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New Derivative Benzothiazole Suspend Diphenyleamine Based Aromatic Polyamides as Electrochromic Light Emitting Devices
Corresponding Author(s) : Azhar Kamil Rashid
Asian Journal of Chemistry,
Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018
Abstract
In this work, a set of some substituted aromatic polyamides containing (benzothiazole)diphenylamine moieties (P1-P5) was prepared via the phosphorylation polycondensation technique from the reaction of several aromatic dicarboxylic acids with synthesized N,N-bis(4-aminophenyl)2-amine-6-methoxybenzothiazol (M). It was prepared from the cesium fluoride-mediated double N-arylation reaction of 6-methoxybenzothiazol (a) with p-fluoronitrobenzene to form dinitro intermediate (I) followed by palladium-catalyzed hydrazine reduction. FTIR, 1H and 13C NMR spectra techniques were utilized to characterize the chemical structures of all the resultant intermediates and polyamides. Thermal analysis revealed that the synthesized polyamides showed perfect thermal stability and superior glass transition temperatures (Tg). Dilute solutions of these polyamides in N-methyl pyrrolidone (10-5 M) showed good optical properties where exhibited intensive photoluminescence in the region of blue colour. Cyclic voltammograms of the synthesized polymers membrane molding onto the basis of ITO-plated glass in the spesial electrolyte contains 10-1 M of tetrabutylammonium perchlorate(TBAP) in dry CH3CN which exhibited one oxidation redox wave couples.
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- J.A. Reglero-Ruiz, M. Trigo-López, F.C. Garcia and J.M. Garcia, Polymers, 9, 414 (2017); https://doi.org/10.3390/polym9090414.
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- K.Y. Law, Chem. Rev., 93, 449 (1993); https://doi.org/10.1021/cr00017a020.
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- S.R. Forrest, Chem. Rev., 97, 1793 (1997); https://doi.org/10.1021/cr941014o.
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References
J.A. Reglero-Ruiz, M. Trigo-López, F.C. Garcia and J.M. Garcia, Polymers, 9, 414 (2017); https://doi.org/10.3390/polym9090414.
E. HaLasa and M. Heneczkowski, Polimery (Warsaw), 43, 1 (1998).
M.Z. Elsabee, R.E. Morsi and S. Selim, 30, 387 (2018); https://doi.org/10.1177/0954008317699259.
S.-H. Hsiao and Y.-H. Chang, Eur. Polym. J., 40, 1749 (2004); https://doi.org/10.1016/j.eurpolymj.2004.04.019.
S.H. Hsiao and S.L. Cheng, J. Polym. Sci. A Polym. Chem., 53, 496 (2015); https://doi.org/10.1002/pola.27465.
M. Ghaemy and S.M. Amini Nasab, React. Funct. Polym., 70, 306 (2010); https://doi.org/10.1016/j.reactfunctpolym.2010.02.004.
R. Friend, R.W. Gymer, A.B. Holmes, J.H. Burroughes, R.N. Marks, C. Taliani, D.D.C. Bradley, D.A.D. Santos, J.L. Brédas, M. Lögdlund and W.R. Salaneck, Nature, 397, 121 (1999); https://doi.org/10.1038/16393.
Y.-H. Chou, H.-J. Yen, C.-L. Tsai, W.-Y. Lee, G.-S. Liou and W.-C. Chen, J. Mater. Chem. C Mater. Opt. Electron. Devices, 1, 3235 (2013); https://doi.org/10.1039/c3tc30252k.
K.Y. Law, Chem. Rev., 93, 449 (1993); https://doi.org/10.1021/cr00017a020.
U. Mitschke and P. Bäuerle, J. Mater. Chem., 10, 1471 (2000); https://doi.org/10.1039/a908713c.
S.R. Forrest, Chem. Rev., 97, 1793 (1997); https://doi.org/10.1021/cr941014o.
T. Zhang, S. Liu, D.G. Kurth and C.F.J. Faul, Adv. Funct. Mater., 19, 642 (2009); https://doi.org/10.1002/adfm.200801409.
P.M. Beaujuge and J.R. Reynolds, Chem. Rev., 110, 268 (2010); https://doi.org/10.1021/cr900129a.
M. Liang and J. Chen, Chem. Soc. Rev., 42, 3453 (2013); https://doi.org/10.1039/c3cs35372a.
W.P. Lin, S.-J. Liu, T. Gong, Q. Zhao and W. Huang, Adv. Mater., 26, 570 (2014); https://doi.org/10.1002/adma.201302637.
J.H. Wu and G.S. Liou, Adv. Funct. Mater., 24, 6422 (2014); https://doi.org/10.1002/adfm.201401608.
S.-H. Cheng, S.-H. Hsiao, T.-H. Su and G.-S. Liou, Macromolecules, 38, 307 (2005);https://doi.org/10.1021/ma048774d.
H.-J. Yen and G.-S. Liou, Polym. Chem., 3, 255 (2012); https://doi.org/10.1039/C1PY00346A.
H.M. Wang and S.H. Hsiao, J. Polym. Sci. A Polym. Chem., 52, 272 (2014); https://doi.org/10.1002/pola.27001.
Y. Wang, Y. Liang, J. Zhu, X. Bai, X. Jiang, Q. Zhang and H. Niu, RSC Adv., 5, 11071 (2015); https://doi.org/10.1039/C4RA12970A.
N. Yamazaki, M. Matsumoto and F. Higashi, J. Polym. Sci.: Polym. Chem., 13, 1373 (1975); https://doi.org/10.1002/pol.1975.170130609.
T.H. Su, S.H. Hsiao and G.S. Liou, J. Polym. Sci. A Polym. Chem., 43, 2085 (2005); https://doi.org/10.1002/pola.20666.
D. De Leeuw, M.M.J. Simenon, A.R. Brown and R.E.F. Einerhand, Synth. Mater., 87, 53 (1997); https://doi.org/10.1016/S0379-6779(97)80097-5.