Applications of ordered porous materials in chromatography separation and analysis

doi:10.3724/SP.J.1123.2024.05032

Abstract

Abstract: Chromatography, a highly efficient and selective separation technology, is broadly applicable and exhibits a range of developmental prospects. The stationary phase of a chromatography column is the most important component of chromatography; hence, the development of advanced stationary-phase materials that exhibit highly resolved separation performance is a continuing research hotspot in this field. In this regard, ordered porous materials (OPMs) are advantageous owing to their precisely controllable pore sizes, morphologies, and regularly arranged pore structures, which are capable of accurately sieving molecules of different sizes and shapes, and reducing disordered molecular diffusion in the flow path. Such materials overcome the limitation of separation accuracy of traditional chromatographic materials, and effectively solve the problems faced by scientific research and industry in the purification of raw materials and products. Over the past few decades, a variety of new OPMs have been developed and used as stationary-phase matrices in chromatography columns. These materials have efficiently and rapidly separated homologues, isomers, isotopes, and other substances with similar properties, and have delivered excellent chromatographic separation and analysis results. In this review, we first discuss the influence of ordered porous structures on column efficiency and resolution during chromatographic separation from a theoretical perspective, which provides a basis for the use of OPMs as stationary phases in chromatography. This review then summarizes research progress on several different OPM types for use in chromatographic separation and analysis applications, including metal organic frameworks (MOFs), covalent organic frameworks (COFs), porous organic cages (POCs), mesoporous silica materials, block copolymer assemblies, and high internal-phase emulsion polymers (PolyHIPEs). The review concludes by discussing current challenges faced by chromatographic OPMs as well as directions for future development.

Key words: ordered porous materials (OPMs), chromatography separation and analysis, framework materials, self-assembly, polymer, review

WANG Zhaoxu, WANG Duanda, WANG Shutao, SONG Yongyang. Applications of ordered porous materials in chromatography separation and analysis[J]. Chinese Journal of Chromatography, DOI: 10.3724/SP.J.1123.2024.05032.

References

1. Sholl D S, Lively R P. Nature, 2016, 532(7600): 435
2. Zhang J, Chen J, Peng S, et al. Chem Soc Rev, 2019, 48(9): 2566
3. Lin C, Xu K, Zheng R, et al. Chem Commun, 2019, 55(40): 5697
4. Ding M, Cai X, Jiang H L. Chem Sci, 2019, 10(44): 10209
5. Zhang P, Wang S, Ma S, et al. Chem Commun, 2020, 56(73): 10631
6. Yang P, Yang W, Zhang H, et al. Materials, 2023, 16(19): 6572
