Application of calixarene stationary phases to liquid chromatography

doi:10.3724/SP.J.1123.2019.08027

Abstract

Abstract:

Calixarenes are cyclic oligomers composed of phenol units linked by methylene bridges. Because of their unique host-guest recognition ability, calixarenes are considered to be the main representatives of the third generation of supramolecular chemistry after crown ethers and cyclodextrins. Calixarenes are widely used in ion channel as well as in organic catalytic reactions, transmembrane transport, purification, and chromatographic separation. A variety of versatile calixarene derivatives with different recognition ability and special selectivity were prepared by modifying different types of compounds due to calixarenes are easy to derivatize. These derivatives were successfully applied to different chromatographic modes to achieve the separation and analysis of complex samples. This review summarizes the recent advances in stationary phases based on calixarenes and their derivatives for liquid chromatography The prospects of calixarenes in chromatographic separation science are also presented.

Key words: calixarenes, heteracalixaromatics, stationary phase, review

CLC Number:

O658

ZHANG Guangrui, ZHANG Wenfen, GUO Yun, ZHANG Suning, ZHANG Shusheng. Application of calixarene stationary phases to liquid chromatography[J]. Chinese Journal of Chromatography, 2020, 38(4): 392-398.

Figures/Tables 4

Fig. 1 Structures of calixarene derivatives for reversed phase chromatography stationary phases

Fig. 2 Structures of calixarene derivatives for chiral chromatography stationary phases

Fig. 3 Structures of calixarene derivatives for mixed-mode chromatography stationary phases

Fig. 4 Structures of heteracalixaromatics for chromatography stationary phases

References

[1]	Shinkai S. Tetrahedron, 1993, 49(40): 8933
[2]	Ersoz M. Adv Colloid Interface Sci, 2007, 134(135): 96
[3]	Delahousse G, Delahousse R, Jabin I, et al. Curr Org Chem, 2015, 19: 2237
[4]	Zhao W J, Hu K, Wang C J, et al. J Chromatogr A, 2012, 1223: 72
[5]	Zhao W J, Wang W J, Chang H, et al. J Chromatogr A, 2012, 1251: 74
[6]	Zhang W F, Wang F, Zhang Y H, et al. Sep Purif Technol, 2019, 211: 227
[7]	Lu G Y, Guo X, Liu F. Chinese Journal of Organic Chemistry, 2005, 25(9): 1021
[7]	陆国元, 郭勋, 刘芳. 有机化学, 2005, 25(9): 1021
[8]	Delahousse G, Peulon-Agasse V, Debray J C, et al. J Chromatogr A, 2013, 1318: 207
[9]	Fan J, Wang Z Z, Li Q, et al. J Chromatogr A, 2014, 1362: 231
[10]	Sun T, Qi L R, Li W W, et al. J Chromatogr A, 2019, 1601: 310
[11]	Hu K, Tian Y L, Yang H, et al. J Liq Chromatogr R T, 2009, 32(18): 2627
[12]	Tian Y, Zhang L F, Zeng Z R, et al. Electrophoresis, 2008, 29: 960
[13]	Xiao X Z, Feng Y Q, Da S L, et al. Chromatogr, 1999, 49(11/12): 6
[14]	Li L S, Liu M, Da S L, et al. Talanta, 2004, 62(3): 643
[15]	Li L S, Liu M, Da S L, et al. Talanta, 2004, 63(2): 433
[16]	Liu M, Li L S, Da S L, et al. Talanta, 2005, 66(2): 479
[17]	Ding C H, Qu K, Li Y B, et al. J Chromatogr A, 2007, 1170: 73
[18]	Hu K, Qu K, Li Y B, et al. J Sep Sci, 2008, 31(13): 2430
[19]	Sliwka-Kaszynska M, Gorczyca G, Slebioda M. J Chromatogr A, 2010, 1217: 329
[20]	Zadmard R, Tabar-Heydar K, Imani M. J Chromatogr Sci, 2015, 53(5): 702
[21]	Hu K, Zhao W J, Wen F Y, et al. Talanta, 2011, 85(1): 317
[22]	Hu K, Liu J W, Tang C, et al. J Sep Sci, 2012, 35(2): 239
[23]	Hu K, Yu A J, Zhang J Q, et al. J Chromatogr Sci, 2012, 50(2): 123
[24]	Mokhtari B, Pourabdollah K. J Chil Chem Soc, 2012, 57: 1150
[25]	Rutkowska M, Płotka-Wasylka J, Morrison C, et al. TrAC-Trends Anal Chem, 2018, 102: 91
[26]	Thamarai C S K, Yong E L, Gong Y H. J Chromatogr A, 2008, 1203: 54
[27]	Thamarai C S K, Zhao J, Chen L J, et al. J Chromatogr A, 2014, 1324: 104
[28]	Yaghoubnejad S, Tabar H K, Ahmadi S H, et al.J Sep Sci, 2018, 41(9): 1903
[29]	Yaghoubnejad S, Tabar H K, Ahmadi S H, et al. Biomed Chromatogr, 2018, 32(3): 1
[30]	Xu J W, Sun Y S, Tang T, et al. Chinese Journal of Chromatography, 2015, 33(11): 1140
[30]	徐基伟, 孙元社, 唐涛, 等. 色谱, 2015, 33(11): 1140
[31]	Zhang L, Dai Q, Qiao X Q, et al. TrAC-Trends Anal Chem, 2016, 82: 143
[32]	Lu J, Zhang W F, Zhang Y H, et al. J Chromatogr A, 2014, 1350: 61
[33]	Qiao L C, Shi X Z, Lu X, et al. J Chromatogr A, 2015, 1396: 62
[34]	Hu K, Zhang W F, Yang H X, et al. Talanta, 2016, 152: 392
[35]	Zhang W F, Zhang Y H, Zhang Y M, et al. Talanta, 2019, 193: 56
[36]	Zhang W F, Zhang Y H, Zhang G R, et al.J Sep Sci, 2019, 42(7): 1374
[37]	Wang M X. Progress in Chemistry, 2018, 30(5): 13
[37]	王梅祥. 化学进展, 2018, 30(5): 13
[38]	Wang X D, Li S, Ao Y F, et al. Org Biomol Chem, 2016, 14: 330
[39]	Liu W, Wang Q Q, Huang Z T, et al. Tetrahedron Lett, 2014, 55: 3172
[40]	Wang M X. Sci China Chem, 2018, 61(8): 993