Alternatives toward proton conductive anhydrous membranes for fuel cells: Heterocyclic protogenic solvents comprising polymer electrolytes

Progress in Polymer Science

Volumn 37, Issue 9, 2012, Pages 1265-1291

  Çelik, Sevim Ünügür ^a   Bozkurt, Ayhan ^a   Hosseini, Seyed Saeid ^b,c  

^a FATIH UNIVERSITY   (Turkey)

^b Keppel Offshore & Marine Limited   (Singapore)

^c TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Fuel cell; Heterocyclic protogenic solvent; Polymer electrolyte; Proton conductivity

Indexed keywords

ANHYDROUS CONDITIONS; DESIGN AND DEVELOPMENT; DESIGN REQUIREMENTS; ELECTROLYTE MEMBRANE; ELECTROLYTE SYSTEMS; FUEL CELL APPLICATION; HETEROCYCLES; LOW TEMPERATURES; PERFORMANCE CHARACTERISTICS; POLYACIDS; POLYMER ELECTROLYTE; POLYMER ELECTROLYTE MEMBRANES; PROTOGENIC SOLVENTS; PROTON CONDUCTING; PROTON-CONDUCTING ELECTROLYTE; RECENT PROGRESS; RESEARCH AND DEVELOPMENT; RESEARCH STUDIES;

DESIGN; DIRECT ENERGY CONVERSION; ENERGY CONVERSION; FUNCTIONAL GROUPS; GAS FUEL PURIFICATION; POLYELECTROLYTES; POLYMERS; PROTON CONDUCTIVITY;

FUEL CELLS;

EID: 84865032687     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2011.11.006     Document Type: Review

References (121)

