Abstract
Metal–organic frameworks (MOFs) have received great attention as stationary phases in chromatographic separation technology because of their unusual properties such as high surface areas, fascinating structures, and excellent chemical and thermal stability. A chiral MOF, [(CH3)2NH2][Cd(bpdc)1.5]·2DMA, possesses a unique chiral nanotube motif built from the covalent linkage of homochiral nanotubes made up of octuple helices. Here, we report the fabrication of a three-dimensional (3D) chiral nanoporous MOF-coated capillary column (2 m long × 75 μm i.d.) for capillary gas chromatographic separation of racemates, Grob’s test mixture, normal alkanes, normal alcohols, and isomers. The MOF-coated capillary column offered good separation efficiency (2,180 plates m−1), which was measured using n-dodecane as the analyte at 120 °C. The relative standard deviations of repeatability for citronellal on MOF-coated capillary column were 0.23 and 2.1 % for retention time and peak area, respectively. The results demonstrated that the capillary column exhibited excellent selectivity and separation ability toward Grob’s test mixture, normal alkanes, normal alcohols and isomers, especially for racemates.
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Rosi N, Eckert J, Eddaoudi M, Vodak D, Kim J, O’Keeffe M, Yaghi OM (2003) Science 300:1127–1129
Zhao XB, Xiao B, Fletcher AJ, Thomas KM, Bradshaw D, Rosseinsky MJ (2004) Science 306:1012–1015
Panella B, Hirscher M (2005) Adv Mater 17:538–541
Rowsell JLC, Yaghi OM (2005) Angew Chem Int Ed 44:4670–4679
McKinlay AC, Xiao B, Wragg DS, Wheatley PS, Megson IL, Morris RE (2008) J Am Chem Soc 130:10440–10444
Yuan D, Zhao D, Sun D, Zhou H-C (2010) Angew Chem Int Ed 49:5357–5361
Seo JS, Whang D, Lee H, Jun SI, Oh J, Jeon YJ, Kim K (2000) Nature 404:982–986
Wu CD, Hu A, Zhang L, Lin WB (2005) J Am Chem Soc 127:8940–8941
Dybtsev DN, Nuzhdin AL, Chun H, Bryliakov KP, Talsi EP, Fedin VP, Kim K (2006) Angew Chem Int Ed 45:916–920
Wang ZQ, Cohen SM (2007) J Am Chem Soc 129:12368–12369
Ding S-Y, Gao J, Wang Q, Zhang Y, Song W-G, Su C-Y, Wang W (2011) J Am Chem Soc 133:19816–19822
Wang B, Cote AP, Furukawa H, O’Keeffe M, Yaghi OM (2008) Nature 453:207–211
Gücüyener C, Bergh J, Gascon J, Kapteijn F (2010) J Am Chem Soc 132:17704–17706
Kauffman KL, Culp JT, Allen AJ, Espinal L, Wong-Ng W, Brown TD, Goodman A, Bernardo MP, Pancoast RJ, Chirdon D, Matranga C (2011) Angew Chem Int Ed 50:10888–10892
Lee CY, Bae Y-S, Jeong NC, Farha OK, Sarjeant AA, Stern CL, Nichias P, Snurr RQ, Hupp JT, Nguyen ST (2011) J Am Chem Soc 133:5228–5231
Sun CY, Qin C, Wang CG, Su ZM, Wang S, Wang XL, Yang GS, Shao KZ, Lan YQ, Wang EB (2011) Adv Mater 23:5629–5632
Horcajada P, Gref R, Baati T, Allan PK, Maurin G, Couvreur P, Ferey G, Morris RE, Serre C (2012) Chem Rev 112:1232–1268
Chen BL, Wang LB, Zapata F, Qian GD, Lobkovsky EB (2008) J Am Chem Soc 130:6718–6719
Lu G, Farha OK, Kreno LE, Schoenecker PM, Walton KS, Van Duyne RP, Hupp JT (2011) Adv Mater 23:4449–4452
He J, Yee K–K, Xu ZT, Zeller M, Hunter AD, Chui SS-Y, Che C-M (2011) Chem Mater 23:2940–2947
