Boronic acid-functionalized porous polycarbazoles: preparation, adsorption performance, and heterogeneous catalysts for selective oxidation
Source abstract
Abstract
Boronic acid-functionalized porous polycarbazoles (PCBA-1 and PCBA-2) which possess special functions as well as permanent porosity have been synthesized by oxidative coupling polymerization, followed by characterization of their chemical structure and porosities. The Brunauer–Emmett–Teller (BET) specific surface area value scope of PCBA-1 and PCBA-2 is from 868 to 768 m2 g−1 and the related dominant pore sizes are centered at about 1.0 nm. PCBA-1 and PCBA-2 exhibit potential adsorption for vapor solvent and small gas molecules. Their adsorption capacity for methanol measured at saturated vapor pressure and room temperature is 534 and 430 mg g−1, respectively. They also show moderate uptake capacity (15.3 and 14.0 wt%) for CO2 at 1.0 bar and 273 K. Also, the obtained porous polymers as effective heterogeneous catalysts can promote transformation of 1,2-diols into α-hydroxy ketones accordingly by selective oxidation.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Metal-Organic Frameworks: Synthesis and Applications · Covalent Organic Framework Applications · Advanced Photocatalysis Techniques
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (45)
Show source-provided references
1. Das S, Heasman P, Ben T, Qiu SL (2017) Porous organic materials: strategic design and structure–function correlation. Chem Rev 117:1515–156310.1021/acs.chemrev.6b00439 ↗
2. Xu Y, Jin S, Xu H, Nagai A, Jiang D (2013) Conjugated microporous polymers: design, synthesis and application. Chem Soc Rev 42:8012–803110.1039/c3cs60160a ↗
3. Cooper AI (2009) Conjugated microporous polymers. Adv Mater 21:1291–129510.1002/adma.200801971 ↗
4. Dawson R, Adams DJ, Cooper AI (2011) Chemical tuning of CO2 sorption in robust nanoporous organic polymers. Chem Sci 2:1173–117710.1039/c1sc00100k ↗
5. Weber J, Thomas A (2008) Toward stable interfaces in conjugated polymers: microporous poly(p-phenylene) and poly(phenyleneethynylene) based on a spirobifluorene building block. J Am Chem Soc 130:6334–633510.1021/ja801691x ↗
6. Chen Q, Luo M, Wang T, Wang JX, Zhou D, Han Y, Yan CG, Han BH (2011) Porous organic polymers based on propeller-like hexaphenylbenzene building units. Macromolecules 44:5573–557710.1021/ma200915f ↗
7. Ding SY, Wang W (2013) Covalent organic frameworks (COFs): from design to applications. Chem Soc Rev 42:548–56810.1039/C2CS35072F ↗
8. Feng X, Ding X, Jiang D (2012) Covalent organic frameworks. Chem Soc Rev 41:6010–602210.1039/c2cs35157a ↗
9. Schmidt J, Weber J, Epping JD, Antonietti M, Thormas A (2009) Microporous conjugated poly(thienylene arylene) networks. Adv Mater 21:702–70510.1002/adma.200802692 ↗
10. Chen Q, Wang JX, Yang F, Zhou D, Bian N, Zhang XJ, Yan CG, Han BH (2011) Tetraphenylethylene-based fluorescent porous organic polymers: preparation, gas sorption properties and photoluminescence properties. J Mater Chem 21:13554–1356010.1039/c1jm11787d ↗
11. Ritter N, Antonietti M, Thomas A, Senkovska I, Kaskel S, Weber J (2009) Binaphthalene-based, soluble polyimides: the limits of intrinsic microporosity. Macromolecules 42:8017–802010.1021/ma901220c ↗
12. Chen L, Yang Y, Jiang D (2010) 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 132:9138–914310.1021/ja1028556 ↗
13. Wu K, Guo J, Wang C (2016) An elastic monolithic catalyst: a microporous metalloporphyrin-containing framework-wrapped melamine foam for process-intensified acyl transfer. Angew Chem Int Ed 55:6013–601710.1002/anie.201600891 ↗