7. Unger K K, Skudas R, Schulte M M. J Chromatogr A, 2008, 1184(1/2): 393
8. Davis M E. Nature, 2002, 417(6891): 813
9. Bennett T D, Coudert F X, James S L, et al. Nat Mater, 2021, 20(9): 1179
10. Zhang M, Liu X, Zhou W, et al. Sep Purif Technol, 2023, 327: 124844
11. Song Y Y, Bao H, Shen X Y, et al. Adv Funct Mater, 2022, 32(20): 2113153
12. Wang H, Liu Y, Li J. Adv Mater, 2020, 32(44): 2002603
13. Yu L, Ullah S, Wang H, et al. Angew Chem Int Ed, 2022, 61(42): e202211359
14. Guo F A, Wang J, Chen C, et al. Angew Chem Int Ed, 2023, 62(24): e202303527
15. Yu L, Zhang J, Ullah S, et al. Angew Chem Int Ed, 2023, 62(41): e202310672
16. Wang Z, Zhang S, Chen Y, et al. Chem Soc Rev, 2020, 49(3): 708
17. Carmichael J B. Macromolecules, 1968, 1(6): 526
18. Vervoort N, Gzil P, Baron G V, et al. J Chromatogr A, 2004, 1030(1/2): 177
19. Billen J, Gzil P, Desmet G. Anal Chem, 2006, 78(17): 6191
20. Minakuchi H, Nakanishi K, Soga N, et al. J Chromatogr A, 1998, 797(1): 121
21. Giddings J C, Dynamics of chromatography: Principles and theory. 1st ed. Boca Raton: CRC Press, 2017
22. Bacskay I, Sepsey A, Felinger A. J Chromatogr A, 2014, 1339: 110
23. Leinweber F C, Tallarek U. J Chromatogr A, 2003, 1006(1): 207
24. Vervoort N, Gzil P, Baron G V, et al. Anal Chem, 2003, 75(4): 843
25. Gzil P, De Smet J, Desmet G. J Sep Sci, 2006, 29(12): 1675
26. Zhou H C, Long J R, Yaghi O M. Chem Rev, 2012, 112(2): 673
27. Li H, Eddaoudi M, Groy T L, et al. J Am Chem Soc, 1998, 120(33): 8571
28. Li H, Eddaoudi M, O'Keeffe M, et al. Nature, 1999, 402(6759): 276
29. Farha O K, Eryazici I, Jeong N C, et al. J Am Chem Soc, 2012, 134(36): 15016
30. Li J R, Sculley J, Zhou H C. Chem Rev, 2011, 112(2): 869
31. Zhao X, Wang Y, Li D S, et al. Adv Mater, 2018, 30(37): 1705189
32. Xie X J, Zeng H, Lu W, et al. J Mater Chem A, 2023, 11(38): 20459
33. Gong Q, Yu L, Ding J, et al. Sep Purif Technol, 2022, 294: 121219
34. Lin Y, Yu L, Ullah S, et al. Angew Chem Int Ed, 2022, 61(50): e202214060
35. Xie F, Wang H, Li J. J Mater Chem A, 2023, 11(24): 12425
36. Xie F, Yu L, Wang H, et al. Angew Chem Int Ed, 2023, 62(20): e202300722
37. Lu Y, Zhang H, Zhu Y, et al. Adv Funct Mater, 2021, 31(25): 2101335
38. Corella-Ochoa M N, Tapia J B, Rubin H N, et al. J Am Chem Soc, 2019, 141(36): 14306
39. Wang H, Warren M, Jagiello J, et al. J Am Chem Soc, 2020, 142(47): 20088
40. Mizutani N, Hosono N, Le Ouay B, et al. J Am Chem Soc, 2020, 142(8): 3701
41. Ding M, Yang L, Zeng J, et al. Anal Chem, 2020, 92(24): 15757
42. Kioka K, Mizutani N, Hosono N, et al. ACS Nano, 2022, 16(4): 6771
43. Kandambeth S, Dey K, Banerjee R. J Am Chem Soc, 2019, 141(5): 1807
44. Geng K, He T, Liu R, et al. Chem Rev, 2020, 120(16): 8814
45. Ma M, Yang Y, Huang Z, et al. Nanoscale, 2024, 16(4): 1600
46. Côté A P, Benin A I, Ockwig N W, et al. Science, 2005, 310(5751): 1166