1. M.F.H. Schuster, and W.H. Meyer Anhydrous proton-conducting polymers Annu Rev Mater Res 33 2003 233 261
2. R. Savinell, E. Yeager, D. Tryk, U. Landau, J. Wainright, D. Weng, K. Lux, M. Litt, and C. Rogers A polymer electrolyte for operation at temperatures up to 200 °C J Electrochem Soc 141 1994 L46 L48
3. C. Heitner-Wirguin Recent advances in perfluorinatedionomer membranes: structure, properties and applications J Membr Sci 120 1996 1 33
4. K.A. Mauritz, and R.B. Moore State of understanding of Nafion Chem Rev 104 2004 4535 4585
5. T.D. Gierke, G.E. Munn, and F.C.J. Wilson The morphology in nafionperfluorinated membrane products, as determined by wide- and small-angle x-ray studies J Polym Sci: Polym Phys Ed. 19 1981 1687 1704
6. K. Schmidt-Rohr, and Q. Chen Parallel cylindrical water nanochannels in Nafion fuel-cell membranes Nat Mater 7 2008 75 83
7. Yeager HJ, Eisenberg A. Transport properties of perfluorosulfonate polymer membranes. In: Eisenberg A, Yeager HL, editors, Perfluorinated ionomer membranes. ACS Symp. Ser. No.180. Washington, DC: American Chemical Society; 1982. p. 41-63.
8. P.J. Brookman, and J.W. Nicholson Ionic polymer membranes A.D. Wilson, H.J. Prosser, Developments in ionic polymers vol. 2 1986 Elsevier Applied Science Publishers London 269 283
9. Kreuer KD, Dippel T, Meyer W, Maier J. NAFION Membranes: molecular diffusion, proton conductivity and proton conduction mechanism. In: Nazri GA, Tarascon JM, Armand M, editors, Solid State Ionics III, Mat. Res. Soc. Symp. Proc. vol. 293. Pittsburgh: MRS; 1993. p. 273-82.
10. K.D. Kreuer On solids with liquidlike properties and the challenge to develop new proton-conducting separator materials for intermediate-temperature fuel cells Chem Phys Chem 3 2002 771 775
11. Q. Li, R. He, J.O. Jensen, and N.J. Bjerrum Approaches and recent development of polymer electrolyte membranes for fuel cells operating above 100 °C Chem Mater 15 2003 4896 4915
12. F. Lecolley, C. Waterson, A.J. Carmichael, G. Mantovani, S. Harrisson, H. Chappell, A. Limer, P. Williams, K. Ohno, and D.M. Haddleton Synthesis of functional polymers by living radical polymerisation J Mater Chem 13 2003 2689 2695
13. J.C. Perrin, S. Lyonnard, A. Guillermo, and P. Levitz Water dynamics in ionomer membranes by field-cycling NMR relaxometry Fuel Cell 6 2006 5 9
14. Q. Li, J.O. Jensen, R.F. Savinell, and N.J. Bjerrum High temperature proton exchange membranes based on polybenzimidazoles for fuel cells Prog Polym Sci 34 2009 449 477
15. H. Pu, L. Qiao, Q. Liu, and Z. Yang A new anhydrous proton conducting material based on phosphoric acid doped polyimide Eur Polym J 41 2005 2505 2510
16. C.J.D. Grotthuss Sur la décomposition de l'eau et des corps qu'elle tient en dissolution à l'aide de l'électricité galvanique Ann Chim (Paris) 58 1806 54 73
17. K.D. Kreuer On the development of proton conducting materials for technological applications Solid State Ionics 97 1997 1 15
18. M. Eigen, and Proton Transfer Acid-base catalysis, and enzymatic hydrolysis. Part I: elementary processes Angew Chem Int Ed 3 1964 1 19
19. N. Agmon The Grotthuss mechanism Chem Phys Lett 244 1995 456 462
20. N. Agmon Hydrogen bonds, water rotation and proton mobility J Chim Phys (Paris) 93 1996 1714 1736
21. K.D. Kreuer Proton conductivity: materials and applications Chem Mater 8 1996 610 641
22. K.D. Kreuer, A. Rabenau, and W. Weppner Vehicle mechanism. A new model for the interpretation of the conductivity of fast proton conductors Angew Chem Int Ed 21 1982 208 209
