Advertisement

Analytical and Bioanalytical Chemistry

, Volume 410, Issue 21, pp 5183–5193 | Cite as

Enhanced molecular recognition for imprinted monolithic column containing polyhedral oligomeric silsesquioxanes by dendritic effect of mesoporous molecular sieve scaffolds

  • Fang-Fang Yang
  • Zai-Xuan Li
  • Yu-Jing Xu
  • Yan-Ping HuangEmail author
  • Zhao-Sheng LiuEmail author
Research Paper

Abstract

The dendritic effect of nano mesoporous molecular sieve was first used to enhance molecular recognition of molecularly imprinted polymers (MIPs)-based polyhedral oligomeric silsesquioxanes (POSS). In this study, the MIPs were made using S-naproxen (S-NAP) as template molecule, 4-vinylpyridine (4-VP) as functional monomer, ethylene glycol dimethacrylate as cross-linker, 1-butyl-3-methylimidazoliumtetrafluoroborate ([BMIM]BF4)/DMSO as binary porogens, 1-propylmethacrylate-heptaisobutyl substituted as POSS monomer, and mesoporous molecular sieve (Mobil composition of matter No. 41, MCM-41) as dendritic scaffold. The influence of synthesis parameters on the imprinting effect, including the content of POSS monomer and derivatized MCM-41-MPS, the ratio of template to monomer, and the ratio of binary porogens were also investigated, respectively. The morphology of the polymers was characterized by scanning electron microscopy, nitrogen adsorption, and X-ray powder diffraction. The results showed that POSS&MCM-41-MPS MIP had a stronger imprinting effect with an imprinting factor 6.86, which is approximately 2.4, 2.3, and 3 times than that of POSS MIP, MCM-41-MPS MIP, and conventional MIP, respectively. The increase of affinity might be attributed to impediment of the chain motion of polymer due to improved POSS aggregation and the dipole interaction between the POSS units by introduce of MCM-41-MPS as scaffolds. The resulting POSS&MCM-41-MPS MIP was used as adsorbent for the enrichment of S-NAP in solid-phase extraction with a high recovery of 97.65% and the value of RSD was 0.94%.

Keywords

Molecularly imprinted polymer Dendritic effect Polyhedral oligomeric silsesquioxanes Mesoporous molecular sieve S-naproxen 

Notes

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant No. 21775109).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

216_2018_1166_MOESM1_ESM.pdf (560 kb)
ESM 1 (PDF 560 kb)

