Water Stability of Metal-Organic Framework HKUST-1

doi:10.21127/yaoyigc20210002

Abstract

Abstract: Metal-organic frameworks (MOFs) are a new class of crystalline porous materials, having wide pores which provide extremely high specific surface areas, larger than those typically observed in more common porous materials like zeolites or activated carbons. This peculiar property combined with the frequent presence of open-metal sites, makes them very promising for a broad range of applications, spacing from gas storage or separation, drug delivery, toxic air removal, chemical detectors, etc. However, the industrialization of MOFs is still facing difficulties because of their low stability to water or even air moisture, a substance difficult to avoid in applications like those mentioned. Another issue concerning MOF industrialization consists in the low bulk density of the micrometric powder grains, which typically constitute such materials. Unfortunately, their low mechanical stability seems to make difficult even to enhance the packaging by simple mechanical compaction. In this review, we will particularly focus on the current state of art involving the MOF HKUST-1, especially on the degradation process involved when this MOF interacts with water molecules. Furthermore, we will show the connection between water and mechanical stability, bringing to attention of a study where solid tablets of HKUST-1 powder have been realized without any loss of crystallinity or porosity because of an accurate study on the effects of different degree of hydration during the tableting phases. In addition, in order to highlight the causes of damages induced in the framework upon interaction with water, a comparison with other two copper carboxylate MOFs will be shown, namely STAM-1 and STAM-17-OEt, which differ from HKUST-1 uniquely for the organic ligands.

Key words: water stability, HKUST-1, mechanical compaction, MOF hydrolysis pattern, degradation process

Angela Terracinaa, and Gianpiero Buscarino. Water Stability of Metal-Organic Framework HKUST-1[J]. General Chemistry, 2021, 7(4): 210002-210002.

References

[1] Yaghi, O. M.; Kalmutzki, M. J.; Diercks, C. S. In Introduction to Reticular Chemistry: Metal-Organic Frameworks and Covalent Organic Frameworks. John Wiley & Sons, 2019.
[2] Furukawa, H.; Cordova, K. E.; O’Keeffe, M.; Yaghi, O. M. The chemistry and applications of metal-organic frameworks. Science 2013, 341, 1230444.
[3] Rowsell, J. L.; Yaghi, O. M. Metal-organic frameworks: a new class of porous materials. Micr. Mes. Mat. 2004, 73, 3–14.
[4] Tan, K.; Nijem, N.; Gao, Y.; Zuluaga, S.; Li, J.; Thonhauser, T.; Chabal, Y. J. Water interactions in metal organic frameworks. CrystEngComm 2015, 17, 247–260.
[5] Moghadam, P. Z.; Li, A.; Wiggin, S. B.; Tao, A.; Maloney, A.G., Wood, P.A.; Ward, S.C. and Fairen-Jimenez, D. Development of a Cambridge Structural Database subset: a collection of metal–organic frameworks for past, present, and future. Chem. Mater. 2017, 29, 2618–2625.
[6] Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keeffe, M.; Yaghi, O. M. Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage. Science 2002, 295, 469–472.
[7] Kuppler, R. J.; Timmons, D. J.; Fang, Q. R.; Li, J. R.; Makal, T. A.; Young, M. D.; Yuan, D.; Zhao, D.; Zhuang, W.; Zhou, H. C. Potential applications of metal-organic frameworks. Coord. Chem. Rev. 2009, 253, 3042–3066.
[8] Burtch, N. C.; Jasuja, H.; Walton, K. S. Water stability and adsorption in metal-organic frameworks. Chem. Rev. 2014, 114, 10575–10612.
[9] Khan, N. A.; Hasan, Z.; Jhung, S. H. Adsorptive removal of hazardous materials using metal–organic frameworks (MOFs): a review. J. Hazard Mater. 2013, 244, 444–456.
[10] McKinlay, A. C.; Morris, R. E.; Horcajada, P.; Férey, G.; Gref, R.; Couvreur, P.; Serre, C. Protecting group and switchable pore-discriminating adsorption properties of a hydrophilic-hydro- phobic metal-organic framework. Angew. Chem. Int. Ed. 2010, 49, 6260–6266.
[11] Li, S. L.; Xu, Q. Metal-organic frameworks as platforms for clean energy. Energ. Environ. Sci. 2013, 6, 1656–1683.
