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One-step synthesis of nitrogen-rich organic polymers for efficient catalysis of CO2 cycloaddition

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Abstract

Nitrogen-rich organic polymer poly(chloride triazole) (PCTs) was synthesized by a one-step method as metal-halogen-free heterogeneous catalyst for the solvent-free CO2 cycloaddition. PCTs had abundant nitrogen sites and hydrogen bond donors, exhibited great activity for the cycloaddition of CO2 and epichlorohydrin, and achieved 99.6% yield of chloropropene carbonate under the conditions of 110 ℃, 6 h, and 0.5 MPa CO2. The activation of epoxides and CO2 by hydrogen bond donor and nitrogen sites was further explained by density functional theory (DFT) calculations. In summary, this study showed that nitrogen-rich organic polymer is a versatile platform for CO2 cycloaddition, and this paper provides a reference for the design of CO2 cycloaddition catalysts.

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References

  • Alves M, Grignard B, Mereau R, Jerome C, Tassaing T, Detrembleur C (2017) Organocatalyzed coupling of carbon dioxide with epoxides for the synthesis of cyclic carbonates: catalyst design and mechanistic studies. Catal Sci Technol 7:2651–2684

    Article  CAS  Google Scholar 

  • Bhin KM, Tharun J, Roshan KR, Kim D-W, Chung Y, Park D-W (2017) Catalytic performance of zeolitic imidazolate framework ZIF-95 for the solventless synthesis of cyclic carbonates from CO2 and epoxides. J CO2 Util 17:112–118

    Article  CAS  Google Scholar 

  • Biswas T, Halder A, Paliwal KS, Mitra A, Tudu G, Banerjee R, Mahalingam V (2020) Triazine-based organic polymer-catalysed conversion of epoxide to cyclic carbonate under ambient CO2 pressure. Chem-An Asian J 15:1683–1687

    Article  CAS  Google Scholar 

  • Buyukcakir O, Je SH, Talapaneni SN, Kim D, Coskun A (2017) Charged covalent triazine frameworks for CO2 capture and conversion. ACS Appl Mater Interfaces 9:7209–7216

    Article  CAS  Google Scholar 

  • Chen J, Li H, Zhong M, Yang Q (2016) Hierarchical mesoporous organic polymer with an intercalated metal complex for the efficient synthesis of cyclic carbonates from flue gas. Green Chem 18:6493–6500

    Article  CAS  Google Scholar 

  • Chen J-J, Xu Y-C, Gan Z-L, Peng X, Yi X-Y (2019) Zinc complexes with tridentate pyridyl-pyrrole ligands and their use as catalysts in co2 fixation into cyclic carbonates. Eur J Inorg Chem 2019:1733–1739

    Article  CAS  Google Scholar 

  • Cokoja M, Wilhelm ME, Anthofer MH, Herrmann WA, Kühn FE (2015) Synthesis of cyclic carbonates from epoxides and carbon dioxide by using organocatalysts. Chemsuschem 8:2436–2454

    Article  CAS  Google Scholar 

  • Dabral S, Schaub T (2019) The use of carbon dioxide (CO2) as a building block in organic synthesis from an industrial perspective. Adv Synth Catal 361:223–246

    Article  CAS  Google Scholar 

  • Dai Z, Bao Y, Yuan J, Yao J, Xiong Y (2021) Different functional groups modified porous organic polymers used for low concentration CO2 fixation. Chem Commun 57:9732–9735

    Article  CAS  Google Scholar 

  • Dinari M, Roghani N (2021) Effect of triazine based silane coupling agent modified LDH on the thermal and mechanical properties of PVC based nanocomposites. J Polym Res 28:320

    Article  CAS  Google Scholar 

  • Ding L-G, Yao B-J, Jiang W-L, Li J-T, Fu Q-J, Li Y-A, Liu Z-H, Ma J-P, Dong Y-B (2017) Bifunctional imidazolium-based ionic liquid decorated UiO-67 type MOF for selective CO2 adsorption and catalytic property for CO2 cycloaddition with epoxides. Inorg Chem 56:2337–2344

    Article  CAS  Google Scholar 

  • Dios JR, Gonzalo B, Tubio CR, Cardoso J, Gonçalves S, Miranda D, Correia V, Viana JC, Costa P, Lanceros-Méndez S (2020) Functional piezoresistive polymer-composites based on polycarbonate and polylactic acid for deformation sensing applications. Macromol Mater Eng 305:2000379