References

  1. 1.
    Wei ZH, Mu LN, Huang YP, Liu ZS. Imprinted monoliths: recent significant progress in analysis field. Trends Anal Chem. 2017;86:84–92.CrossRefGoogle Scholar
  2. 2.
    Huang YP, Zheng C, Liu ZS. Molecularly imprinted polymers for the separation of organic compounds in capillary electrochromatography. Curr Org Chem. 2011;15:1863–70.CrossRefGoogle Scholar
  3. 3.
    Ansari S, Karimi M. Challenges and trends in trace determination of drug analysis using molecularly imprinted solid-phase microextraction technology. Talanta. 2017;164:612–25.CrossRefPubMedGoogle Scholar
  4. 4.
    Haupt K, Linares AV, Bompart M, Bernadette TSB. Molecularly imprinted polymers. Top Curr Chem. 2012;325:1–28.PubMedGoogle Scholar
  5. 5.
    Phillips SH, Haddad TS, Tomczak SJ. Developments in nanoscience: polyhedral oligomeric silsesquioxane (POSS)-polymers. Curr Opin Solid State Mater Sci. 2004;8:21–9.CrossRefGoogle Scholar
  6. 6.
    Xiong XY, Yang ZH, Li YX, Xiao LH, Jiang LB, Chen YZ, et al. Preparation of a polyhedral oligomeric silsesquioxane-based perfluorinated monolithic column. J Chromatogr A. 2013;1304:85–91.CrossRefPubMedGoogle Scholar
  7. 7.
    Lin H, Zhang ZB, Dong J, Zou HF. Ring-opening polymerization reaction of polyhedral oligomeric silsesquioxanes (POSSs) for preparation of well-controlled 3D skeletal hybrid monoliths. Chem Commun. 2013;49:231–3.CrossRefGoogle Scholar
  8. 8.
    Chen CY, Liang XT, Wang JP, Zou Y, Hu HP, Cai QY, et al. Development of a polymeric ionic liquid coating for direct-immersion solid-phase microextraction using polyhedral oligomeric silsesquioxane as cross-linker. J Chromatogr A. 2014;1348:80–6.CrossRefPubMedGoogle Scholar
  9. 9.
    Ou JJ, Zhang ZB, Lin H, Dong J, Wu MH, Zou HF. Preparation and application of hydrophobic hybrid monolithic columns containing polyhedral oligomeric silsesquioxanes for capillary electrochromatography. Electrophoresis. 2012;33:1660–8.CrossRefPubMedGoogle Scholar
  10. 10.
    Carroll JB, Frankamp BL, Rotello VM. Self-assembly of gold nanoparticles through tandem hydrogen bonding and polyoligosilsequioxane (POSS)-POSS recognition processes. Chem Commun. 2002;17:1892–3.CrossRefGoogle Scholar
  11. 11.
    Li F, Chen XX, Huang YP, Liu ZS. Preparation of polyhedral oligomeric silsesquioxane based imprinted monolith. J Chromatogr A. 2015;1425:180–8.CrossRefPubMedGoogle Scholar
  12. 12.
    Gao SP, Zhang X, Zhang LS, Huang YP, Liu ZS. Molecularly imprinted polymer prepared with polyhedral oligomeric silsesquioxane through reversible addition–fragmentation chain transfer polymerization. Anal Bioanal Chem. 2017;409:3741–8.CrossRefPubMedGoogle Scholar
  13. 13.
    Zhao QL, Zhou J, Zhang LS, Huang YP, Liu ZS. Coatings of molecularly imprinted polymers based on polyhedral oligomeric silsequioxane for open tubular capillary electrochromatography. Talanta. 2016;152:277–82.CrossRefPubMedGoogle Scholar
  14. 14.
    Xu H, Kuo SW, Huang CF, Chang FC. Poly (acetoxystyrene-co-isobutylstyryl POSS) nanocomposites: characterization and molecular interaction. J Polym Res. 2002;9:239–44.CrossRefGoogle Scholar
  15. 15.
    Xu Y, Cao Q, Svec F, Fréchet JMJ. Porous polymer monolithic column with surface-bound gold nanoparticles for the capture and separation of cysteine containing peptides. Anal Chem. 2010;82:3352–8.CrossRefPubMedPubMedCentralGoogle Scholar
  16. 16.
    Boal AK, Rotello VM. Radial control of recognition and redox processes with multivalent nanoparticle hosts. J Am Chem Soc. 2002;124:5019–24.CrossRefPubMedGoogle Scholar
  17. 17.
    Drechsler U, Erdogan B, Rotell VM. Nanoparticles: scaffolds for molecular recognition. Chem Eur J. 2004;10:5570–9.CrossRefPubMedGoogle Scholar
  18. 18.
    Shenhar R, Rotello VM. Nanoparticles: scaffolds and building blocks. J Chem Inform. 2003;36:549–61.Google Scholar
  19. 19.
