Tunable Water and CO2 Sorption Properties in Isostructural Azine-Based Covalent Organic Frameworks through Polarity Engineering

Chemistry of Materials

Volumn 27, Issue 23, 2015, Pages 7874-7881

  Stegbauer, Linus ^a,b,c   Hahn, Maximilian W ^d   Jentys, Andreas ^d   Savasci, Gökcen ^b   Ochsenfeld, Christian ^b   Lercher, Johannes A ^d   Lotsch, Bettina V ^a,b,c  

^a MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

^c NANOSYSTEMS INITIATIVE MUNICH NIM   (Germany)

^d TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC CHEMISTRY; PORE PRESSURE; QUAY WALLS; RESERVOIRS (WATER); SORPTION; WALLS (STRUCTURAL PARTITIONS); WATER CONSERVATION; ZINC; ZINC COMPOUNDS;

ATMOSPHERIC WATER; CHEMICAL NATURE; COVALENT ORGANIC FRAMEWORKS; KINETIC CONDITIONS; SORPTION CHARACTERISTICS; SORPTION ISOTHERMS; SORPTION PROPERTIES; WATER VAPOR UPTAKE;

CARBON DIOXIDE;

EID: 84948178149     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.5b02151     Document Type: Article

References (57)

1. Stocker, T.; Alexander, L.; Allen, M. Climate Change 2013: The Physical Science Basis; Working Group I Contribution to the Fifth Assessment Report of the Intergovernmental Panel on Climate Change; WMO IPCC: Geneva, 2014.
2. Boot-Handford, M. E.; Abanades, J. C.; Anthony, E. J.; Blunt, M. J.; Brandani, S.; Mac Dowell, N.; Fernandez, J. R.; Ferrari, M.-C.; Gross, R.; Hallett, J. P.; Haszeldine, R.; Stuart; Heptonstall, P.; Lyngfelt, A.; Makuch, Z.; Mangano, E.; Porter; Richard, T. J.; Pourkashanian, M.; Rochelle, G. T.; Shah, N.; Yao, J. G.; Fennell, P. S. Carbon capture and storage update Energy Environ. Sci. 2014, 7, 130-189 10.1039/C3EE42350F
3. D'Alessandro, D. M.; Smit, B.; Long, J. R. Carbon Dioxide Capture: Prospects for New Materials Angew. Chem., Int. Ed. 2010, 49, 6058-6082 10.1002/anie.201000431
4. International Energy Agency. Carbon Capture and Storage: Legal and Regulatory Review: Edition 4. http://www.iea.org/publications/insights/insightpublications/CCSReview-4thEd-FINAL.pdf (accessed April 24, 2015).
5. Furukawa, H.; Yaghi, O. M. Storage of Hydrogen, Methane, and Carbon Dioxide in Highly Porous Covalent Organic Frameworks for Clean Energy Applications J. Am. Chem. Soc. 2009, 131, 8875-8883 10.1021/ja9015765
6. Bhunia, A.; Vasylyeva, V.; Janiak, C. From a supramolecular tetranitrile to a porous covalent triazine-based framework with high gas uptake capacities Chem. Commun. (Cambridge, U. K.) 2013, 49, 3961-3963 10.1039/c3cc41382a
7. Bhunia, A.; Boldog, I.; Möller, A.; Janiak, C. Highly stable nanoporous covalent triazine-based frameworks with an adamantane core for carbon dioxide sorption and separation J. Mater. Chem. A 2013, 1, 14990-14999 10.1039/c3ta13407e
8. European Environment Agency. Household energy consumption by end-use in the EU-27. http://www.eea.europa.eu/data-and-maps/figures/households-energy-consumption-by-end-uses-4 (accessed April 24, 2015).
9. Ng, E.-P.; Mintova, S. Nanoporous materials with enhanced hydrophilicity and high water sorption capacity Microporous Mesoporous Mater. 2008, 114, 1-26 10.1016/j.micromeso.2007.12.022
10. NASA. Earth Fact Sheet. http://nssdc.gsfc.nasa.gov/planetary/factsheet/earthfact.html (accessed April 24, 2015).
11. Jeremias, F.; Lozan, V.; Henninger, S. K.; Janiak, C. Programming MOFs for water sorption: amino-functionalized MIL-125 and UiO-66 for heat transformation and heat storage applications Dalton Trans. 2013, 42, 15967-15973 10.1039/c3dt51471d
