Sulfonated poly(arylene ether)s with high content of phosphine oxide moieties for proton exchange membranes

Journal of Membrane Science

Volumn 389, Issue , 2012, Pages 407-415

  Fu, Lingchao ^a   Liao, Huiying ^a   Xiao, Guyu ^a   Yan, Deyue ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Decafluorobiphenyl; Phosphine oxide; Poly(arylene ether)s; Proton exchange membrane; Sulfonated

Indexed keywords

DECAFLUOROBIPHENYL; PHOSPHINE OXIDE; POLY(ARYLENE ETHER)S; PROTON EXCHANGE MEMBRANE; SULFONATED;

ETHERS; ORGANIC COMPOUNDS; OXIDATION RESISTANCE; PHOSPHORUS COMPOUNDS; POLYCONDENSATION; PROTON EXCHANGE MEMBRANE FUEL CELLS (PEMFC); PROTONS; STABILITY;

MEMBRANES;

BIS(4 FLUORODIPHENYL)PHENYL PHOSPHINE OXIDE; BIS(4 FLUOROPHENYL)PHENYL PHOSPHINE OXIDE; BIS(4 HYDROXYPHENYL)PHENYL PHOSPHINE OXIDE; PHOSPHINE OXIDE DERIVATIVE; POLY(ARYLENE ETHER); POLYMER; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CLUSTER ANALYSIS; HYDROPHOBICITY; MEMBRANE; MEMBRANE STABILIZATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; SULFONATION; THERMOSTABILITY;

EID: 83855165095     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2011.11.006     Document Type: Article

References (50)

