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Synthesis of Octyl-Quaternary Ammonium Mixed-Mode Stationary Phase by Vapor Deposition Approach and Its Application in Compound Preparation Separation

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Abstract

An octyl-quaternary ammonium (Sil-C8-QA)-modified silica stationary phase was prepared by a two-step vapor deposition method which can substantially reduce the consumption of toxic organic solvents. The structure of the dual-functional ligands stationary phase was characterized by Fourier transform infrared spectroscopy and solid-state 13C CP/MAS NMR. Following elemental analysis, the surface density of octyl and quaternary ammonium bonding amount is 2.13 µmol m−2 and 0.77 µmol m−2, respectively. The efficiency and selectivity of the two-ligand phases were compared with two sole functional ligand phases: quaternary ammonium (Sil-QA)- and octyl-modified silica (Sil-C8). Chromatographic evaluation demonstrated a mixed-mode reversed-phase/anion-exchange retention property on the Sil-C8-QA column. The retention behavior of a homologous series of alkylbenzoic acids on the synthesized phase was systematically studied by changing the pH, ionic, and solvent strength of the mobile phase. A well-established mixed-model mechanism was confirmed. The Sil-C8-QA phase can predominantly enhance the retention of acidic drugs and improve their selectivity. It was also successfully applied to the simultaneous separation and determination of three kinds of compound preparations with large differences in component polarity.

