Citation: HUANG Zhi-Feng, JIA Wen-Yan, YUAN Li-Ming. Three Kinds of Chiral Covalent Organic Frameworks Used as Stationary Phases for Gas Chromatography[J]. Chinese Journal of Analytical Chemistry, ;2023, 51(3): 436-444. doi: 10.19756/j.issn.0253-3820.221309 shu

Three Kinds of Chiral Covalent Organic Frameworks Used as Stationary Phases for Gas Chromatography

Department of Chemistry, Yunnan Normal University, Kunming 650500, China

Corresponding author: YUAN Li-Ming, yuan_limingpd@126.com
Received Date: 23 June 2022
Revised Date: 22 February 2023

Fund Project: Supported by the National Natural Science Foundation of China (No. 22174125).

Chiral covalent organic frameworks (CCOFs) have important applications in many fields such as asymmetric catalysis and chiral recognition. Chiral separation has become one of the most important applications of CCOFs due to its convenience, rapidity and high efficiency. To further develop the application value of CCOFs in chromatographic chiral separation, three kinds of CCOFs were obtained by post-synthetic modification method, e.g. L-valine was modified on covalent organic frameworks (COFs) TpPa(NH₂)₂, L-isoleucine was modified on COFs TpPa(NH₂)₂ and TpBD(NH₂)₂, respectively. The three CCOFs were used as gas chromatography chiral stationary phases(CSPs), and mixed with polysiloxane OV-1701 at a mass ratio of 3∶7 to prepare a 4.5 mg/mL coating solution. Three capillary chromatographic columns were prepared by dynamic coating method for chiral separation and analysis. The results showed that the chromatographic columns coated with three kinds of CCOFs had good chiral selectivity and repeatability, which could be used for rapid separation of 25 kinds of chiral compounds such as amino acids, alcohols, aldehydes, esters, ethers, acids and ketones, as well as n-alkanes, n-alkanols, aromatic mixtures and Grob mixtures. Among them, the three CCOFs had wide chiral selectivity and good complementarity in gas chromatography chiral separation, which broadened the range of CCOFs used as gas chromatography CSPs to separate chiral compounds to some extent. This study provided an example of the synthesis of CCOFs by postsynthetic modification, expanded the application of COFs in the field of chiral separation, and showed that CCOFs as a new CSPs had a good application prospect in chromatographic chiral separation.
- Chiral covalent organic frameworks,
- Chiral stationary phase,
- Chiral separation,
- Gas chromatography
1. [1]
2. [2]
  WARD T J, WARD K D. Anal. Chem., 2012, 84(2):626-635.
3. [3]
4. [4]
  DOBÓ M, FOROUGHBAKHSHFASAEI M, HORVÁTH P, SZABÓ Z I, TÓTH G. J. Chromatogr. A, 2022, 1662:462741.
5. [5]
  ZHANG J, XIE S, YUAN L. J. Sep. Sci., 2022, 45(1):51-77.
6. [6]
  BETZENBICHLER G, HUBER L, KRÄH S, MORKOS M-K, SIEGLE A F, TRAPP O. Chirality, 2022, 34(5):732-759.
7. [7]
  GUS'KOV V Y, MAISTRENKO V N. J Anal. Chem., 2018, 73(10):937-945.
8. [8]
  SCHURIG V. J. Chromatog. A, 1994, 666(1-2):111-129.
9. [9]
  SCHURIG V. J. Chromatogr. A, 2001, 906(1-2):275-299.
10. [10]
  XIE S M, CHEN X X, ZHANG J H, YUAN L M. TrAC, Trends Anal. Chem., 2020, 124:115808.
11. [11]
  FRANK H, GRAEME J N, BAYER E. Angew. Chem., Int. Ed., 1978, 17(5):363-365.
12. [12]
  KEIM W, KOHNES A, MELTZOW W, ROMER H. J. Sep. Sci., 1991, 14(8):507-529.
13. [13]
  NIE M Y, ZHOU L M, WANG Q H, ZHU D Q. Chromatographia, 2000, 51(11-12):736-740.
14. [14]
15. [15]
  LI Y X, FU S G, ZHANG J H, XIE S M, LI L, HE Y Y, ZI M, YUAN L M. J. Chromatogr. A, 2018, 1557:99-106.
16. [16]
  TANG B, ZHANG X, GENG L, SUN L, LUO A. J. Chromatogr. A, 2021, 1636:461792.
17. [17]
  WANG Z, XIONG W, HUANG Z, QIN G, ZI M, YUAN L. Chirality, 2022, 34(3):462-472.
18. [18]
  XIE S M, ZHANG Z J, WANG Z Y, YUAN L M. J. Am. Chem. Soc., 2011, 133(31):11892-11895.
19. [19]
  SCHURIG V. Angew. Chem., Int. Ed., 1984, 23(10):747-765.
20. [20]
  DING J, WELTON T, ARMSTRONG D W. Anal. Chem., 2004, 76(22):6819-6822.
21. [21]
  YUAN L M, HAN Y, ZHOU Y, MENG X, LI Z Y, ZI M, CHANG Y X. Anal. Lett., 2006, 39(7):1439-1449.
22. [22]
23. [23]
  HAN X, YUAN C, HOU B, LIU L, LI H, LIU Y, CUI Y. Chem. Soc. Rev., 2020, 49(17):6248-6272.
24. [24]
  ZHANG J, HAN X, WU X, LIU Y, CUI Y. J. Am. Chem. Soc., 2017, 139(24):8277-8285.
25. [25]
  QIAN H L, YANG C X, YAN X P. Nat. Commun., 2016, 7:12104.
26. [26]