    Dehghani S, Haghighi M. Sono-sulfated zirconia nanocatalyst supported on MCM-41 for biodiesel production from sunflower oil: influence of ultrasound irradiation power on catalytic properties and performance. Ultrason Sonochem. 2017;35:142–51.CrossRefPubMedGoogle Scholar
  20. 20.
    Wu YC, Yang XF, Hao L. Improved oxygen optical sensing performance from Re(I) complex doped MCM-41 composite samples by incorporating oxadiazole ring into diamine ligand: synthesis, characterization and sensing response. Sensors Actuators B Chem. 2017;244:1113–20.CrossRefGoogle Scholar
  21. 21.
    Brady R, Brad W, Gee ML, O'Connor AJ. Hierarchical mesoporous silica materials for separation of functional food ingredients—A review. Innovative Food Sci Emerg Technol. 2008;9:243–8.CrossRefGoogle Scholar
  22. 22.
    Boccardi E, Philippart A, Juhasz-Bortuzzo JA, Beltrán AM, Novajra G, Vitale-Brovarone C, et al. Uniform surface modification of 3D Bioglass (®)-based scaffolds with mesoporous silica particles (MCM-41) for enhancing drug delivery capability. Front Bioeng Biotechnol. 2015;3:177–99.CrossRefPubMedPubMedCentralGoogle Scholar
  23. 23.
    Hasanzadeh M, Shadjou N, Omidinia E. Mesoporous silica (MCM-41)-Fe2O3 as a novel magnetic nanosensor for determination of trace amount of amino acid. Colloid Surf B: Biointerfaces. 2013;108:52–9.CrossRefPubMedGoogle Scholar
  24. 24.
    He H, Gu X, Shi L, Hong J, Zhang H, Gao Y, et al. Molecularly imprinted polymers based on SBA-15 for selective solid-phase extraction of baicalein from plasma sample. Anal Bioanal Chem. 2015;407:509–19.CrossRefPubMedGoogle Scholar
  25. 25.
    Yang JJ, Li Y, Wang JC, Sun XL, Syed MS, Cao R, et al. Novel sponge-like molecularly imprinted mesoporous silica material for selective isolation of bisphenol A and its analogues from sediment extract. Anal Chim Acta. 2015;853:311–9.CrossRefPubMedGoogle Scholar
  26. 26.
    Cheng WJ, Ma HT, Zhang L, Wang Y. Hierarchically imprinted mesoporous silica polymer: an efficient solid-phase extractant for bisphenol A. Talanta. 2014;120:255–61.CrossRefPubMedGoogle Scholar
  27. 27.
    Wang L, Yan HY, Yang CL, Li Z, Qiao FX. Synthesis of mimic molecularly imprinted ordered mesoporous silica adsorbent by thermally reversible semicovalent approach forpipette-tip solid-phase extraction-liquid chromatography fluorescence determination of estradiol in milk. J Chromatogr A. 2016;1456:58–67.CrossRefPubMedGoogle Scholar
  28. 28.
    Grün M, Unger KK, Matsumoto A, Tsutsumi K. Novel pathways for the preparation of mesoporous MCM-41 materials: control of porosity and morphology. Microporous Mesoporous Mater. 1999;27:207–16.CrossRefGoogle Scholar
  29. 29.
    Zhou XS, Wu TB, Ding KL, Hu BJ, Hou MQ, Han BX. The dispersion of carbon nanotubes in water with the aid of very small amounts of ionic liquid. Chem Commun. 2009;14:1897–9.CrossRefGoogle Scholar
  30. 30.
    Ban L, Zhao L, Deng BL, Huang YP, Liu ZS. Preparation and characterization of an imprinted monolith by atom transfer radical polymerization assisted by crowding agents. Anal Bioanal Chem. 2013;405:2245–53.CrossRefPubMedGoogle Scholar
  31. 31.
    Madikizela LM, Tavengwa NT, Chimuka L. Applications of molecularly imprinted polymers for solid-phase extraction of non-steroidal anti-inflammatory drugs and analgesics from environmental waters and biological samples. J Pharm Biomed Anal. 2018;147:624–33.CrossRefPubMedGoogle Scholar
  32. 32.
    Umpleby RJ II, Baxter SC, Chen YZ, Shah RN, Shimizu KD. Characterization of molecularly imprinted polymers with the Langmuir-Freundlich isotherm. Anal Chem. 2001;73:4584–91.CrossRefPubMedGoogle Scholar
  33. 33.
    Sing KSW. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Provisional). Pure Appl Chem. 1982;54:2201–18.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of PharmacyTianjin Medical UniversityTianjinChina

Personalised recommendations