High capacity gas capture and selectivity properties of triazatruxene-based ultramicroporous hyper-crosslinked covalent polymer

High capacity gas capture and selectivity properties of triazatruxene-based ultramicroporous hyper-crosslinked covalent polymer

Tuning the selective sorption features of microporous organic networks is of great importance for subsequent applications in gas uptake and hiding, while it is more attractive in terms of being both time and cost effective to realize these optimizations without using functional groups in the core and linker. “Knitting” is one of the easiest and most used method to obtain a broad scope of hyper-crosslinked polymers on a large scale from aromatic structures that do not contain functional groups for polymerization. By the use of Knitting method, a hypercrosslinked covalent ultramicroporous organic polymer was obtained via stepwise process from using triazatruxene (TAT) as core -a planar indole trimer- through anhydrous $FeCl_3$ catalyzed Friedel–Crafts alkylation using dimethoxybenzene as a linker. The resulting microporous polymer, namely TATHCCP was completely identified by analytical and spectral techniques after examined for gas properties $(CO_2 , CH_4 , O_2 , CO, and H_2 ) $and selectivity $(CO_2 /N_2 , CO_2 /O_2 , for CO_2 /CO and CO_2 /CH_4 )$ up to 1 bar and increased temperatures (273 K, 296 K and 320 K). Although it has a relatively low (Brunauer–Emmett–Teller) BET specific surface area around 557 $m_2 /g,$ it was seen to have a high $CO_2$ capture capacity approaching 10% wt. at 273 K. In accordance with (ideal adsorbed solution theory) IAST computations, it was revealed that interesting selectivity features hitting up to 60 for $CO_2 /N_2 , 45 for CO_2 /O_2 , 35 for CO_2 /CO, 13 for CO_2 /CH4$ at lower temperatures revealed that the material has much better selectivity values than many HCP (hyper-crosslinked polymer) derivatives in the literature even from its most similar analog dimethoxymethane derivative TATHCP, which has a surface area of 950 $m^2 /g.$

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  • 1. Liebl MR, Senker J. Microporous functionalized triazine-based polyimides with high CO2 capture capacity. Chemistry of Materials 2013; 25: 970-980.
  • 2. Dawson R, Cooper AI, Adams DJ. Chemical functionalization strategies for carbon dioxide capture in microporous organic polymers. Polymer International 2013; 62: 345-352.
  • 3. Rabbani MG, El-Kaderi HM. Template-free synthesis of a highly porous benzimidazole-linked polymer for CO2 capture and H2 storage. Chemistry of Materials 2011; 23: 1650-1653.
  • 4. Demessence A, D’Alessandro DM, Foo ML, Long JR. Strong CO2 binding in a water-stable, triazolate-bridged metal− organic framework functionalized with ethylenediamine. Journal of the American Chemical Society 2009; 131: 8784-8786.
  • 5. Lu W, Yuan D, Sculley J, Zhao D, Krishna Ret al. Sulfonate-grafted porous polymer networks for preferential CO2 adsorption at low pressure. Journal of the American Chemical Society 2011; 133: 18126-18129.
  • 6. Kuhn P, Forget A, Su D, Thomas A, Antonietti M. From microporous regular frameworks to mesoporous materials with ultrahigh surface area: dynamic reorganization of porous polymer networks. Journal of the American Chemical Society 2008; 130: 13333-13337.
  • 7. Kuhn P, Antonietti M, Thomas A. Porous covalent triazine-based frameworks prepared by ionothermal synthesis. Angewandte Chemie International Edition 2008; 47: 3450-3453.
  • 8. Xiang Z, Cao D. Porous covalent–organic materials: synthesis, clean energy application and design. Journal of Materials Chemistry A 2013; 1: 2691-2718.
  • 9. Cooper AI. Conjugated microporous polymers. Advanced Materials 2009; 21: 1291-1295.
  • 10. Jiang JX, Su F, Trewin A, Wood CD, Campbell NLet al. Conjugated microporous poly (aryleneethynylene) networks. Angewandte Chemie International Edition 2007; 46: 8574-8578.
  • 11. Budd PM, Butler A, Selbie J, Mahmood K, McKeown NB et al. The potential of organic polymer-based hydrogen storage materials. Physical Chemistry Chemical Physics 2007; 9: 1802-1808.
  • 12. McKeown NB, Budd PM. Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage. Chemical Society Reviews 2006; 35: 675-683.
  • 13. Ben T, Ren H, Ma S, Cao D, Lan Jet al. Targeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area. Angewandte Chemie 2009; 121: 9621-9624.
