• No se han encontrado resultados

2. MARCO DE REFERENCIA

2.1 MARCO TEÓRICO

2.1.2 Administración de la educación universitaria

Main-chain cobaltocenium containing polymers for AAEMs:

Along with side-chain cobaltocenium containing polymers, main-chaing cobaltocenium containing polymers should be investigated for AAEMs. Polyolefins (saturated hydrocarbon backbon) is relatively inert to nucleophilic attack, or deprotonation by hydroxide ion. Random copolymers norbornene, cyclooctene and diene containing cobaltocenium are promising candidate materials for stable AAEMs. The synthetic routes to these norbornene, cyclooctene and diene containing cobaltocenium monomer are shown in Figure 4.1. The diene containing monomer can be polymerized via acyclic diene metathesis polymerization, and other two monomers can be copolymerized with norbornene, or cyclooctene monomers via ring-opening metathesis polymerization (ROMP) followed by hydrogenation to fabricate flexible, robust and alkaline stable membranes.

Figure 4.1 Proposed synthetic route to the norbornene, cyclooctene and diene containing cobaltocenium monomer

REFERENCES

1. Hardy, C. G.; Zhang, J.; Yan, Y.; Ren, L.; Tang, C., Metallopolymers with transition metals in the side-chain by living and controlled polymerization techniques. Progress in Polymer Science 2014,39 (10), 1742-1796.

2. Abd-El-Aziz, A. S.; Strohm, E. A., Transition metal-containing macromolecules: En route to new functional materials. Polymer 2012,53 (22), 4879-4921.

3. Whittell, G. R.; Hager, M. D.; Schubert, U. S.; Manners, I., Functional soft materials from metallopolymers and metallosupramolecular polymers. Nature materials

2011,10 (3), 176-188.

4. Sobransingh, D.; Kaifer, A. E., New dendrimers containing a single cobaltocenium unit covalently attached to the apical position of newkome dendrons: electrochemistry and guest binding interactions with cucurbit [7] uril. Langmuir 2006,22 (25), 10540-10544.

5. Whittell, G. R.; Manners, I., Metallopolymers: New multifunctional materials. Advanced Materials 2007,19 (21), 3439-3468.

6. Andres, P. R.; Schubert, U. S., New functional polymers and materials based on 2, 2': 6', 2"-terpyridine metal complexes. Advanced Materials 2004,16 (13), 1043-1070. 7. Al-Badri, Z. M.; Tew, G. N., Well-defined acetylene-functionalized oxanorbornene polymers and block copolymers. Macromolecules 2008, 41 (12), 4173- 4179.

8. Schatzschneider, U.; Metzler‐Nolte, N., New principles in medicinal organometallic chemistry. Angewandte Chemie International Edition 2006, 45 (10), 1504-1507.

9. Ornelas, C., Application of ferrocene and its derivatives in cancer research. New Journal of Chemistry 2011,35 (10), 1973-1985.

10. Zhou, J.; Whittell, G. R.; Manners, I., Metalloblock Copolymers: New Functional Nanomaterials. Macromolecules 2014,47 (11), 3529-3543.

11. Chen, Y.; Wilbon, P. A.; Chen, Y. P.; Zhou, J.; Nagarkatti, M.; Wang, C.; Chu, F.; Decho, A. W.; Tang, C., Amphipathic antibacterial agents using cationic methacrylic polymers with natural rosin as pendant group. RSC Advances 2012,2 (27), 10275-10282.

12. Li, P.; Poon, Y. F.; Li, W.; Zhu, H.-Y.; Yeap, S. H.; Cao, Y.; Qi, X.; Zhou, C.; Lamrani, M.; Beuerman, R. W., A polycationic antimicrobial and biocompatible hydrogel with microbe membrane suctioning ability. Nature materials 2011,10 (2), 149-156. 13. Nederberg, F.; Zhang, Y.; Tan, J. P.; Xu, K.; Wang, H.; Yang, C.; Gao, S.; Guo, X. D.; Fukushima, K.; Li, L., Biodegradable nanostructures with selective lysis of microbial membranes. Nature chemistry 2011,3 (5), 409-414.