23. G. Alberti, and M. Casciola Solid state protonic conductors, present main applications and future prospects Solid State Ionics 145 2001 3 16
24. A. Bozkurt, and W.H. Meyer Proton-conducting poly(vinylpyrrolidon)- polyphosphoric acid blends J Polym Sci Part B Polym Phys 39 2001 1987 1994
25. A. Bozkurt, W.H. Meyer, J. Gutmann, and G. Wegner Proton conducting copolymers on the basis of vinylphosphonic acid and 4-vinylimidazole Solid State Ionics 164 2003 169 176
26. K.D. Kreuer On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells J Membr Sci 185 2001 29 39
27. A. Bozkurt, M. Ise, K.D. Kreuer, W.H. Meyer, and G. Wegner Proton-conducting polymer electrolytes based on phosphoric acid Solid State Ionics 125 1999 225 233
28. Wei J, Stone C, Steck AE. Trifluorostyrene and substituted trifluorostyrenecopolymeric compositions and ion-exchange membranes formed therefrom. US 5422411; 1995.
29. Q. Li, R. He, J.O. Jensen, and N.J. Bjerrum PBI-based polymer membranes for high temperature fuel cells - preparation, characterization and fuel cell demonstration Fuel Cells 4 2004 147 159
30. M. Schuster, T. Rager, A. Noda, K.D. Kreuer, and J. Maier About the choice of the protogenic group in PEM separator materials for intermediate temperature, low humidity operation: a critical comparison of sulfonic acid, phosphonic acid and imidazole functionalized model compounds Fuel Cells 5 2005 355 365
31. K.D. Kreuer, A. Fuchs, M. Ise, M. Spaeth, and J. Maier Imidazole and pyrazole-based proton conducting polymers and liquids Electrochim Acta 43 1998 1281 1288
32. K.D. Kreuer New proton conducting polymers for fuel cell applications B.V.R. Chowdari, K. Lal, S.A. Agnihotry, N. Khare, S.S. Sekhon, P.C. Srivastava, S. Chandra, Solid state ionics: science & technology 1998 World Scientific Singapore 263 274
33. V.D.Z. Bermudez, M. Armand, C. Poinsignon, L. Abello, and J.Y. Sanchez Proton-vacancy conducting polymers based on polyethylene oxide and sulfamide-type salts Electrochim Acta 37 1992 1603 1609
34. A. Bozkurt, and T. Pakula Dielectric and dynamic mechanical relaxations in polymer-heterocycle hybrid materials Chem Phys Lett 422 2006 496 499
35. W. Münch, K.D. Kreuer, W. Silvestri, J. Maier, and G. Seifert The diffusion mechanism of an excess proton in imidazole molecule chains: first results of an ab initio molecular dynamics study Solid State Ionics 145 2001 437 443
36. H. Erdemi, A. Bozkurt, and W.H. Meyer PAMPSA-IM based proton conducting polymer electrolytes Synth Met 143 2004 133 138
37. M. Yamada, and I. Honma Anhydrous proton conducting polymer electrolytes based on poly(vinylphosphonic acid)-heterocycle composite material Polymer 46 2005 2986 2992
38. Z. Zhou, S. Li, Y. Zhang, M. Liu, and W. Li Promotion of proton conduction in polymer electrolyte membranes by 1H-1,2,3-triazole J Am Chem Soc 127 2005 10824 10825
39. M. Iannuzzi, and M. Parrinello Proton transfer in heterocycle crystals Phys Rev Lett 93 2004 025901 025905
40. M.F.H. Schuster, W.H. Meyer, M. Schuster, and K.D. Kreuer Toward a new type of anhydrous organic proton conductor based on immobilized imidazole Chem Mater 16 2004 329 337
41. M. Schuster, W.H. Meyer, G. Wegner, H.G. Herz, M. Ise, M. Schuster, K.D. Kreuer, and J. Maier Proton mobility in oligomer-bound proton solvents: imidazole immobilization via flexible spacers Solid State Ionics 145 2001 85 92
42. G. Scharfenberger, W.H. Meyer, G. Wegner, M. Schuster, K.D. Kreuer, and J. Maier Anhydrous polymeric proton conductors based on imidazole functionalized polysiloxane Fuel Cells 6 2006 237 250