    Article  CAS  Google Scholar 

  • Fan M, Wang WD, Zhu Y, Sun X, Zhang F, Dong Z (2019) Palladium clusters confined in triazinyl-functionalized COFs with enhanced catalytic activity. Appl Catal B 257:117942

    Article  CAS  Google Scholar 

  • Goodarzi F, Karimi AR (2020) New PEG-modified ladder-like silsesquioxane as an antifoaming agent. ChemistrySelect 5:12411–12416

    Article  CAS  Google Scholar 

  • Guha N, Gupta AK, Chatterjee S, Krishnan S, Singh MK, Rai DK (2021) Environmentally benign melamine functionalized silica-coated iron oxide for selective CO2 capture and fixation into cyclic carbonate. J CO2 Util 49:101575

    Article  CAS  Google Scholar 

  • Gulsu MS, Bagci F, Can S, Yilmaz AE, Akaoglu B (2020) Metamaterial-based sensor with a polycarbonate substrate for sensing the permittivity of alcoholic liquids in a WR-229 waveguide. Sens Actuators A 312:112139

    Article  CAS  Google Scholar 

  • Hu T-d, Jiang Y, Ding Y-h (2019) Computational screening of metal-substituted HKUST-1 catalysts for chemical fixation of carbon dioxide into epoxides. J Mater Chem A 7:14825–14834

    Article  CAS  Google Scholar 

  • Jiao S, Deng L, Zhang X, Zhang Y, Liu K, Li S, Wang L, Ma D (2021) Evaluation of an ionic porous organic polymer for water remediation. ACS Appl Mater Interfaces 13:39404–39413

    Article  CAS  Google Scholar 

  • Kim D, Ji H, Hur MY, Lee W, Kim TS, Cho D-H (2018) Polymer-supported Zn-containing imidazolium salt ionic liquids as sustainable catalysts for the cycloaddition of CO2: a kinetic study and response surface methodology. ACS Sustain Chem Eng 6:14743–14750

    Article  CAS  Google Scholar 

  • Kurisingal JF, Rachuri Y, Gu Y, Kim G-H, Park D-W (2019) Binary metal-organic frameworks: catalysts for the efficient solvent-free CO2 fixation reaction via cyclic carbonates synthesis. Appl Catal A 571:1–11

    Article  CAS  Google Scholar 

  • Lai S, Gao J, Zhang H, Cheng L, Xiong X (2020) Luffa sponge supported dendritic imidazolium ILs with high-density active sites as highly efficient and environmentally friendly catalysts for CO2 chemical fixation. J CO2 Util 38:148–157

    Article  CAS  Google Scholar 

  • Lan J, Liu M, Lu X, Zhang X, Sun J (2018) Novel 3D nitrogen-rich metal organic framework for highly efficient CO2 adsorption and catalytic conversion to cyclic carbonates under ambient temperature. ACS Sustain Chem Eng 6:8727–8735

    Article  CAS  Google Scholar 

  • Li G, Zhang B, Wang Z (2016a) Facile synthesis of fluorinated microporous polyaminals for adsorption of carbon dioxide and selectivities over nitrogen and methane. Macromolecules 49:2575–2581

    Article  CAS  Google Scholar 

  • Li G, Zhang B, Yan J, Wang Z (2016b) The cost-effective synthesis of furan- and thienyl-based microporous polyaminals for adsorption of gases and organic vapors. Chem Commun 52:1143–1146

    Article  Google Scholar 

  • Li Y-M, Yang L, Sun L, Ma L, Deng W-Q, Li Z (2019) Chemical fixation of carbon dioxide catalyzed via covalent triazine frameworks as metal free heterogeneous catalysts without a cocatalyst. J Mater Chem A 7:26071–26076

    Article  CAS  Google Scholar 

  • Li X, Cai W, Guan H, Zhao S, Cao S, Chen C, Liu M, Zang Z (2021a) Highly stable CsPbBr 3 quantum dots by silica-coating and ligand modification for white light-emitting diodes and visible light communication. Chem Eng J 419:129551

    Article  CAS  Google Scholar 

  • Li Z, Zhi Y, Ni Y, Su H, Miao Y, Shan S (2021b) Novel melamine-based porous organic materials as metal-free catalysts for copolymerization of SO2 with epoxide. Polymer 217:123434