14. Chen Q, Luo M, Hammershøj P, Zhou D, Han Y, Laursen BW, Yan CG, Han BH (2012) Microporous polycarbazole with high specific surface area for gas storage and separation. J Am Chem Soc 134:6084–608710.1021/ja300438w ↗
15. Chen Q, Liu DP, Luo M, Feng LJ, Zhao YC, Han BH (2014) Nitrogen-containing microporous conjugated polymers via carbazole-based oxidative coupling polymerization: preparation, porosity, and gas uptake. Small 10:308–31510.1002/smll.201301618 ↗
16. Jiang F, Jin T, Zhu X, Tian Z, Do-Thanh CL, Hu J, Jiang DE, Wang H, Liu H, Dai S (2016) Substitution effect guided synthesis of task-specific nanoporous polycarbazoles with enhanced carbon capture. Macromolecules 49:5325–533010.1021/acs.macromol.6b01342 ↗
17. Zhu X, Ding S, Abney CW, Browning KL, Sacci RL, Veith GM, Tian C, Dai S (2017) Superacid-promoted synthesis of highly porous hypercrosslinked polycarbazoles for efficient CO2 capture. Chem Commun 53:7645–764810.1039/C7CC03620E ↗
18. Gu C, Huang N, Chen Y, Zhang H, Zhang S, Li F, Ma Y, Jiang D (2016) Porous organic polymer films with tunable work functions and selective hole and electron flows for energy conversions. Angew Chem Int Ed 55:3049–305310.1002/anie.201510723 ↗
19. Liu C, Luo H, Shi G, Nian L, Chi Z, Ma Y (2017) Electrochemical route to fabricate porous organic polymers film and its application for polymer solar cells. Dyes Pigments 142:132–13810.1016/j.dyepig.2017.03.017 ↗
20. Palma-Cando A, Scherf U (2015) Electrogenerated thin films of microporous polymer networks with remarkably increased electrochemical response to nitroaromatic analytes. ACS Appl Mater Interfaces 7:11127–1113310.1021/acsami.5b02233 ↗
21. Räupke A, Palma-Cando A, Shkura E, Teckhausen P, Polywka A, Görrn P, Scherf U, Riedl T (2016) Highly sensitive gas-phase explosive detection by luminescent microporous polymer networks. Sci Rep 6:2911810.1038/srep29118 ↗
22. Palma-Cando A, Preis E, Scherf U (2016) Silicon-or carbon-cored multifunctional carbazolyl monomers for the electrochemical generation of microporous polymer films. Macromolecules 49:8041–804710.1021/acs.macromol.6b02025 ↗
23. Pan L, Chen Q, Zhu JH, Yu J, He YJ, Han BH (2015) Cross-linked porous polycarbazoles via one-step oxidative coupling reaction and Friedel-Crafts alkylation. Polym Chem 6:2478–248710.1039/C4PY01797H ↗
24. Eduard P, Christian W, Ullrich S, Satish P, Gunther B, Johannes S, Thomasd Arne (2011) Aromatic, microporous polymer networks with high surface area generated in Friedel–Crafts-type polycondensations. Polym Chem 2:2186–218910.1039/c1py00251a ↗
25. Preis E, Widling C, Brunklaus G, Schmidt J, Thomas A, Scherf U (2013) Microporous polymer networks (MPNs) made in metal-free regimes: systematic optimization of a synthetic protocol toward N-arylcarbazole-based MPNs. Acs Macro Lett 2:380–38310.1021/mz400126f ↗
26. Chen Q, Han BH (2018) Microporous polycarbazole materials: from preparation and properties to applications. Macromol Rapid Commun 39:201800040
27. Cao Q, Chen Q, Han BH (2015) Recent advance in organic porous polycarbazoles: preparation and properties. Acta Chim Sin 73:541–55610.6023/A15020126 ↗
28. Molla RA, Bhanja P, Ghosh K, Islam SS, Bhaumik A, Islam SM (2017) Pd nanoparticles decorated on hypercrosslinked microporous polymer: a highly efficient catalyst for the formylation of amines through carbon dioxide fixation. ChemCatChem 9:1939–194610.1002/cctc.201700069 ↗
