Abstract
A series of new organosoluble poly(amide-ether-imidazole)s with different functional groups, such as flexible ether linkages, substituted imidazole and carbazole rings, and electron withdrawing CF3 groups, were synthesized from a new diamine and various dicarboxylic acids using two methods: (1) direct polycondensation with triphenyl phosphite (TPP) as an activating agent, N-methyl-2-pyrrolidone (NMP), pyridine (Py) and LiCl; and (2) direct polycondensation using ionic liquids (ILs) and TPP without Py, LiCl or NMP. Room temperature ILs containing anions such as Br−, BF−4 and PF−6 with symmetrical 1,3-dialkylimidazolium cations were prepared and used as polycondensation media. The polymers were obtained with good yields in ILs with moderate viscosities (0.34–0.62 dl g−1) in a shorter reaction time (2.5 vs 12 h) than in NMP. All of the polymers were amorphous in nature and showed excellent solubility in amide-type polar aprotic solvents. They showed good thermal stability with glass transition temperatures (Tg) between 162 and 303 °C and 10% weight loss temperatures of 388 and 421 °C in O2 and N2 atmospheres, respectively. These polymers showed blue fluorescence emission upon irradiation with ultraviolet light and are candidates for applications in electroluminescent devices.
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References
Wasserscheid, P. & Welton, T. Ionic Liquids in Synthesis (Wiley-VCH, KGaA, Weinheim, 2002).
Lu, J., Yan, F. & Texter, J. Advanced applications of ionic liquids in polymer science. Prog. Polym. Sci. 34, 431–448 (2009).
Kubisa, P. Application of ionic liquids as solvents for polymerization processes. Prog. Polym. Sci. 29, 3–12 (2004).
Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2084 (1999).
Lozinskaya, E. I., Shaplov, A. S. & Vygodskii, Y. S. Direct polycondensation in ionic liquids. Eur. Polym. J. 40, 2065–2075 (2004).
Kubisa, P. Ionic liquids in the synthesis and modification of polymers. J. Polym. Sci. Part A 43, 4675–4683 (2005).
Lozinskaya, E. I., Shaplov, A. S., Kotseruba, M. V., Komarova, L. I., Lyssenko, K. A., Antipin, M. Y., Golovanov, D. G. & Vygodskii, Y. S. “One-pot” synthesis of aromatic poly(1,3,4-oxadiazole)s in novel solvents-ionic liquids. J. Polym. Sci. Part A 44, 380–394 (2006).
Yoneyama, M. Direct polycondensation of aromatic tetracarboxylic acids with aromatic diamines in ionic liquids. High Perform. Polymer (Guildf) 18, 817–823 (2006).
Paraknowitsch, J. P., Thomas, A. & Antonietti, M. A detailed view on the polycondensation of ionic liquid monomers towards nitrogen doped carbon materials. J. Mater. Chem. 20, 6746–6758 (2010).
Vygodskii, Y. S., Lozinskaya, E. I., Shaplov, A. S., Lyssenko, K. A., Antipin, M. Y. & Urman, Y. G. Implementation of ionic liquids as activating media for polycondensation processes. Polym. J. 45, 5031–5045 (2004).
Cassidy, P. E. Thermally Stable Polymer Chapter 4 (Dekker, New York, 1980).
García, J. M., García, F. C., Serna, F. & de la Peña, J. L. High-performance aromatic polyamides. Prog. Polym. Sci. 5, 623–686 (2010).
Hearle, J. W. High-Performance Fibres, (Woodhead Publishing, Cambridge, UK, 2001).
Gaudiana, R. A., Minns, R. A., Sinta, R., Weeks, N. & Rogers, H. G. Amorphous rigid-rod polymers. Prog. Polym. Sci. 14, 47–89 (1989).
Hsiao, S. H. & Lin, K. H. Soluble aromatic polyamides bearing asymmetrical diaryl ether groups. Polymer (Guildf) 45, 7877–7885 (2004).
Kricheldorf, H. R., Bohme, S. & Schwarz, G. Macrocycles. 17. The role of cyclization in kinetically controlled polycondensations. 2. Polyamides. Macromolecules 34, 8879–8885 (2001).
Liou, G. S., Hsiao, S. H., Ishida, M., Kakimoto, M. & Imai, Y. Synthesis and characterization of novel soluble triphenylamine-containing aromatic polyamides based on N,N′-bis(4-aminophenyl)-N,N′-diphenyl-1,4-phenylenediamine. J. Polym. Sci. Part A 40, 2810–2818 (2002).
Liu, Y. -L., Li, S. -H., Lee, H. -C. & Hsu, K. -Y. Selective reactivity of aromatic amines toward 5-maleimidoisophthalic acid for preparation of polyamides bearing N-phenylmaleimide moieties. React. Funct. Polym. 66, 924–930 (2006).
Mallakpour, S. & Taghavi, M. Kinetics and thermal degradation study of optically active and thermally stable aromatic polyamides with flame-retardancy properties. Polym. J. 41, 308–318 (2009).
Ghaemy, M., Amini Nasab, S. M. & Alizadeh, R. Synthesis and characterization of new soluble polyamides from an unsymmetrical diamine bearing a bulky triaryl pyridine pendent group. J. Appl. Polym. Sci. 116, 3725–3731 (2010).
Ghaemy, M. & Alizadeh, R. Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2, 4, 5-triaryl imidazole pendent group. Eur. Polym. J. 45, 1681–1688 (2009).
Ghaemy, M. & Amini Nasab, S. M. Synthesis and characterization of organo-soluble polyamides containing triaryl imidazole pendant and ether linkage moieties: thermal, photophysical, and chemiluminescent properties. Polym. Adv. Technol. 22, 2311–2318 (2011).