14. Ramos, J.; Forcada, J.; Hidalgo-Alvarez, R., Cationic polymer nanoparticles and nanogels: from synthesis to biotechnological applications. Chemical reviews 2013, 114 (1), 367-428.

15. Samal, S. K.; Dash, M.; Van Vlierberghe, S.; Kaplan, D. L.; Chiellini, E.; Van Blitterswijk, C.; Moroni, L.; Dubruel, P., Cationic polymers and their therapeutic potential. Chemical Society Reviews 2012,41 (21), 7147-7194.

16. Wang, J.; Chen, Y. P.; Yao, K.; Wilbon, P. A.; Zhang, W.; Ren, L.; Zhou, J.; Nagarkatti, M.; Wang, C.; Chu, F., Robust antimicrobial compounds and polymers derived from natural resin acids. Chemical Communications 2012,48 (6), 916-918. 17. Yan, Y.; Deaton, T. M.; Zhang, J.; He, H.; Hayat, J.; Pageni, P.; Matyjaszewski, K.; Tang, C., Syntheses of Monosubstituted Rhodocenium Derivatives, Monomers, and Polymers. Macromolecules 2015,48 (6), 1644-1650.

18. Neuse, E. W.; Rosenberg, H., Metallocene polymers. Journal of Macromolecular Science—Reviews in Macromolecular Chemistry 1970,4 (1), 1-145.

19. Kenaree, A. R.; Berven, B. M.; Ragogna, P. J.; Gilroy, J. B., Highly-metallized phosphonium polyelectrolytes. Chemical Communications 2014,50 (73), 10714-10717. 20. Hardy, C. G.; Ren, L.; Ma, S.; Tang, C., Self-assembly of well-defined ferrocene triblock copolymers and their template synthesis of ordered iron oxide nanoparticles. Chemical Communications 2013,49 (39), 4373-4375.

21. Yan, Y.; Zhang, J.; Qiao, Y.; Ganewatta, M.; Tang, C., Ruthenocene-containing homopolymers and block copolymers via ATRP and RAFT polymerization. Macromolecules 2013,46 (22), 8816-8823.

22. Kundu, S.; Chakraborty, A.; Mondal, K.; Chandrasekhar, V., Multi-Ruthenocene Assemblies on an Organostannoxane Platform. Supramolecular Signatures and Conversion to (Ru–Sn) O2. Crystal Growth & Design 2014,14 (2), 861-870.

23. Zhang, J.; Yan, Y.; Chance, M. W.; Chen, J.; Hayat, J.; Ma, S.; Tang, C., Charged Metallopolymers as Universal Precursors for Versatile Cobalt Materials. Angewandte Chemie 2013,125 (50), 13629-13633.

24. Mayer, U. F.; Gilroy, J. B.; O’Hare, D.; Manners, I., Ring-opening polymerization of 19-electron [2] cobaltocenophanes: a route to high-molecular-weight, water-soluble polycobaltocenium polyelectrolytes. Journal of the American Chemical Society 2009,

131 (30), 10382-10383.

25. Zhang, J.; Pellechia, P. J.; Hayat, J.; Hardy, C. G.; Tang, C., Quantitative and qualitative counterion exchange in cationic metallocene polyelectrolytes. Macromolecules 2013,46 (4), 1618-1624.

26. Zhang, J.; Chen, Y. P.; Miller, K. P.; Ganewatta, M. S.; Bam, M.; Yan, Y.; Nagarkatti, M.; Decho, A. W.; Tang, C., Antimicrobial metallopolymers and their bioconjugates with conventional antibiotics against multidrug-resistant bacteria. Journal of the American Chemical Society 2014,136 (13), 4873-4876.

27. Sheats, J. E.; Hlatky, G., Cobalt sandwich compounds. J. Chem. Educ 1983, 60 (12), 1015.

28. Balkus, K.; Gabrielov, A.; Shepelev, S., Synthesis of aluminum phosphate molecular sieves using cobalticinium hydroxide. Microporous Materials 1995, 3 (4), 489-495.

29. Ito, T.; Kenjo, T., A new anion exchanger containing cobalticinium cation. Bulletin of the Chemical Society of Japan 1968,41 (3), 614-619.

