Skip to main content
SpringerLink
Log in

Metal–Organic Framework InH(d-C10H14O4)2 for Improved Enantioseparations on a Chiral Cyclodextrin Stationary Phase in GC

  • Original
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

The chiral MOF InH(d-C10H14O4)2 has a left-handed helical structure and adopts a diamond network. In this work, three capillary columns (A, B, and C) containing InH(d-C10H14O4)2, peramylated β-cyclodextrin and sodium chloride, and InH(d-C10H14O4)2 and peramylated β-cyclodextrin have been prepared and their respective enantioseparation abilities have been investigated. The polarity of the MOF is moderate, whereas peramylated β-cyclodextrin provides a stationary phase of low polarity. The numbers of theoretical plates (plate m−1) of the three columns have been measured with n-dodecane at 120 °C, which followed an increasing order of A (2,973) < B (3,563) < C (3,665). 1-Phenylethanol, dihydrocarvyl acetate, citronellal, leucine, methyl l-β-hydroxyisobutyrate, limonene, and menthol were separated with different resolutions on columns A, B, and C. The relative standard deviations (RSDs) in the run-to-run and column-to-column retention times were 0.50 and 2.50 %, respectively. The test results indicated that the incorporated InH(d-C10H14O4)2 enhanced the separations of racemates on a peramylated β-cyclodextrin stationary phase, resulting in high column efficiency and good reproducibility in gas chromatography.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Gu ZY, Yang CX, Chang N, Yan XP (2012) Acc Chem Res 45:734–745

    Article  CAS  Google Scholar 

  2. Salles F, Ghoufi A, Maurin G, Bell RG, Mellot Draznieks C, Ferey G (2008) Angew Chem Int Ed 47:8487–8491

    Article  CAS  Google Scholar 

  3. Chang N, Gu ZY, Yan XP (2010) J Am Chem Soc 132:13645–13647

    Article  CAS  Google Scholar 

  4. Gu ZY, Yan XP (2010) Angew Chem Int Ed 49:1477–1480

    Article  CAS  Google Scholar 

  5. Li LM, Yang F, Wang HF, Yan XP (2013) J Chromatogr A 1316:97–103

    Article  CAS  Google Scholar 

  6. Yu LQ, Yang CX, Yan XP (2014) J Chromatogr A 1343:188–194

    Article  CAS  Google Scholar 

  7. Ma LF, Wang LY, Wang YY, Du M, Wang JG (2009) CrystEng Comm 11:109–117

    Article  CAS  Google Scholar 

  8. Suh KQ, Yutkin MP, Dybtsev DN, Fedin VP, Kim K (2012) Chem Commun 48:513–515

    Article  CAS  Google Scholar 

  9. Xu YY, Xu LF, Qi SD, Dong YL, Rahman Z, Chen HL, Chen XG (2013) Anal Chem 85:11369–11375

    Article  CAS  Google Scholar 

  10. Chang N, Gu ZY, Wang HF, Yan XP (2011) Anal Chem 83:7094–7101

    Article  CAS  Google Scholar 

  11. Yang CX, Liu SS, Wang HF, Wang SW, Yan XP (2012) Analyst 137:133–139

    Article  CAS  Google Scholar 

  12. Fu YY, Yang CX, Yan XP (2012) Langmuir 28:6794–6802

    Article  CAS  Google Scholar 

  13. Chang N, Yan XP (2012) J Chromatogr A 1257:116–124

    Article  CAS  Google Scholar 

  14. Gu ZY, Jiang JQ, Yan XP (2011) Anal Chem 83:5093–5100

    Article  CAS  Google Scholar 

  15. Yang CX, Yan XP (2011) Anal Chem 83:7144–7150

    Article  CAS  Google Scholar 

  16. Liu SS, Yang CX, Wang SW, Yan XP (2012) Analyst 137:816–818

    Article  CAS  Google Scholar 

  17. Yang CX, Chen YJ, Wang HF, Yan XP (2011) Chem Eur J 17:11734–11737

    Article  CAS  Google Scholar 

  18. Fu YY, Yang CX, Yan XP (2013) J Chromatogr A 1274:137–144

    Article  CAS  Google Scholar 

  19. Li LM, Wang HF, Yan XP (2012) Electrophoresis 33:2896–2902

    Article  CAS  Google Scholar 

  20. Xie SM, Zhang ZJ, Wang ZY, Yuan LM (2011) J Am Chem Soc 133:11892–11895

    Article  CAS  Google Scholar 

  21. Xiang SC, Zhang Z, Zhao CG, Hong K, Zhao X, Ding DR, Xie MH, Wu CD, Das MC, Gill R, Thomas KM, Chen B (2011) Nat Comms 2:204

