Naphthalene-based microporous polyimides: Adsorption behavior of CO 2 and toxic organic vapors and their separation from other gases

Journal of Physical Chemistry C

Volumn 117, Issue 46, 2013, Pages 24428-24437

  Li, Guiyang ^a   Wang, Zhonggang ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CRITICAL TEMPERATURES; ELECTRON DELOCALIZATION; HIGH ADSORPTION CAPACITY; HYDROPHOBIC/HYDROPHILIC; MICROPOROUS ORGANIC POLYMERS; NARROW PORE SIZE DISTRIBUTIONS; ONE-POT POLYCONDENSATION; POROUS CHARACTERISTICS;

BENZENE; CARBON DIOXIDE; METHANE; MICROPOROSITY; POLYIMIDES; SEPARATION; VAPORS;

NAPHTHALENE;

EID: 84888633209     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp408502t     Document Type: Article

References (65)

1. McKeown, N. B.; Budd, P. M. Polymers of Intrinsic Microporosity (PIMs): Organic Materials for Membrane Separations, Heterogeneous Catalysis and Hydrogen Storage Chem. Soc. Rev. 2006, 35, 675-683
2. Dawson, R.; Cooper, A. I.; Adams, D. J. Nanoporous Organic Polymer Networks Prog. Polym. Sci. 2012, 37, 530-563
3. Wu, D.; Xu, F.; Sun, B.; Fu, R.; He, H.; Matyjaszewski, K. Design and Preparation of Porous Polymers Chem. Rev. 2012, 112, 3959-4015
4. Ding, S. Y.; Wang, W. Covalent Organic Frameworks (COFs): from Design to Applications Chem. Soc. Rev. 2013, 42, 548-568
5. Zou, X.; Ren, H.; Zhu, G. Topology-Directed Design of Porous Organic Frameworks and Their Advanced Applications Chem. Commun. 2013, 49, 3925-3936
6. 2 Gas and Organic Vapors Macromolecules 2013, 46, 3058-3066
7. 2 Capturing Materials Adv. Mater. 2012, 46, 3058-3066
8. Chen, Q.; Luo, M.; Hammershøj, P.; Zhou, D.; Han, Y.; Laursen, B. W.; Yan, C. G.; Han, B. H. Microporous Polycarbazole with High Specific Surface Area for Gas Storage and Separation J. Am. Chem. Soc. 2012, 134, 6014-6087
9. 2 Adsorption at Low Pressure J. Am. Chem. Soc. 2011, 133, 18126-18129
10. Dawson, R.; Stöckel, E.; Holst, J. R.; Adams, D. J.; Cooper, A. I. Microporous Organic Polymers for Carbon Dioxide Capture Energy Environ. Sci. 2011, 4, 4239-4245
11. Wang, Z. G.; Zhang, B. F.; Yu, H.; Sun, L. X.; Jiao, C. L.; Liu, W. S. Microporous Polyimide Networks with Large Surface Areas and Their Hydrogen Storage Properties Chem. Commun. 2010, 46, 7730-7732
12. Preis, E.; Widling, C.; Brunklaus, G.; Schmidt, J.; Thomas, A.; Scherf, U. Microporous Polymer Networks (MPNs) Made in Metal-Free Regimes: Systematic Optimization of a Synthetic Protocol toward N-Arylcarbazole-Based MPNs ACS Macro Lett. 2013, 2, 380-383
13. Ghanem, B. S.; Msayib, K. J.; McKeown, N. B.; Harris, K. D. M.; Pan, Z.; Budd, P. M.; Butler, A.; Selbie, J.; Book, D.; Walton, A. A Triptycene-Based Polymer of Intrinsic Microposity That Displays Enhanced Surface Area and Hydrogen Adsorption Chem. Commun. 2007, 43, 67-69
14. Germain, J.; Svec, F.; Fréchet, J. M. J. Preparation of Size-Selective Nanoporous Polymer Networks of Aromatic Rings: Potential Adsorbents for Hydrogen Storage Chem. Mater. 2008, 20, 7069-7076
