Abstract
We propose four types of poly(arylene ether)s (PAEs) polymers with remarkable thermal stability and high optical transmittance. The PAEs were synthesized by means of nucleophilic displacement through polymerization on a 2-trifluoromethyl-activated bisfluoro monomer to react with bisphenols. Thermal analysis indicated that PAEs possessed a high glass-transition point of ∼300 °C and a decomposition temperature of Td=500 °C at a weight loss of 5%. In addition, a high transmittance of 92%, a low dielectric constant of ∼1.9 and the mechanical properties of PAE films were experimentally determined. The physical properties of PAEs related to the arylene ether positions and phenyl substituents, which showed great potential as substrates for flexible electronics.
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References
Bottino, F. A., Pasquale, G.Di. & Iannelli, P. Synthesis, characterization, and study of the thermal properties of new poly(arylene ether 134-oxadiazole)s. Macromolecules 34, 33–37 (2001).
Hedrick, J. L. Poly (aryl ether amides). Macromolecules 24, 812–813 (1991).
Huang, W. Y., Liaw, B. R., Chang, M. Y., Han, Y. K. & Huang, P. T. High glass-transition temperature and organosoluble novel arylene ether polymers. Macromolecules 40, 8649–8657 (2007).
Chikashige, Y., Chikyu, Y., Miyatake, K. & Watanabe, M. Poly (arylene ether) ionomers containing sulfofluorenyl groups for fuel cell applications. Macromolecules 38, 7121–7126 (2005).
Liaw, B. R., Huang, W. Y., Huang, P. T., Chang, M. Y. & Han, Y. K. Novel poly(arylene ether)s containing multi-substituted pentaphenylene moiety. Polymer 48, 7087–7097 (2007).
Hedrick, J. L. & Labadie, J. W. Poly (aryl ether phenylquinoxalines). Macromolecules 23, 1561 (1990).
Xu, Z., Dannenberg, C., Springer, J., Banerjee, S. & Maier, G. Gas separation properties of polymers containing fluorene moieties. Chem. Mater. 14, 3271–3276 (2002).
Bourgeois, Y., Charlier, Y., Devaux, J. & Legras, R. Synthesis of a poly(aryl ether sulfone)-poly(aryl ether ketone) triblock copolymer. Polymer 37, 5503–5511 (1996).
Banerjee, S. & Maier, G. Novel high Tg high-strength poly(aryl ether)s. Chem. Mater. 11, 2179–2184 (1999).
Chikashige, Y., Chikyu, Y., Miyatake, K. & Watanabe, M. Poly (arylene ether) ionomers containing sulfofluorenyl groups for fuel cell applications. Macromolecules 38, 7121–7126 (2005).
Qi, Y., Ding, J., Day, M., Jiang, J. & Callender, C. L. Cross-linkable highly fluorinated poly(arylene ether ketones/sulfones) for optical waveguiding applications. Chem. Mater. 17, 676–682 (2005).
Aitken, C. L., McHattie, J. S. & Paul, D. R. Dynamic mechanical behavior of polysulfones. Macromolecules 25, 2910–2922 (1992).
Attwood, T. E., Barr, D. A., Feasey, G. G., Leslie, V. J., Newton, A. B. & Rose, J. B. Poly(arylene ether sulphones) by polyetherification: 1 synthesis of halogenophenols. Polymer 18, 354–358 (1997).
Palmans Anja, R. A., Smith, P. & Weder, C. Polarizing energy transfer in photoluminescent conjugated polymers with covalently attached sensitizers. Macromolecules 32, 4677–4685 (1999).
Tullos, G. L. & Cassidy, P. E. Polymers derived from hexafluoroacetone: 12F-Poly(ether ketone). Macromolecules 24, 6059–6064 (1991).
Saran, N., Parikh, K., Suh, D. S., Muñoz, E., Kolla, H. & Manohar, S. K. Fabrication and characterization of thin films of single-walled carbon nanotube bundles on flexible plastic substrates. J. Am. Chem. Soc. 126, 4462–4463 (2004).
Tullos, G. L., Cassidy, P. E. & St Clair, A. K. Polymers derived from hexafluoroacetone: 12F-poly (ether ketone). Macromolecules 24, 6059–6064 (1991).
Park, S. K. & Kim, S. Y. Synthesis of poly(arylene ether ketone)s containing trifluoromethyl groups via nitro displacement reaction. Macromolecules 31, 3385–3387 (1998).
Liu, P., Wu, Y., Li, Y., Ong, B. S. & Zhu, S. Enabling gate dielectric design for all solution-processed high-performance flexible organic thin-film transistors. J. Am. Chem. Soc. 128, 4554–4555 (2006).
Zhao, G., Ishizaka, T., Kasai, H., Oikawa, H. & Nakanishi, H. Fabrication of unique porous polyimide nanoparticles using a reprecipitation method. Chem. Mater. 19, 1901–1905 (2007).