  YUAN C, JIA W, YU Z, LI Y, ZI M, YUAN L M, CUI Y. J. Am. Chem. Soc., 2022, 144(2):891-900.
27. [27]
  GUO J X, YANG C, YAN X P. J. Mater. Chem. A, 2021, 9(37):21151-21157.
28. [28]
  TANG B, WANG W, HOU H, LIU Y, LIU Z, GENG L, SUN L, LUO A. Chin. Chem. Lett., 2022, 33(2):898-902.
29. [29]
  YUAN C, FU S, YANG K, HOU B, LIU Y, JIANG J, CUI Y. J. Am. Chem. Soc., 2021, 143(1):369-381.
30. [30]
  KANG X, STEPHENS E R, SPECTOR-WATTS B M, LI Z, LIU Y, LIU L, CUI Y. Chem. Sci., 2022, 13(34):9811-9832.
31. [31]
  CHONG J H, SAUER M, PATRICK B O, MACLACHLAN M J. Org. Lett., 2003, 5(21):3823-3826.
32. [32]
  CHANDRA S, KANDAMBETH S, BISWAL B P, LUKOSE B, KUNJIR S M, CHAUDHARY M, BABARAO R, HEINE T, BANERJEE R. J. Am. Chem. Soc., 2013, 135(47):17853-17861.
33. [33]
  LOHSE M S, STASSIN T, NAUDIN G, WUTTKE S, AMELOOT R, DE VOS D, MEDINA D D, BEIN T. Chem. Mater., 2016, 28(2):626-631.
34. [34]
  BONNEFOY J, LEGRAND A, QUADRELLI E A, CANIVET J, FARRUSSENG D. J. Am. Chem. Soc., 2015, 137(29):9409-9416.
35. [35]
  KOU W T, YANG C X, YAN X P. J. Mater. Chem. A, 2018, 6(37):17861-17866.
36. [36]
  ZHANG J H, XIE S M, CHEN L, WANG B J, HE P G, YUAN L M. Anal. Chem., 2015, 87(15):7817-7824.
37. [37]
  IDREES K B, LI Z, XIE H, KIRLIKOVALI K O, KAZEM-ROSTAMI M, WANG X, WANG X, TAI T Y, ISLAMOGLU T, STODDART J F, SNURR R Q, FARHA O K. J. Am. Chem. Soc., 2022, 144(27):12212-12218.
38. [38]
  WANG W, ZHANG Y, TANG B, HOU H, TANG S, LUO A. J. Chromatogr. A, 2022, 1675:463150.
1. [1]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
2. [2]
  Shunü Peng , Huamin Li , Zhaobin Chen , Yiru Wang . Simultaneous Application of Multiple Quantitative Analysis Methods in Gas Chromatography for the Determination of Active Ingredients in Traditional Chinese Medicine Preparations. University Chemistry, 2025, 40(10): 243-249. doi: 10.12461/PKU.DXHX202412043
3. [3]
  Zelin Wang , Gang Liu , Mengran Wang , Peiyu Zhang , Aixin Song , Jingcheng Hao , Jiwei Cui . Application of Instrumental Analysis in the Detection of Organic Components in Liquor. University Chemistry, 2025, 40(11): 318-326. doi: 10.12461/PKU.DXHX202502077
4. [4]
  Jingming Li , Bowen Ding , Nan Li , Nurgul . Application of Comparative Teaching Method in Experimental Project Design of Instrumental Analysis Course: A Case Study in Chromatography Experiment Teaching. University Chemistry, 2024, 39(8): 263-269. doi: 10.3866/PKU.DXHX202312078
5. [5]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059
6. [6]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
7. [7]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
8. [8]
  Zhengjie Miao , Chuanqiang Zhou , Yuanyuan Ren , Xiangping Xu , Ju Xie , Jie Han . Hierarchical chiral nanoribbons of achiral oligoaniline: temperature induced helicity inversion and enantioselective crystallization application. Acta Physico-Chimica Sinica, 2026, 42(10): 100256-0. doi: 10.1016/j.actphy.2026.100256
9. [9]
  Qi Liang , Xinxin Wang , Xinmiao Zhao , Mohan Yu , Yue Sun . 电子圆二色谱结合量子化学计算的氨基酸手性解析——介绍一个计算化学综合实验. University Chemistry, 2026, 41(5): 380-390. doi: 10.12461/PKU.DXHX202511096
10. [10]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
11. [11]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
12. [12]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
13. [13]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
14. [14]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
15. [15]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
16. [16]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
17. [17]
  Xinhe Wu , Chang Cheng . Chiral COF-based S-scheme heterojunction for spin-polarized photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2026, 42(9): 100303-0. doi: 10.1016/j.actphy.2026.100303
18. [18]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
19. [19]
  Heyu Li , Lingjiao Li , Haiyu Wang , Bin Liu , Lianfen Chen , Zhiliang Jin . Chirality regulated CdS/Co-doped Ti₃C₂ MXene Schottky heterojunction for microplastic photoreforming to hydrogen and pyruvic acid. Acta Physico-Chimica Sinica, 2026, 42(10): 100350-0. doi: 10.1016/j.actphy.2026.100350
20. [20]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011

Get Citation

PDF

XML

Metrics

PDF Downloads(21)
Abstract views(2508)
HTML views(181)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142