15. Tan, D. Z.; Fan, W. J.; Xiong, W. N.; Sun, H. X.; Li, A.; Deng, W. Q.; Meng, C. G. Study on Adsorption Performance of Conjugated Microporous Polymers for Hydrogen and Organic Solvents: The Role of Pore Volume Eur. Polym. J. 2012, 48, 705-711
16. Palkovits, R.; Antonietti, M.; Kuhn, P.; Thomas, A.; Schüth, F. Solid Catalysts for the Selective Low-Temperature Oxidation of Methane to Methanol Angew. Chem., Int. Ed. 2009, 48, 6909-6912
17. Chen, L.; Yang, Y.; Jiang, D. L. CMPs as Scaffolds for Constructing Porous Catalytic Frameworks: A Built-in Heterogeneous Catalyst with High Activity and Selectivity Based on Nanoporous Metalloporphyrin Polymers J. Am. Chem. Soc. 2010, 132, 9138-9143
18. Carta, M.; Malpass-Evans, R.; Croad, M.; Rogan, Y.; Jansen, J. C.; Bernardo, P.; Bazzarelli, F.; McKeown, N. B. An Efficient Polymer Molecular Sieve for Membrane Gas Separations Science 2013, 339, 303-307
19. Qian, H.; Zheng, J.; Zhang, S. Preparation of Microporous Polyamide Networks for Carbon Dioxide Capture and Nanofiltration Polymer 2013, 54, 557-564
20. Du, N.; Dal-Cin, M. M.; Robertson, G. P.; Guiver, M. D. Decarboxylation-Induced Cross-Linking of Polymers of Intrinsic Microporosity (PIMs) for Membrane Gas Separation Macromolecules 2013, 45, 5134-5139
21. Zhang, B. F.; Wang, Z. G. Microporous Thermosetting Film Constructed from Hyperbranched Polyarylate Precursors Containing Rigid Tetrahedral Core: Synthesis, Characterization, and Properties Chem. Mater. 2010, 22, 2780-2789
22. 2 Capture Science 2009, 325, 1652-1654
23. Khan, F. I.; Ghoshal, A. K. Removal of Volatile Organic Compounds from Polluted Air J. Loss Prevent. Process Ind. 2000, 13, 527-545
24. Ramos, M. E.; Bonelli, P. R.; Cukierman, A. L.; Ribeiro Carrott, M. M. L.; Carrott, P. J. M. Adsorption of Volatile Organic Compounds onto Activated Carbon Cloths Derived from A Novel Regenerated Cellulosic Precursor J. Hazard. Mater. 2010, 177, 175-182
25. Shim, W. G.; Moon, H.; Lee, J. W. Performance Evaluation of Wash-Coated MCM-48 Monolith for Adsorption of Volatile Organic Compounds and Water Vapors Microporous Mesoporous Mater. 2006, 94, 15-28
26. Shen, C. J.; Bao, Y. J.; Wang, Z. G. Tetraphenyladamantane-Based Microporous Polyimide for Adsorption of Carbon Dioxide, Hydrogen, Organic and Water Vapors Chem. Commun. 2013, 49, 3321-3323
27. Wang, X. S.; Liu, J.; Bonefont, J. M.; Yuan, D. Q.; Thallapally, P. K.; Ma, S. Q. A Porous Covalent Porphyrin Framework with Exceptional Uptake Capacity of Saturated Hydrocarbons for Oil Spill Cleanup Chem. Commun. 2013, 49, 1533-1535
28. Luo, J.; Xu, H.; Liu, Y.; Zhao, Y.; Daemen, L. L.; Brown, C.; Timofeeva, T. V.; Ma, S.; Zhou, H. C. Hydrogen Adsorption in A Highly Stable Porous Rare-Earth Metal-Organic Framework: Sorption Properties and Neutron Diffraction Studies J. Am. Chem. Soc. 2008, 130, 9626-9627
29. Rzepka, M.; Lamp, P.; de la Casa-Lillo, M. A. Physisorption of Hydrogen on Microporous Carbon and Carbon Nanotubes J. Phys. Chem. B 1998, 102, 10894-10898