Su, K., Bujalski, D. R., Eguchi, K., Gordon, G. V., Ou, D. L., Chevalier, P., Hu, S. & Boisvert, R. P. Low-k interlayer dielectric materials: synthesis and properties of alkoxy-functional silsesquioxanes. Chem. Mater. 17, 2520–2529 (2005).
US patent no. 4835197, 5658994, 5108840, 5114780, 5145936 and 5155175.
Lu, Z., Shao, P., Li, J., Hua, J., Qin, J., Qin, A. & Ye, C. Two novel fluorinated poly(arylene ether)s with pendant chromophores for second-order nonlinear optical application. Macromolecules 37, 7089–7096 (2004).
Ding, J., Du, X., Day, M., Jiang, J., Callender, C. L. & Stupak, J. Highly fluorinated poly(arylene alkylene ether sulfone)s: synthesis and thermal properties. Macromolecules 40, 3145–3153 (2007).
Ganapathy, H. S., Hwang, H. S. & Lim, K. T. Synthesis and properties of fluorinated ester-functionalized polythiophenes in supercritical carbon dioxide. Ind. Eng. Chem. Res. 45, 3406–3411 (2006).
Hill, D. J., Mio, M. J., Prince, R. B., Hughes, T. S. & Moore, J. S. A field guide to foldamers. Chem. Rev. 101, 3893–4011 (2001).
Huang, C., Zhen, C. G., Su, S. P., Loh, K. P. & Chen, Z. K. Solution-processable polyphenylphenyl dendron bearing molecules for highly efficient blue light-emitting diodes. Org. Lett. 7, 391–394 (2005).
Johnson, B. C., Yilgör, İ., Tran, C., Iqbal, M., Wightman, J. P., Lloyd, D. R. & McGrath, J. E. Synthesis and characterization of sulfonated poly(acrylene ether sulfones). J. Polym. Sci. Polym. Chem. Ed. 22, 721–737 (1984).
Pixton, M. R. & Paul, D. R. Gas transport properties of adamantane-based polysulfones. Polymer 36, 3165–3172 (1995).
Bottino, F. A., Pasquale, G.Di. & Iannelli, P. Synthesis characterization and study of the thermal properties of new poly(arylene ether 134-oxadiazole)s. Macromolecules 34, 33–37 (2001).
Wolfe, J. F. & Arnold, F. E. Rigid-rod polymers 1 synthesis and thermal properties of para-aromatic polymers with 26-benzobisoxazole units in the main chain. Macromolecules 14, 909–915 (1981).
Huang, W. Y., Gao, W., Kwei, T. K. & Okamoto, Y. Synthesis and characterization of poly(alkyl-substituted p-phenylene ethynylene)s. Macromolecules 34, 1570–1578 (2001).
McHattie, J. S., Koros, W. J. & Paul, D. R. Effect of isopropylidene replacement on gas transport properties of polycarbonates. J. Polym. Sci. B Polym. Phys. 29, 731–746 (1991).
Huang, W. Y., Matsuoka, S., Kwei, T. K. & Okamoto, Y. Aggregation and gelation of fully conjugated rigid-rod polymers poly(2,5-dialkyl-1,4-phenyleneethynylene)s. Macromolecules 34, 7166–7171 (2001).
Hansen, E. F., Derrick, M. R., Schilling, M. R. & Garcia, R. The effects of solution application on some mechanical and physical properties of thermoplastic amorphous polymers used in conservation: poly(vinyl acetate)s. J. Am. Inst. Conser. 30, 203–213 (1991).
Ikeda, K., Ogoma, Y., Fujii, T., Hachimori, A., Kondo, Y., Hayakawaa, T., Iwatsuki, M. & Akaike, T. Conformation of polyamino acids containing fluorine. Polymer 31, 344–347 (1990).
Lee, S. H., Jang, B. B. & Kafafi, Z. H. Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives. J. Am. Chem. Soc. 127, 9071–9078 (2005).
Ohshita, J., Lee, K. H., Hamamoto, D., Kunugi, Y., Ikadai1, J., Kwak, Y. W. & Kunai, A. Synthesis of novel spiro-condensed dithienosiloles and the application to organic FET. Chem. Lett. 33, 892–893 (2004).
Jang, W., Shin, D., Choi, S., Park, S. & Han, H. Effects of internal linkage groups of fluorinated diamine on the optical and dielectric properties of polyimide thin films. Polymer 48, 2130–2143 (2007).
Colquhoun, H. M. & Williams, D. J. Crystal and molecular simulation of high-performance polymers. Acc. Chem. Res. 33, 189–198 (2000).
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Lee, CC., Huang, WY. The influence of arylene ether positions and phenyl substituents on the physical properties of functional fluorinated polymers. Polym J 43, 180–185 (2011). https://doi.org/10.1038/pj.2010.116
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DOI: https://doi.org/10.1038/pj.2010.116