    Article  CAS  Google Scholar 

  • Li X, Ma W, Liang D, Cai W, Zhao S, Zang Z (2022) High-performance CsPbBr3@Cs4PbBr6/SiO2 nanocrystals via double coating layers for white light emission and visible light communication. eScience 2:646–654

    Article  Google Scholar 

  • Liu A, Zhang J, Lv X (2018a) Novel hydrazine-bridged covalent triazine polymer for CO2 capture and catalytic conversion. Chin J Catal 39:1320–1328

    Article  CAS  Google Scholar 

  • Liu M, Lu X, Jiang Y, Sun J, Arai M (2018b) Zwitterionic imidazole-urea derivative framework bridged mesoporous hybrid silica: a highly efficient heterogeneous nanocatalyst for carbon dioxide conversion. ChemCatChem 10:1860–1868

    Article  CAS  Google Scholar 

  • Liu C, Ye Y, Jiang Z, Xu P, Zhang J, Sun J (2019) Carbon dioxide activation and conversion by hyperbranched polyethylenimine/ZnI2 catalysts. Ind Eng Chem Res 58:872–878

    Article  CAS  Google Scholar 

  • Lohse MS, Bein T (2018) Covalent organic frameworks: structures, synthesis, and applications. Adv Func Mater 28:1705553

    Article  Google Scholar 

  • Luo R, Xu W, Chen M, Liu X, Fang Y, Ji H (2020) Covalent triazine frameworks obtained from nitrile monomers for sustainable co2 catalysis. Chemsuschem 13:6509–6522

    Article  CAS  Google Scholar 

  • Luo R, Yang Y, Chen K, Liu X, Chen M, Xu W, Liu B, Ji H, Fang Y (2021) Tailored covalent organic frameworks for simultaneously capturing and converting CO2 into cyclic carbonates. J Mater Chem A 9:20941–20956

    Article  CAS  Google Scholar 

  • Mo Q, Chen C, Cai W, Zhao S, Yan D, Zang Z (2021) Room temperature synthesis of stable zirconia-coated CsPbBr 3 nanocrystals for white light-emitting diodes and visible light communication. Laser Photonics Rev 15:2100278

    Article  CAS  Google Scholar 

  • Moslan MS, Othman MHD, Samavati A, Theodosiou A, Kalli K, Ismail AF, Rahman MA (2023) Real-time fluid flow movement identification in porous media for reservoir monitoring application using polycarbonate optical fibre Bragg grating sensor. Sens Actuators, A 354:114246

    Article  CAS  Google Scholar 

  • Peng J, Wang S, Yang H-J, Ban B, Wei Z, Wang L, Lei B (2018) Highly efficient fixation of carbon dioxide to cyclic carbonates with new multi-hydroxyl bis-(quaternary ammonium) ionic liquids as metal-free catalysts under mild conditions. Fuel 224:481–488

    Article  CAS  Google Scholar 

  • Qi S-C, Wu J-K, Lu J, Yu G-X, Zhu R-R, Liu Y, Liu X-Q, Sun L-B (2019) Underlying mechanism of CO2 adsorption onto conjugated azacyclo-copolymers: N-doped adsorbents capture CO2 chiefly through acid–base interaction? J Mater Chem A 7:17842–17853

    Article  CAS  Google Scholar 

  • Qian Y, Chu Y, Zheng Z, Shadike Z, Han B, Xiang S, Kang Y, Hu S, Cao C, Zhong L, Shi Q, Lin M, Zeng H, Wang J, Hu E, Weiland C, Yang X-Q, Deng Y (2022) A new cyclic carbonate enables high power/ low temperature lithium-ion batteries. Energy Storage Mater 45:14–23

    Article  Google Scholar 

  • Sharma R, Muhammad R, Chandra Srivastava V, Mohanty P (2021) Heteroatom driven activation and conversion of CO2 using cyclophosphazene based inorganic–organic hybrid nanoporous materials. Sustain Energy Fuels 5:3213–3218

    Article  CAS  Google Scholar 

  • Sun J, Cheng W, Yang Z, Wang J, Xu T, Xin J, Zhang S (2014) Superbase/cellulose: an environmentally benign catalyst for chemical fixation of carbon dioxide into cyclic carbonates. Green Chem 16:3071–3078