43. P. Jannasch Recent developments in high-temperature proton conducting polymer electrolyte membranes Curr Opin Coll Int Sci 8 2003 96 102
44. K.D. Kreuer Proton conduction in fuel cells J.T. Hynes, J.P. Klinman, H.H. Limbach, R.L. Schowen, Hydrogen-transfer reactions 2007 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim 709 736
45. H. Steininger, M. Schuster, K.D. Kreuer, A. Kaltbeitzel, B. Bingöl, W.H. Meyer, S. Schauff, G. Brunklaus, J. Maier, and H.W. Spiess Intermediate temperature proton conductors for PEM fuel cells based on phosphonic acid as protogenic group: A progress report Phys Chem Chem Phys 9 2007 1764 1773
46. J. Sun, L.R. Jordan, M. Forsyth, and D.R. MacFarlane Acid-Organic base swollen polymer membranes Electrochim Acta 46 2001 1703 1708
47. A. Noda, M.H. Susan, K. Kudo, S. Mitsushima, K. Hayamizu, and M. Watanabe Bronsted acid-base ionic liquids as proton-conducting nonaqueous electrolytes J Phys Chem B 107 2003 4024 4033
48. M. Casciola, S. Chieli, U. Costantino, and A. Peraio Intercalation compounds of [alpha]-zirconium hydrogen phosphate with heterocyclic bases and their ac conductivity Solid State Ionics 46 1991 53 59
49. F. Sevil, and A. Bozkurt Proton conducting polymer electrolytes on the basis of poly(vinylphosphonic acid) and imidazole J Phys Chem Solids 65 2004 1659 1662
50. C. Yang, P. Costamagna, S. Srinivasan, J. Benziger, and A.B. Bocarsly Approaches and technical challenges to high temperature operation of proton exchange membrane fuel cells J Power Sources 103 2001 1 9
51. W.Q. Deng, V. Molinero, and W.A. Goddard Fluorinated imidazoles as proton carriers for water-free fuel cell membranes J Am Chem Soc 126 2004 15644 15645
52. S. Li, Z. Zhou, Y. Zhang, and M. Liu 1H-1,2,4-triazole: an effective solvent for proton-conducting electrolytes Chem Mater 17 2005 5884 5886
53. A. Schechter, and R.F. Savinell Imidazole and 1-methyl imidazole in phosphoric acid doped polybenzimidazole, electrolyte for fuel cells Solid State Ionics 147 2002 181 187
54. R.A. Munson Self-dissociative equilibria in molten phosphoric acid J Phys Chem 68 1964 3374 3377
55. R.A. Munson, and M.E. Lazarus Influence of ionic solutes upon the conductivity of molten phosphoric acid J Phys Chem 71 1967 3245 3248
56. R.M. Acheson An introduction to the chemistry of heterocyclic compounds 3rd ed. 1976 Wiley-Interscience New York p. 501
57. T. Dippel, K.D. Kreuer, J.C. Lassègues, and D. Rodriguez Proton conductivity in fused phosphoric acid; A 1H/31P PFG-NMR and QNS study Solid State Ionics 61 1993 41 46
58. Z. Zhou, R. Liu, J. Wang, S. Li, M. Liu, and J.L. Brédas Intra- and intermolecular proton transfer in 1H(2H)-1,2,3-triazole based systems J Phys Chem A 110 2006 2322 2324
59. G. Rauhut Modulation of reaction barriers by generating reactive intermediates: double proton transfer reactions Phys Chem Chem Phys 5 2003 791 800
60. V. Minkin, A. Garnovsk, J. Elguero, A. Katritzky, and O. Denisko The tautomerism of heterocycles: Five-membered rings with two or more heteroatoms Adv Heterocycl Chem 76 2000 157 323
61. S.T. Günday, A. Bozkurt, W.H. Meyer, and G. Wegner Effects of different acid functional groups on proton conductivity of polymer-1,2,4- triazole blends J Polym Sci Part B Polym Phys 44 2006 3315 3322
62. J.S. Mihina, and R.M. Herbst The reaction of nitriles with hydrazoic acid: synthesis of monosubstituted tetrazoles J Org Chem 15 1950 1082 1092
