Self-assembled highly ordered acid layers in precisely sulfonated polyethylene produce efficient proton transport

Nature Materials - Tập 17 Số 8 - Trang 725-731 - 2018
Edward B. Trigg1, Taylor W. Gaines2, Manuel Maréchal3, Demi E. Moed1, Patrice Rannou3, Kenneth B. Wagener2, Mark J. Stevens4, Karen I. Winey1
1University of Pennsylvania (3451 Walnut Street, Philadelphia, PA 19104 | 215-898-5000 - United States)
2UF - University of Florida [Gainesville] (Gainesville, FL 32611 - United States)
3SYMMES - SYstèmes Moléculaires et nanoMatériaux pour l’Energie et la Santé (17, rue des Martyrs 38054 Grenoble cedex 09 - France)
4SNL - Sandia National Laboratories [Albuquerque] (PO Box 5800 Albuquerque, NM 87185 - United States)

Tóm tắt

Từ khóa


Tài liệu tham khảo

Dobson, C. M. Protein folding and misfolding. Am. Sci. 90, 445–453 (2002).

Hill, D. J., Mio, M. J., Prince, R. B., Hughes, T. S. & Moore, J. S. A field guide to foldamers. Chem. Rev. 101, 3893–4011 (2001).

Ortmann, P. & Mecking, S. Long-spaced aliphatic polyesters. Macromolecules 46, 7213–7218 (2013).

Le Fevere de Ten Hove, C., Penelle, J., Ivanov, D. A. & Jonas, A. M. Encoding crystal microstructure and chain folding in the chemical structure of synthetic polymers. Nat. Mater. 3, 33–37 (2004).

Atallah, P., Wagener, K. B. & Schulz, M. D. ADMET: the future revealed. Macromolecules 46, 4735–4741 (2013).

Gaines, T. W., Trigg, E. B., Winey, K. I. & Wagener, K. B. High melting precision sulfone polyethylenes synthesized by ADMET chemistry. Macromol. Chem. Phys. 217, 2351–2359 (2016).

Caire da Silva, L., Rojas, G., Schulz, M. D. & Wagener, K. B. Acyclic diene metathesis polymerization: history, methods and applications. Prog. Polym. Sci. 69, 79–107 (2017).

Baughman, T., Chan, C., Winey, K. & Wagener, K. B. Synthesis and morphology of well-defined poly(ethylene-co-acrylic acid) copolymers. Macromolecules 40, 6564–6571 (2007).

Trigg, E. B., Stevens, M. J. & Winey, K. I. Chain folding produces a multilayered morphology in a precise polymer: simulations and experiments. J. Am. Chem. Soc. 139, 3747–3755 (2017).

Trigg, E. B., Middleton, L. R., Moed, D. E. & Winey, K. I. Transverse orientation of acid layers in the crystallites of a precise polymer. Macromolecules 50, 8988–8995 (2017).

Mandal, J., Krishna Prasad, S., Rao, D. S. S. & Ramakrishnan, S. Periodically clickable polyesters: study of intrachain self-segregation induced folding, crystallization, and mesophase formation. J. Am. Chem. Soc. 136, 2538–2545 (2014).

Gierke, T. D., Munn, G. E. & Wilson, F. C. The morphology in nafion perfluorinated membrane products, as determined by wide- and small- angle X-ray studies. J. Polym. Sci. Polym. Phys. Ed. 19, 1687–1704 (1981).

Eisenberg, A. Clustering of ions in organic polymers. A theoretical approach. Macromolecules 3, 147–154 (1970).

Diat, O. & Gebel, G. Fuel cells: proton channels. Nat. Mater. 7, 13–14 (2008).

Kreuer, K. D. & Portale, G. A critical revision of the nano-morphology of proton conducting ionomers and polyelectrolytes for fuel cell applications. Adv. Funct. Mater. 23, 5390–5397 (2013).

Mauritz, K. A. & Moore, R. B. State of Understanding of Nafion. Chem. Rev. 104, 4535–4585 (2004).

Kusoglu, A., Mosdestino, M. A., Hexemer, A., Segalman, R. A. & Weber, A. Z. Subsecond morphological changes in Nafion during water uptake detected by small-angle X-ray scattering. ACS Macro Lett. 1, 33–36 (2012).

Kreuer, K. D. Ion conducting membranes for fuel cells and other electrochemical devices. Chem. Mater. 26, 361–380 (2013).

Rubatat, L., Rollet, A. L., Gebel, G. & Diat, O. Evidence of elongated polymeric aggregates in Nafion. Macromolecules 35, 4050–4055 (2002).

Schmidt-rohr, K. & Chen, Q. Parallel cylindrical water nanochannels in Nafion fuel-cell membranes. Nat. Mater. 7, 75–83 (2008).