  • 14. Sadak AE. A comparative gas sorption study of dicarbazole-derived microporous hyper-crosslinked polymers. Microporous and Mesoporous Materials 311: 110727.
  • 15. Sadak AE, Karakuş E, Chumakov YM, Dogan NA, Yavuz CT. Triazatruxene-based ordered porous polymer: high capacity CO2, CH4, and H2 capture, heterogeneous Suzuki–Miyaura catalytic coupling, and thermoelectric properties. ACS Applied Energy Materials 2020; 3: 4983-4994.
  • 16. Wood CD, Tan B, Trewin A, Su F, Rosseinsky MJ et al. Microporous organic polymers for methane storage. Advanced Materials 2008; 20: 1916-1921.
  • 17. Luo Y, Li B, Wang W, Wu K, Tan B. Hypercrosslinked aromatic heterocyclic microporous polymers: a new class of highly selective CO2 capturing materials. Advanced Materials 2012; 24: 5703-5707.
  • 18. Ji L, Fang Q, Yuan M-s, Liu Z-q, Shen Y-xet al. Switching high two-photon efficiency: from 3, 8, 13-substituted triindole derivatives to their 2, 7, 12-isomers. Organic Letters 2010; 12: 5192-5195.
  • 19. Bura T, Leclerc N, Bechara R, Lévêque P, Heiser T et al. Triazatruxene-diketopyrrolopyrrole dumbbell-shaped molecules as photoactive electron donor for high-efficiency solution processed organic solar cells. Advanced Energy Materials 2013; 3: 1118-1124.
  • 20. Ruiz C, Lopez Navarrete JT, Ruiz Delgado MC, Gómez-Lor B. Triindole-bridge-triindole dimers as models for two dimensional microporous polymers. Organic Letters 2015; 17: 2258-2261.
  • 21. Shao J, Guan Z, Yan Y, Jiao C, Xu Q-Het al. Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores. The Journal of organic chemistry 2011; 76: 780-790.
  • 22. Lai WY, He QY, Zhu R, Chen QQ, Huang W. Kinked star-shaped fluorene/triazatruxene co-oligomer hybrids with enhanced functional properties for high-performance, solution-processed, blue organic light-emitting diodes. Advanced Functional Materials 2008; 18: 265- 276.
  • 23. Sadak AE, Gören AC, Bozdemir ÖA, Saraçoğlu N. Synthesis of novel meso-indole- and meso-triazatruxene-bodipy dyes. Chemistry Select 2017; 2: 10512-10516.
  • 24. Xu S, Luo Y, Tan B. Recent development of hypercrosslinked microporous organic polymers. Macromolecular Rapid Communications 2013; 34: 471-484.
  • 25. Shen R, Yan X, Guan Y-J, Zhu W, Li Tet al. One-pot synthesis of a highly porous anionic hypercrosslinked polymer for ultrafast adsorption of organic pollutants. Polymer Chemistry 2018; 9: 4724-4732.
  • 26. Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA et al. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (recommendations 1984). Pure and Applied Chemistry 1985; 57: 603-619.
  • 27. Saleh M, Lee HM, Kemp KC, Kim KS. Highly stable CO2/N2 and CO2/CH4 selectivity in hyper-cross-linked heterocyclic porous polymers. ACS applied materials & interfaces 2014; 6: 7325-7333.
  • 28. Ben T, Pei C, Zhang D, Xu J, Deng F et al. Gas storage in porous aromatic frameworks (PAFs). Energy & Environmental Science 2011; 4: 3991-3999.
  • 29. Jeon HJ, Choi JH, Lee Y, Choi KM, Park JH et al. Highly selective CO2-capturing polymeric organic network structures. Advanced Energy Materials 2012; 2: 225-228.
  • 30. Jackson KT, Rabbani MG, Reich TE, El-Kaderi HM. Synthesis of highly porous borazine-linked polymers and their application to H-2, CO2, and CH4 storage. Polymer Chemistry 2011; 2: 2775-2777.
  • 31. Dawson R, Adams DJ, Cooper AI. Chemical tuning of CO2 sorption in robust nanoporous organic polymers. Chemical Science 2011; 2: 1173-1177.
  • 32. Li P-Z, Zhao Y. Nitrogen-rich porous adsorbents for CO2 capture and storage. Chemistry – An Asian Journal 2013; 8: 1680-1691.
  • 33. Erdogan FO. Freundlich, Langmuir, Temkin, DR and Harkins-Jura isotherm studies on the adsorption of CO2 on various porous adsorbents. International Journal of Chemical Reactor Engineering 2019; 17.