30. Ito, T.; Kenjo, T., Ion-exchange Properties of Anion-exchanger Containing Cobalticinium Cations. Bulletin of the Chemical Society of Japan 1968, 41 (7), 1600- 1605.

31. Ren, L.; Hardy, C. G.; Tang, C., Synthesis and solution self-assembly of side- chain cobaltocenium-containing block copolymers. Journal of the American Chemical Society 2010,132 (26), 8874-8875.

32. Chen, B.; Xiang, S.; Qian, G., Metal− organic frameworks with functional pores for recognition of small molecules. Accounts of chemical research 2010, 43 (8), 1115- 1124.

33. Bonizzoni, M.; Long, S. R.; Rainwater, C.; Anslyn, E. V., PAMAM Dendrimer- Induced Aggregation of 5 (6)-Carboxyfluorescein. The Journal of organic chemistry

2012,77 (3), 1258-1266.

34. Sheats, J. E.; Rausch, M. D., Synthesis and properties of cobalticinium salts. I. Synthesis of monosubstituted cobalticinium salts. The Journal of Organic Chemistry

1970,35 (10), 3245-3249.

35. anicek, S.; opacka, H.; Wurst, .; M ller, T.; Schottenberger, H.; Bildstein, B., Chemoselective, Practical Synthesis of Cobaltocenium Carboxylic Acid Hexafluorophosphate. Organometallics 2014,33 (5), 1152-1156.

36. Yan, Y.; Zhang, J.; Qiao, Y.; Tang, C., Facile Preparation of Cobaltocenium‐Containing Polyelectrolyte via Click Chemistry and RAFT Polymerization. Macromolecular rapid communications 2014,35 (2), 254-259.

37. Jolly, A. M.; Bonizzoni, M., PAMAM dendrimers as supramolecular hosts through non-covalent interactions. Supramolecular Chemistry 2015,27 (3), 151-160. 38. Mallet, A. M.; Liu, Y.; Bonizzoni, M., An off-the-shelf sensing system for physiological phosphates. Chemical Communications 2014,50 (39), 5003-5006.

39. Jolly, A. M.; Bonizzoni, M., PAMAM dendrimers as supramolecular hosts through non-covalent interactions. Supramol. Chem. 2014, 1-11.

40. Jolly, A. M.; Bonizzoni, M., Intermolecular Forces Driving Encapsulation of Small Molecules by PAMAM Dendrimers in Water. Macromolecules 2014, 47 (18), 6281-6288.

41. Wang, Y.; Chen, K. S.; Mishler, J.; Cho, S. C.; Adroher, X. C., A review of polymer electrolyte membrane fuel cells: technology, applications, and needs on fundamental research. Applied Energy 2011,88 (4), 981-1007.

42. Cheng, J.; He, G.; Zhang, F., A mini-review on anion exchange membranes for fuel cell applications: Stability issue and addressing strategies. International Journal of Hydrogen Energy 2015,40 (23), 7348-7360.

43. Appleby, A. J., Fuel cell handbook. 1988.

44. Whittingham, M. S.; Zawodzinski, T., Introduction: batteries and fuel cells. Chemical reviews 2004,104 (10), 4243-4244.

45. Lee, C. H.; Park, H. B.; Lee, Y. M.; Lee, R. D., Importance of proton conductivity measurement in polymer electrolyte membrane for fuel cell application. Industrial & engineering chemistry research 2005,44 (20), 7617-7626.

46. Gil, M.; Ji, X.; Li, X.; Na, H.; Hampsey, J. E.; Lu, Y., Direct synthesis of sulfonated aromatic poly (ether ether ketone) proton exchange membranes for fuel cell applications. Journal of membrane science 2004,234 (1), 75-81.

47. Thomas, S. C.; Ren, X.; Gottesfeld, S.; Zelenay, P., Direct methanol fuel cells: progress in cell performance and cathode research. Electrochimica Acta 2002, 47 (22), 3741-3748.

48. Varcoe, J. R.; Slade, R. C., Prospects for alkaline anion‐exchange membranes in low temperature fuel cells. Fuel cells 2005,5 (2), 187-200.

49. Cifrain, M.; Kordesch, K., Advances, aging mechanism and lifetime in AFCs with circulating electrolytes. Journal of Power Sources 2004,127 (1), 234-242.

