Synthesis of poly(arylene ether)s containing triphenylamine units via nitro displacement reaction

Macromolecules

Volumn 38, Issue 14, 2005, Pages 5844-5845

  Lee, Mong Sup ^a   Kim, Sang Youl ^b  

^a Department of Chemistry   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOPHORES; ELECTROLUMINESCENCE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; KETONES; MONOMERS; NUCLEAR MAGNETIC RESONANCE; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

BIS(4-NITRO-3-TRIFLUOROMETHYLPHENYL)PHENYLAMINE; NUCLEOPHILIC AROMATIC SUBSTITUTION REACTION; ORGANIC ELECTROLUMINESCENT DEVICES; POLY(ARYLENE ETHER TRIPHENYLAMINE);

AROMATIC POLYMERS;

EID: 22944475792     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma048170+     Document Type: Article

References (25)

1. Cotter, R. J. Engineering Plastics: A Handbook of Polyarylethers; Gordon and Breach Publishers: Amsterdam, 1995.
2. (a) Labadie, J. W.; Hedrick, J. L.; Ueda, M. In Step-Growth Polymers for High-Performance Materials, New Synth. Methods; Hedrick, J. L., Labadie, J. W., Eds.; ACS Symposium Series 624; American Chemical Society: Washington, DC, 1996; p 210.
3. (b) Terrier, F. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group; VCH Publishers: New York, 1991.
4. (c) Kricheldorf, H. R. In Handbook of Polymer Synthesis; Kricheldorf, H. R., Ed.; Marcel Dekker: New York, 1992; p 545.
5. Bartoli, G.; Todesco, P. E. Acc. Chem. Res. 1977, 10, 125.
6. (a) Williams, F. J.; Donahue, P. E. J. Org. Chem. 1977, 42, 3414.
7. (b) Markezich, R. L.; Zamek, O. S. J. Org. Chem. 1977, 42, 3431.
8. (c) Markezich, R. L.; Zamek, O. S.; Donahue, P. E.; Williams, F. J. J. Org. Chem. 1977, 42, 3435.
9. (d) White, D. M.; Takekoshi, T.; Williams, F. J.; Relles, H. M.; Donahue, P. E.; Klopfer, H. J.; Loucks, G. R.; Manello, J. S.; Matthews, R. O.; Schlvenz, R. W. J. Polym. Sci., Polym. Chem. Ed. 1981, 19, 1635.
10. (e) Takekoshi, T. Polym. J. 1987, 19, 191.
11. (a) Chung, I. S.; Kim, S. Y. Macromolecules 2000, 33, 9474.
12. (b) Chung, I. S.; Kim, S. Y. J. Am. Chem. Soc. 2001, 123, 11071.
13. Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
14. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489.
15. Moylan, C. R.; Twieg, R. J.; Lee, V. Y.; Swanson, S. A.; Betterton, K. M.; Miller, R. D. J. Am. Chem. Soc.. 1993, 115, 12599.
16. (a) Miller, R. D.; Burland, D. M.; Jurich, M.; Lee, V. Y.; Moylan, C. R.; Thackara, J. I.; Twieg, R. J.; Verbiest, T.; Volksen, W. Macromolecules 1995, 28, 4970.
17. (b) Kido, J.; Harada, G.; Nagai, K. Polym. Adv. Technol. 1996, 7, 31.
18. (c) Lu, J.; Hlil, A. R.; Hay, A. S.; Maindron, T.; Dodelet, J.; Lam, J.; D'Iorio, M. J. Polym. Sci., Polym., Part A: Polym. Chem. 2000, 38, 2740.
19. (d) Liaw, D. J.; Hsu, P. N.; Chen, W. H.; Lin, S. L. Macromolecules 2002, 35, 4669.
20. (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
21. (b) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213.
22. (c) Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960.
23. The detailed synthetic procedure and the spectroscopic data of the monomer and the model compound are in the Supporting Information.
24. The band gaps of polymers, calculated from absorption band edges of 393, 392, and 392 nm in UV-vis spectra, are 3.15, 3.16, and 3.16 eV, respectively. The HOMO levels of polymers were calculated from cyclic voltammetry using the ferrocene value of -4.8 eV as a standard.
25. Thelakkat, M.; Fink, R.; Poesch, P.; Ring, J.; Schmidt, H.-W. Polym. Prepr. 1997, 38 (1), 394.