  • 34. Furukawa H, Yaghi OM. Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications. Journal of the American Chemical Society 2009; 131: 8875-8883.
  • 35. Germain J, Svec F, Fréchet JMJ. Preparation of size-selective nanoporous polymer networks of aromatic rings: potential adsorbents for hydrogen storage. Chemistry of Materials 2008; 20: 7069-7076.
  • 36. Jiang J-X, Su F, Trewin A, Wood CD, Niu H et al. Synthetic control of the pore dimension and surface area in conjugated microporous polymer and copolymer networks. Journal of the American Chemical Society 2008; 130: 7710-7720.
  • 37. Oguz Erdogan F, Kopac T. Comparison of activated carbons produced from zonguldak kozlu and zonguldak karadon hard coals for hydrogen sorption. Energy Sources, Part A: Recovery Utilization and Environmental Effects 2020; 1-17.
  • 38. Tozawa T, Jones JTA, Swamy SI, Jiang S, Adams DJ et al. Porous organic cages. Nature Materials 2009; 8: 973.
  • 39. Rabbani MG, Sekizkardes AK, El-Kadri OM, Kaafarani BR, El-Kaderi HM. Pyrene-directed growth of nanoporous benzimidazole-linked nanofibers and their application to selective CO2 capture and separation. Journal of Materials Chemistry 2012; 22: 25409-25417.
  • 40. Mastalerz M, Hauswald H-JS, Stoll R. Metal-assisted salphen organic frameworks (MaSOFs) with high surface areas and narrow pore-size distribution. Chemical Communications 2012; 48: 130-132.
  • 41. Katsoulidis AP, Kanatzidis MG. Mesoporous hydrophobic polymeric organic frameworks with bound surfactants. selective adsorption of C2H6 versus CH4. Chemistry of Materials 2012; 24: 471-479.
  • 42. Rabbani MG, El-Kaderi HM. Synthesis and characterization of porous benzimidazole-linked polymers and their performance in small gas storage and selective uptake. Chemistry of Materials 2012; 24: 1511-1517.
  • 43. Oguz Erdogan F. A comparative study on methane adsorption onto various adsorbents including activated carbons, zeolites, MWCNT, and MCM-41. International Journal of Coal Preparation and Utilization 2020; 1-21.
  • 44. Oguz Erdogan F. Carbon dioxide and methane adsorption behaviour of zeolite/biomass-based activated carbon and zeolite/multiwalled carbon nanotube composites. International Journal of Environmental Analytical Chemistry 2020; 1-19.
  • 45. Myers AL, Prausnitz JM. Thermodynamics of mixed-gas adsorption. AIChE Journal 1965; 11: 121-127.
  • 46. Yang X, Yu M, Zhao Y, Zhang C, Wang X et al. Hypercrosslinked microporous polymers based on carbazole for gas storage and separation. RSC Advances 2014; 4: 61051-61055.
  • 47. Xie Y-F, Ding S-Y, Liu J-M, Wang W, Zheng QY. Triazatruxene based covalent organic framework and its quick-response fluorescence-on nature towards electron rich arenes. Journal of Materials Chemistry C 2015; 3: 10066-10069.
  • 48. Zhu Y, Long H, Zhang W. Imine-linked porous polymer frameworks with high small gas (H2, CO2, CH4, C2H2) uptake and CO2/N2 selectivity. Chemistry of Materials 2013; 25: 1630-1635.
  • 49. Yang X, Yao S, Yu M, Jiang J-X. Synthesis and gas adsorption properties of tetra-armed microporous organic polymer networks based on triphenylamine. Macromolecular Rapid Communications 2014; 35: 834-839.
  • 50. Wang ZG, Liu X, Wang D, Jin J. Tröger’s base-based copolymers with intrinsic microporosity for CO2 separation and effect of Tröger’s base on separation performance. Polymer Chemistry 2014; 5: 2793-2800.
  • 51. Qiao S, Du Z, Yang R. Design and synthesis of novel carbazole–spacer–carbazole type conjugated microporous networks for gas storage and separation. Journal of Materials Chemistry A 2014; 2: 1877-1885.
  • 52. Zhang X, Lu J, Zhang J. Porosity enhancement of carbazolic porous organic frameworks using dendritic building blocks for gas storage and separation. Chemistry of Materials 2014; 26: 4023-4029.
  • 53. Nguyen TS, Yavuz CT. Quantifying the nitrogen effect on CO2 capture using isoporous network polymers. Chemical Communications 2020; 56: 4273-4275.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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