47. Qin Y, Zhu X, Huang R. Biomater Sci, 2023, 11(21): 6942
48. Yuan C, Wu X, Gao R, et al. J Am Chem Soc, 2019, 141(51): 20187
49. Wang S, Yang Y, Zhang Z. Acc Mater Res, 2023, 4(11): 953
50. Zhang L, Wang D, Cong M, et al. Chem Commun, 2023, 59(33): 4911
51. Oh H, Kalidindi S B, Um Y, et al. Angew Chem Int Ed, 2013, 52(50): 13219
52. Jin F, Lin E, Wang T, et al. J Am Chem Soc, 2022, 144(50): 23081
53. Li Z, Liao Z, Hu J, et al. J Chromatogr A, 2023, 1694: 463905
54. Wang G, Lv W, Pan C, et al. Chem Commun, 2022, 58(3): 403
55. Song Q, Yang J, Zheng K, et al. J Am Chem Soc, 2024, 146(11): 7594
56. Chen Y, Huang S, Xia L, et al. Anal Chem, 2024, 96(3): 1380
57. Zhang S, Zheng Y, An H, et al. Angew Chem Int Ed, 2018, 57(51): 16754
58. Jin F, Wang T, Zheng H, et al. J Am Chem Soc, 2023, 145(11): 6507
59. Guan Q, Zhou L L, Dong Y B. Chem Soc Rev, 2022, 51(15): 6307
60. Kumar S, Kulkarni V V, Jangir R. ChemistrySelect, 2021, 6(41): 11201
61. Tozawa T, Jones J T, Swamy S I, et al. Nat Mater, 2009, 8(12): 973
62. Yang X, Ullah Z, Stoddart J F, et al. Chem Rev, 2023, 123(8): 4602
63. Bojdys M J, Briggs M E, Jones J T A, et al. J Am Chem Soc, 2011, 133(41): 16566
64. Su K, Wang W, Du S, et al. Nat Commun, 2021, 12(1): 3703
65. Vogel D J, Nenoff T M, Rimsza J M. ACS Omega, 2022, 7(9): 7963
66. Li H X, Xie T P, Yan K Q, et al. Microchimica Acta, 2020, 187(5): 269
67. Cui D X, Geng Y, Kou J N, et al. Nat Commun, 2022, 13(1): 4011
68. Zhang J H, Xie S M, Zi M, et al. J Sep Sci, 2020, 43(1): 134
69. Su K, Wang W, Du S, et al. J Am Chem Soc, 2020, 142(42): 18060
70. Liu J, Wang Z, Cheng P, et al. Nat Rev Chem, 2022, 6(5): 339
71. Zhu Q, Wang X, Clowes R, et al. J Am Chem Soc, 2020, 142(39): 16842
72. Thommes M, Kaneko K, Neimark A V, et al. Pure Appl Chem, 2015, 87(9/10): 1051
73. Lan K, Zhao D. Nano Lett, 2022, 22(8): 3177
74. Jiang L, Wang X, Raza F, et al. Biomater Sci, 2023, 11(15): 5301
75. Kirkland J J. J Chromatogr Sci, 1972, 10(10): 593
76. Majors R E. Anal Chem, 1972, 44(11): 1722
77. Kresge C T, Leonowicz M E, Roth W J, et al. Nature, 1992, 359(6397): 710
78. Meyer U, Larsson A, Hentze H P, et al. Adv Mater, 2002, 14(23): 1768
79. Fait F, Steinbach J C, Kandelbauer A, et al. J Chromatogr A, 2023, 1705: 464190
80. Steinbach J C, Fait F, Mayer H A, et al. ACS Omega, 2023, 8(33): 30273
81. Cao L, Shi Y, Geng J, et al. Mater Chem Phys, 2011, 130(3): 1280
82. Wong C K, Qiang X, Müller A H E, et al. Prog Polym Sci, 2020, 102: 101211
83. Duan L, Wang C, Zhang W, et al. Chem Rev, 2021, 121(23): 14349
84. Zhang S, Bao H, Shen X, et al. Droplet, 2023, 2(4): e81
85. Chen X, Yang X, Song D P, et al. Macromolecules, 2021, 54(8): 3668
86. Li Y L, Chen X, Geng H K, et al. Angew Chem Int Ed, 2021, 60(7): 3647
87. Peinemann K V, Abetz V, Simon P F. Nat Mater, 2007, 6(12): 992
88. Yu H, Qiu X, Nunes S P, et al. Nat Commun, 2014, 5: 4110
89. Lee J S, Hirao A, Nakahama S. Macromolecules, 1988, 21(1): 274