12. Küsgens, P.; Rose, M.; Senkovska, I.; Fröde, H.; Henschel, A.; Siegle, S.; Kaskel, S. Characterization of metal-organic frameworks by water adsorption Microporous Mesoporous Mater. 2009, 120, 325-330 10.1016/j.micromeso.2008.11.020
13. László, K.; Czakkel, O.; Dobos, G.; Lodewyckx, P.; Rochas, C.; Geissler, E. Water vapour adsorption in highly porous carbons as seen by small and wide angle X-ray scattering Carbon 2010, 48, 1038-1048 10.1016/j.carbon.2009.11.023
14. Brennan, J. K.; Bandosz, T. J.; Thomson, K. T.; Gubbins, K. E. Water in porous carbons Colloids Surf., A 2001, 187-188, 539-568 10.1016/S0927-7757(01)00644-6
15. Burtch, N. C.; Jasuja, H.; Walton, K. S. Water Stability and Adsorption in Metal-Organic Frameworks Chem. Rev. (Washington, DC, U. S.) 2014, 114, 10575-10612 10.1021/cr5002589
16. Biswal, B. P.; Chandra, S.; Kandambeth, S.; Lukose, B.; Heine, T.; Banerjee, R. Mechanochemical Synthesis of Chemically Stable Isoreticular Covalent Organic Frameworks J. Am. Chem. Soc. 2013, 135, 5328-5331 10.1021/ja4017842
17. Shinde, D. B.; Kandambeth, S.; Pachfule, P.; Kumar, R. R.; Banerjee, R. Bifunctional covalent organic frameworks with two dimensional organocatalytic micropores Chem. Commun. 2015, 51, 310-313 10.1039/C4CC07104B
18. Kandambeth, S.; Venkatesh, V.; Shinde, D. B.; Kumari, S.; Halder, A.; Verma, S.; Banerjee, R. Self-templated chemically stable hollow spherical covalent organic framework Nat. Commun. 2015, 6, 6786 10.1038/ncomms7786
19. Dalapati, S.; Jin, S.; Gao, J.; Xu, Y.; Nagai, A.; Jiang, D. An Azine-Linked Covalent Organic Framework J. Am. Chem. Soc. 2013, 135, 17310-17313 10.1021/ja4103293
20. Chandra, S.; Kandambeth, S.; Biswal, B. P.; Lukose, B.; Kunjir, S. M.; Chaudhary, M.; Babarao, R.; Heine, T.; Banerjee, R. Chemically Stable Multilayered Covalent Organic Nanosheets from Covalent Organic Frameworks via Mechanical Delamination J. Am. Chem. Soc. 2013, 135, 17853-17861 10.1021/ja408121p
21. Kandambeth, S.; Mallick, A.; Lukose, B.; Mane, M. V.; Heine, T.; Banerjee, R. Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route J. Am. Chem. Soc. 2012, 134, 19524-19527 10.1021/ja308278w
22. Gao, F.; Ding, Z.; Meng, S. Three-dimensional metal-intercalated covalent organic frameworks for near-ambient energy storage Sci. Rep. 2013, 3, 1882 10.1038/srep01882
23. Guo, J.-H.; Zhang, H.; Gong, M.; Cheng, X.-L. Ca2+- and Mg2+-doped covalent organic frameworks exhibiting high hydrogen and acetylene storage Struct. Chem. 2013, 24, 691-703 10.1007/s11224-012-0120-1
24. Guo, J.-H.; Zhang, H.; Miyamoto, Y. New Li-doped fullerene-intercalated phthalocyanine covalent organic frameworks designed for hydrogen storage Phys. Chem. Chem. Phys. 2013, 15, 8199-8207 10.1039/c3cp50492a
25. Guo, J.-H.; Zhang, H.; Liu, Z.-P.; Cheng, X.-L. Multiscale Study of Hydrogen Adsorption, Diffusion, and Desorption on Li-Doped Phthalocyanine Covalent Organic Frameworks: The Journal of Physical Chemistry C J. Phys. Chem. C 2012, 116, 15908-15917 10.1021/jp305949q
26. Feng, X.; Liu, L.; Honsho, Y.; Saeki, A.; Seki, S.; Irle, S.; Dong, Y.; Nagai, A.; Jiang, D. High-Rate Charge-Carrier Transport in Porphyrin Covalent Organic Frameworks: Switching from Hole to Electron to Ambipolar Conduction Angew. Chem., Int. Ed. 2012, 51, 2618-2622 10.1002/anie.201106203
27. Bae, Y.-S.; Hauser, B. G.; Farha, O. K.; Hupp, J. T.; Snurr, R. Q. Enhancement of CO2/CH4 selectivity in metal-organic frameworks containing lithium cations Microporous Mesoporous Mater. 2011, 141, 231-235 10.1016/j.micromeso.2010.10.048