    Article  Google Scholar 

  22. Xie SM, Zhang XH, Zhang ZJ, Zhang M, Jia J, Yuan LM (2013) Anal Bioanal Chem 405:3407–3412

    Article  CAS  Google Scholar 

  23. Das MC, Guo Q, He Y, Kim J, Zhao CG, Hong K, Xiang S, Zhang Z, Thomas KM, K-rishna R, Chen B (2012) J Am Chem Soc 134:8703–8710

    Article  CAS  Google Scholar 

  24. Zhang M, Pu ZJ, Chen XL, Gong XL, Zhu AX, Yuan LM (2013) Chem Commun 49:5201–5203

    Article  CAS  Google Scholar 

  25. Zhang M, Zhang JH, Zhang Y, Wang BJ, Xie SM, Yuan LM (2014) J Chromatogr A 1325:163–170

    Article  CAS  Google Scholar 

  26. Zhang M, Xue XD, Zhang JH, Xie SM, Zhang Y, Yuan LM (2014) Anal Methods 6:341–346

    Article  CAS  Google Scholar 

  27. Kuang X, Ma Y, Su H, Zhang J, Dong YB, Tang B (2014) Anal Chem 86:1277–1281

    Article  CAS  Google Scholar 

  28. Fei ZX, Zhang M, Zhang JH, Yuan LM (2014) Anal Chim Acta 830:49–55

    Article  CAS  Google Scholar 

  29. Li ZF, Ban XF, Gu ZB, Li CM, Huang M, Hong Y, Li C (2014) Carbohydr Polym 108:112–117

    Article  CAS  Google Scholar 

  30. Qi QS, Zimmermann WG (2005) Appl Microbiol Biotechnol 66:475–485

    Article  CAS  Google Scholar 

  31. Saenger W (1980) Angew Chem Int Ed 19:344–362

    Article  Google Scholar 

  32. Harada A (2001) Acc Chem Res 34:456–464

    Article  CAS  Google Scholar 

  33. Juvancz Z, Alexander G, Szejtli J (1987) J High Resolut Chromatogr 10:105–107

    Article  CAS  Google Scholar 

  34. Alexander G, Juvancz Z, Szejtli J (1988) J High Resolut Chromatogr 11:110–113

    Article  CAS  Google Scholar 

  35. Venema A, Tolsma PJA (1989) J High Resolut Chromatogr 12:32–34

    Article  CAS  Google Scholar 

  36. Sybliska D, Koscielski T (1983) J Chromatogr A 261:357–362

    Article  Google Scholar 

  37. König WA, Lutz DCS, Wenz G (1988) Angew Chem Int Ed 27:979–980

    Article  Google Scholar 

  38. König WA, Lutz S, Mischnick-Lübbecke P, Brassat B, Wenz G (1988) J Chromatogr A 447:193–197

    Article  Google Scholar 

  39. Armstrong DW, Stalcup AM, Hilton ML, Duncan JD, Faulkner JR Jr, Chang SC (1990) Anal Chem 62:1610–1615

    Article  CAS  Google Scholar 

  40. Armstrong DW, Li WY, Stalcup AM, Secor HV, Izac RR, Seeman JI (1990) Anal Chim Acta 234:365–380

    Article  CAS  Google Scholar 

  41. Bicchi C, D’Amato A, Rubiolo P (1999) J Chromatogr A 843:99–121

    Article  CAS  Google Scholar 

  42. Bicchi C, D’Amato A, Manzin V, Rubiolo P (1997) Flavour Fragr J 12:55–61

    Article  CAS  Google Scholar 

  43. Liu H, Xie SM, Ai P, Zhang JH, Yuan LM (2014) Chempluschem 79:1103–1108

    Article  CAS  Google Scholar 

  44. Wang LP, Song TY, Huang LL, Xu JN, Li C, Ji CX, Shan L, Wang L (2011) CrystEng Comm 13:4005–4009

    Article  CAS  Google Scholar 

  45. Zhou LM (1994) New technology of gas chromatography. Science Press, Beijing, p 51

    Google Scholar 

  46. Lee ML, Yang FJ, Bartle KD (1984) Open tubular column gas chromatography—theory and practice. Wiley, New York, p 71

    Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation (No. 21275126, 21127012) of China.

Author information

Authors and Affiliations

  1. Department of Chemistry, Yunnan Normal University, Kunming, 650500, People’s Republic of China

    Jiang-rong Yang, Sheng-ming Xie, Hong Liu & Li-ming Yuan

  2. Department of Chemistry, East China Normal University, Shanghai, 200241, People’s Republic of China

    Jun-hui Zhang & Li-ming Yuan

Authors
  1. Jiang-rong Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sheng-ming Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hong Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jun-hui Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Li-ming Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Li-ming Yuan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yang, Jr., Xie, Sm., Liu, H. et al. Metal–Organic Framework InH(d-C10H14O4)2 for Improved Enantioseparations on a Chiral Cyclodextrin Stationary Phase in GC. Chromatographia 78, 557–564 (2015). https://doi.org/10.1007/s10337-015-2863-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10337-015-2863-5

Keywords

Search

Navigation