2018 (1) 6

Synthesis of meta-linked fluorinated oligo(arylene ether) with hydroxyl end groups

 

Ihor Tkachenko, Yaroslav Kobzar, Oleg Shekera, Valery Shevchenko

 

Institute of Macromolecular Chemistry of the National Academy of Sciences of Ukraine

48, Kharkivske shose, Kyiv, 02160, Ukraine

 

Polym. J., 2018, 40, no. 1: 41-45

 

Section: Synthesis polymers.

 

Language: English.

 

Abstract:

 

Reactive aromatic oligoethers with perfluoroaromatic units attract much interest as efficient building blocks for the construction low-loss optical waveguide materials and highly ion conductive membranes. Significant progress has been made on the synthesis of fluorine-terminated oligo(arylene ether)s (FAOs). Due to the side reactions as branching and crosslinking, hydroxyl-terminated FAOs are significantly less developed therefore efficient strategies of synthesis mentioned oligomers are paramount. In this work, the strategy to the synthesis of the hydroxyl-terminated FAO containing meta-oxyphenylene fragments was proposed. This oligomer is the first example of meta-linked FAO with reactive OH end-groups and was prepared by condensation polymerization of decafluorobiphenyl and resorcinol, where an excess of resorcinol was used. The structure of the synthesized oligomer was determined by Fourier transform infrared, 1H NMR and 19F NMR spectroscopy techniques. The molecular weight and thermal properties of the synthesized fluorinated oligo(arylene ether) were studied.

 

Keywords: reactive oligomers, fluorinated aromatic oligomers, synthesis, properties, meta-fragments.

 

References

1. Shevchenko V.V., Tkachenko I.M., Shekera O.V. Nucleus-fluorinated aromatic polyethers. Polymer Sci. B., 2010, 52, no. 7–8: 408–430.
https://doi.org/10.1134/S1560090410070055
 
2. Dhara M.G., Banerjee S. Fluorinated high-performance polymers: poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups. Prog. Polym. Sci., 2010, 35, no. 8: 1022–1077.
https://doi.org/10.1016/j.progpolymsci.2010.04.003
 
3. Wan Y., Zhang Y., Shi Z., Xu W., Zhang X., Zhao L., Cui Z. Direct UV-written highly fluorinated aromatic-aliphatic copolyethers for optical waveguides. Polymer, 2012, 53, no. 8: 967–975.
https://doi.org/10.1016/j.polymer.2011.12.021
 
4. Nakabayashi K., Higashihara T., Ueda M. Polymer electrolyte membranes based on poly (phenylene ether) s with pendant perfluoroalkyl sulfonic acids. Macromolecules, 2011, 44, no. 6: 1603–1609.
https://doi.org/10.1021/ma102813y
 
5. Endo K., Yamade T. Synthesis and characterization of polymers from bisphenol derivatives and perfluorinated aromatic compounds. Polymer J., 2008, 40, no. 3: 212–216.
https://doi.org/10.1295/polymj.PJ2007168
 6. Tkachenko I.M., Belov N.A., Yakovlev Y.V., Vakuliuk P.V., Shekera О.V., Yampolskii Y.P., Shevchenko V.V. Synthesis, gas transport and dielectric properties of fluorinated poly(arylene ether)s based on decafluorobiphenyl. Mater. Chem. Phys., 2016, 183: 279–287.
7. Kim J.P., Lee W.Y., Kang J.W., Kwon S.K., Kim J.J., Lee J.S. Fluorinated poly(arylene ether sulfide) for polymeric optical waveguide devices. Macromolecules, 2001, 34, no. 22: 7817–7821.
https://doi.org/10.1021/ma010439r
 
8. Lee H.J., Lee E.M., Lee M.H., Oh M.C., Ahn J.H., Han S.G., Kim H.G. Crosslinkable fluorinated poly(arylene ethers) bearing phenyl ethynyl moiety for low-loss polymer optical waveguide devices. J. Polym. Sci. A., 1998, 36, no. 16: 2881–2887.
https://doi.org/10.1002/(SICI)1099-0518(19981130)36:16<2881::AID-POLA6>3.0.CO;2-#
 
9. Lee K.S., Jeong M.H., Lee J.P., Lee J.S. End-group cross-linked poly(arylene ether) for proton exchange membranes. Macromolecules, 2009, 42, no. 3: 584–590.
https://doi.org/10.1021/ma802233j
 
10. Yu X., Roy A., Dunn S., Badami A.S., Yang J., Good A.S., McGrath J.E. Synthesis and characterization of sulfonated-fluorinated, hydrophilic-hydrophobic multiblock copolymers for proton exchange membranes. J. Polym. Sci. A., 2009, 47, no. 4: 1038–1051.
https://doi.org/10.1002/pola.23194
 
11. Roy A., Yu X., Dunn S., McGrath J.E. Influence of microstructure and chemical composition on proton exchange membrane properties of sulfonated–fluorinated, hydrophilic–hydrophobic multiblock copolymers. J. Membr. Sci., 2009, 327, no. 1: 118–124.
https://doi.org/10.1016/j.memsci.2008.11.016
 
12. Ghassemi H., McGrath J.E., Zawodzinski T.A. Multiblock sulfonated-fluorinated poly (arylene ether) s for a proton exchange membrane fuel cell. Polymer, 2006, 47, no. 11: 4132–4139.
https://doi.org/10.1016/j.polymer.2006.02.038
 
13. Sannigrahi A., Takamuku S., Jannasch P. Block copolymers combining semi-fluorinated poly (arylene ether) and sulfonated poly (arylene ether sulfone) segments for proton exchange membranes. Int. J. Hydrog. Energy, 2014, 39, no. 28: 15718–15727.
https://doi.org/10.1016/j.ijhydene.2014.07.155
 
14. Yokota N., Ono H., Miyake J., Nishino E., Asazawa K., Watanabe M., Miyatake K. Anion conductive aromatic block copolymers containing diphenyl ether or sulfide groups for application to alkaline fuel cells. ACS Appl. Mater. Interfaces, 2014, 6, no. 19: 17044–17052.
https://doi.org/10.1021/am5046586
 
15. Higashihara T., Matsumoto K., Ueda M. Sulfonated aromatic hydrocarbon polymers as proton exchange membranes for fuel cells. Polymer, 2009, 50, no. 23: 5341–5357.
https://doi.org/10.1016/j.polymer.2009.09.001
 
16. Tkachenko I.M., Kobzar Y.L., Yakovlev Y.V., Shekera O.V., Klepko V.V., Shevchenko V.V. Synthesis of perfectly alternating and statistical meta-linked fluorinated poly (arylene ether) copolymers containing octafluorobiphenylene and trifluoromethyl units. Macromol. Res., 2017, 25, no. 4: 112–119.
https://doi.org/10.1007/s13233-017-5012-1
 
17. Kobzar Y.L., Tkachenko I.M., Bliznyuk V.N., Shekera O.V., Turiv T.M., Soroka P.V., Nazarenko V.V., Shevchenko V.V. Synthesis and characterization of fluorinated poly(azomethine ether)s from new core-fluorinated azomethine-containing monomers. Designed Monomers Polym., 2016, 19, no. 1: 1–11.
https://doi.org/10.1080/15685551.2015.1092007