Abstract
A new triphenylpyridine-containing aromatic diamine monomer named 4-phenyl-2,6-bis(4-aminophenyl) pyridine was successfully synthesized. A series of polyimides (PIs) with triphenylpyridine moieties were prepared from the newly synthesized diamine monomer via a one-step polymerization with oxydiphthalicanhydride. All the PIs were amorphous and showed excellent solubility in many polar aprotic solvents at room temperature and most of them could afford flexible, transparent, and tough films with good mechanical properties. All the PIs had useful levels of thermal stability associated with high glass-transition temperatures (299–341 °C), 10 % weight-loss temperatures in excess of 537 °C, and char yields at 800 °C in nitrogen higher than 54.9 %.
Similar content being viewed by others
References
Li W, Guo X, Fang J (2014) Synthesis and properties of sulfonated polyimide–polybenzimidazole copolymers as proton exchange membranes. J Mater Sci 49:2745–2753. doi:10.1007/s10853-013-7977-2
Standage AE, Turner WN (1967) A high-temperature polyimide reinforced with silica fibre. J Mater Sci 2:103–111. doi:10.1007/BF00549568
Xu Y, Wang S, Li Z, Xu Q, Zhang Q (2013) Polyimide fibers prepared by dry-spinning process: imidization degree and mechanical properties. J Mater Sci 48:7863–7868. doi:10.1007/s10853-013-7310-0
Li W, Wu Z, Jiang H, Eashoo M, Harris FW, Cheng SZD (1996) High-performance aromatic polyimide fibres: part V compressive properties of BPDA-DMB fibre. J Mater Sci 31:4423–4431. doi:10.1007/BF00356470
Barzic AI, Rusu RD, Stoica I, Damaceanu MD (2014) Chain flexibility versus molecular entanglement response to rubbing deformation in designing poly(oxadiazolenaphthylimide)s as liquid crystal orientation layers. J Mater Sci 49:3080–3098. doi:10.1007/s10853-013-8010-5
Gong S, Liu M, Sun Z, Xia S, Wang Y (2014) Synthesis and characterisation of novel soluble polyimides for the application as liquid crystal vertical alignment layers. Liq Cryst 41:1831–1842
Behniafar H, Hosseinpour M (2013) Novel ortho-linked fluorinated poly(ether-imide)s based on 2,2′-substituted 1,1′-binaphthyl units. Polym Adv Technol 24:118–125
Chung IS, Park CE, Ree M, Kim SY (2001) Soluble polyimides containing benzimidazole rings for interlevel dielectrics. Chem Mater 13:2801–2806
Liaw DJ, Liaw BY, Yang CM (1999) Synthesis and properties of new polyamides based on bis[4-(4-aminophenoxy)phenyl]diphenylmethane. Macromolecules 32:7248–7250
Salbeck J, Bauer J, Weissörtel F (1998) Spiro linked compounds for use as active materials in organic light emitting diodes. Macromol Symp 125:121–132
Liaw DJ, Chang FC (2004) Highly organosoluble and flexible polyimides with color lightness and transparency based on 2,2-bis[4-(2-trifluoromethyl-4-aminophenoxy)-3,5-dimethylphenyl] propane. J Polym Sci A 42:5766–5774
Chern YT, Tsai JY (2008) Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-bis(4-aminophenoxy)-2,6-di-tert-butylbenzene. Macromolecules 41:9556–9564
Calle M, LozanoÁE Campa JGDL, Abajo JD (2010) Novel aromatic polyimides derived from 5′-t-butyl-2′-pivaloylimino-3,4,3′′,4′′-m-terphenyltetracarboxylic dianhydride with potential application on gas separation processes. Macromolecules 43:2268–2275
Tao LM, Yang HX, Liu JG, Fan L, Yang SY (2009) Synthesis and characterization of highly optical transparent and low dielectric constant fluorinated polyimides. Polymer 50:6009–6018
Dong J, Yin C, Luo W, Zhang Q (2013) Synthesis of organ-soluble copolyimides by one-step polymerization and fabrication of high performance fibers. J Mater Sci 48:7594–7602. doi:10.1007/s10853-013-7576-2
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Grant No. 51173115), the Ministry of Education (the Foundation for Ph.D. training, Grant No. 20110181110030) of China.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Gu, Y., Sun, Z., Gong, S. et al. Synthesis and characterization of soluble and thermally stable triphenylpyridine-containing aromatic polyimides. J Mater Sci 50, 6552–6558 (2015). https://doi.org/10.1007/s10853-015-9186-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-015-9186-7