aromatic dialdehydes, including terephthalaldehyde and isophthalaldehyde, produced a series of co-poly (azomethine-ether)s incorporating cardo cyclopentane units in the polymer backbone. The influence of the cardo cyclopentane structure and pendant methyl group on the solubility and thermal stability of the resulting co-poly (azomethine-ether)s was examined. The polymers exhibited glass transition temperatures (Tg) in the range of 165-178°C and thermal degradation temperatures (Td) between 456 and 486°C, indicating thermal stability. The polyazomethines were soluble in polar aprotic solvents such as DMF, NMP, DMAc, and DMSO at ambient temperature or upon heating. X-ray diffraction analysis indicated that SPAM-2, SPAM-3, SPAM-4, and SPAM-5 exhibited amorphous characteristics with a broad diffraction peak around 2θ ≈ 20°, whereas SPAM-1 showed semicrystalline behaviour. The inherent viscosities of the co-poly (azomethine-ether)s ranged from 0.20 to 0.39 dL g-1.
GrigorasMColotinGDobreanuA, et al.Synthesis and characterization of some aliphatic-aromatic poly(schiff base)s. Eur Polym J2001; 37: 2213–2220. https://doi.org/10.1016/S0014-3057(01)00119-7
2.
RiberaDManteconASerraA. Synthesis and crosslinking of a series of dimeric liquid-crystalline diglycidylester compounds containing imine groups. J Polym Sci Polym Chem2002; 40: 4344–4356. https://doi.org/10.1002/pola.10510ss
3.
SuhSCShimSC. Synthesis and properties of a novel polyazomethine with high photoconductivity and second-order optical nonlinearity. Synth Met2000; 114: 91–95. https://doi.org/10.1016/S0379-6779(99)00253-8
4.
JaglarzJCisowskiJJurusikJ, et al.Reflectance studies of polyazomethine thin films. Rev Adv Mater Sci2004; 8: 82–85.
5.
JarzabekBWeszkaJDomanskiM, et al.Optical properties of amorphous polyazomethine thin films. Thin Solid Films2006; 510: 230–234. https://doi.org/10.1016/j.tsf.2005.12.238
6.
AlyKIKhalafAA. New polymer syntheses IX: synthesis and properties of new conducting polyazomethine polymers containing main chain cycloalkanone and pyridine moieties. J Appl Polym Sci2000; 77(77:6): 1218–1229. https://doi.org/10.1002/(SICI)1097-4628/20000808
7.
GrigorasMAntonoaiaNC. Synthesis of isoelectronic polyazomethine and poly(arylene vinylene) by a palladium-catalyzed suzuki coupling method. Polym Int2005; 54: 1641–1646. https://doi.org/10.1002/pi.1895
8.
El-ShekeilAAl-KhaderMAbu-BakrAO. Synthesis, characterization and dc electrical conductivity of some oligomer mixed metal complexes. Synth Met2004; 143: 147–152. https://doi.org/10.1016/j.synthmet.2003.11.001
9.
PuertolasJACarodEDiaz-CallejaR, et al.Influence of the metal cross-linking on the dielectric, mechanical and thermal properties of a liquid crystalline polyazomethine. Macromolecules1997; 30: 773–779. https://doi.org/10.1021/ma961119o
10.
NiuHHuangYBaiX, et al.Study on crystallization, thermal stability and hole transport properties of conjugated polyazomethine materials containing 4,4′-bisamine-triphenylamine. Mater Chem Phys2004; 86(1): 33–37. https://doi.org/10.1016/j.matchemphys.2004.01.023
DuttaPKJainPSenP, et al.Synthesis and characterization of a novel polyazomethine ether for NLO application. Eur Polym J2003; 39: 1007–1011. https://doi.org/10.1016/S0014-3057(02)00328-2
13.
WeaverMSBradleyDDC. Organic electroluminescence devices fabricated with chemical vapour deposited polyazomethine films. Synth Met1996; 83: 61–66. https://doi.org/10.1016/S0379-6779(96)03817-9
14.
TatsuuraSSotoyamaWMotoyoshiK, et al.Polyazomethine conjugated polymer film with second-order nonlinear optical properties fabricated by electric-field-assisted chemical vapor deposition. Appl Phys Lett1993; 62(18): 2182–2184. https://doi.org/10.1063/1.109462
ChevrotCHenriT. Electrosynthesis and oxidation of new oligoazomethines containing N-ethylcarbazole groups. Synth Met2001; 118(1-3): 157–166. https://doi.org/10.1016/S0379-6779(00)00403-3
17.
ShuklaURaoKVRakshitAK. Synthesis and characterization of polyazomethines containing flexible ether linkages. J Appl Polym Sci2003; 88(1): 153–160. https://doi.org/10.1002/app.11652
CozanVAvramE. Side-chain thermotropic liquid crystalline polysulfone obtained from polysulfone Udel by chemical modification. Eur Polym J2003; 39(1): 107–114. https://doi.org/10.1016/S0014-3057(02)00181-7
26.