63. J.F. Satchell, and B.J. Smith Calculation of aqueous dissociation constants of 1,2,4-triazole and tetrazole: A comparison of solvation models Phys Chem Chem Phys 4 2002 4314 4318
64. A.I. Lesnikovich, O.A. Ivashkevich, S.V. Levchik, A.I. Balabanovich, P.N. Gaponik, and A.A. Kulak Thermal decomposition of aminotetrazoles Thermochimica Acta 388 2002 233 251
65. S.V. Levchik, G.A. Ivashkcvich, A.I. Balabanovich, A.I. Lesnikovich, P.N. Gaponik, and L. Costa Thermal decomposition of aminotetrazoles. Pat I. 5-Aminotetrazole Thermochim Acta 207 1992 115 130
66. J.C. Lassegues Mixed inorganic-organic systems: the acid/polymer blends P. Colomban, Proton conductors, solids membranes, and gels-materials and devices 1992 Cambridge University Press Cambridge 311 326
67. F. Göktepe, A. Bozkurt, and Ş.T. Günday Synthesis and proton conductivity of poly(styrene sulfonic acid)/heterocycle-based membranes Polym Int 57 2008 133 138
68. R. He, Q. Li, G. Xiao, and N.J. Bjerrum Proton conductivity of phosphoric acid doped polybenzimidazole and its composites with inorganic proton conductors J Membr Sci 226 2003 169 184
69. B. Karadedeli, A. Bozkurt, and A. Baykal Proton conduction in adipic acid/benzimidazole hybrid electrolytes Physica B 364 2005 279 284
70. A. Bozkurt, W.H. Meyer, and G. Wegner PAA/imidazol-based proton conducting polymer electrolytes J Power Sources 123 2003 126 131
71. M. Yamada, and I. Honma Alginic acid-imidazole composite material as anhydrous proton conducting membrane Polymer 45 2004 8349 8354
72. S.T. Gunday, and A. Bozkurt Preparation and proton conductivity of polymer electrolytes based on alginic acid and 1,2,4-triazole Polym J 40 2007 104 108
73. Y.J. Lee, B. Bingöl, T. Murakhtina, D. Sebastiani, W.H. Meyer, G. Wegner, H.W. Spiess, and High-resolution solid-state NMR studies of poly(vinyl phosphonic acid) proton-conducting polymer: molecular structure and proton dynamics J Phys Chem B 111 2007 9711 9721
74. A. Kaltbeitzel, S. Schauff, H. Steininger, B. Bingöl, G. Brunklaus, W.H. Meyer, and H.W. Spiess Water sorption of poly(vinylphosphonic acid) and its influence on proton conductivity Solid State Ionics 178 2007 469 474
75. F. Sevil, and A. Bozkurt Proton conduction in PVPA - benzimidazole hybrid electrolytes Turk J Chem 29 2005 377 383
76. M. Yamada, and I. Honma Proton conducting acid-base mixed materials under water-free condition Electrochim Acta 48 2003 2411 2415
77. M. Kufaci, A. Bozkurt, and M. Tülü Poly(ethyleneglycol methacrylate phosphate) and heterocycle based proton conducting composite materials Solid State Ionics 177 2006 1003 1007
78. B. Smitha, S. Sridhar, and A.A. Khan Solid polymer electrolyte membranes for fuel cell applications - a review J Membr Sci 259 2005 10 26
79. J. Yu, B. Yi, D. Xing, F. Liu, Z. Shao, Y. Fu, and H. Zhang Degradation mechanism of polystyrene sulfonic acid membrane and application of its composite membranes in fuel cells Phys Chem Chem Phys 5 2003 611 615
80. A. Bozkurt Anhydrous proton conductive polystyrene sulfonic acid membranes Turk J Chem 29 2005 117 123
81. B. Baradie, C. Poinsignon, J.Y. Sanchez, Y. Piffard, G. Vitter, N. Bestaoui, D. Foscallo, A. Denoyelle, D. Delabouglise, and M. Vaujany Thermostable ionomeric filled membrane for H2/O2 fuel cell J Power Sources 74 1998 8 16
82. F. Lufrano, G. Squadrito, A. Patti, and E. Passalacqua Sulfonated polysulfone as promising membranes for polymer electrolyte fuel cells J Appl Polym Sci 77 2000 1250 1256