1. Hickner M.A., Ghassemi H., Kim Y.S., Einsla B.R., McGrath J.E. Alternative polymer systems for proton exchange membranes (PEMs). Chem. Rev. 2004, 104:4587-4612.
2. Kreuer K.D. On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells. J. Membr. Sci. 2001, 185:29-39.
3. Li Q.F., He R.H., Jensen J.O., Bjerrum N.J. Approaches and recent development of polymer electrolyte membranes for fuel cells operating above 100°C. Chem. Mater. 2003, 15:4896-4915.
4. Savadogo O. Emerging membranes for electrochemical systems: Part II. High temperature composite membranes for polymer electrolyte fuel cell (PEFC) applications. J. Power Sources 2004, 127:135-161.
5. Shao Y., Yin G., Wang Z., Gao Y. Proton exchange membrane fuel cell from low temperature to high temperature: material challenges. J. Power Sources 2007, 167:235-242.
6. Jones D.J., Rozière J. Non-fluorinated polymer materials for proton exchange membrane fuel cells. Annu. Rev. Mater. Res. 2003, 33:503-555.
7. Kerres J.A. Development of ionomer membranes for fuel cells. J. Membr. Sci. 2001, 185:3-27.
8. Matsumoto K., Higashihara T., Ueda M. Locally and densely sulfonated poly(ether sulfone)s as proton exchange membrane. Macromolecules 2009, 42:1161-1166.
9. Parvole J., Jannasch P. Poly(arylene ether sulfone)s with phosphonic acid and bis(phosphonic acid) on short alkyl side chains for proton-exchange membranes. J. Mater. Chem. 2008, 18:5547-5556.
10. Miyatake K., Zhou H., Uchida H., Watanabe M. Highly proton conductive polyimide electrolytes containing fluorenyl groups. Chem. Commun. 2003, 3:368-369.
11. Zhang Y., Zhang G., Wan Y., Zhao C.J., Shao K., Li H.T., Han M.M., Zhu J., Xu S., Liu Z.G., Na H. Synthesis and characterization of poly(arylene ether ketone)s bearing pendant sulfonic acid groups for proton exchange membrane materials. J. Polym. Sci.: Polym. Chem. 2010, 48:5824-5832.
12. Liu B.J., Robertson G.P., Kim D.S., Guiver M.D., Hu W., Jiang Z.H. Aromatic poly(ether ketone)s with pendant sulfonic acid phenyl groups prepared by a mild sulfonation method for proton exchange membranes. Macromolecules 2007, 40:1934-1944.
13. Pang J.H., Zhang H.B., Li X.F., Jiang Z.H. Novel wholly aromatic sulfonated poly(arylene ether) copolymers containing sulfonic acid groups on the pendants for proton exchange membrane materials. Macromolecules 2007, 40:9435-9442.
14. Xiao G.Y., Sun G.M., Yan D.Y. Sulfonated poly(thioether ketone)s with high oxidation resistance to peroxides. Abstr. Pap. Am. Chem. Soc. 2003, 225:U558.
15. Bai Z.W., Shumaker J.A., Houtz M.D., Mirau P.A., Dang T.D. Fluorinated poly(arylene thioether sulfone) copolymers containing pendant sulfonic acid groups for proton exchange membrane materials. Polymer 2009, 50:1463-1469.
16. Matsumura S., Hlil A.R., Lepiller C., Gaudet J., Guay D., Hay A.S. Ionomers for proton exchange membrane fuel cells with sulfonic acid groups on the end groups: novel linear aromatic poly(sulfide-ketone)s. Macromolecules 2008, 41:277-280.
17. Fang J.H., Guo X.X., Harada S., Watari T., Tanaka K., Kita H., Okamoto K.-I. Novel sulfonated polyimides as polyelectrolytes for fuel cell application. 1. Synthesis, proton conductivity, and water stability of polyimides from 4,4'-diaminodiphenyl ether-2,2'-disulfonic acid. Macromolecules 2002, 35:9022-9028.
18. Li N.W, Zhang S.B., Liu J., Zhang F. Synthesis and properties of sulfonated poly[bis(benzimidazobenzisoquinolinones)] as hydrolytically and thermooxidatively stable proton conducting ionomers. Macromolecules 2008, 41:4165-4172.
19. Marestin C., Gebel G., Diat O., Mercier R. Sulfonated polyimides. Adv. Polym. Sci. 2008, 216:185-258.
20. Xiao G.Y., Sun G.M., Yan D.Y., Zhu P.F., Tao P. Synthesis of sulfonated poly(phthalazinone ether sulfone)s by direct polymerization. Polymer 2002, 43:5335-5339.
21. Zhu X.L., Liang Y.F., Pan H.Y., Jian X.G., Zhang Y.X. Synthesis and properties of novel H-bonded composite membranes from sulfonated poly(phthalazinone ether)s for PEMFC. J. Membr. Sci. 2008, 312:59-65.
22. Shen L.P., Xiao G.Y., Yan D.Y., Sun G.M., Zhu P.F., Zhu N. Comparison of the water uptake and swelling between sulfonated poly(phthalazinone ether ketone ketone)s and sulfonated poly(arylene ether ketone ketone)s. Polym. Bull. 2005, 54:57-64.
23. Allcock H.R., Wood R.M. Design and synthesis of ion-conductive polyphosphazenes for fuel cell applications: review. J. Polym. Sci.: Polym. Phys. 2006, 44:2358-2368.
24. Wycisk R., Pintauro P.N. Polyphosphazene membranes for fuel cells. Adv. Polym. Sci. 2008, 216:157-183.
25. Staiti P., Lufrano F., Arico A.S., Passalacqua E., Antonucci V. Sulfonated polybenzimidazole membranes-preparation and physico-chemical characterization. J. Membr. Sci. 2001, 188:71-78.
26. Mader J., Xiao L.X., Schmidt T.J., Benicewicz B.C. Polybenzimidazole/acid complexes as high-temperature membranes. Adv. Polym. Sci. 2008, 216:63-124.