29. Ding S, Tian C, Zhu X, Abney CW, Tian Z, Chen B, Li M, Jiang DE, Zhang N, Dai S (2017) Pd-metalated conjugated nanoporous polycarbazoles for additive-free cyanation of aryl halides: boosting catalytic efficiency through spatial modulation. Chemsuschem 10:2348–235110.1002/cssc.201700329 ↗
30. Huang YJ, Ouyang WJ, Wu X, Li Z, Fossey JS, James TD, Jiang YB (2013) Glucose sensing via aggregation and the use of “knock-out” binding to improve selectivity. J Am Chem Soc 135:1700–170310.1021/ja311442x ↗
31. Wu X, Li Z, Chen XX, Fossey JS, James TD, Jiang YB (2013) Selective sensing of saccharides using simple boronic acids and their aggregates. Chem Soc Rev 42:8032–804810.1039/c3cs60148j ↗
32. Maki T, Ushijima N, Matsumura Y, Onomura O (2009) Catalytic monoalkylation of 1,2-diols. Tetrahedron Lett 50:1466–146810.1016/j.tetlet.2009.01.063 ↗
33. William JM, Kuriyama M, Onomura O (2014) Boronic acid-catalyzed selective oxidation of 1,2-diols to α-hydroxy ketones in water. Adv Synth Catal 356:934–94010.1002/adsc.201300961 ↗
34. Chen Q, Liu DP, Zhu JH, Han BH (2014) Mesoporous conjugated polycarbazole with high porosity via structure tuning. Macromolecules 47:5926–593110.1021/ma501330v ↗
35. Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquérol J, Siemieniewska T (1985) Reporting physisorption date for gas/solid systems with special reference to the determination of surface area and porosity. Pure Appl Chem 57:603–61910.1351/pac198557040603 ↗
36. Weber J, Schmidt J, Thomas A, Böhlmann W (2010) Micropore analysis of polymer networks by gas sorption and 129Xe NMR spectroscopy: toward a better understanding of intrinsic microporosity. Langmuir 26:15650–1565610.1021/la1028806 ↗
37. Dawson R, Adams DJ, Cooper AI (2011) Chemical tuning of CO2 sorption in robust nanoporous organic polymers. Chem Sci 2:1173–117710.1039/c1sc00100k ↗
38. Lu W, Yuan D, Sculley J, Zhao D, Krishna R, Zhou HC (2011) Sulfonate-grafted porous polymer networks for preferential CO2 adsorption at low pressure. J Am Chem Soc 133:18126–1812910.1021/ja2087773 ↗
39. Feng LJ, Chen Q, Zhu JH, Liu DP, Zhao YC, Han BH (2014) Adsorption performance and catalytic activity of porous conjugated polyporphyrins via carbazole-based oxidative coupling polymerization. Polym Chem 5:3081–308810.1039/c3py01430d ↗
40. Zhu JH, Chen Q, Sui ZY, Pan L, Yu JG, Han BH (2014) Preparation and adsorption performance of cross-linked porous polycarbazoles. J Mater Chem A 2:16181–1618910.1039/C4TA01537A ↗
41. Ben T, Pei C, Zhang D, Xu J, Deng F, Jing X, Qiu SL (2011) Gas storage in porous aromatic frameworks (PAFs). Energy Environ Sci 4:3991–399910.1039/c1ee01222c ↗
42. Banerjee R, Phan A, Wang B, Knobler C, Furukawa H, O’Keeffe M, Yaghi OM (2008) High-throughput synthesis of zeolitic imidazolate frameworks and application to CO2 capture. Science 319:939–94310.1126/science.1152516 ↗
43. Furukawa H, Yaghi OM (2009) Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications. J Am Chem Soc 131:8875–888310.1021/ja9015765 ↗
44. Zhang X, Lu JZ, Zhang J (2014) Porosity enhancement of carbazolic porous organic frameworks using dendritic building blocks for gas storage and separation. Chem Mater 26:4023–402910.1021/cm501717c ↗
45. Jiang F, Jin T, Zhu X, Tian ZQ, Do-Thanh CL, Hu J, Jiang DE, Wang HL, Liu HL, Dai S (2016) Substitution effect guided synthesis of task-specific nanoporous polycarbazoles with enhanced carbon capture. Macromolecules 49:5325–533010.1021/acs.macromol.6b01342 ↗