Liu, J.; Thallapally, P. K.; McGrail, B. P.; Brown, D. R.; Liu, J. Progress in adsorption-based CO2 capture by metal-organic frameworks. Chem. Soc. Rev. 2012, 41, 2308–2322.
[12] Editorial Staff. Frameworks for Commercial Success. Nat. Chem. 2016, 8, p. 987.
[13] Kim, H.; Yang, S.; Narayanan, S.; Umans, A. S.; Wang, E. N.; Rao, S. R. Sorption–based Atmospheric Water Harvesting Device. US 10,640,954, 2020.
[14] Canivet, J.; Fateeva, A.; Guo, Y.; Coasne, B.; Farrusseng, D. Water adsorption in MOFs: fundamentals and applications. Chem. Soc. Rev. 2014, 43, 5594–5617.
[15] Nandasiri, M. I.; Jambovane, S. R.; McGrail, B. P.; Schaef, H. T.; Nune, S. K. Adsorption, separation, and catalytic properties of densified metal-organic frameworks. Coord. Chem. Rev. 2016, 311, 38–52.
[16] Ren, J.; Langmi, H. W.; North, B. C.; Mathe, M. Review on processing of metal-organic framework (MOF) materials towards system integration for hydrogen storage. Int. J. Energ. Res. 2015, 39, 607–620.
[17] Chui, S. S. Y.; Lo, S. M. F.; Charmant, J. P.; Orpen, A. G.; Williams, I. D. A chemically functionalizable nanoporous material [Cu₃(TMA)₂(H₂O)₃]_n. Science 1999, 283, 1148–1150.
[18] Hendon, C. H.; Walsh, A. Chemical principles underpinning the performance of the metal-organic framework HKUST-1. Chem. Sci. 2015, 6, 3674–3683.
[19] Mohideen, M. I. H.; Xiao, B.; Wheatley, P. S.; McKinlay, A. C.; Li, Y.; Slawin, A. M.; Aldous, D. W.; Cessford, N. F.; Düren, T.; Zhao, X.; Gill, R. Protecting group and switchable pore-discriminating adsorption properties of a hydrophilic-hydrophobic metal-organic framework. Nat. Chem. 2011, 3, 304–310.
[20] McHugh, L. N.; McPherson, M. J.; McCormick, L. J.; Morris, S. A.; Wheatley, P. S.; Teat, S. J.; McKay, D.; Dawson, D. M.; Sansome, C. E.; Ashbrook, S. E.; Stone, C. A. Hydrolytic stability in hemilabile metal-organic frameworks. Nat. Chem. 2018, 10, 1096–1102.
[21] Dawson, D. M.; Jamieson, L. E.; Mohideen, M. I. H.; McKinlay, A. C.; Smellie, I. A.; Cadou, R.; Keddie, N. S.; Morris, R. E. and Ashbrook, S. E. High-resolution solid-state 13C NMR spectroscopy of the paramagnetic metal-organic frameworks, STAM-1 and HKUST-1. Phys. Chem. Chem. Phys. 2013, 15, 919–929.
[22] Dawson, D. M.; Sansome, C. E.; McHugh, L. N.; McPherson, M. J.; McPherson, L. J. M.; Morris, R. E.; Ashbrook, S. E. 13C NMR of “crumple zone” Cu(II) isophthalate metal-organic frameworks. Solid State Nucl. Mag. 2019, 101, 44–50.
[23] Makal, T. A.; Li, J. R.; Lu, W.; Zhou, H. C. Methane storage in advanced porous materials. Chem. Soc. Rev. 2012, 41, 7761–7779.
[24] Yang, S.; Sun, J.; Ramirez-Cuesta, A. J.; Callear, S. K.; David, W. I.; Anderson, D. P.; Newby, R.; Blake, A. J.; Parker, J. E.; Tang, C. C.; Schröder, M. Selectivity and direct visualization of carbon dioxide and sulfur dioxide in a decorated porous host. Nat. Chem. 2012, 4, 887–894.
[25] Taylor, J. M.; Dawson, K. W.; Shimizu, G. K. A water-stable metal-organic framework with highly acidic pores for proton-conducting applications. J. Am. Chem. Soc. 2013, 135, 1193–1196.
[26] Low, J. J.; Benin, A. I.; Jakubczak, P.; Abrahamian, J. F.; Faheem, S. A.; Willis, R. R. Virtual high throughput screening confirmed experimentally: porous coordination polymer hydration. J. Am. Chem. Soc. 2009, 131, 15834–15842.