28. Bosch, M.; Zhang, M.; Feng, D.; Yuan, S.; Wang, X.; Chen, Y.-P.; Zhou, H.-C. Lithium inclusion in indium metal-organic frameworks showing increased surface area and hydrogen adsorption APL Mater. 2014, 2, 124103 10.1063/1.4897475
29. Kubo, M.; Shimojima, A.; Okubo, T. Effect of Lithium Doping into MIL-53(Al) through Thermal Decomposition of Anion Species on Hydrogen Adsorption J. Phys. Chem. C 2012, 116, 10260-10265 10.1021/jp211029y
30. Xiang, Z.; Hu, Z.; Cao, D.; Yang, W.; Lu, J.; Han, B.; Wang, W. Metal-Organic Frameworks with Incorporated Carbon Nanotubes: Improving Carbon Dioxide and Methane Storage Capacities by Lithium Doping Angew. Chem., Int. Ed. 2011, 50, 491-494 10.1002/anie.201004537
31. Li, Z.; Feng, X.; Zou, Y.; Zhang, Y.; Xia, H.; Liu, X.; Mu, Y. A 2D azine-linked covalent organic framework for gas storage applications Chem. Commun. (Cambridge, U. K.) 2014, 50, 13825-13828 10.1039/C4CC05665E
32. Li, Z.; Zhi, Y.; Feng, X.; Ding, X.; Zou, Y.; Liu, X.; Mu, Y. An Azine-Linked Covalent Organic Framework: Synthesis, Characterization and Efficient Gas Storage Chem.-Eur. J. 2015, 21, 12079-12084 10.1002/chem.201501206
33. Makal, A.; Schilf, W.; Kamieński, B.; Szady-Chelmieniecka, A.; Grech, E.; Woźniak, K. Hydrogen bonding in Schiff bases - NMR, structural and experimental charge density studies Dalton Trans. 2011, 40, 421-430 10.1039/C0DT00298D
34. Feldscher, B.; Stammler, A.; Bögge, H.; Glaser, T. Aromatic versus heteroradialene character in extended thiophloroglucinol ligands and their trinuclear nickel(II) complexes Chem.-Asian J. 2014, 9, 2205-2218 10.1002/asia.201402272
35. Kussmann, J.; Ochsenfeld, C. Pre-selective screening for matrix elements in linear-scaling exact exchange calculations J. Chem. Phys. 2013, 138, 134114 10.1063/1.4796441
36. Kussmann, J.; Ochsenfeld, C. Preselective Screening for Linear-Scaling Exact Exchange-Gradient Calculations for Graphics Processing Units and General Strong-Scaling Massively Parallel Calculations J. Chem. Theory Comput. 2015, 11, 918-922 10.1021/ct501189u
37. Hug, S.; Mesch, M. B.; Oh, H.; Popp, N.; Hirscher, M.; Senker, J.; Lotsch, B. V. A fluorene based covalent triazine framework with high CO2 and H2 capture and storage capacities J. Mater. Chem. A 2014, 2, 5928-5936 10.1039/C3TA15417C
38. Hao, G.-P.; Mondin, G.; Zheng, Z.; Biemelt, T.; Klosz, S.; Schubel, R.; Eychmüller, A.; Kaskel, S. Unusual Ultra-Hydrophilic, Porous Carbon Cuboids for Atmospheric-Water Capture Angew. Chem., Int. Ed. 2015, 54, 1941-1945 10.1002/anie.201409439
39. Akiyama, G.; Matsuda, R.; Kitagawa, S. Highly Porous and Stable Coordination Polymers as Water Sorption Materials Chem. Lett. 2010, 39, 360-361 10.1246/cl.2010.360
40. Dubinin, M. M. The Potential Theory of Adsorption of Gases and Vapors for Adsorbents with Energetically Nonuniform Surfaces Chem. Rev. (Washington, DC, U. S.) 1960, 60, 235-241 10.1021/cr60204a006
41. Thommes, M.; Morell, J.; Cychosz, K. A.; Fröba, M. Combining Nitrogen, Argon, and Water Adsorption for Advanced Characterization of Ordered Mesoporous Carbons (CMKs) and Periodic Mesoporous Organosilicas (PMOs) Langmuir 2013, 29, 14893-14902 10.1021/la402832b
42. Furukawa, H.; Gándara, F.; Zhang, Y.-B.; Jiang, J.; Queen, W. L.; Hudson, M. R.; Yaghi, O. M. Water Adsorption in Porous Metal-Organic Frameworks and Related Materials J. Am. Chem. Soc. 2014, 136, 4369-4381 10.1021/ja500330a