30. Dou, B.; Li, J.; Hua, Q.; Ma, C.; He, C.; Li, P.; Hu, Q.; Hao, Z.; Qiao, S. Hydrophobic Micro/Mesoporous Silica Spheres Assembled from Zeolite Precursors in Acidic Media for Aromatics Adsorption Microporous Mesoporous Mater. 2010, 133, 115-123
31. Farha, O. K.; Bae, Y. S.; Hauser, B. G.; Spokoyny, A. M.; Snurr, R. Q.; Mirkin, C. A.; Hupp, J. T. Chemical Reduction of A Diimide Based Porous Polymer for Selective Uptake of Carbon Dioxide Versus Methane Chem. Commun. 2010, 46, 1056-1058
32. Wang, Z. G.; Zhang, B. F.; Yu, H.; Li, G. Y.; Bao, Y. J. Synthetic Control of Network Topology and Pore Structure in Microporous Polyimides Based on Triangular Triphenylbenzene and Triphenylamine Units Soft Matter 2011, 7, 5723-5730
33. Yang, Y. Q.; Zhang, Q.; Zhang, Z. G.; Zhnag, S. B. Functional Microporous Polyimides Based on Sulfonated Binaphthalene Dianhydride for Uptake and Separation of Carbon Dioxide and Vapors J. Mater. Chem. A 2013, 1, 10368-10374
34. Miller, R. D.; Burland, D. M.; Jurich, M.; Lee, V. Y.; Moylan, C. R.; Thackara, J. I.; Twieg, R. J.; Verbiest, T.; Volksen, W. Donor-Embedded Nonlinear-Optical Side-Chain Polyimides Containing No Flexible Tether-Materials of Exceptional Thermal-Stability for Electrooptic Applications Macromolecules 1995, 28, 4970-4974
35. Yeh, R. M.; Xu, J.; Seeber, G.; Raymond, K. N. Large M4L4 (M = Al(III), Ga(III), In(III), Ti(IV)) Tetrahedral Coordination Cages: An Extension of Symmetry-Based Design Inorg. Chem. 2005, 44, 6228-6239
36. Dawson, R.; Laybourn, A.; Clowes, R.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Functionalized Conjugated Microporous Polymers Macromolecules 2009, 42, 8809-8816
37. Weber, J.; Thomas, A. Toward Stable Interfaces in Conjugated Polymers: Microporous Poly(p-Phenylene) and Poly(Phenyleneethynylene) Based on a Spirobifluorene Building Block J. Am. Chem. Soc. 2008, 130, 6334-6335
38. Lillo-Ródenas, M. A.; Cazorla-Amorós, D.; Linares-Solano, A. Benzene and Toluene Adsorption at Low Concentration on Activated Carbon Fibres Adsorption 2011, 17, 473-481
39. Zhang, J. P.; Chen, X. M. Exceptional Framework Flexibility and Sorption Behavior of A Multifunctional Porous Cuprous Triazolate Framework J. Am. Chem. Soc. 2008, 130, 6010-6017
40. Yu, H.; Shen, C. J.; Tian, M. Z.; Qu, J.; Wang, Z. G. Microporous Cyanate Resins: Synthesis, Porous Structure, and Correlations with Gas and Vapor Adsorptions Macromolecules 2012, 45, 5140-5150
41. Yu, H.; Shen, C. J.; Wang, Z. G. Micro- and Mesoporous Polycyanurate Networks Based on Triangular Units ChemPlusChem 2013, 78, 498-505
42. Rose, M.; Bohlmann, W.; Sabo, M.; Kaskel, S. Element-Organic Frameworks with High Permanent Porosity Chem. Commun. 2008, 2462-2464
43. Banerjee, R.; Furukawa, H.; Britt, D.; Knobler, C.; O'Keeffe, M.; Yaghi, O. M. Control of Pore Size and Functionality in Isoreticular Zeolitic Imidazolate Frameworks and their Carbon Dioxide Selective Capture Properties J. Am. Chem..Soc. 2009, 131, 3875-3877