[27] Bellarosa, L.; Castillo, J. M.; Vlugt, T.; Calero, S.; López, N. On the mechanism behind the instability of isoreticular metal-organic frameworks (irmofs) in humid environments. Chem.-Eur. J. 2012, 18, 12260–12266.
[28] De Toni, M.; Jonchiere, R.; Pullumbi, P.; Coudert, F. X.; Fuchs, A. H. How Can a Hydrophobic MOF be Water-Unstable? Insight into the Hydration Mechanism of IRMOFs. ChemPhysChem 2012, 13, 3497–3503.
[29] Worrall, S. D.; Bissett, M. A.; Hill, P. I.; Rooney, A. P.; Haigh, S. J.; Attfield, M. P.; Dryfe, R. A. Metal-organic framework templated electrodeposition of functional gold nanostructures. Electrochim. Acta 2016, 222, 361–369.
[30] Prestipino, C.; Regli, L.; Vitillo, J. G.; Bonino, F.; Damin, A.; Lamberti, C.; Zecchina, A.; Solari, P. L.; Kongshaug, K. O.; Bordiga, S. Local structure of framework Cu(II) in HKUST-1 metallorganic framework: spectroscopic characterization upon activation and interaction with adsorbates. Chem. Mat. 2006, 18, 1337–1346.
[31] Chowdhury, P.; Bikkina, C.; Meister, D.; Dreisbach, F.; Gumma, S. Comparison of adsorption isotherms on Cu-BTC metal organic frameworks synthesized from different routes. Micropor. Mesopor. Mat. 2009, 117, 406–413.
[32] Tian, T.; Zeng, Z.; Vulpe, D.; Casco, M. E.; Divitini, G.; Midgley, P. A.; Silvestre-Albero, J.; Tan, J. C.; Moghadam, P. Z. and Fairen-Jimenez, D. A sol-gel monolithic metal-organic framework with enhanced methane uptake. Nat. Mat. 2018, 17, 174–179.
[33] Peng, Y.; Krungleviciute, V.; Eryazici, I.; Hupp, J. T.; Farha, O. K.; Yildirim, T. Methane storage in metal-organic frameworks: current records, surprise findings, and challenges. J. Am. Chem. Soc. 2013, 135, 11887–11894.
[34] Todaro, M.; Buscarino, G.; Sciortino, L.; Alessi, A.; Messina, F.; Taddei, M.; Ranocchiari, M.; Cannas, M.; Gelardi, F. M. Decomposition process of carboxylate MOF HKUST-1 unveiled at the atomic scale level. J. Phys. Chem. C 2016, 120, 12879–12889.
[35] Todaro, M.; Alessi, A.; Sciortino, L.; Agnello, S.; Cannas, M.; Gelardi, F. M.; Buscarino, G. Investigation by Raman spectroscopy of the decomposition process of HKUST-1 upon exposure to air. J. Spectrosc. 2016.
[36] Todaro, M.; Sciortino, L.; Gelardi, F. M. and Buscarino, G. Determination of Geometry Arrangement of Copper Ions in HKUST-1 by XAFS during a Prolonged Exposure to Air. J. Phys. Chem. C 2017, 121, 24853–24860.
[37] Decoste, J. B.; Peterson, G. W.; Smith, M. W.; Stone, C. A.; Willis, C. R. Enhanced stability of Cu-BTC MOF via perfluorohexane plas-ma-enhanced chemical vapor deposition. J. Am. Chem. Soc. 2012, 134, 1486–1489.
[38] Küsgens, P.; Rose, M.; Senkovska, I.; Fröde, H.; Henschel, A.; Siegle, S.; Kaskel, S. Characterization of metal-organic frameworks by water adsorption. Micropor. Mesopor. Mat. 2009, 120, 325–330.
[39] Schoenecker, P. M.; Carson, C. G.; Jasuja, H.; Flemming, C. J.; Walton, K. S. Effect of water adsorption on retention of structure and surface area of metal-organic frameworks. Ind. Eng. Chem. Res. 2012, 51, 6513–6519.
[40] DeCoste, J. B.; Peterson, G. W.; Schindler, B. J.; Killops, K. L.; Browe, M. A.; Mahle, J. J. The effect of water adsorption on the structure of the carboxylate containing metal-organic frameworks Cu-BTC, Mg-MOF-74, and UiO-66. J. Mat. Chem. A 2013, 1, 11922–11932.