27. Wang G., Xiao G.Y., Yan D.Y. Synthesis and properties of soluble sulfonated polybenzimidazoles derived from asymmetric dicarboxylic acid monomers with sulfonate group as proton exchange membrane. J. Membr. Sci. 2011, 369:388-396.
28. Ng F., Péron J., Jones D.J., Rozière J. Synthesis of novel proton-conducting highly sulfonated polybenzimidazoles for PEMFC and the effect of the type of bisphenyl bridge on polymer and membrane properties. J. Polym. Sci.: Polym. Chem. 2011, 49:2107-2117.
29. Tan N., Xiao G.Y., Yan D.Y. Sulfonated polybenzothiazoles: a novel candidate for proton exchange membranes. Chem. Mater. 2010, 22:1022-1031.
30. Ma X.H., Zhang C.J., Xiao G.Y., Yan D.Y. Synthesis and properties of sulfonated poly(arylene ether phosphine oxide)s for proton exchange membranes. J. Power Sources 2009, 188:57-63.
31. Gui L.Y., Zhang C.J., Kang S., Tan N., Xiao G.Y., Yan D.Y. Synthesis and properties of hexafluoroisopropylidene containing sulfonated poly(arylene thioether phosphine oxide)s for proton exchange membranes. Int. J. Hydrogen Energy 2010, 35:2436-2445.
32. Zhang C.J., Kang S., Ma X.H., Xiao G.Y., Yan D.Y. Synthesis and characterization of sulfonated poly(arylene ether phosphine oxide)s with fluorenyl groups by direct polymerization for proton exchange membranes. J. Membr. Sci. 2009, 329:99-105.
33. Ma X.H., Shen L.P., Zhang C.J., Xiao G.Y., Yan D.Y., Sun G.M. Sulfonated poly(arylene thioether phosphine oxide)s copolymers for proton exchange membrane fuel cells. J. Membr. Sci. 2008, 310:303-311.
34. Yang Y., Siu A., Peckham T.J., Holdcroft S. Structural and morphological features of acid-bearing polymers for PEM fuel cells. Adv. Polym. Sci. 2008, 216:55-126.
35. Lee J.K., Kerres J. Synthesis and characterization of sulfonated poly(arylene thioether)s and their blends with polybenzimidazole for proton exchange membranes. J. Membr. Sci. 2007, 294:75-83.
36. Bi H.P., Wang J.L., Chen S.W., Hu Z.X., Gao Z.L., Wang L.J., Okamoto K.-I. Preparation and properties of cross-linked sulfonated poly(arylene ether sulfone)/sulfonated polyimide blend membranes for fuel cell application. J. Membr. Sci. 2010, 350:109-116.
37. Feng S.G., Shang Y.M., Wang S.B., Xie X.F., Wang Y.Z., Wang Y.W., Xu J.M. Novel method for the preparation of ionically crosslinked sulfonated poly(arylene ether sulfone)/polybenzimidazole composite membranes via in situ polymerization. J. Membr. Sci. 2010, 346:105-112.
38. 40) for proton exchange membranes. Solid State Ionics 2006, 177:1123-1128.
39. Liu D., Liao H.Y., Tan N., Xiao G.Y., Yan D.Y. Sulfonated poly(arylene thioether phosphine oxide)/sulfonated benzimidazole blends for proton exchange membranes. J. Membr. Sci. 2011, 372:125-133.
40. Ma X.H., Zhang C.J., Xiao G.Y., Yan D.Y., Sun G.M. Synthesis and characterization of sulfonated poly(phthalazinone ether phosphine oxide)s by direct polycondensation for proton exchange membranes. J. Polym. Sci.: Polym. Chem. 2008, 46:1758-1769.
41. Fu L.C., Xiao G.Y., Yan D.Y. Sulfonated poly(arylene ether sulfone)s with phosphine oxide moieties: a promising material for proton exchange membranes. ACS Appl. Mater. Interfaces 2010, 2:1601-1607.
42. Fu L.C., Xiao G.Y., Yan D.Y. Synthesis and characterization of sulfonated poly(arylene ether ketone/ketone phosphine oxide)s as proton exchange membranes. J. Membr. Sci. 2010, 362:509-516.
43. Hsu F.M., Chien C.H., Shih P.I., Shu C.F. Phosphine-oxide-containing bipolar host material for blue electrophosphorescent devices. Chem. Mater. 2009, 21:1017-1022.
44. Laskoski M., Dominguez D.D., Keller T.M. Synthesis and properties of aromatic ether phosphine oxide containing oligomeric phthalonitrile resins with improved oxidative stability. Polymer 2007, 48:6234-6240.
45. Watson K.A., Palmieri F.L., Connell J.W. Space environmentally stable polyimides and copolyimides derived from [2,4-bis(3-aminophenoxy)phenyl] diphenylphosphine oxide. Macromolecules 2002, 35:4968-4974.
46. Kerres J.A., Xing D.M., Schönberger F. Comparative investigation of novel PBI blend ionomer membranes from nonfluorinated and partially fluorinated poly arylene ethers. J. Polym. Sci.: Polym. Phys. 2006, 44:2311-2326.
47. NO iron. Inorg. Chim. Acta 1989, 155:11-12.
48. Valle G., Casotto G., Zanonato P.L., Zarli B. Crystal and molecular structures of two europium (III) nitrate complexes with triphenylphosphine oxide. Polyhedron 1986, 5:2093-2096.
49. Gao Y., Robertson G.P., Guiver M.D., Wang G., Jian X., Mikhailenko S.D., Li X., Kaliaguine S. Sulfonated copoly(phthalazinone ether ketone nitrile)s as proton exchange membrane materials. J. Membr. Sci. 2006, 278:26-34.
50. Dai H., Zhang H., Luo Q., Zhang Y., Bi C. Properties and fuel cell performance of proton exchange membranes prepared from disulfonated poly(sulfide sulfone). J. Power Sources 2008, 185:19-25.