43. Seo, Y.-K.; Yoon, J. W.; Lee, J. S.; Hwang, Y. K.; Jun, C.-H.; Chang, J.-S.; Wuttke, S.; Bazin, P.; Vimont, A.; Daturi, M.; Bourrelly, S.; Llewellyn, P. L.; Horcajada, P.; Serre, C.; Férey, G. Energy-Efficient Dehumidification over Hierachically Porous Metal-Organic Frameworks as Advanced Water Adsorbents Adv. Mater. (Weinheim, Ger.) 2012, 24, 806-810 10.1002/adma.201104084
44. Lu, G. Q.; Zhao, X. S. Nanoporous Materials: Science and Engineering; Series on Chemical Engineering; Imperial College Press: London, 2004; Vol. 4.
45. Xu, D.; Xiao, P.; Zhang, J.; Li, G.; Xiao, G.; Webley, P. A.; Zhai, Y. Effects of water vapour on CO2 capture with vacuum swing adsorption using activated carbon Chem. Eng. J. (Amsterdam, Neth.) 2013, 230, 64-72 10.1016/j.cej.2013.06.080
46. Frohlich, D.; Henninger, S. K.; Janiak, C. Multicycle water vapour stability of microporous breathing MOF aluminium isophthalate CAU-10-H Dalton Trans. 2014, 43, 15300-15304 10.1039/C4DT02264E
47. Jeremias, F.; Khutia, A.; Henninger, S. K.; Janiak, C. MIL-100(Al, Fe) as water adsorbents for heat transformation purposes-a promising application J. Mater. Chem. 2012, 22, 10148-10151 10.1039/C2JM15615F
48. Henninger, S. K.; Jeremias, F.; Kummer, H.; Janiak, C. MOFs for Use in Adsorption Heat Pump Processes Eur. J. Inorg. Chem. 2012, 16, 2625-2634 10.1002/ejic.201101056
49. Khutia, A.; Rammelberg, H. U.; Schmidt, T.; Henninger, S.; Janiak, C. Water Sorption Cycle Measurements on Functionalized MIL-101Cr for Heat Transformation Application Chem. Mater. 2013, 25, 790-798 10.1021/cm304055k
50. Rabbani, M. G.; Sekizkardes, A. K.; El-Kadri, O. M.; Kaafarani, B. R.; El-Kaderi, H. M. Pyrene-directed growth of nanoporous benzimidazole-linked nanofibers and their application to selective CO2 capture and separation J. Mater. Chem. 2012, 22, 25409-25417 10.1039/c2jm34922a
51. Lu, W.; Yuan, D.; Sculley, J.; Zhao, D.; Krishna, R.; Zhou, H.-C. Sulfonate-Grafted Porous Polymer Networks for Preferential CO2 Adsorption at Low Pressure J. Am. Chem. Soc. 2011, 133, 18126-18129 10.1021/ja2087773
52. Ren, S.; Bojdys, M. J.; Dawson, R.; Laybourn, A.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Porous, Fluorescent, Covalent Triazine-Based Frameworks Via Room-Temperature and Microwave-Assisted Synthesis Adv. Mater. (Weinheim, Ger.) 2012, 24, 2357-2361 10.1002/adma.201200751
53. Lan, J.; Cao, D.; Wang, W.; Smit, B. Doping of Alkali, Alkaline-Earth, and Transition Metals in Covalent-Organic Frameworks for Enhancing CO2 Capture by First-Principles Calculations and Molecular Simulations ACS Nano 2010, 4, 4225-4237 10.1021/nn100962r
54. Zhao, Y.; Yao, K. X.; Teng, B.; Zhang, T.; Han, Y. A perfluorinated covalent triazine-based framework for highly selective and water-tolerant CO2 capture Energy Environ. Sci. 2013, 6, 3684-3692 10.1039/c3ee42548g
55. Huang, N.; Chen, X.; Krishna, R.; Jiang, D. Two-Dimensional Covalent Organic Frameworks for Carbon Dioxide Capture through Channel-Wall Functionalization Angew. Chem., Int. Ed. 2015, 54, 2986-2990 10.1002/anie.201411262
56. Kanniche, M.; Gros-Bonnivard, R.; Jaud, P.; Valle-Marcos, J.; Amann, J.-M.; Bouallou, C. Pre-combustion, post-combustion and oxy-combustion in thermal power plant for CO2 capture Appl. Therm. Eng. 2010, 30, 53-62 10.1016/j.applthermaleng.2009.05.005
57. Hahn, M. W.; Steib, M.; Jentys, A.; Lercher, J. A. Tailoring hierarchically structured SiO2 spheres for high pressure CO2 adsorption J. Mater. Chem. A 2014, 2, 13624-13634 10.1039/C4TA02145B