90. Abetz V. Macromol Rapid Comm, 2015, 36(1): 10
91. Nunes S P. Macromolecules, 2016, 49(8): 2905
92. Hampu N, Werber J R, Chan W Y, et al. ACS Nano, 2020, 14(12): 16446
93. Lang C, Kumar M, Hickey R J. Soft Matter, 2021, 17(46): 10405
94. Li Y, Qi L, Li N, et al. Talanta, 2016, 152: 244
95. Babanejad N, Mfoafo K, Zhang E, et al. J Chromatogr A, 2022, 1683: 463546
96. Peng W S, Lin Y Y, Sun Y J, et al. Macromol Rapid Comm, 2021, 42(14): 2100154
97. Kimmins S D, Cameron N R. Adv Funct Mater, 2011, 21(2): 211
98. Silverstein M S. Prog Polym Sci, 2014, 39(1): 199
99. Zhang T, Sanguramath R A, Israel S, et al. Macromolecules, 2019, 52(15): 5445
100. Luo J, Huang Z, Liu L, et al. J Sep Sci, 2020, 44(1): 169
101. Stubenrauch C, Menner A, Bismarck A, et al. Angew Chem Int Ed, 2018, 57(32): 10024
102. Niu H Y, Cao L Q, Yang X L, et al. Polym Adv Technol, 2021, 32(8): 3194
103. Yadav A, Ghosh S, Samanta A, et al. Chem Commun, 2022, 58(10): 1468
104. Barrulas R V, Zanatta M, Casimiro T, et al. Chem Eng J, 2021, 411: 128528
105. Azhar U, Zong C, Wan X, et al.Chem-Eur J, 2018, 24(45): 11619
106. Li J J, Wu Y, Luo Z H, et al. J Polym Sci, 2022, 60(17): 2562
107. Yi F, Xu F, Gao Y, et al. RSC Adv, 2015, 5(50): 40227
108. Fresco C B, Cárdenas S. Anal Chim Acta, 2022, 1208: 339669
109. Tunç Y, Gölgelioğlu Ç, Hasirci N, et al. J Chromatogr A, 2010, 1217(10): 1654
110. Khodabandeh A, Arrua R D, Mansour F R, et al. Sci Rep, 2017, 7(1): 7847
111. Choudhury S, Duffy E, Connolly D, et al. Separations, 2017, 4(1): 5
112. Desire C T, Arrua R D, Mansour F R, et al. RSC Adv, 2019, 9(13): 7301
113. Alla A J, Stine K J. Separations, 2022, 9(2): 44
114. Gokmen M T, Van Camp W, Colver P J, et al. Macromolecules, 2009, 42(23): 9289
115. Wang B, Prinsen P, Wang H, et al. Chem Soc Rev, 2017, 46(3): 855
116. Dabrowski M L, Jenkins D, Cosgriff H E, et al. Phys Chem Chem Phys, 2020, 22(1): 155
117. Dabrowski M L, Stubenrauch C. Adv Eng Mater, 2021, 23(3): 2001013
118. Broeckhoven K, Desmet G. Anal Chem, 2020, 93(1): 257
119. Kotova A A, Thiebaut D, Vial J, et al. Coordin Chem Rev, 2022, 455(15): 214364
120. Salmean C, Dimartino S. Chromatographia, 2019, 82(1): 443
121. Moleirinho M G, Feast S, Moreira A S, et al. Sep Purif Technol, 2021, 254: 1176
122. Testouri A, Ranft M, Honorez C, et al. Adv Eng Mater, 2013, 15(11): 1086

[1]	LUO Yana, CHEN Jia, HU Yuyu, GAO Shijie, WANG Yanli, LIU Yanming, FENG Juanjuan, SUN Min. Research progress in material preparation and application of magnetism-enhanced in-tube solid-phase microextraction [J]. Chinese Journal of Chromatography, 2025, 43(6): 606-619.
[2]	QIAN Jiankun, HE Runming, FANG Ke, LI Chenlong, BAO Shan, GU Wen, TANG Song. Progress in the metabolic and biotransformation of polycyclic aromatic hydrocarbons and their derivatives in humans [J]. Chinese Journal of Chromatography, 2025, 43(6): 571-584.