Li, N. & Guiver, M. D. Ion transport by nanochannels in ion-containing aromatic copolymers. Macromolecules 47, 2175–2198 (2014).

Vetter, S., Ruffmann, B., Buder, I. & Nunes, S. P. Proton conductive membranes of sulfonated poly(ether ketone ketone). J. Memb. Sci. 260, 181–186 (2005).

Fujimoto, C. H., Hickner, M. A., Cornelius, C. J. & Loy, D. A. Ionomeric poly(phenylene) prepared by Diels-Alder polymerization: synthesis and physical properties of a novel polyelectrolyte. Macromolecules 38, 5010–5016 (2005).

Elabd, Y. A. & Hickner, M. A. Block copolymers for fuel cells. Macromolecules 44, 1–11 (2011).

Elabd, Y. A., Napadensky, E., Walker, C. W. & Winey, K. I. Transport properties of sulfonated poly(styrene-b-isobutylene-b-styrene) triblock copolymers at high ion-exchange capacities. Macromolecules 39, 399–407 (2006).

Kim, H. K., Zhang, M., Yuan, X., Lvov, S. N. & Chung, T. C. M. Synthesis of polyethylene-based proton exchange membranes containing PE backbone and sulfonated poly(arylene ether sulfone) side chains for fuel cell applications. Macromolecules 45, 2460–2470 (2012).

Nakabayashi, K., Higashihara, T. & Ueda, M. Polymer electrolyte membranes based on cross-linked highly sulfonated multiblock copoly(ether sulfone)s. Macromolecules 43, 5756–5761 (2010).

Miyanishi, S., Fukushima, T. & Yamaguchi, T. Synthesis and property of semicrystalline anion exchange membrane with well-defined ion channel structure. Macromolecules 48, 2576–2584 (2015).

Gadjourova, Z., Andreev, Y. G., Tunstall, D. P. & Bruce, P. G. Ionic conductivity in crystalline polymer electrolytes. Nature 412, 520–523 (2001).

Cheng, S., Smith, D. M. & Li, C. Y. How does nanoscale crystalline structure affect ion transport in solid polymer electrolytes? Macromolecules 47, 3978–3986 (2014).

Schulz, M. D., Sauty, N. F. & Wagener, K. B. Morphology control in precision polyolefins. Appl. Petrochem. Res. 5, 3–8 (2015).

Buitrago, C. F. et al. Room temperature morphologies of precise acid- and ion-containing polyethylenes. Macromolecules 46, 9003–9012 (2013).

Middleton, L. R. et al. Hierarchical acrylic acid aggregate morphologies produce strain-hardening in precise polyethylene-based copolymers. Macromolecules 48, 3713–3724 (2015).

Seitz, M. E. et al. Nanoscale morphology in precisely sequenced poly(ethylene-co-acrylic acid) zinc ionomers. J. Am. Chem. Soc. 132, 8165–8174 (2010).

Gaines, T. W., Bell, M.H., Trigg, E. B., Winey, K. I. & Wagener, K. B. Precision sulfonic acid polyolefins via heterogenous to homogenous deprotection. Macromol. Chem. Phys. https://doi.org/10.1002/macp.201700634 (2018).

Kreuer, K. D., Paddison, S. J., Spohr, E. & Schuster, M. Transport in proton conductors for fuel cell applications: simulation, elementary reactions and phenomenology. Chem. Rev. 104, 4637–4678 (2004).

Feng, S. & Voth, G. A. Proton solvation and transport in hydrated Nafion. J. Phys. Chem. B 115, 5903–5912 (2011).

Choi, P., Jalani, N. H. & Datta, R. Thermodynamics and proton transport in Nafion. J. Electrochem. Soc. 152, E123–E130 (2005).

Suarez, S. N., Jayakody, J. R. P., Greenbaum, S. G., Zawodzinski, T. & Fontanella, J. J. A fundamental study of the transport properties of aqueous superacid solutions. J. Phys. Chem. B 114, 8941–8947 (2010).

Urata, S. et al. Molecular dynamics simulation of swollen membrane of perfluorinated ionomer. J. Phys. Chem. B 109, 4269–4278 (2005).

Lane, J. M. D., Chandross, M., Stevens, M. J. & Grest, G. S. Water in nanoconfinement between hydrophilic self-assembled monolayers. Langmuir 24, 5209–5212 (2008).

Leng, Y. & Cummings, P. T. Fluidity of hydration layers nanoconfined between mica surfaces. Phys. Rev. Lett. 94, 19–22 (2005).

Savage, J. & Voth, G. A. Persistent subdiffusive proton transport in perfluorosulfonic acid membranes. J. Phys. Chem. Lett. 5, 3037–3042 (2014).