50. Gülzow, E.; Schulze, M., Long-term operation of AFC electrodes with CO 2 containing gases. Journal of Power Sources 2004,127 (1), 243-251.

51. Chempath, S.; Boncella, J. M.; Pratt, L. R.; Henson, N.; Pivovar, B. S., Density functional theory study of degradation of tetraalkylammonium hydroxides. The Journal of Physical Chemistry C 2010,114 (27), 11977-11983.

52. Chempath, S.; Einsla, B. R.; Pratt, L. R.; Macomber, C. S.; Boncella, J. M.; Rau, J. A.; Pivovar, B. S., Mechanism of tetraalkylammonium headgroup degradation in alkaline fuel cell membranes. The Journal of Physical Chemistry C 2008,112 (9), 3179- 3182.

53. Danks, T. N.; Slade, R. C.; Varcoe, J. R., Alkaline anion-exchange radiation- grafted membranes for possible electrochemical application in fuel cells. Journal of Materials Chemistry 2003,13 (4), 712-721.

54. Herman, H.; Slade, R. C.; Varcoe, J. R., The radiation-grafting of vinylbenzyl chloride onto poly (hexafluoropropylene-co-tetrafluoroethylene) films with subsequent conversion to alkaline anion-exchange membranes: optimisation of the experimental conditions and characterisation. Journal of Membrane Science 2003,218 (1), 147-163. 55. Varcoe, J. R.; Slade, R. C., An electron-beam-grafted ETFE alkaline anion- exchange membrane in metal-cation-free solid-state alkaline fuel cells. Electrochemistry Communications 2006,8 (5), 839-843.

56. Varcoe, J. R.; Slade, R. C.; Lam How Yee, E.; Poynton, S. D.; Driscoll, D. J.; Apperley, D. C., Poly (ethylene-co-tetrafluoroethylene)-derived radiation-grafted anion- exchange membrane with properties specifically tailored for application in metal-cation- free alkaline polymer electrolyte fuel cells. Chemistry of Materials 2007,19 (10), 2686- 2693.

57. Hibbs, M. R.; Hickner, M. A.; Alam, T. M.; McIntyre, S. K.; Fujimoto, C. H.; Cornelius, C. J., Transport properties of hydroxide and proton conducting membranes. Chemistry of materials 2008,20 (7), 2566-2573.

58. Wang, G.; Weng, Y.; Chu, D.; Chen, R.; Xie, D., Developing a polysulfone-based alkaline anion exchange membrane for improved ionic conductivity. Journal of Membrane Science 2009,332 (1), 63-68.

59. Wang, J.; Zhao, Z.; Gong, F.; Li, S.; Zhang, S., Synthesis of soluble poly (arylene ether sulfone) ionomers with pendant quaternary ammonium groups for anion exchange membranes. Macromolecules 2009,42 (22), 8711-8717.

60. Yan, J.; Hickner, M. A., Anion exchange membranes by bromination of benzylmethyl-containing poly (sulfone) s. Macromolecules 2010,43 (5), 2349-2356.

61. Hibbs, M. R.; Fujimoto, C. H.; Cornelius, C. J., Synthesis and characterization of poly (phenylene)-based anion exchange membranes for alkaline fuel cells. Macromolecules 2009,42 (21), 8316-8321.

62. Li, N.; Leng, Y.; Hickner, M. A.; Wang, C.-Y., Highly stable, anion conductive, comb-shaped copolymers for alkaline fuel cells. Journal of the American Chemical Society 2013,135 (27), 10124-10133.

63. Robertson, N. J.; Kostalik IV, H. A.; Clark, T. J.; Mutolo, P. F.; Abruña, H. D.; Coates, G. W., Tunable high performance cross-linked alkaline anion exchange membranes for fuel cell applications. Journal of the American Chemical Society 2010,

132 (10), 3400-3404.

64. Price, S. C.; Ren, X.; Jackson, A. C.; Ye, Y.; Elabd, Y. A.; Beyer, F. L., Bicontinuous alkaline fuel cell membranes from strongly self-segregating block copolymers. Macromolecules 2013,46 (18), 7332-7340.