83. C. Poinsignon, I. Imodio, D. Foscallo, and J.Y. Sanchez Low cost filled thermostable ionomer membrane for PEMFC Mater Res Soc Symp Proc 548 1999 307 312
84. C. Brousse, R. Chapurlat, and J.P. Quentin New membranes for reverse osmosis I Characteristics of the base polymer: sulphonated polysulphones Desalination 18 1976 137 153
85. V. Deimede, G.A. Voyiatzis, J.K. Kallitsis, L. Qingfeng, and N.J. Bjerrum Miscibility behavior of polybenzimidazole/sulfonated polysulfone blends for use in fuel cell applications Macromolecules 33 2000 7609 7617
86. M. Rikukawa, and K. Sanui Proton-conducting polymer electrolyte membranes based on hydrocarbon polymers Prog Polym Sci 25 2000 1463 1502
87. N. Takimotoa, L. Wu, A. Ohira, Y. Takeokaa, and M. Rikukawa Hydration behavior of perfluorinated and hydrocarbon-type proton exchange membranes: Relationship between morphology and proton conduction Polymer 50 2009 534 540
88. M. Casciola, G. Alberti, M. Sganappa, and R. Narducci On the decay of Nafion proton conductivity at high temperature and relative humidity J Power Sources 162 2006 141 145
89. T.A. Zawodzinski, T.E. Springer, J. Davey, R. Jestel, C. Lopez, J. Valerio, and S. Gottesfeld A comparative study of water uptake by and transport through ionomeric fuel cell membranes J Electrochem Soc 140 1993 1981 1985
90. L.M. Onishi, J.M. Prausnitz, and J. Newman Water-Nafion equilibria absence of Schroeder's paradox J Phys Chem B 111 2007 10166 10173
91. J.D. Kim, T. Mori, S. Hayashi, and I. Honma Anhydrous proton-conducting properties of Nafion-1,2,4-triazole and Nafion-benzimidazole membranes for polymer electrolyte fuel cells J Electrochem Soc 154 2007 A290 A294
92. U. Sen, Çelik SÜ, A. Ata, and A. Bozkurt Anhydrous proton conducting membranes for PEM fuel cells based on Nafion/Azole composites Int J Hydr Energy 33 2008 2808 2815
93. A. Bozkurt, and W.H. Meyer Proton conducting blends of poly(4-vinylimidazole) with phosphoric acid Solid State Ionics 138 2001 259 265
94. H. Pu, W.H. Meyer, and G. Wegner Proton conductivity in acid-blended poly(4-vinylimidazole) Macromol Chem Phys 202 2001 1478 1482
95. 4 J Polym Sci Part B Polym Phys 40 2002 663 669
96. H.T. Pu, J. Wu, D.C. Wan, and Z.H. Chang Synthesis and anhydrous proton conductivity of poly(5-vinyltetrazole) prepared by free radical polymerization J Membr Sci 322 2008 392 399
97. Çelik SÜ, A. Aslan, and A. Bozkurt Phosphoric acid-doped poly(1-vinyl-1,2,4-triazole) as water-free proton conducting polymer electrolytes Solid State Ionics 179 2008 683 688
98. H. Pu, Q. Liu, and G. Liu Methanol permeation and proton conductivity of acid-doped poly(N-ethylbenzimidazole) and poly(N-methylbenzimidazole) J Membr Sci 241 2004 169 175
99. A. Aslan, Çelik SÜ, Ü. Şen, R. Haser, and A. Bozkurt Intrinsically proton-conducting poly(1-vinyl-1,2,4-triazole)/triflic acid blends Electrochim Acta 54 2009 2957 2961
100. Ş. Özden, Çelik SÜ, and A. Bozkurt Polymer electrolyte membranes based on p-toluenesulfonic acid doped poly(1-vinyl-1,2,4- triazole): Synthesis, thermal and proton conductivity properties J Polym Sci Part B Polym Phys 48 2010 1016 1021
101. A. Aslan, and A. Bozkurt Development and characterization of polymer electrolyte membranes based on ionical cross-linked poly(1-vinyl-1,2,4 triazole) and poly(vinylphosphonic acid) J Power Sources 191 2009 442 447
102. A. Aslan, U. Sen, and A. Bozkurt Preparation, properties, and characterization of polymer electrolyte membranes based on poly(1-vinyl-1,2,4 triazole) and poly(styrene sulfonic acid) J Electrochem Soc 156 2009 B1112 B1116
