Synthesis and Characterization of Novel Photoactive ‎Poly(ether-amide)s Based on Highly Substituted ‎Phenanthrimidazole

Document Type : Research Article

Authors

1 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, I.R. Iran

2 Department of Chemistry, Bojnourd Branch, Islamic Azad University, Bojnourd, I.R. Iran

Abstract

A new aromatic diamine monomer containing ether linkage based on the phenanthrimidazole ring, ‎1,1´-(4,4´- oxy bis(1,4-phenylene))bis(2-(4-aminophenyl)-1H-phenanthro[9,10-d]imidazole) was synthesized through four-‎components condensation of 4,4´-diamino diphenyl ether, 4-nitrobenzaldehyde, phenanthrene-9,10-dione and ammonium ‎acetate in presence of acetic acid, followed by palladium-catalyzed hydrazine monohydrate reduction. This new monomer ‎was further confirmed by FT-IR, 1H NMR, and 13C NMR spectroscopy. A series of new aromatic polyamides containing ‎phenanthrimidazole ring in the main chain was prepared by direct polycondensation of the prepared diamine with four ‎commercially available aromatic and aliphatic diacids. These polymers are essentially amorphous and were soluble in polar ‎aprotic solvents such as DMF, NMP, DMAc, and DMSO. Inherent viscosities of polyamides were in the range 0.42–0.53 ‎dL/g indicating the formation of medium molecular weight polymers. Polyamides exhibited glass-transition temperature (Tg) in ‎the range 260-280 °C. The 10% weight loss temperature in air atmosphere measured by TGA was in the range 454-526 °C ‎indicating their good thermal stabilities. The photophysical properties of diamine and polyamides were investigated by UV-Vsible and fluorescence spectroscopy.

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References

[1] Mallakpour S., Taghavi M., A Facile, Microwave-Assisted Synthesis of Novel Optically Active Polyamides Derived from 5-(3-methyl-2-Phthalimidylpentanoylamino)Isophthalic Acid and Different Diisocyanates, Eur. Polym. J., 44 (1): 87-97 (2008).
[2] Majo M.A., Alla A., Bou J.J., Herranz C., Munoz-Guerra S., Synthesis and Characterization of Polyamides Obtained from Tartaric Acid and l-Lysine, Eur. Polym. J., 40 (12): 2699-2708 (2004).
[3] Behniafar H., Banihashemi A., Synthesis and Characterization of New Soluble and Thermally Stable Aromatic Poly(amide-imide)s Based on N-[3,5-bis(N-trimellitoyl)phenyl]phthalimide, Eur. Polym. J. 40 (7): 1409-1415 (2004).
[4] Cui X., Li W., Yan D., Yuan C., Di Silvestro G., Synthesis and Characterization of Polyamides X 18, J. Appl. Polym. Sci., 98 (4): 1565-1571 (2005).
[5] Hearle J.W.S., ‎"‎High-Performance Fibres", Woodhead Publishing Ltd, Cambridge (2001).
[6] Mark H.F., "Encyclopedia of Polymer Science and Technology", Wiley Interscience, 12 Volume Set, 3rd Edition, New York (2004).
[7] Imai Y., Recent Advances in Synthesis of High-Temperature Aromatic Polymers, React. Funct. Polym., 30 (1-3): 3-15 (1996).
[8] Liou G.Sh., Fang Y.K., Yen H.J., Synthesis, and Properties of Noncoplanar Rigid-rod Aromatic Polyamides Containing Phenyl or Naphthyl Substituents, J. Polym. Res., 14 (2): 147-155 (2007).
[9] Amini Nasab S.M., Ghaemy M., Synthesis and Characterization of New Polyamides and Polyimides Containing Dioxypyrimidine Moiety in the Main Chain with Bulky Imidazole Pendent Group: Solubility, Thermal and Photophysical Properties, J. Polym. Res., 18 (6): 1575-1586 (2011).
[10] Ghaemy M., Alizadeh R., Behmadi H., Synthesis of Soluble and Thermally Stable Polyimide from New Diamine Bearing N-[4-(9H-carbazol-9-yl)phenyl] Formamide Pendent Group, Eur. Polym. J., 45 (11):3108-3115 (2009).
[11] Sava I., Iosip M.D., Bruma M., Hamciuc C., Robison J., Okrasa L., Aromatic Polyamides with Pendent Acetoxybenzamide Groups and Thin Films Made Therefrom, Eur. Polym. J., 39 (4): 725-738 (2003).
[12] Faghihi Kh., Mozaffari Z., New Polyamides Based on 2,5-bis[(4-carboxyanilino) carbonyl] Pyridine and Aromatic Diamines: Synthesis and Characterization, J. Appl. Polym. Sci., 108 (2): 1152-1158 (2008).
[13] In I., Kim S.Y., Soluble Wholly Aromatic Polyamides Containing Unsymmetrical Pyridyl Ether linkages, Polymer, 47 (2): 547-552 (2006).
[14] Abdolmaleki A., Novel Aromatic Poly(amide-hydrazide)s Based on the Bipyridine. Part I: Synthesis, Characterization and Thermal Stability, Polym. Degrad. Stab., 92 (2): 292-298 (2007).
[15] Bottino F.A., Di Pasquale G., Scalia L., Pollicino L.A., Synthesis and Characterisation of New Polyamides Containing 6,6′-oxy or 6,6′-Carbonyldiquinoline Units, Polymer, 42 (8): 3323-3332 (2001).
[16] Bottino F.A., Di Pasquale G., Pollicino A., Scalia L., Synthesis and Characterization of New Polyamides Containing 6,6′-Methylenediquinoline Units, Polymer, 39 (20): 4949-4954 (1998).
[17] Saadati S.M., Mosslemin M.H., Behmadi H., Shams A., Synthesis, Characterisation and Fluorescence Studies of New Bis-phenanthrimidazole Derivatives, J. Chem. Res., 37 (8): 487-512 (2013).
[18] Yamazaki N., Higashi F., Kawataba J., Studies on Reactions of the N-phosphonium Salts of Pyridines. XI. Preparation of Polypeptides and Polyamides by Means of Triaryl Phosphites in Pyridine, J. Polym. Sci. A: Polym. Chem., 12 (9): 2149-2154 (1974).
[19] Dey J., Dogra S.K., Dual Fluorescence in 2-(4’-N,N-Dimethylamino-phenyl)benzazole and its Benzimidazole Analog – Effect of Solvent and pH on Electronic Spectra, J. Phys. Chem., 98 (14): 3638-3644 (1994).
Iranian Journal of Chemistry and Chemical Engineering
Volume 36, Issue 6 - Serial Number 86
November and December 2017
Pages 69-76

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