Jia J, Xu FJ, Long Z, Hou XD, Sepaniak MJ (2013) Chem Commun 49:4670–4672
Ni Z, Jerrell JP, Cadwallader KR, Masel RI (2007) Anal Chem 79:1290–1293
Gu ZY, Wang G, Yan XP (2010) Anal Chem 82:1365–1370
Zhou YY, Yan XP, Kim KN, Wang SW, Liu MG (2006) J Chromatogr A 1116:172–178
Barreto AS, da Silva RL, Dos Santos Silva SC, Rodrigues MO, de Simone CA, de Sá GF, Júnior SA, Navickiene S, de Mesquita ME (2010) J Sep Sci 33:3811–3816
Gu ZY, Chen YJ, Jiang JQ, Yan XP (2011) Chem Commun 47:4787–4789
Cui XY, Gu ZY, Jiang DQ, Li Y, Wang HF, Yan XP (2009) Anal Chem 81:9771–9777
Chang N, Gu ZY, Wang HF, Yan XP (2011) Anal Chem 83:7094–7101
Yu LQ, Yan XP (2013) Chem Commun 49:2142–2144
Gu ZY, Yan XP (2010) Angew Chem Int Ed 49:1477–1480
Chang N, Gu ZY, Yan XP (2010) J Am Chem Soc 132:13645–13647
Chang N, Yan XP (2012) J Chromatogr A 1257:116–124
Gu ZY, Jiang JQ, Yan XP (2011) Anal Chem 83:5093–5100
Fan L, Yan XP (2012) Talanta 99:944–950
Yang CX, Yan XP (2011) Anal Chem 83:7144–7150
Yang CX, Chen YJ, Wang HF, Yan XP (2011) Chem A Eur J 17:11734–11737
Fu YY, Yang CX, Yan XP (2012) Langmuir 28:6794–6802
Yang CX, Liu SS, Wang HF, Wang SW, Yan XP (2012) Analyst 137:133–139
Liu SS, Yang CX, Wang SW, Yan XP (2012) Analyst 137:816–818
Fu YY, Yang CX, Yan XP (2013) J Chromatogr A 1274:137–144
Fu YY, Yang CX, Yan XP (2013) Chem A Eur J 19:13484–13491
Li LM, Wang HF, Yan XP (2012) Electrophoresis 33:2896–2902
Nuzhdin AL, Dybtsev DN, Bryliakov KP, Talsi EP, Fedin VP (2007) J Am Chem Soc 129:12958–12959
Padmanaban M, Muller P, Lieder C, Gedrich K, Grunker R, Bon V, Senkovska I, Baumgartner S, Opelt S, Paasch S, Brunner E, Glorius F, Klemm E, Kaskel S (2011) Chem Commun 47:12089–12091
Tanaka K, Muraoka T, Hirayama D, Ohnish A (2012) Chem Commun 48:8577–8579
Zhang M, Pu ZJ, Chen XL, Gong XL, Zhu AX, Yuan LM (2013) Chem Commun 49:5201–5203
Zhang M, Zhang JH, Zhang Y, Wang BJ, Xie SM, Yuan LM (2014) J Chromatogr A 1325:163–170
Zhang M, Xue XD, Zhang JH, Xie SM, Zhang Y, Yuan LM (2014) Anal Methods 6:341–346
Xue XD, Zhang M, Xie SM, Yuan LM (2013) Acta Chromatogr Adv
Xie SM, Zhang ZJ, Wang ZY, Yuan LM (2011) J Am Chem Soc 133:11892–11895
Xie SM, Zhang XH, Zhang ZJ, Yuan LM (2013) Anal Lett 46:753–763
Xie SM, Zhang XH, Zhang ZJ, Zhang M, Jia J, Yuan LM (2013) Anal Bioanal Chem 405:3407–3412
Zhang XH, Xie SM, Duan AH, Wang BJ, Yuan LM (2013) Chromatographia 76:831–836
Xie SM, Wang BJ, Zhang XH, Zhang JH, Zhang M, Yuan LM (2014) Chirality 26:27–32
Hao XR, Wang XL, Qin C, Su ZM, Wang EB, Lana YQ, Shao KZ (2007) Chem Commun 44:4620–4622
Ikai T, Okamoto Y (2009) Chem Rev 109:6077–6101
Acknowledgments
This work is supported by the National Natural Science Foundation (No. 21275126, 21365024) and the Yunnan Province’s Basic Research Program (No. 2013FB035) of China.
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Xie, Sm., Zhang, Xh., Wang, Bj. et al. 3D Chiral Nanoporous Metal–Organic Framework for Chromatographic Separation in GC. Chromatographia 77, 1359–1365 (2014). https://doi.org/10.1007/s10337-014-2719-4
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DOI: https://doi.org/10.1007/s10337-014-2719-4