New C2 symmetric chiral stationary phases based on L-proline derivatives as chains

doi:10.3724/SP.J.1123.2017.02029

Abstract

Abstract:

C₂ symmetric chiral compounds overlap themselves when rotating with an axis of 180° with an axis and have important applications in chiral catalysis and chiral separation fields. A novel C₂ symmetric stationary phase based on phenyl substituted L-proline derivatives was prepared and compared with the similar stationary phase based on mono-substituted brush-type stationary phase. The C₂ symmetric stationary phase showed higher enantiodiscrimination capability than the mono-substituted stationary phase for 31 acidic, neutral and alkaline analytes. The influence of the substitution groups on the terminal phenyl moiety on enantioselectivity was investigated. In summary, the best separation capability was achieved by the stationary phase with none substitution on the endmost phenyl ring. An unusual thermodynamic behavior of the enantioseparation property was observed on the C₂ symmetric stationary phase for some analytes, which showed the different separation mechanism comparing with the corresponding mono-substituted stationary phase. The appearance of this novel chiral stationary phase has an important significance in enriching the type of brush-type stationary phases and widening their applications.

Key words: C₂ symmetric, chiral stationary phase (CSP), enantiomer separation, proline derivatives

CLC Number:

O658

CHEN Long, CHENG Lingping, HE Shanshan, HE Yunchao, WU Yaling, KE Yanxiong, LIANG Xinmiao. New C₂ symmetric chiral stationary phases based on L-proline derivatives as chains[J]. Chinese Journal of Chromatography, 2017, 35(7): 703-711.

References

[1] Lin X J, Gong R J, Li P, et al. Chinese Journal of Chromatography, 2014, 32(8):880林小建, 龚如金, 李平, 等. 色谱, 2014, 32(8):880
[2] Chen B P, Li L S, Zhou R D, et al. Chinese Journal of Chromatography, 2014, 32(11):1219程彪平, 李来生, 周仁丹, 等. 色谱, 2014, 32(11):1219
[3] Chen L, Li Y, Nong R Y, et al. Chinese Journal of Analysis Laborator, 2015, 34(12):1365陈玲, 李扬, 农蕊瑜, 等. 分析试验室, 2015, 34(12):1365
[4] Zhang W J, Liang L, Li H. Fine Chemicals, 2012, 29(3):272章文军, 梁莉, 李慧. 精细化工, 2012, 29(3):272
[5] Hou J G, Zhou Z Q, Chen L R, et al. Chinese Journal of Chromatography, 1997, 15(3):206侯经国, 周志强, 陈立仁, 等. 色谱, 1997, 15(3):206
[6] Zheng W L, Song H, Liang Y M, et al. Chinese Journal of Chromatography, 2003, 21(3):239郑文丽, 宋航, 梁彦明, 等. 色谱, 2003, 21(3):239
[7] Yu J J, Lee J M, Ryoo J J. Chirality, 2016, 28:276
[8] Wu H B, Ji S Y, Yang B, et al. J Sep Sci, 2012, 35:351
[9] Pirkle W H, Murray P G. J Chromatogr A, 1996, 719:299
[10] Delgado B, Perez E, Santano M C, et al. J Chromatogr A, 2005, 1092:36
[11] Ashtari M, Cann N M. J Chromatogr A, 2015, 1409:89
[12] Zhou H, Long Y D, Huang T B, Chinese Journal of Chromatography, 1997, 15(1):26周华, 龙远德, 黄天宝. 色谱, 1997, 15(1):26
[13] Huang J, Zhang P, Chen H, et al. Anal Chem, 2005, 77(10):3301
[14] Huang J, Chen H, Li T. J Chromatogr A, 2006, 1113:109
[15] Huang J, Chen H, Zhang P, et al. J Chromatogr A, 2006, 1109:307
[16] Wu H B, Song G J, Liang X M, et al. Chin J Chem, 2012, 30:2791
[17] Wu H B, Song G J, Wang D Q, et al. J Chromatogr A, 2013, 1298:152
[18] Wu H B, Wang D Q, Song G J, et al. J Sep Sci, 2014, 37:934
[19] Kagan H B, Dang T P. J Am Chem Soc, 1972, 94:29
[20] Jin Y, Zhang T Y, Wang L M, et al. Chemical Reagents, 2013, 35(9):789金瑛, 张天一, 王黎明, 等. 化学试剂, 2013, 35(9):789
[21] Ma M L, Zhang Y Y, Yang J, et al. Journal of Xihua University, 2013, 32(1):7马梦林, 张园园, 杨静, 等. 西华大学学报, 2013, 32(1):7
[22] Cai W S, Feng C L, Ma X Y, et al. Electrochim Acta, 2015, 169:424
[23] Mikes F, Boshart G. J Chromatogr A, 1978, 149:455
[24] Feibush B, Figueroa A, Charles R, et al. J Am Chem Soc, 1986, 108(12):3310
[25] Shinbo T, Yamaguchi T, Nishimura K, et al. J Chromatogr A, 1987, 405:145
[26] Tichy M, Holnaova J, Zavada J. J Chromatogr A, 1994, 667:11
[27] Gasparrini F, Misiti D, Villani C. J Org Chem, 1995, 60(14):4314
[28] Yu J, Ryoo D, Lee J, et al. Chirality, 2016, 28:186
[29] Kelly S E, LaCour T G. Synth Commun, 1992, 22(6):859
[30] Tu S J, Fang F, Zhu S L, et al. Synlett, 2004, 3:537
[31] Zhang H, Guo D L, Deng Y W, et al. Chinese Journal of Analytical Chemistry, 2013, 41(8):1209张华, 郭丹丽, 邓毓文, 等. 分析化学, 2013, 41(8):1209
[32] Yao B, Zhan F, Yu G, et al. J Chromatogr A, 2009, 1216:5429
[33] Jonsson S, Schon A, Isaksson R, et al. Chirality, 1992, 4:505
[34] Fornstedt T, Sajonz P, Guiochon G. J Am Chem Soc, 1997, 119(6):1252

New C₂ symmetric chiral stationary phases based on L-proline derivatives as chains

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