Naphthalene proton exchange

Genies, G., Mercier, R., Sillion, B., Gomet, N., Gebel, G. and Pineri, M. 2001. Soluble sulfonated naphthalenic polyimides as materials for proton exchange membranes. Polymer 42 359-373. 

Einsla, B. R., Hong, Y. T., Kim, Y. S., Wang, F., Gunduz, N. and McGrath, J. E. 2004. Sulfonated naphthalene dianhydride based polyimide copolymers for proton-exchange-membrane fuel cells. 1. Monomer and copolymer synthesis. Journal of Polymer Science Part A Polymer Chemistry 42 862-874. 

Y. Gao, G.P. Robertson, M.D. Guiver, S.D. Mikhailenko, X. Li, S. Kaliaguine, Synthesis of poly(arylene ether ether ketone ketone) copolymers containing pendant sulfonic acid groups bonded to naphthalene as proton exchange membrane materials. Macromolecules 2004, 37(18), 6748-6754. 

The copolymers of polyarylketones, containing imits of naphthalene-sulfonic acid in lateral links, are use in manuiacturing of proton-exchange membranes [392],... 

A major goal of the research in proton exchange membrane fuel cells is the development of high-temperature membranes that may operate at 120 °C and low humidity. One route are multi-block copolymers with completely disulfonated PAES and naphthalene polyimide oligomers [107]. 

Badami AS, Roy A, Lee HS, Li Y, McGrath JE. Morphological investigations of disulfonated poly(arylene ether sulfone)-fe-naphthalene dianhydride-based polyimide multiblock copolymers as potential high temperature proton exchange membranes. J Membr Sci 2009 328 (l-2) 156-64. 

E.A. Mistri, A.K. Mohanty, S. Banerjee, H. Komber, B. Voit, Naphthalene dianhydride based semifluorinated sulfonated copoly(ether imide)s synthesis, characterization and proton exchange properties, J. Membr. Sci. 441 (2013)168-177. 

Scheme 6.90. Potential pathways for the exchange of protons at C-1 (C-a) and C-2 (C-p) of naphthalene. The exchange of tritium ( H) at C-1 is 8 to 10 times faster than at C-2.

P. Xing, G. P. Robertson, M. D. Guiver, S. D. Mikhailenko, S. Kaliaguine, Sulfonated poly(aryl ether ketones) containing naphthalene moieties obtained by direct copolymerization as novel polymers for proton exchange membranes. J. Polym. Sci. A 42, 2866-2876 (2004). 

The initiator system 2a/DBU was formed by addition of DBU ([2a]/[DBU] = 1 1), which leads to the thiolate/thiol equilibrium through proton exchange The polymerization of MT using this initiator system was carried out in DMF at 0 °C and was quenched by l-(chloromethyl)naphthalene, which has been reported to be effective for termination of thiirane polymerization. With a feed ratio of [MT]o/[2a/DBU]o = 30, the reartion was complete within 5 min to afford the corresponding star-shaped polymer the nrrmber-average molecular weight (M ) and MWD (Mw/MJ, which were 3500 and 1.05, respectively. 

Suda et al. [288] reported the synthesis and characterization of a series of sulfonated star-hb polyimides (S-hb-Pls) without any crosslinking for use as proton exchange membranes. Sulfonated anhydride-terminated polyimides with different molecular weights (M v = 59,000, 200,000 and 300,000 Da) based on monomer combination 1,4,5,8-naphthalene tetracarboxylic dianhydride/4,4 -diaminobiphenyl 2,2 -disulfonic acid (NTDA/BDSA) were synthesized using different molar ratios of BDSA NTDA. The amine-terminated hb-Pl based on monomer combination 4,4-(hexafluoroisopropylidene)diphthalic anhydride/tris(4-aminophenyl)amine (6EDA/TAPA) was also prepared. Scheme 33 shows the monomer combinations used for the preparation of (S-hb-Pl). 

Genies, C., Mercier, R., SiUion, B., Comet, N., Gebel, G., and Pineri, M. (2001b). Stability stody of sulfonated phthalic and naphthalenic polyimide stmctores in aqueous medium. Polymer 42, 5097. Gil, M., Ji, X. L., Li, X. F., Na, H. Hampsey, J. E., and Lu, Y. F. (2004). Direct synthesis of sulfonated aromatic poly (ether ether ketone) proton exchange membranes for fuel cell applications. J. Membr. Sci. 234, 75. 

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