Perrin, J., Lyonnard, S., Guillermo, A. & Levitz, P. Water dynamics in ionomer membranes by field-cycling NMR relaxometry. J. Phys. Chem. B 110, 5439–5444 (2006).

Jankowska, A., Zalewska, A., Skalska, A., Ostrowski, A. & Kowalak, S. Proton conductivity of imidazole entrapped in microporous molecular sieves. Chem. Commun. 53, 2475–2478 (2017).

Trigg, E. B., Tiegs, B. J., Coates, W. & Winey, K. I. High morphological order in a nearly precise acid-containing polymer and ionomer. ACS Macro Lett. 6, 947–951 (2017).

Zawodzinski, T. A. et al. Water uptake by and transport through Nafion 117 membranes. J. Electrochem. Soc. 140, 1041–1047 (1993).

Yin, Y. et al. Synthesis, proton conductivity and methanol permeability of a novel sulfonated polyimide from 3-(2′,4′-diaminophenoxy)propane sulfonic acid. Polymer 44, 4509–4518 (2003).

Abbott, L. J. & Frischknecht, A. L. Nanoscale structure and morphology of sulfonated polyphenylenes via atomistic simulations. Macromolecules 50, 1184–1192 (2017).

Gaines, T. W. Oxidized Sulfur Functionalized Polymers via ADMET Polymerization. PhD thesis, Univ. Florida (2015).

Gaines, T. W. & Wagener, K. B. Sulfonated polyethylene. US patent 9,724,686 (2017).

Salas-De La Cruz, D. et al. Environmental chamber for in situ dynamic control of temperature and relative humidity during X-ray scattering. Rev. Sci. Instrum. 83, 025112 (2012).

Heiney, P. Datasqueeze: a software tool for powder and small-angle X-ray diffraction analysis. Comm. Powder Diffr. Newsl. 32, 9–11 (2005).

Abràmoff, M. D., Magalhães, P. J. & Ram, S. J. Image processing with ImageJ. Biophoton. Int. 11, 36–41 (2004).

Plimpton, S. Fast parallel algorithms for short-range molecular dynamics. J. Comput. Phys. 117, 1–19 (1995).

Siu, S. W. I., Pluhackova, K. & Böckmann, R. A. Optimization of the OPLS-AA force field for long hydrocarbons. J. Chem. Theory Comput. 8, 1459–1470 (2012).

Middleton, L. R. et al. Heterogeneous chain dynamics and aggregate lifetimes in precise acid-containing polyethylenes: experiments and simulations. Macromolecules 49, 9176–9185 (2016).

Canongia Lopes, J. N., Pádua, A. A. H. & Shimizu, K. Molecular force field for ionic liquids IV: trialkylimidazolium and alkoxycarbonyl-imidazolium cations; alkylsulfonate and alkylsulfate anions. J. Phys. Chem. B 112, 5039–5046 (2008).

Price, D. J. & Brooks, C. L. A modified TIP3P water potential for simulation with Ewald summation. J. Chem. Phys. 121, 10096–10103 (2004).

Baaden, M., Burgard, M. & Wipff, G. TBP at the water−oil interface: the effect of TBP concentration and water acidity investigated by molecular dynamics simulations. J. Phys. Chem. B 105, 11131–11141 (2001).

Hockney, R. W. & Eastwood, J. W. Computer Simulation Using Particles (Taylor & Francis, New York, NY, 1988).

Bolintineanu, D. S., Stevens, M. J. & Frischknecht, A. L. Atomistic simulations predict a surprising variety of morphologies in precise ionomers. ACS Macro Lett. 2, 206–210 (2013).

Lueth, C. A., Bolintineanu, D. S., Stevens, M. J. & Frischknecht, A. L. Hydrogen-bonded aggregates in precise acid copolymers. J. Chem. Phys. 140, 054902 (2014).

Bolintineanu, D. S., Stevens, M. J. & Frischknecht, A. L. Influence of cation type on ionic aggregates in precise ionomers. Macromolecules 46, 5381–5392 (2013).

Brubach, J. B. et al. Performance of the AILES THz-infrared beamline at SOLEIL for high resolution spectroscopy. AIP Conf. Proc. 1214, 81–84 (2010).

Roy, P., Rouzieres, M., Qi, Z. & Chubar, O. The AILES infrared beamline on the third generation synchrotron radiation facility SOLEIL. Infrared Phys. Technol. 49, 139–146 (2006).

Bernardina, S. D. et al. New experimental set-ups for studying nanoconfined water on the AILES beamline at SOLEIL. Vib. Spectrosc. 75, 154–161 (2014).

Voute, A. et al. New high-pressure/low-temperature set-up available at the AILES beamline. Vib. Spectrosc. 86, 17–23 (2016).