65. Clark, T. J.; Robertson, N. J.; Kostalik IV, H. A.; Lobkovsky, E. B.; Mutolo, P. F.; Abruna, H. D.; Coates, G. W., A ring-opening metathesis polymerization route to alkaline anion exchange membranes: development of hydroxide-conducting thin films from an ammonium-functionalized monomer. Journal of the American Chemical Society

2009,131 (36), 12888-12889.

66. Long, H.; Kim, K.; Pivovar, B. S., Hydroxide degradation pathways for substituted trimethylammonium cations: a DFT study. The Journal of Physical Chemistry C 2012,116 (17), 9419-9426.

67. Edson, J. B.; Macomber, C. S.; Pivovar, B. S.; Boncella, J. M., Hydroxide based decomposition pathways of alkyltrimethylammonium cations. Journal of membrane science 2012,399, 49-59.

68. Neagu, V.; Bunia, I.; Plesca, I., Ionic polymers VI. Chemical stability of strong base anion exchangers in aggressive media. Polymer degradation and Stability 2000,70 (3), 463-468.

69. Wang, J.; Li, S.; Zhang, S., Novel hydroxide-conducting polyelectrolyte composed of an poly (arylene ether sulfone) containing pendant quaternary guanidinium groups for alkaline fuel cell applications. Macromolecules 2010,43 (8), 3890-3896. 70. Kim, D. S.; Labouriau, A.; Guiver, M. D.; Kim, Y. S., Guanidinium- functionalized anion exchange polymer electrolytes via activated fluorophenyl-amine reaction. Chemistry of Materials 2011,23 (17), 3795-3797.

71. Thomas, O. D.; Soo, K. J.; Peckham, T. J.; Kulkarni, M. P.; Holdcroft, S., A stable hydroxide-conducting polymer. Journal of the American Chemical Society 2012,

72. Lin, B.; Dong, H.; Li, Y.; Si, Z.; Gu, F.; Yan, F., Alkaline stable C2-substituted imidazolium-based anion-exchange membranes. Chemistry of Materials 2013, 25 (9), 1858-1867.

73. Zhang, F.; Zhang, H.; Qu, C., Imidazolium functionalized polysulfone anion exchange membrane for fuel cell application. Journal of Materials Chemistry 2011, 21 (34), 12744-12752.

74. Noonan, . J.; Hugar, . M.; ostalik I , H. A.; Lobkovsky, E. B.; Abru a, H. c. D.; Coates, G. W., Phosphonium-functionalized polyethylene: a new class of base-stable alkaline anion exchange membranes. Journal of the American Chemical Society 2012,

134 (44), 18161-18164.

75. Zha, Y.; Disabb-Miller, M. L.; Johnson, Z. D.; Hickner, M. A.; Tew, G. N., Metal-cation-based anion exchange membranes. Journal of the American Chemical Society 2012,134 (10), 4493-4496.

76. Wilkinson, G., The Preparation and Some Properties of the Cobalticinium Salts. Journal of the American Chemical Society 1952,74 (23), 6148-6149.

77. Ren, L.; Hardy, C. G.; Tang, S.; Doxie, D. B.; Hamidi, N.; Tang, C., Preparation of side-chain 18-e cobaltocenium-containing acrylate monomers and polymers. Macromolecules 2010,43 (22), 9304-9310.

78. Zhang, J.; Ren, L.; Hardy, C. G.; Tang, C., Cobaltocenium-containing methacrylate homopolymers, block copolymers, and heterobimetallic polymers via RAFT polymerization. Macromolecules 2012,45 (17), 6857-6863.

79. Pittman, C.; Ayers, O.; Suryanarayanan, B.; McManus, S.; Sheats, J., Organometallic polymers, 28 Condensation polymerization of cobalticinium salts. Die Makromolekulare Chemie 1974,175 (5), 1427-1437.

80. Carraher, C. E.; Sheats, J. E., Synthesis of organometallic polymers by the interfacial technique. XXVI. Synthesis of poly [bis (oxycarbonylcyclopentadienyl)‐cobalt (III)(dicyclopentadienyltitan (IV)) hexafluorophosphate]. Die Makromolekulare Chemie

Documento similar