MarinLCozanVBrumaM, et al.Synthesis and properties of aromatic polyazomethines In: Proceedings of the 8th international symposium on polymers for advanced technologies. Springer, 2005, pp. 13–16.
27.
ChoiMKKimHLSuhDH. Changes of fluorescence color in novel poly(azomethine) by the acidity variation. J Appl Polym Sci2006; 101(2): 1228–1233. https://doi.org/10.1002/app.24209
28.
YangJSunWLJiangHJ, et al.Synthesis and properties of two novel poly(schiff base)s and their rare-earth complexes. Polymer2005; 46(23): 10478–10483. https://doi.org/10.1016/j.polymer.2005.08.037
29.
LiouGSLinHYHsiehYL, et al.Synthesis and characterization of wholly aromatic poly(azomethine)s containing donor–acceptor triphenylamine moieties. J Polym Sci Polym Chem2007; 45(21): 4921–4932. https://doi.org/10.1002/pola.22228
30.
NiuHJHuangYDBaiXD, et al.Novel poly-schiff bases containing 4,4′-diamino-triphenylamine as hole transport material for organic electronic devices. Mater Lett2004; 58(24): 2979–2983. https://doi.org/10.1016/j.matlet.2004.05.007
31.
NiuHJKangHCaiJ, et al.Novel soluble polyazomethines with pendant carbazole and triphenylamine derivatives: preparation, characterization, and optical, electrochemical and electrochromic properties. Polym Chem2011; 2(12): 2804–2817. https://doi.org/10.1039/C1PY00237F
WangCShiehSLeGoffE, et al.Synthesis and characterization of a new conjugated aromatic poly(azomethine) derivative based on the 3′,4′-dibutyl-α-terthiophene building block. Macromolecules1996; 29(9): 3147–3156. https://doi.org/10.1021/ma9514131
35.
TsaiFCChangCCLiuCL, et al.New thiophene-linked conjugated poly(azomethine)s: synthesis, photophysical properties, and theoretical electronic structures. Macromolecules2005; 38(5): 1958–1966. https://doi.org/10.1021/ma048112o
36.
KimHCKimJSKimKS, et al.Synthesis and characterization of new soluble polyazomethines bearing fluorine and carbazole units in the backbone and solubility-improving moieties in the side group. J Polym Sci Polym Chem2004; 42(4): 825–834. https://doi.org/10.1002/pola.11045
37.
YangCJJenekheSA. Effects of structure on refractive index of conjugated polyimines. Chem Mater1994; 6(2): 196–203. https://doi.org/10.1021/cm00038a016
ParkSBKimHZinWC, et al.Synthesis and properties of polyazomethines having flexible (n-alkyloxy)methyl side chains. Macromolecules1993; 26(7): 1627–1632. https://doi.org/10.1021/ma00059a021
40.
YangCJJenekheSA. Conjugated aromatic polyimines. 2. Synthesis, structure, and properties of new aromatic polyazomethines. Macromolecules1995; 28(4): 1180–1196. https://doi.org/10.1021/ma00108a054
41.
ThomasOInganäsOAnderssonMR. Synthesis and properties of a soluble conjugated poly(azomethine) with high molecular weight. Macromolecules1998; 31(8): 2676–2678. https://doi.org/10.1021/ma9701090
42.
MatsumotoTYamadaFKurosakiT. Fully conjugated and soluble polyazomethines. Macromolecules1997; 30(12): 3547–3552. https://doi.org/10.1021/ma9614104
43.
AnkushraoSSGugwadVMUbaleVP, et al.High performance poly(ether-amide)s derived from 1,1-bis[4-(4-carboxy methylene phenoxy)-3-methyl phenyl] cyclopentane and aromatic diamines. Polym Sci Ser B2018; 60(3): 263–272. https://doi.org/10.1134/S1560090418030107
44.
AnkushraoSSPatilYSUbaleVP, et al.Synthesis and characterization of thermally stable poly(ether-azomethine)s derived from 1,1-bis[4-(4-benzaldehyde oxy)-3-methyl phenyl] cyclopentane. J Macromol Sci A Pure Appl Chem2017; 54(6): 411–417. https://doi.org/10.1080/10601325.2017.1313155
45.
MahindrakarJNPatilYSSalunkhePH, et al.Optically transparent, organosoluble poly(ether-amide)s bearing triptycene unit: synthesis and characterization. J Macromol Sci A Pure Appl Chem2018; 55(9): 658–667. https://doi.org/10.1080/10601325.2018.1510291
46.
AnkushraoSSGhanwatAAPatilYS, et al.Synthesis, characterization and properties of processable polyazomethines for high temperature applications. J Adv Sci Res2021; 12(3): 306–314. https://doi.org/10.55218/jasr.s2202112336