    Article  CAS  Google Scholar 

  • Tahmasbi B, Ghorbani-Choghamarani A (2019) Magnetic MCM-41 nanoparticles as a support for the immobilization of a palladium organometallic catalyst and its application in C-C coupling reactions. New J Chem 43:14485–14501

    Article  CAS  Google Scholar 

  • Takaishi K, Nath BD, Yamada Y, Kosugi H, Ema T (2019) Unexpected macrocyclic multinuclear zinc and nickel complexes that function as multitasking catalysts for CO2 fixations. Angew Chem Int Ed 58:9984–9988

    Article  CAS  Google Scholar 

  • Verma S, Kumar G, Ansari A, Kureshy RI, N-uH K (2017) A nitrogen rich polymer as an organo-catalyst for cycloaddition of CO2 to epoxides and its application for the synthesis of polyurethane. Sustain Energy Fuels 1:1620–1629

    Article  CAS  Google Scholar 

  • Wang L, Dong B, Ge R, Jiang F, Xiong J, Gao Y, Xu J (2016) A thiadiazole-functionalized covalent organic framework for efficient CO2 capture and separation. Microporous Mesoporous Mater 224:95–99

    Article  CAS  Google Scholar 

  • Xiao Y, Zhang J, Lang M (2018) Melamine driven supramolecular self-assembly of nucleobase derivatives in water. J Polym Sci Part A: Polym Chem 56:789–796

    Article  CAS  Google Scholar 

  • Xu K, Dai Y, Ye B, Wang H (2017a) Two dimensional covalent organic framework materials for chemical fixation of carbon dioxide: excellent repeatability and high selectivity. Dalton Trans 46:10780–10785

    Article  CAS  Google Scholar 

  • Xu L, Chen J, Song J, Li J, Xue J, Dong Y, Cai B, Shan Q, Han B, Zeng H (2017b) Double-protected all-inorganic perovskite nanocrystals by crystalline matrix and silica for triple-modal anti-counterfeiting codes. ACS Appl Mater Interfaces 9:26556–26564

    Article  CAS  Google Scholar 

  • Xu Y, Yu H, Shi B, Gao S, Zhang L, Li X, Liao X, Huang K (2020) Room-temperature synthesis of hollow carbazole-based covalent triazine polymers with multiactive sites for efficient iodine capture-catalysis cascade application. ACS Appl Polymer Mater 2:3704–3713

    Article  CAS  Google Scholar 

  • Xu W, Wang W, Hao L, Liu H, Hai F, Wang X (2021) Synthesis and properties of novel triazine-based fluorinated chain extender modified waterborne polyurethane hydrophobic films. Prog Org Coat 157:106282

    Article  CAS  Google Scholar 

  • Yang C, Liu M, Zhang J, Wang X, Jiang Y, Sun J (2018) Facile synthesis of DBU-based ionic liquids cooperated with ZnI2 as catalysts for efficient cycloaddition of CO2 to epoxides under mild and solvent-free conditions. Mol Catal 450:39–45

    Article  CAS  Google Scholar 

  • Yang F, Li Y, Zhang T, Zhao Z, Xing G, Chen L (2020) Docking site modulation of isostructural covalent organic frameworks for CO2 fixation. Chem-A Eur J 26:4510–4514

    Article  CAS  Google Scholar 

  • Yang Q, Luo M, Liu K, Cao H, Yan H (2020b) Covalent organic frameworks for photocatalytic applications. Appl Catal B 276:119174

    Article  CAS  Google Scholar 

  • Yang Q, Peng H, Zhang Q, Qian X, Chen X, Tang X, Dai S, Zhao J, Jiang K, Yang Q, Sun J, Zhang L, Zhang N, Gao H, Lu Z, Chen L (2021) Atomically dispersed high-density Al–N4 sites in porous carbon for efficient photodriven CO2 cycloaddition. Adv Mater 33:2103186

    Article  CAS  Google Scholar 

  • You D, Hu W, Song L, Wei W, Xiong H (2022) High-energy metallic lithium batteries enabled by polymer-in-salt electrolytes of cyclic carbonate substituted polyethers. ACS Appl Polymer Mater 4:8584–8593