[3]	WANG Zhaoxu, WANG Duanda, WANG Shutao, SONG Yongyang. Applications of ordered porous materials in chromatography separation and analysis [J]. Chinese Journal of Chromatography, 2025, 43(6): 594-605.
[4]	YANG Yanwei, ZHANG Xu, LIN Xiao, SUN Qi, FU Hui, LU Yifu, QIU Tian, ZHANG Zhuona, XIE Linna, ZHANG Haijing, ZHANG Miao, HU Xiaojian, QU Yingli, ZHAO Feng, LYU Yuebin, ZHU Ying, SHI Xiaoming. Quality control strategy for targeted quantitative analysis of chemical pollutants in China National Human Biomonitoring Program [J]. Chinese Journal of Chromatography, 2025, 43(6): 559-570.
[5]	SU Yating, QIAN Xiaohong, QIN Weijie. Research advances of liposomes and exosomes in drug delivery and biomarker screening [J]. Chinese Journal of Chromatography, 2025, 43(5): 472-486.
[6]	BU Aixiang, WU Guangyao, HU Lianghai. Progress and prospect of separation and analysis of single-cell and single-particle exosomes [J]. Chinese Journal of Chromatography, 2025, 43(5): 399-412.
[7]	HU Yangyang, YANG Ge, QU Feng. Research advances in non-immobilized aptamer screening techniques for small-molecule targets [J]. Chinese Journal of Chromatography, 2025, 43(4): 297-308.
[8]	JIANG Liushan, ZHOU Qingxiang. Recent progress in magnetic covalent organic framework materials for the enrichment and detection of typical organic pollutants [J]. Chinese Journal of Chromatography, 2025, 43(2): 107-119.
[9]	CHENG Yingchao, GAO Yiyang, LI Xiaomin, CHEN Luyu, DU Fang, GUO Jie, MENG Yitong, SUN Min, FENG Juanjuan. Research advance of solid-phase microextraction based on covalent organic framework materials [J]. Chinese Journal of Chromatography, 2025, 43(2): 120-130.
[10]	YUAN Keyu, XIONG Jun, YUAN Bifeng. Research advances in the transplacental transfer efficiencies of environmental pollutants [J]. Chinese Journal of Chromatography, 2025, 43(1): 13-21.
[11]	ZHANG Pengcheng, WANG Yuan, LIU Kunling, SUN Yaming, HE Lijun, ZHAO Wenjie. Analysis of phthalate esters from vegetable oils by gas chromatography-mass spectrometry coupled with headspace solid-phase microextraction using cyclodextrin-based hypercrosslinked polymer coated fiber [J]. Chinese Journal of Chromatography, 2024, 42(9): 881-890.
[12]	JIANG Bo, GAO Bo, WEI Shuxian, LIANG Zhen, ZHANG Lihua, ZHANG Yukui. Progress in enrichment methods for protein N-phosphorylation [J]. Chinese Journal of Chromatography, 2024, 42(7): 623-631.
[13]	XUE Jieying, LIU Zheyi, WANG Fangjun. Applications of native mass spectrometry and ultraviolet photodissociation in protein structure and interaction analysis [J]. Chinese Journal of Chromatography, 2024, 42(7): 681-692.
[14]	LIU Jiawei, TANG Changwei, XIA Yiran, BAI Quan. Recent progress of chromatographic techniques for antibody purification [J]. Chinese Journal of Chromatography, 2024, 42(6): 533-543.
[15]	CHEN Xin, QIAN Wenping, CHEN Tianqi, SHAO Lingyun, ZHANG Wenfen, ZHANG Shusheng. Synthesis of fluorinated nitrogen-rich porous organic polymers and removal of perfluorooctanoic acid from water [J]. Chinese Journal of Chromatography, 2024, 42(6): 572-580.