Abstract
The economical and convenient one-pot approach plays a substantial role in chemical synthesis and material design. However, the related reports on the synthesis and functionalization of covalent organic frameworks (COFs) by the one-pot approach are limited. Herein, we selectively introduced three different functional groups (fluoroalkyl, borate, and alkyl groups) to verify that the multi-component one-pot tandem reaction could be applied into surface post-functionalization of COFs as an economical strategy. After proving the practicability of the economical strategy, we also prepared two kinds of fluorine-containing COFs (COF-F0.5 and COF-F) and butyl-containing COF (COF-Bu) via the economical strategy to explore the effect of COF nature (porosity and the number of functional groups) on fipronil adsorption. The results showed that COF-F0.5 possessing the largest Brunauer–Emmett–Teller (BET) specific surface area (1573 m2 g−1) exhibited a larger saturated adsorption capacity (194.7 mg g−1) than COF-F (149.8 mg g−1). Furthermore, comparing with COF-Bu (122.4 mg g−1), COF-F (149.8 mg g−1) containing functional groups showed a greater adsorption capacity.
Graphical abstract
Post-functionalization of covalent organic frameworks by multiple-component one-pot tandem reactions was reported and the related application in the adsorption of pesticides was also studied.
Similar content being viewed by others
References
Hayashi Y (2016) Pot economy and one-pot synthesis. Chem Sci 7: 866–880
Cui P, Liu Q, Wang J et al (2019) One-pot synthesis of chiral β-hydroxysulfones from alkynes via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O. Green Chem 21:634–639
KraEm J, Ollevier T (2017) Atom economical synthesis of N-alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant. Green Chem 19:1263–1267
Talekar S, Joshi A, Kambale S et al (2017) A tri-enzyme magnetic nanobiocatalyst with one pot starch hydrolytic activity. Chem Eng J 325:80–90
Behr A, Vorholt AJ, Ostrowski KA, Seidensticker T (2014) Towards resource efficient chemistry: tandem reactions with renewables. Green Chem 16:982–1006
Hernandez JG, Juaristi E (2012) Recent efforts directed to the development of more sustainable asymmetric organocatalysis. Chem Commun 48:5396–5409
Cioc RC, Ruijter E, Orru RVA (2014) Multicomponent reactions: advanced tools for sustainable organic synthesis. Green Chem 16:2958–2975
Wu S, Zhou Y, Li Z (2019) Biocatalytic selective functionalisation of alkenes via single-step and one-pot multi-step reactions. Chem Commun 55:883–896
Liu L, Meng WK, Zhou YS et al (2019) β-Ketoenamine-linked covalent organic framework coating for ultra-high-performance solid-phase microextraction of polybrominated diphenyl ethers from environmental samples. Chem Eng J 356:926–933
Huang N, Zhai L, Xu H, Jiang D (2017) Stable covalent organic frameworks for exceptional mercury removal from aqueous solutions. J Am Chem Soc 139:2428–2434
Li Y, Chen W, Xing G et al (2020) New synthetic strategies toward covalent organic frameworks. Chem Soc Rev 49:2852–2868
Wang T, Wu H, Zhao S et al (2019) Interfacial polymerized and pore-variable covalent organic framework composite membrane for dye separation. Chem Eng J 384:123347
Feng T, Wang JM, Gao ST et al (2018) Covalent triazine frameworks supported CoPd nanoparticles for boosting hydrogen generation from formic acid. Appl Surf Sci 469:431–436
Li J, Jing X, Li Q et al (2020) Bulk COFs and COF nanosheets for electrochemical energy storage and conversion. Chem Soc Rev 49:3565–3604
Nguyen HL, Gropp C, Yaghi OM (2020) Reticulating 1D ribbons into 2D covalent organic frameworks by imine and imide linkages. J Am Chem Soc 142:2771–2776
Zhang B, Mao H, Matheu R et al (2019) Reticular synthesis of multinary covalent organic frameworks. J Am Chem Soc 141:11420–11424
Cui W-R, Jiang W, Zhang C-R et al (2020) Regenerable carbohydrazide-linked fluorescent covalent organic frameworks for ultrasensitive detection and removal of mercury. ACS Sustain Chem Eng 8:445–451
Liang Y, Feng L, Liu X et al (2021) Enhanced selective adsorption of NSAIDs by covalent organic frameworks via functional group tuning. Chem Eng J 404:127095
Uribe-Romo FJ, Doonan CJ, Furukawa H et al (2011) Crystalline covalent organic frameworks with hydrazone linkages. J Am Chem Soc 133:11478–11481
Huang N, Krishna R, Jiang D (2015) Tailor-made pore surface engineering in covalent organic frameworks: systematic functionalization for performance screening. J Am Chem Soc 137:7079–7082
Pyles DA, Crowe JW, Baldwin LA, McGrier PL (2016) Synthesis of benzobisoxazole-linked two-dimensional covalent organic frameworks and their carbon dioxide capture properties. ACS Macro Lett 5:1055–1058
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 131:8875–8883
Yu Y, Li G, Liu J, Yuan D (2020) A recyclable fluorescent covalent organic framework for exclusive detection and removal of mercury(II). Chem Eng J 401:126139
Lu Y, Liang Y, Zhao Y et al (2021) Fluorescent test paper via the in situ growth of COFs for rapid and convenient detection of Pd(II) ions. ACS Appl Mater Interfaces 13:1644–1650
Liu Z, Su Q, Ju P et al (2020) A hydrophilic covalent organic framework for photocatalytic oxidation of benzylamine in water. Chem Commun 56:766–769