    Article  CAS  Google Scholar 

  • Yu W, Gu S, Fu Y, Xiong S, Pan C, Liu Y, Yu G (2018a) Carbazole-decorated covalent triazine frameworks: novel nonmetal catalysts for carbon dioxide fixation and oxygen reduction reaction. J Catal 362:1–9

    Article  CAS  Google Scholar 

  • Yu X, Sun J, Yuan J, Zhang W, Pan C, Liu Y, Yu G (2018b) One-pot synthesis of an ionic porous organic framework for metal-free catalytic CO2 fixation under ambient conditions. Chem Eng J 350:867–871

    Article  CAS  Google Scholar 

  • Yue Z, Pudukudy M, Chen S, Liu Y, Zhao W, Wang J, Shan S, Jia Q (2020) A non-metal Acen-H catalyst for the chemical fixation of CO2 into cyclic carbonates under solvent- and halide-free mild reaction conditions. Appl Catal A 601:117646

    Article  CAS  Google Scholar 

  • Zhang B, Yan J, Li G, Wang Z (2019a) Carboxyl-, hydroxyl-, and nitro-functionalized porous polyaminals for highly selective CO2 capture. ACS Appl Polymer Mater 1:1524–1531

    Article  CAS  Google Scholar 

  • Zhang B, Yan J, Li G, Wang Z (2019b) Cost-effective preparation of microporous polymers from formamide derivatives and adsorption of CO2 under dry and humid conditions. Polym Chem 10:3371–3379

    Article  CAS  Google Scholar 

  • Zhi Y, Shao P, Feng X, Xia H, Zhang Y, Shi Z, Mu Y, Liu X (2018) Covalent organic frameworks: efficient, metal-free, heterogeneous organocatalysts for chemical fixation of CO2 under mild conditions. J Mater Chem A 6:374–382

    Article  CAS  Google Scholar 

  • Zhong H, Gao J, Sa R, Yang S, Wu Z, Wang R (2020) Carbon dioxide conversion upgraded by host-guest cooperation between nitrogen-rich covalent organic framework and imidazolium-based ionic polymer. Chemsuschem 13:6323–6329

    CAS  Google Scholar 

  • Zhou X, Jin C, Liu G, Wu G, Huo S, Kong Z (2021) Functionalized lignin-based magnetic adsorbents with tunable structure for the efficient and selective removal of Pb(II) from aqueous solution. Chem Eng J 420:130409

    Article  CAS  Google Scholar 

  • Ziaee MA, Tang Y, Zhong H, Tian D, Wang R (2019) Urea-functionalized imidazolium-based ionic polymer for chemical conversion of CO2 into organic carbonates. ACS Sustain Chem Eng 7:2380–2387

    Article  CAS  Google Scholar 

  • Zou L, Sun Y, Che S, Yang X, Wang X, Bosch M, Wang Q, Li H, Smith M, Yuan S, Perry Z, Zhou H-C (2017) Porous organic polymers for post-combustion carbon capture. Adv Mater 29:1700229

    Article  Google Scholar 

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Funding

This work was supported by the National Natural Science Foundation of China (Grant Nos. 22068023, 21766016, and 52163003), Science and Technology Planning Project of Yunnan Provincial Department of Science and Technology (202002AB080002), Youth Project of Basic Research Program of Yunnan Province (202001AU070023), Yunnan Ten Thousand Talents Plan Young & Elite Talents Project (YNWR-QNBJ2018-198), Kunming Science and Technology Planning Project (2019–1-G-25318000003480), Kunming Key Laboratory of Efficient Conversion and Utilization of Forest Resources (2019–1-A-24657), and Enterprise Basic Research Applied Basic Research Joint Special Project (202101BC070001-024).

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All authors contributed to this study. Catalyst preparation, characterization test, and data analysis were performed by Zewen Chen, Yi Liu, Wenlong Li, and Yunfei Zhi. The DFT calculation was conducted by Shuangjiang Li, Lan Shi, Xiaoning Tang, and Tianding Hu. The manuscript was written by Zewen Chen and Shaoyun Shan.

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Correspondence to Shaoyun Shan.

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Chen, Z., Zhi, Y., Li, W. et al. One-step synthesis of nitrogen-rich organic polymers for efficient catalysis of CO2 cycloaddition. Environ Sci Pollut Res 30, 67290–67302 (2023). https://doi.org/10.1007/s11356-023-26728-5

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