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Theoretical design and preparation of molecularly imprinted polymers of formaldehyde and acrylamide

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Abstract

The B3LYP/6-31G(d,p) level was performed to simulated the formaldehyde (HCHO), a molecularly imprinted self-assembly system with acrylamide (AM) as the functional monomer. HCHO–molecularly imprinted polymers (MIPs) were prepared using thermally initiated precipitation polymerisation based on the calculation results. The adsorption, selectivity and stability of HCHO–MIPs were characterised and analysed. The results revealed that the complex with an orderly arrangement of HCHO and AM had the lowest configurational energy (−109.51 kJ/mol) when the ratio of HCHO and AM was 1:4, and the cross-linking agent was pentaerythritol triacrylate. HCHO–MIPS prepared using HCHO, AM and PETA in the ratio of 1:4:16 had the best imprinting effect under certain conditions: 289-K temperature, 400-mg/L HCHO solution concentration, and 400-min absorption time. The maximum clear adsorption capacity and dissociation-equilibrium constants were 54.67 mg/g and 72.46 mg/L, respectively. The pseudo-second-order kinetic equation was used to fit the adsorption capacity. Thermodynamic studies showed that the adsorption of HCHO by HCHO–MIPs was an exothermic process. The selectivity study showed that the adsorption capacity of HCHO–MIPs for HCHO was higher than that of benzaldehyde, propionaldehyde and glyoxylic acid, showing a strong specific adsorption capacity. The HCHO–MIPs prepared using this synthetic strategy exhibited better adsorption, selectivity and stability.

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References

  1. Kuru CI, Ulucan F, Kuat K, Akgl S (2020) A model study by using polymeric molecular imprinting nanomaterials for removal of penicillin G. Environ Monit Assess 192:367–373

    Article  CAS  Google Scholar 

  2. Lai C, Zhou X, Huang D, Zeng G, Cheng M, Lei QL, Yi H, Zhang C, Xu P, Zhou C, Wang RZ, Huang C (2018) A review of titanium dioxide and its highlighted application in molecular imprinting technology in environment. J Taiwan Inst Chem E 8:1–15

    Google Scholar 

  3. Shadabfar M, Abdouss M, Khonakdar HA (2020) Synthesis, characterization, and evaluation of a magnetic molecular imprinted polymer for 5-fluorouracil as an intelligent drug delivery system for breast cancer treatment. J Mater Sci 2:1–18

    Google Scholar 

  4. Suravajhala R, Burri HR, Malik B (2020) Selective Targeted Drug Delivery Mechanism via Molecular Imprinted Polymers in Cancer Therapeutics. Curr Top Med Chem 20:1993–1998

    Article  CAS  Google Scholar 

  5. Ik D, Ahin S, Caglayan MO, Stünda Z (2021) Electrochemical impedimetric detection of kanamycin using molecular imprinting for food safety. Microchem J 160:105713–105724

    Article  Google Scholar 

  6. Cheubong C, Yoshida A, Mizukawa Y, Hayakawa N, Takeuchi T (2020) Molecularly Imprinted Nanogels Capable of Porcine Serum Albumin Detection in Raw Meat Extract for Halal Food Control. Anal Chem 92:6401–6407

    Article  CAS  Google Scholar 

  7. Subasinghe ND (2014) Theoretical study of phenol and hydroxyl radical reaction mechanism in aqueous medium by DFT/B3LYP/6-31+G(d, p)/CPCM model. Canadian J Chem 92:809–813

    Article  Google Scholar 

  8. Sun JN, Liu JB, Tang SS, Jin RF (2013) Theoretical Researches on the Self-assembly System of Ciprofloxacin Imprinted Polymers. Chinese J Struct Chem 32:1204–1210

    CAS  Google Scholar 

  9. Shi Y, Liu JB, Tang SS (2015) Jin RF, Computational Simulation on Molecular Imprinted Mechanism between Salbutamol and Trifuoromethacrylic acid. J Mol Sci 31:53–58

    CAS  Google Scholar 

  10. Gao Q, Liu JB, Tang SS, Jin RF (2018) Theoretical and experimental researches on the molecular imprinted polymer formed from chloramphenicol and 4-vinylpyridine. Chinese J Vet Drug 52:52–59