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, 1575–1586 (2011).
Ghaemy, M. & Amini Nasab, S. M. Synthesis and identification of organosoluble polyamides bearing a triaryl imidazole pendent: thermal, photophysical, chemiluminescent, and electrochemical characterization with a modified carbon nanotube electrode. React. Funct. Polym. 70, 306–313 (2010).
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, 3108–3115 (2009).
Ghaemy, M. & Amini Nasab, S. M. Synthesis and identification of organosoluble polyimides: thermal, photophysical and chemiluminescence properties. Polym. J. 42, 648–656 (2010).
Ghaemy, M. & Alizadeh, R. Synthesis, characterization and photophysical properties of organosoluble and thermally stable polyamides containing pendent N-carbazole group. React. Funct. Polym. 71, 425–432 (2011).
Kim, H. C., Kim, J. S., Kim, K. S., Park, H. K., Baek, S. & Ree, M. Synthesis and characterization of new, soluble polyazomethines bearing fluorene and carbazole units in the backbone and solubility-improving moieties in the side group. J. Polym. Sci. Part A 42, 825–834 (2004).
Grigalevicius, S., Grazulevicius, J. V., Gaidelis, V. & Jankauskas, V. Synthesis and properties of poly(3,9-carbazole) and low-molar-mass glass-forming carbazole compounds. Polymer (Guildf) 43, 2603–2608 (2002).
Grazulevicius, J. V., Strohriegl, P., Pielichowski, J. & Pielichowski, K. Carbazole-containing polymers: synthesis, properties and applications. Prog. Polym. Sci. 28, 1297–1353 (2003).
Angiolini, L., Giorgini, L., Li, H., Golemme, A., Mauriello, F. & Termine, R. Synthesis, characterization and photoconductive properties of optically active methacrylic polymers bearing side-chain 9-phenylcarbazole moieties. Polymer (Guildf) 51, 368–377 (2010).
Liou, G. S., Hsiao, S. H., Huang, N. K. & Yang, Y. L. Synthesis, photophysical, and electrochromic characterization of wholly aromatic polyamide blue-light-emitting materials. Macromolecules 39, 5337–5346 (2006).
Barghamadi, M., Ghaemy, M. & Alizadeh, R. Non-isothermal cure kinetics of diglycidyl ether of bisphenol-a with various aromatic diamines. Iran. Polym. J. 18, 431–443 (2009).
Liou, G. S., Chen, H. W. & Yen, H. J. Synthesis and photoluminescent and electrochromic properties of aromatic poly(amine amide)s bearing pendent N-carbazolylphenyl moieties. J. Polym. Sci. Part A 44, 4108–4121 (2006).
Vygodskii, Y. S., Lozinskaya, E. I. & Shaplov, A. S. Ionic liquids as novel reaction media for the synthesis of condensation polymers. Macromol. Rapid Commun. 23, 676–680 (2002).
Chauveau, E., Marestin, C., Martin, V. & Mercier, R. G. Microwave-assisted polymerization process: a way to design new, high molecular weight poly(arylimidazole)s. Polymer (Guildf) 49, 5209–5214 (2008).
Hsiao, S.-H. & Chang, Y.-H. New soluble aromatic polyamides containing ether linkages and laterally attached p-terphenyls. Eur. Polym. J. 40, 1749–1757 (2004).
Ge, Z., Yang, S., Tao, Z., Liu, J. & Fan, L. Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines. Polymer (Guildf) 45, 3627–3635 (2004).
Hsiao, S. H., Chen, C. W. & Liou, G. S. Novel aromatic polyamides bearing pendent diphenylamino or carbazolyl groups. J. Polym. Sci. Part A 42, 3302–3313 (2004).
Sheng, S. -R., Pei, X. -L., Huang, Z. -Z., Liu, X. -L. & Song, C. -S. Novel soluble fluorinated aromatic polyamides derived from 2-(4-trifluoromethylphenoxy)terephthaloyl chloride with various aromatic diamines. Eur. Polym. J. 45, 230–236 (2009).
Feng, K., Hsub, F. L., Van DerVeer, D., Bota, K. & Xiu, R. Tuning fluorescence properties of imidazole derivatives with thiophene and thiazole. J. Photochem. Photobiol. A 165, 223–228 (2004).
Liou, G. S. & Chang, C. W. Highly stable anodic electrochromic aromatic polyamidescontaining N,N,Ń,Ń-tetraphenyl-p-phenylenediamine moieties: synthesis, electrochemical, and electrochromic properties. Macromolecules 41, 1667–1674 (2008).
Van Krevelen, D. W. & Hoftyzer, P. J. Properties of Polymers 3rd edn (Elsevier Scientific Publishing, Amsterdam, 1976).
Yin, D., Li, Y., Shao, Y., Zhao, X., Yang, S. & Fan, L. Synthesis and characterization of soluble polyimides based on trifluoromethylated aromatic dianhydride and substitutional diaminetriphenylmethanes. J. Fluorine Chem. 126, 819–823 (2005).
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We thank the Research Affairs Division of the University of Mazandaran (UMZ), Babolsar (Iran), for partial financial support.
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Ghaemy, M., Hassanzadeh, M., Amini Nasab, S. et al. Ionic liquids in the synthesis of high-performance fluorinated polyamides with backbones containing derivatives of imidazole and carbazole rings. Polym J 45, 622–630 (2013). https://doi.org/10.1038/pj.2012.217
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DOI: https://doi.org/10.1038/pj.2012.217
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