Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Study of Spectral, Thermal and Electrochemical Properties of New Thermally Stable Blue Light Emitting Materials Based Aromatic Polyamides
Corresponding Author(s) : Azhar Kamil Rashid
Asian Journal of Chemistry,
Vol. 28 No. 8 (2016): Vol 28 Issue 8
Abstract
In this study, new triphenylamine with aromatic diacid monomers, 4,4'-dicarboxy-4''-acetyl-triphenylamine (AC1), 4,4'-dicarboxy-4''-ethyl-triphenylamine (AC2), 4,4'-dicarboxy-4''-methoxy-triphenylamine (AC3) were successfully synthesized by the aromatic nucleophilic displacement reaction of 4-fluorobenzonitrile with three aniline-derivatives using sodium hydride as the base, followed by alkaline hydrolysis of the di-cyanides intermediates (CY1, CY2, CY3). From these di-acids monomers, a series of poly(amine-amide)s were prepared by the phosphorylation poly-condensation reaction with different aromatic diamines. FTIR, 1H and 13C NMR spectroscopic techniques were used to identify the chemical structures of all resultant compounds and poly(amine-amide)s. These aromatic poly(amine-amide)s have a good solubility in several organic solvents and gave strong and tough thin films via solution casting. They exhibited excellent thermal stability associated with high glass transition temperatures (Tg). In dilute N-methyl pyrrolidone solution, these polymers exhibited a strong photoluminescence in the blue region. Cyclic voltammetry of the results polyamides films cast onto an ITO-coated glass substrate in dry acetonitrile containing 0.1 M of tetrabutylammonium perchlorate as an electrolyte exhibited one oxidation redox couples.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- C.W. Tang and S.A. VanSlyke, Appl. Phys. Lett., 51, 913 (1987); doi:10.1063/1.98799.
- C.W. Tang, S.A. VanSlyke and C.H. Chen, J. Appl. Phys., 65, 3610 (1989); doi:10.1063/1.343409.
- C.K. Adachi, K. Nagai and N. Tamoto, Appl. Phys. Lett., 66, 2679 (1995); doi:10.1063/1.113123.
- JJ. Lu, A.R. Hlil, Y. Sun, A.S. Hay, T. Maindron, J.-P. Dodelet and M. D’Iorio, Chem. Mater., 11, 2501 (1999); doi:10.1021/cm9902063.
- J.F. Yarn, High Performance Polymers, Sage Publications, New York (2008).
- A.P. Kulkarni, C.J. Tonzola, A. Babel and S.A. Jenekhe, J. Mater. Chem., 16, 4556 (2004); doi:10.1021/cm049473l.
- M. Thelakkat and H.W. Schmidt, Aromatic High-Strength Fibers, Wiley, New York (1989).
- K. Ogino, A. Kanegae, R. Yamaguchi, H. Sato and J. Kurjata, J. Macromol. Rapid Commun., 20, 103 (1999); doi:10.1002/(SICI)1521-3927(19990301)20:3<103::AID-MARC103>3.0.CO;2-Q.
- M.Y. Chou, M.-k. Leung, Y.O. Su, C.L. Chiang, C.-C. Lin, J.-H. Liu, C.-K. Kuo and C.-Y. Mou, Chem. Mater., 16, 654 (2004); doi:10.1021/cm034735p.
- S.H. Cheng and G.S. Liou, Macromolecules, 38, (2005).
- S.-H. Hsiao, Y.-M. Chang, H.-W. Chen and G.-S. Liou, J. Polym. Sci. A Polym. Chem., 44, 4579 (2006); doi:10.1002/pola.21547.
- S. Beaupre and J.D.M. Leclerc, Chem. Mater., 18, 4011 (2006); doi:10.1021/cm060407o.
- F. Fleischhaker, A.C. Arsenault, J. Schmidtke, R. Zentel and G.A. Ozin, Chem. Mater., 18, 5640 (2006); doi:10.1021/cm061948g.
- J. Si and C.W. Tang, Appl. Phys. Lett., 80, 3201 (1987); doi:0.1063/1.1475361.
- M. Strukelj, F. Papadimitrakopoulos, T.M. Miller and L.J. Rothberg, Science, 267, 1969 (1995); doi:10.1126/science.267.5206.1969.
- U. Mitschke and P. Bauerle, J. Mater. Chem., 10, 1471 (2000); doi:10.1039/a908713c.
- N.V. Sadavarte, C.V. Avadhani, P.V. Naik and P.P. Wadgaonkar, Eur. Polym. J., 46, 1307 (2010); doi:10.1016/j.eurpolymj.2010.03.007.
- Y. Imai, High Perform. Polym., 7, 337 (1995); doi:10.1088/0954-0083/7/3/010.
- Y. Imai, React. Funct. Polym., 30, 3 (1996); doi:10.1016/1381-5148(95)00109-3.
- Y. Oishi, M. Kakimoto and Y. Imai, J. Polym. Sci. A Polym. Chem., 28, 1763 (1990); doi:10.1002/pola.1990.080280708.
- G.-S. Liou, S.-H. Hsiao, M. Ishida, M. Kakimoto and Y. Imai, Polym. Chem., 40, 2810 (2002); doi:10.1002/pola.10364.