103. U. Sen, A. Bozkurt, and A. Ata Nafion/poly(1-vinyl-1,2,4-triazole) blends as proton conducting membranes for polymer electrolyte membrane fuel cells J Power Sources 195 2010 7720 7726
104. S. Martwiset, R.C. Woudenberg, S. Granados-Focil, O. Yavuzcetin, M.T. Tuominen, and E.B. Coughlin Intrinsically conducting polymers and copolymers containing triazole moieties Solid State Ionics 178 2007 1398 1403
105. R.C. Woudenberg, O. Yavuzcetin, M.T. Tuominen, and E.B. Coughlin Intrinsically proton conducting polymers and copolymers containing benzimidazole moieties: Glass transition effects Solid State Ionics 178 2007 1135 1141
106. S. Granados-Focil, R.C. Woudenberg, O. Yavuzcetin, M.T. Tuominen, and E.B. Coughlin Water-free proton-conducting polysiloxanes: a study on the effect of heterocycle structure Macromolecules 40 2007 8708 8713
107. Çelik SÜ, U. Akbey, R. Graf, A. Bozkurt, and H.W. Spiess Anhydrous proton-conducting properties of triazole-phosphonic acid copolymers: a combined study with MAS NMR Phys Chem Chem Phys 10 2008 6058 6066
108. H. Pu, S. Ye, and D. Wan Anhydrous proton conductivity of acid doped vinyltriazole-based polymers Electrochim Acta 52 2007 5879 5883
109. Çelik SÜ, and A. Bozkurt The synthesis and proton-conducting properties of the copolymers based on 1-vinyl-1,2,4-triazole and 2-acrylamido-2-methyl-1-propanesulfonic acid Solid State Ionics 181 2010 525 530
110. H.G. Herz, K.D. Kreuer, J. Maier, G. Scharfenberger, M.F.H. Schuster, and W.H. Meyer New fully polymeric proton solvents with high proton mobility Electrochim Acta 48 2003 2165 2171
111. G.R. Goward, F.H.M. Schuster, D. Sebastiani, I. Schnell, and H.W. Spiess High-resolution solid-state nmr studies of imidazole-based proton conductors: structure motifs and chemical exchange from 1H NMR J Phys Chem B 106 2002 9322 9334
112. J.C. Persson, and P. Jannasch Self-conducting benzimidazole oligomers for proton transport Chem Mater 15 2003 3044 3045
113. R. Subbaraman, H. Ghassemi, and T.A. Zawodzinski 4,5-Dicyano-1H-[1,2,3]- triazole as a proton transport facilitator for polymer electrolyte membrane fuel cells J Am Chem Soc 129 2007 2238 2239
114. Çelik SÜ, and A. Bozkurt Preparation and proton conductivity of acid-doped 5-aminotetrazole functional poly(glycidyl methacrylate) Eur Polym J 44 2008 213 218
115. Çelik SÜ, Ü. Akbey, A. Bozkurt, R. Graf, and H.W. Spiess Proton-conducting properties of acid-doped poly(glycidyl methacrylate)-1,2,4- triazole systems Macrom Chem Phys 209 2008 593 603
116. M. Garcia-Viloca, A. Gonzalez-Lafont, and J.M. Lluch On pKa matching as a requirement to form a low-barrier hydrogen bond a theoretical study in gas phase J Phys Chem A 101 1997 3880 3886
117. J.C. Persson, and P. Jannasch Intrinsically proton-conducting benzimidazole units tethered to polysiloxanes Macromolecules 38 2005 3283 3289
118. S.T. Günday, A. Bozkurt, N.M. Atabay, and A. Baykal Benzimidazole tethered proton conducting organic electrolytes Mater Chem Phys 105 2007 240 244
119. Ş. Özden, Çelik SÜ, and A. Bozkurt Synthesis and proton conductivity studies of doped azole functional polymer electrolyte membranes Electrochim Acta 55 2010 8498 8503
120. Ş. Özden, Çelik SÜ, and A. Bozkurt Synthesis and proton conductivity studies of polystyrene-based triazole functional polymer membranes J Polym Sci Part A Polym Chem 48 2010 4974 4980
121. J.C. Persson, K. Josefsson, and P. Jannasch Polysulfones tethered with benzimidazole Polymer 47 2006 991 998