44. 2 Uptake in a Cobalt Adeninate Metal-Organic Framework Exhibiting Pyrimidine- and Amino-Decorated Pores J. Am. Chem. Soc. 2010, 132, 38-39
45. 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
46. Ren, S. J.; Dawson, R.; Laybourn, A.; Jiang, J. X.; Khimyak, Y.; Adams, D. J.; Cooper, A. I. Functional Conjugated Microporous Polymers: from 1,3,5-Benzene to 1,3,5-Triazine Polym. Chem. 2012, 3, 928-934
47. Ben, T.; Pei, C. Y.; Zhang, D. L.; Xu, J.; Deng, F.; Jing, X. F.; Qiu, S. L. Gas Storage in Porous Aromatic Frameworks (PAFs) Energy Environ. Sci. 2011, 4, 3991-3999
48. Krungleviciute, V.; Heroux, L.; Migone, A. D. Isosteric Heat of Argon Adsorbed on Single-Walled Carbon Nanotubes Prepared by Laser Ablation J. Phys. Chem. B 2005, 109, 9317-9320
49. Cole, J. H.; Everett, D. H.; Marshall, C. T.; Paniego, A. R.; Powl, J. C.; Rodriguez-Reinoso, F. Thermodynamics of High Temperature Adsorption of Some Permanent Gases by Porous Carbons J. Chem. Soc., Faraday Trans. 1974, 70, 2154-2169
50. 2 Capture J. Mater. Chem. 2011, 21, 5475-5483
51. 2 Storage Chem. Mater. 2011, 23, 1650-1653
52. 2 Uptake and Selectivity by Triptycene-Derived Benzimidazole-Linked Polymers Chem. Commun. 2012, 48, 1141-1143
53. 2 Gas, Organic and Water Vapors Polym. Chem. 2013, 4, 961-968
54. 4 Storage Polym. Chem. 2011, 2, 2775-2777
55. 4 Gas Uptake by a Halogen-Decorated Borazine-Linked Polymer J. Mater. Chem. 2012, 22, 13524-13528
56. 2 Binding in a Water-Stable, Triazolate-Bridged Metal-Organic Framework Functionalized with Ethylenediamine J. Am. Chem. Soc. 2009, 131, 8784-8786
57. 2 Reduction Angew. Chem., Int. Ed. 2012, 51, 3364-3367
58. Lewinski, J.; Kaczorowski, Y.; Prochowicz, D.; Lipinska, T.; Justyniak, I.; Kaszkur, Z.; Lipkowski, J. Cinchona Alkaloid-Metal Complexes: Noncovalent Porous Materials with Unique Gas Separation Properties Angew. Chem., Int. Ed. 2010, 49, 7035-7039
59. 2 Uptake in a Cobalt Adeninate Metal-Organic Framework Exhibiting Pyrimidine- and Amino-Decorated Pores J. Am. Chem. Soc. 2010, 132, 38-39
60. Li, J. R.; Kuppler, R. J.; Zhou, H. C. Selective Gas Adsorption and Separation in Metal-Organic Frameworks Chem. Soc. Rev. 2009, 38, 1477-1504
61. Panda, T.; Pachfule, P.; Chen, Y.; Jiang, J.; Banerjee, R. Amino Functionalized Zeolitic Tetrazolate Framework (ZTF) with High Capacity for Storage of Carbon Dioxide Chem. Commun. 2011, 47, 2011-2013
62. Arstad, B.; Fjellvag, H.; Kongshaug, K. O.; Swang, O.; Blom, R. Amine Functionalised Metal Organic Frameworks (Mofs) as Adsorbents for Carbon Dioxide Adsorption 2008, 14, 755-762
63. Breck, D. W. Zeolite Molecular Sieves; John Wiley & Sons: New York, 1994.
64. Jeans, J. An Introduction to the Kinetic Theory of Gases; Cambridge University Press: London, 1982.
65. Shah, V. M.; Hardy, B. J.; Stern, S. A. Solubility Of Carbon-Dioxide, Methane, and Propane in Silicone Polymers-Effect of Polymer Side-Chains J. Polym. Sci., Polym. Phys. Ed. 1986, 24, 2033-2047