- G.S. Liou and S.-H. Hsiao, J. Polym. Sci. A Polym. Chem., 41, 94 (2003); doi:10.1002/pola.10552.
- N. Yamazaki, F. Higashi and J. Kawabata, J. Polym. Sci. A Polym. Chem., 12, 2149 (1974); doi:10.1002/pol.1974.170120935.
- G.S. Liou and H.J. Yen, J. Polym. Sci. A Polym. Chem., 44, 6094 (2006); doi:10.1002/pola.21708.
- R. Uma, C. Crévisy and R. Grée, Chem. Rev., 103, 27 (2003); doi:10.1021/cr0103165.
- D.M. de Leeuw, M.M.J. Simenon, A.R. Brown and R.E.F. Einerhand, Synth. Met., 87, 53 (1997); doi:10.1016/S0379-6779(97)80097-5.
References
C.W. Tang and S.A. VanSlyke, Appl. Phys. Lett., 51, 913 (1987); doi:10.1063/1.98799.
C.W. Tang, S.A. VanSlyke and C.H. Chen, J. Appl. Phys., 65, 3610 (1989); doi:10.1063/1.343409.
C.K. Adachi, K. Nagai and N. Tamoto, Appl. Phys. Lett., 66, 2679 (1995); doi:10.1063/1.113123.
JJ. Lu, A.R. Hlil, Y. Sun, A.S. Hay, T. Maindron, J.-P. Dodelet and M. D’Iorio, Chem. Mater., 11, 2501 (1999); doi:10.1021/cm9902063.
J.F. Yarn, High Performance Polymers, Sage Publications, New York (2008).
A.P. Kulkarni, C.J. Tonzola, A. Babel and S.A. Jenekhe, J. Mater. Chem., 16, 4556 (2004); doi:10.1021/cm049473l.
M. Thelakkat and H.W. Schmidt, Aromatic High-Strength Fibers, Wiley, New York (1989).
K. Ogino, A. Kanegae, R. Yamaguchi, H. Sato and J. Kurjata, J. Macromol. Rapid Commun., 20, 103 (1999); doi:10.1002/(SICI)1521-3927(19990301)20:3<103::AID-MARC103>3.0.CO;2-Q.
M.Y. Chou, M.-k. Leung, Y.O. Su, C.L. Chiang, C.-C. Lin, J.-H. Liu, C.-K. Kuo and C.-Y. Mou, Chem. Mater., 16, 654 (2004); doi:10.1021/cm034735p.
S.H. Cheng and G.S. Liou, Macromolecules, 38, (2005).
S.-H. Hsiao, Y.-M. Chang, H.-W. Chen and G.-S. Liou, J. Polym. Sci. A Polym. Chem., 44, 4579 (2006); doi:10.1002/pola.21547.
S. Beaupre and J.D.M. Leclerc, Chem. Mater., 18, 4011 (2006); doi:10.1021/cm060407o.
F. Fleischhaker, A.C. Arsenault, J. Schmidtke, R. Zentel and G.A. Ozin, Chem. Mater., 18, 5640 (2006); doi:10.1021/cm061948g.
J. Si and C.W. Tang, Appl. Phys. Lett., 80, 3201 (1987); doi:0.1063/1.1475361.
M. Strukelj, F. Papadimitrakopoulos, T.M. Miller and L.J. Rothberg, Science, 267, 1969 (1995); doi:10.1126/science.267.5206.1969.
U. Mitschke and P. Bauerle, J. Mater. Chem., 10, 1471 (2000); doi:10.1039/a908713c.
N.V. Sadavarte, C.V. Avadhani, P.V. Naik and P.P. Wadgaonkar, Eur. Polym. J., 46, 1307 (2010); doi:10.1016/j.eurpolymj.2010.03.007.
Y. Imai, High Perform. Polym., 7, 337 (1995); doi:10.1088/0954-0083/7/3/010.
Y. Imai, React. Funct. Polym., 30, 3 (1996); doi:10.1016/1381-5148(95)00109-3.
Y. Oishi, M. Kakimoto and Y. Imai, J. Polym. Sci. A Polym. Chem., 28, 1763 (1990); doi:10.1002/pola.1990.080280708.
G.-S. Liou, S.-H. Hsiao, M. Ishida, M. Kakimoto and Y. Imai, Polym. Chem., 40, 2810 (2002); doi:10.1002/pola.10364.
G.S. Liou and S.-H. Hsiao, J. Polym. Sci. A Polym. Chem., 41, 94 (2003); doi:10.1002/pola.10552.
N. Yamazaki, F. Higashi and J. Kawabata, J. Polym. Sci. A Polym. Chem., 12, 2149 (1974); doi:10.1002/pol.1974.170120935.
G.S. Liou and H.J. Yen, J. Polym. Sci. A Polym. Chem., 44, 6094 (2006); doi:10.1002/pola.21708.
R. Uma, C. Crévisy and R. Grée, Chem. Rev., 103, 27 (2003); doi:10.1021/cr0103165.
D.M. de Leeuw, M.M.J. Simenon, A.R. Brown and R.E.F. Einerhand, Synth. Met., 87, 53 (1997); doi:10.1016/S0379-6779(97)80097-5.