[41] Tan, K.; Nijem, N.; Canepa, P.; Gong, Q.; Li, J.; Thonhauser, T.; Chabal, Y. J. Stability and hydrolyzation of metal organic frameworks with paddle-wheel SBUs upon hydration. Chem. Mat. 2012, 24, 3153–3167.
[42] Pöppl, A.; Jee, B.; Icker, M.; Hartmann, M.; Himsl, D. Untersuchungen zur chemischen Stabilität von Cu₃(btc)₂ (HKUST-1) durch N2-Adsorption, Röntgenpulverdiffraktometrie und EPR-Spektroskopie. Chem-Ing-Tech 2010, 82, 1025–1029.
[43] Jee, B. Cw and Pulsed EPR Spectroscopy of Cu (II) and V (IV) in Metal-Organic Framework Compounds: Metal Ion Coordination and Adsorbate Interactions, Ph.D. Dissertation, Universität Leipzig, Leipzig, Germany, 2013.
[44] Mazaj, M.; Čendak, T.; Buscarino, G.; Todaro, M.; Logar, N.Z. Confined crystallization of a HKUST-1 metal-organic framework within mesostructured silica with enhanced structural resistance towards water. J. Mat. Chem. A 2017, 5, 22305–22315.
[45] Gul-E-Noor, F.; Michel, D.; Krautscheid, H.; Haase, J.; Bertmer, M. Time dependent water uptake in Cu₃(btc)₂ MOF: Identification of different water adsorption states by 1H MAS NMR. Micropor. Mesopor. Mat. 2013, 180, 8–13.
[46] Castillo, J. M.; Vlugt, T. J.; Calero, S. Understanding water adsorption in Cu-BTC metal-organic frameworks. J. Phys. Chem. C 2008, 112, 15934–15939.
[47] Panella, B.; Hirscher, M.; Pütter, H.; Müller, U. Hydrogen adsorption in metal-organic frameworks: Cu-MOFs and Zn-MOFs compared. Adv. Funct. Mater. 2006, 16, 520–524.
[48] Wang, Q. M.; Shen, D.; Bülow, M.; Lau, M. L.; Deng, S.; Fitch, F. R.; Lemcoff, N. O.; Semanscin, J. Metallo-organic molecular sieve for gas separation and purification. Micropor. Mesopor. Mater. 2002, 55, 217–230.
[49] Schlichte, K.; Kratzke, T.; Kaskel, S. Improved synthesis, thermal stability and catalytic properties of the metal-organic framework compound Cu₃(BTC)₂. Micropor. Mesopor. Mater. 2004, 73, 81–88.
[50] Al-Janabi, N.; Hill, P.; Torrente-Murciano, L.; Garforth, A.; Gorgojo, P.; Siperstein, F.; Fan, X. Mapping the Cu-BTC metal-organic framework HKUST-1 stability envelope in the presence of water vapour for CO₂ adsorption from flue gases Chem. Eng. J. 2015, 281, 669–677.
[51] Kim, H. K.; Yun, W. S.; Kim, M. B.; Kim, J. Y.; Bae, Y. S.; Lee, J.; Jeong, N. C. A chemical route to activation of open metal sites in the copper-based metal-organic framework materials HKUST-1 and Cu-MOF-2. J. Am. Chem. Soc. 2015, 137, 10009–10015.
[52] Grajciar, L.; Bludsky, O.; Nachtigall, P. Water adsorption on coordinatively unsaturated sites in CuBTC MOF. J. Phys. Chem. Lett. 2010, 1, 3354–3359.
[53] Toda, J.; Fischer, M.; Jorge, M.; Gomes, J. R. Water adsorption on a copper formate paddlewheel model of CuBTC: A comparative MP2 and DFT study. Chem. Phys. Lett. 2013, 587, 7–13.