Liu W, Li X, Wang C et al (2019) A scalable general synthetic approach toward ultrathin imine-linked two-dimensional covalent organic framework nanosheets for photocatalytic CO2 reduction. J Am Chem Soc 141:17431–17440
Dalapati S, Addicoat M, Jin S et al (2015) Rational design of crystalline supermicroporous covalent organic frameworks with triangular topologies. Nat Commun 6:7786
Jiang Q, Li Y, Zhao X et al (2018) Inverse-vulcanization of vinyl functionalized covalent organic frameworks as efficient cathode materials for Li–S batteries. J Mater Chem A 6:17977–17981
Cheng W, Yi M, Guiqing L et al (2018) Impregnation of sulfur into a 2D pyrene-based covalent organic framework for high-rate lithium–sulfur batteries. J Mater Chem A 6:17186–17191
Wang S, Liang Y, Dai T et al (2021) Cationic covalent-organic framework for sulfur storage with high-performance in lithium-sulfur batteries. J Colloid Interface Sci 591:264–272
Wang K, Jia Z, Bai Y et al (2020) Synthesis of stable thiazole-linked covalent organic frameworks via a multicomponent reaction. J Am Chem Soc 142:11131–11138
Li X-T, Zou J, Wang T-H et al (2020) Construction of covalent organic frameworks via three-component one-pot Strecker and Povarov reactions. J Am Chem Soc 142:6521–6526
Wang P-L, Ding S-Y, Zhang Z-C et al (2019) Constructing robust covalent organic frameworks via multicomponent reactions. J Am Chem Soc 141:18004–18008
Wu N, Zhao LX, Jiang CY et al (2020) A naked-eye visible colorimetric and fluorescent chemosensor for rapid detection of fluoride anions: Implication for toxic fluorine-containing pesticides detection. J Mol Liq 302:112549
Lin C, Qiu Y, Fan J et al (2020) Fabrication of photo-responsive cellulose based intelligent imprinted material and selective adsorption on typical pesticide residue. Chem Eng J 394:124841
Zhang B, Li B, Wang Z (2020) Creation of carbazole-based fluorescent porous polymers for recognition and detection of various pesticides in water. ACS Sensors 5:162–170
Xu H, Gao J, Jiang D (2015) Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts. Nat Chem 7:905–912
Merí-Bofí L, Royuela S, Zamora F et al (2017) Thiol grafted imine-based covalent organic frameworks for water remediation through selective removal of Hg(II). J Mater Chem A 5:8933–8938
Rohde RD, Agnew HD, Yeo W-S et al (2006) A non-oxidative approach toward chemically and electrochemically functionalizing Si(111). J Am Chem Soc 128:9518–9525
Jiang Y, Liu C, Li Y, Huang A (2019) Stainless-steel-net-supported superhydrophobic COF coating for oil/water separation. J Memb Sci 587:117177
Dong A, Zhu Y, Ren M et al (2019) Remarkably enhanced CO2 uptake and uranium extraction by functionalization of cyano-bearing conjugated porous polycarbazoles. Eng Sci 6:44–52
Dong A, Wang D, Dai T et al (2018) Micro/mesoporous conjugated fluorinated iron-porphyrin polymer: porosity and heterogeneous catalyst for oxidation. Adv Compos Hybrid Mater 1:696–704
Dong A, Dai T, Ren M et al (2018) Functionalization and fabrication of soluble polymers of intrinsic microporosity for CO2 transformation and uranium extraction. Eng Sci 5:56–65
Liu S, Liang L, Meng L et al (2020) Synergy of plasmonic silver nanorod and water for enhanced planar perovskite photovoltaic devices. Sol RRL 4:1900231
Zhang J, Zhang W, Wei L et al (2019) Alternating multilayer structural epoxy composite coating for corrosion protection of steel. Macromol Mater Eng 304:1970035
Zhang Z, Zhang J, Li S et al (2019) Effect of graphene liquid crystal on dielectric properties of polydimethylsiloxane nanocomposites. Compos Part B Eng 176:107338
Chang Z, Liang Y, Wang S et al (2020) A novel fluorescent covalent organic framework containing boric acid groups for selective capture and sensing of cis-diol molecules. Nanoscale 12:23748–23755
Liu X, Wang S, Liang Y et al (2021) Adenine-bearing covalent organic frameworks via one-pot tandem reaction for selective adsorption of Ag+. Microporous Mesoporous Mater 315:110923
Du Z, Deng S, Zhang S et al (2017) Selective and fast adsorption of perfluorooctanesulfonate from wastewater by magnetic fluorinated vermiculite. Environ ence Technol 51:8027–8035
Sun Q, Aguila B, Perman JA et al (2018) Integrating superwettability within covalent organic frameworks for functional coating. Chem 4:1726–1739
Du Z, Deng S, Bei Y et al (2014) Adsorption behavior and mechanism of perfluorinated compounds on various adsorbents–a review. J Hazard Mater 274:443–454
Funding
This work was supported by the Hainan Science and Technology Major Project (ZDKJ2019013), the National Natural Science Foundation of China (52063014, 51873053, 51775152, 61761016, and U1967213), the National Key R&D program of China (2019YFC1904304 and 2018YFE0103500), and the Fundamental Research Funds for the Central Universities (2020YQHH01). Ning Yuan also received funding from the Foundation of State Key Laboratory of Structural Chemistry (20190003).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
There authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, S., Yuan, N., Dai, T. et al. Surface post-functionalization of COFs by economical strategy via multiple-component one-pot tandem reactions and their application in adsorption of pesticides. Adv Compos Hybrid Mater 5, 1439–1449 (2022). https://doi.org/10.1007/s42114-021-00241-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s42114-021-00241-0