    Google Scholar 

  11. Korth HG, Heer MD, Mulder P (2002) A DFT Study on Intramolecular Hydrogen Bonding in 2-Substituted Phenols: Conformations, Enthalpies, and Correlation with Solute Parameters. J Phys Chem A 106:8779–8789

    Article  CAS  Google Scholar 

  12. Liu JB, Zhao WS, Wang GY, Tang SS, Jin RF (2020) Simulation of Phenobarbital Molecularly Imprinted Polymerization Self-assembly System and Its Adsorption Property. Anal Methods 12:813–821

    Article  CAS  Google Scholar 

  13. Liu JB, Zhao WS, Tang SS, Jin RF (2019) Theoretical Design and Adsorption Properties of Molecularly Imprinted Polymers Obtained from Chloramphenicol and Acrylamide. Chem Res Chinese Universities 36:1–6

    Google Scholar 

  14. Zhao WS, Liu JB, Tang SS, Jin RF (2020) Theoretical research of molecular imprinted polymers formed from formaldehyde and methacrylic acid. J Mol Model 26:1–8

    Article  Google Scholar 

  15. Paizs B, Suhai S (2015) Comparative study of BSSE correction methods at DFT and MP2 levels of theory. J Comput Chem 19:575–584

    Article  Google Scholar 

  16. Sheikhi M, Shahab S, Filippovich L, Dikusar E, Khaleghian M (2018) DFT Investigations (Geometry Optimization, UV/Vis, FT-IR, NMR, HOMO-LUMO, FMO, MEP, NBO, Excited States) and the Syntheses of New Pyrimidine Dyes. Chinese J Struct Chem 37:1201–1222

    Google Scholar 

  17. Oliveira BG, Pereira FS, Araújo RCMUD, Ramos MN (2006) The hydrogen bond strength: new proposals to evaluate the intermolecular interaction using DFT calculations and the AIM theory. Chem Phys Lett 427:181–184

    Article  CAS  Google Scholar 

  18. Anil K, Shruthi DL (2021) The nature of the chemical bond in sodium tungstate based on ab initio, DFT and QTAIM topological analysis of electron density. Mater Today: Proceedings 44:3127–3132

    Google Scholar 

  19. Bader R (1991) A Theory of Molecules. (Book Reviews: Atoms in Molecules. A Quantum Theory.) Science 252:1566–1567

  20. Lipkowski J, Ross PN (1994) The Electrochemistry of Novel Materials. VCH

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Acknowledgements

The Science and Technology Development Planning of Jilin Province (20200201202JC) is gratefully acknowledged.

Funding

The Science and Technology Development Planning of Jilin Province (20200201202JC).

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Authors and Affiliations

  1. College of Resource and Environmental Science, Jilin Agricultural University, Changchun, China

    Jun-bo Liu, Hanqi Chang, Wensi Zhao & Dadong Liang

  2. College of Life Sciences, The Key Laboratory of Straw Biology and Utilization, The Ministry of Education, Jilin Agricultural University, Changchun, 130118, China

    Shanshan Tang

  3. College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, China

    Ruifa Jin

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  1. Jun-bo Liu
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  2. Hanqi Chang
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  3. Wensi Zhao
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  4. Dadong Liang
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  6. Ruifa Jin
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Contributions

Junbo Liu: Conceived and designed the experiments, Funding acquisition. Wensi Zhao: Performed the experiments, Writing—original draft. Hanqi Chang: Analyzed the data. Dadong Liang: Analyzed the data. Shanshan Tang: Conceived and designed the experiments, Writing—original draft. Ruifa Jin: Provided the software.

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Correspondence to Dadong Liang or Shanshan Tang.

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Liu, Jb., Chang, H., Zhao, W. et al. Theoretical design and preparation of molecularly imprinted polymers of formaldehyde and acrylamide. J Polym Res 28, 433 (2021). https://doi.org/10.1007/s10965-021-02724-6

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  • DOI: https://doi.org/10.1007/s10965-021-02724-6

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