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References

  1. Yan JL, Li M, Li RY, Wu LP, Sun YF, Li HL (2013) Chin J Tissue Eng Res 33:6055–6060

    Google Scholar 

  2. Li QP, Liu XM, Dai JD (2014) China J Chin Mater Med 39:402–406

    CAS  Google Scholar 

  3. Snyder LR, Kirkland JJ, Dolan JW (2010) Introduction to modern liquid chromatography, 3rd edn. Wiley, Weinheim

    Google Scholar 

  4. Fekete S, Oláh E, Fekete J (2012) J Chromatogr A 1228:57–71

    Article  CAS  PubMed  Google Scholar 

  5. Qiu HD, Liang XJ, Sun M, Jiang SX (2011) Anal Bioanal Chem 399:3307–3322

    Article  CAS  PubMed  Google Scholar 

  6. Yang Y, Geng XD (2011) J Chromatogr A 1218:8813–8825

    Article  CAS  PubMed  Google Scholar 

  7. Hu K, Feng SX, Wu MX, Wang S, Zhao WJ, Jiang Q, Yu AJ, Zhang SS (2014) Talanta 130:63–70

    Article  CAS  PubMed  Google Scholar 

  8. Sun M, Qiu HD, Wang LC, Liu X, Jiang SX (2009) J Chromatogr A 1216:3904–3909

    Article  CAS  PubMed  Google Scholar 

  9. Sun M, Feng JJ, Luo CN, Liu X, Jiang SX (2013) Talanta 105:135–141

    Article  CAS  PubMed  Google Scholar 

  10. Sun M, Feng JJ, Liu SJ, Xiong CM, Liu X, Jiang SX (2011) J Chromatogr A 1218:3743–3749

    Article  CAS  PubMed  Google Scholar 

  11. Zimmermann A, Greco R, Walker I, Horak J, Cavazzini A (2014) J Chromatogr A 1354:43–55

    Article  CAS  PubMed  Google Scholar 

  12. Yang F, Bai Q, Zhao KL, Gao D, Tian L (2015) Anal Bioanal Chem 407:1721–1734

    Article  CAS  PubMed  Google Scholar 

  13. Shen GB, Zhang FF, Yang BC, Chu CG, Liang XM (2013) Talanta 115:129–132

    Article  CAS  PubMed  Google Scholar 

  14. Qiao LZ, Wang SY, Li H, Shan YH, Dou A, Shi XZ, Xu GW (2014) J Chromatogr A 1360:240–247

    Article  CAS  PubMed  Google Scholar 

  15. Iverson CD, Lucy CA (2014) J Chromatogr A 1373:17–24

    Article  CAS  PubMed  Google Scholar 

  16. Sun M, Feng JJ, Wang XW, Duan HM, Li LL, Luo CN (2014) J Sep Sci 37:2153–2159

    Article  CAS  PubMed  Google Scholar 

  17. Abbood A, Smadja C, Herrenknecht C, Alahmad Y, Tchapla A, Taverna M (2009) J Chromatogr A 1216:3244–3251

    Article  CAS  PubMed  Google Scholar 

  18. Abbood A, Smadja C, Taverna M, Herrenknecht C (2010) J Chromatogr A 1217:450–458

    Article  CAS  PubMed  Google Scholar 

  19. Liu QX, Liang T, Li KY, Ke YX, Jin Y, Liang XM (2012) J Sep Sci 35:2685–2692

    Article  CAS  PubMed  Google Scholar 

  20. Wikström P, Mandenius CF, Larsson PO (1988) J Chromatogr A 455:105–117

    Article  Google Scholar 

  21. Li RS, Wan QH (2018) Chromatographia 81:1623–1630

    Article  CAS  Google Scholar 

  22. Chen M, Chen L (2018) Anal Methods 10:1538–1546

    Article  CAS  Google Scholar 

  23. Guo ZQ, Chen F, Deng Y, Wan QH, Chen L (2009) Chem J Chin Univ 30:2017–2023

    CAS  Google Scholar 

  24. Giri S, Inostroza-Rivera R, Herrera B, Núñez AS, Lund F, Toro-Labbé A (2014) J Mol Model 20:2353

    Article  CAS  PubMed  Google Scholar 

  25. Cao W, Wang ZQ, Zeng QL, Shen CH (2016) Appl Surf Sci 389:404–410

    Article  CAS  Google Scholar 

  26. Huang XJ, Wang JD, Liu XL, Shang ZH (2001) Chromatographia 54:350–354

    Article  CAS  Google Scholar 

  27. Berendsen G, Galan LD (1978) J Liq Chromatogr 5:561–586

    Article  Google Scholar 

  28. Zhang MY, Wang HB, Chen H, Sun XL, Jiang R (2011) Acta Chim Slov 58:60–68

    CAS  PubMed  Google Scholar 

  29. Hu K, Zhang WF, Yang HX, Cui YX, Zhang JY, Zhao WJ, Yu AJ, Zhang SS (2016) Talanta 152:392–400

    Article  CAS  PubMed  Google Scholar 

  30. Ståhlberg J (1999) J Chromatogr A 855:3–55

    Article  PubMed  Google Scholar 

  31. Ford MS (1969) Analyst 91:15–22

    Article  Google Scholar 

  32. Yang X, Dai J, Carr PW (2003) J Chromatogr A 996:13–31

    Article  CAS  PubMed  Google Scholar 

  33. Neue UD, Tran KV, Méndez A, Carr PW (2005) J Chromatogr A 1063:35–45

    Article  CAS  PubMed  Google Scholar 

  34. Li LX, Lai CY, Xuan XY, Gao CK, Li N (2016) J Chromatogr Sci 54:1415–1420

    Article  CAS  PubMed  Google Scholar 

  35. Wang YH, Liu GR, Fu CG, Wang XS, Cao XQ, Wang SE (2006) Chin J Pharm Anal 26:692–695

    CAS  Google Scholar 

  36. Burdan F (2002) Hum Exp Toxicol 21:25–31

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We thank Prof. Qian-Hong Wan from Tianjin University for his technical assistance with chromatography evaluation. We also thank Dr. Xinghua Jin of Tianjin University for performing the elemental analysis.

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  1. School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin, 300072, China

    Fan Zhang & Lei Chen

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  1. Fan Zhang
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  2. Lei Chen
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Correspondence to Lei Chen.

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Zhang, F., Chen, L. Synthesis of Octyl-Quaternary Ammonium Mixed-Mode Stationary Phase by Vapor Deposition Approach and Its Application in Compound Preparation Separation. Chromatographia 82, 1437–1447 (2019). https://doi.org/10.1007/s10337-019-03774-1

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