[54] Xue, W.; Zhang, Z.; Huang, H.; Zhong, C.; Mei, D. Theoretical Insight into the Initial Hydrolytic Breakdown of HKUST-1. J. Phys. Chem. C 2019, 124, 1991–2001. [55] Terracina, A.; Todaro, M.; Mazaj, M.; Agnello, S.; Gelardi, F. M. and Buscarino, G. Unveiled the Source of the Structural Instability of HKUST-1 Powders upon Mechanical Compaction: Definition of a Fully Preserving Tableting Method. J. Phys. Chem. C 2018, 123, 1730–1741. [56] Giovine, R.; Pourpoint, F.; Duval, S.; Lafon, O.; Amoureux, J. P.; Loiseau, T.; Volkringer, C. The Surprising Stability of Cu3(btc)2 Metal-Organic Framework under Steam Flow at High Temperature. Cryst. Growth Des. 2018, 18, 6681–6693. [57] Gul-E-Noor, F.; Jee, B.; Pöppl, A.; Hartmann, M.; Himsl, D.; Bertmer, M. Effects of varying water adsorption on a Cu3(BTC)2 metal-organic framework (MOF) as studied by 1H and 13C solid-state NMR spectroscopy. Phys. Chem. Chem. Phys. 2011, 13, 7783–7788. [58] St. Petkov, P.; Vayssilov, G. N.; Liu, J.; Shekhah, O.; Wang, Y.; Wöll, C.; Heine, T. Defects in MOFs: a thorough characterization. ChemPhysChem 2012, 13, 2025–2029. [59] Terracina, A.; McHugh, L. N.; Todaro, M.; Agnello, S.; Wheatley, P. S.; Gelardi, F. M.; Morris, R. E.; Buscarino, G. Multitechnique Analysis of the Hydration in Three Different Copper Paddle-Wheel Metal-Organic Frameworks. J. Phys. Chem. C 2019, 123, 28219–28232. [60] Wang, T.; Zhu, H.; Zeng, Q. and Liu, D. Strategies for Overcoming Defects of HKUST-1 and Its Relevant Applications. Adv. Mater. Interfaces 2019, 6, 1900423. [61] Safy, M. E.; Amin, M.; Haikal, R. R.; Elshazly, B.; Wang, J.; Wang, Y.; Wöll, C.; Alkordi, M. H. Probing the Water Stability Limits and Degradation Pathways of Metal-Organic Frameworks (MOFs). Chem.-Eur. J. 2020. [62] Pöppl, A.; Kunz, S.; Himsl, D.; Hartmann, M. CW and Pulsed ESR Spectroscopy of Cupric Ions in the Metal-Organic Framework Compound Cu3(BTC)2. J. Phys. Chem. C 2008, 112, 2678–2684. [63] Carné‐Sánchez, A.; Stylianou, K. C.; Carbonell, C.; Naderi, M.; Imaz, I. and Maspoch, D. Protecting Metal-Organic Framework Crystals from Hydrolytic Degradation by Spray-Dry Encapsulating Them into Polystyrene Microspheres. Adv. Mater. 2015, 27, 869–873. [64] Lin, Z.; Lv, Z.; Zhou, X.; Xiao, H.; Wu, J.; Li, Z. Postsynthetic strategy to prepare ACN@Cu-BTCs with enhanced water vapor stability and CO2/CH4 separation selectivity. Ind. Eng. Chem. Res. 2018, 57, 3765–3772. [65] Müller, K.; Vankova, N.; Schöttner, L.; Heine, T. and Heinke, L. Dissolving uptake-hindering surface defects in metal-organic frameworks. Chem. Sci. 2019, 10, 153–160. [66] Majano, G.; Martin, O.; Hammes, M.; Smeets, S.; Baerlocher, C. and Pérez‐Ramírez, J. Solvent–Mediated Reconstruction of the Metal-Organic Framework HKUST-1 (Cu3(BTC)2). Adv. Funct. Mater. 2014, 24, 3855–3865. [67] Sun, X.; Li, H.; Li, Y.; Xu, F.; Xiao, J.; Xia, Q.; Li, Y.; Li, Z. A novel mechanochemical method for reconstructing the moisture-degraded HKUST-1. Chem. Commun. 2015, 51, 10835–10838. [68] Das, S. K.; Chatterjee, S.; Bhunia, S.; Mondal, A.; Mitra, P.; Kumari, V.; Pradhan, A. and Bhaumik, A. A new strongly paramagnetic ce-rium-containing microporous MOF for CO2 fixation under ambient conditions. Dalton Trans. 2017, 46, 13783–13792. [69] Gumilar, G.; Kaneti, Y. V.; Henzie, J.; Chatterjee, S.; Na, J.; Yuliarto, B.; Nugraha, N.; Patah, A.; Bhaumik, A. and Yamauchi, Y. General synthesis of hierarchical sheet/plate-like M-BDC (M = Cu, Mn, Ni, and Zr) metal-organic frameworks for electrochemical non-enzymatic glucose sensing. Chem. Sci. 2020 11, 3644–3655.