注册 English

基于手性共价有机框架材料的气相色谱固定相的合成和分离性能研究

黄芝凤 ,  贾文燕 ,  袁黎明

downloadPDF
引用本文: 黄芝凤, 贾文燕, 袁黎明. 基于手性共价有机框架材料的气相色谱固定相的合成和分离性能研究[J]. 分析化学, 2023, 51(3): 436-444. doi: 10.19756/j.issn.0253-3820.221309 shu
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

基于手性共价有机框架材料的气相色谱固定相的合成和分离性能研究

  • 云南师范大学化学化工学院, 昆明 650500

    • 通讯作者: 袁黎明,E-mail:yuan_limingpd@126.com
  • 基金项目:

    国家自然科学基金项目(No.22174125)资助。

摘要: 手性共价有机框架材料(CCOFs)在不对称催化、手性识别等诸多领域中具有重要的应用价值,其中,手性分离以其方便、快速和高效的特点成为CCOFs最重要的应用之一。为了进一步开拓CCOFs在色谱手性分离方面的应用,本研究利用后合成修饰法将L-缬氨酸修饰在共价有机框架材料(COFs) TpPa (NH2)2上、L-异亮氨酸分别修饰在COFs TpPa (NH2)2和TpBD (NH2)2上,得到3种CCOFs。将这3种CCOFs分别用作气相色谱手性固定相(CSPs),与聚硅氧烷OV-1701以质量比为3:7混合配制成4.5 mg/mL的涂渍液,采用动态涂敷法制备了3根毛细管色谱柱进行手性分离分析。研究结果表明,3根色谱柱均具有良好的手性选择性和重复性,可用于氨基酸、醇、醛、酯、醚、酸和酮等25种手性化合物以及正构烷烃、正构醇、芳香族混合物和Grob试剂的快速分离,并且3根柱分离的手性化合物类型具有一定的互补性。3种CCOFs在气相色谱手性分离方面具有较广的手性选择性和良好的互补性。本研究提供了一种利用后合成修饰法合成CCOFs的新策略,拓展了CCOFs在手性分离领域的应用,证明CCOFs作为一种新型CSPs在色谱手性分离方面具有良好的应用前景。

English


    1. [1]

      ZHONG Hui, ZENG Qing-Li, ZHANG Tian-Ci, SHUANG Ya-Zhou, LI Lai-Sheng. Chin. J. Anal. Chem., 2022, 50(3):433-451. 钟慧, 曾庆丽, 张天赐, 双亚洲, 李来生. 分析化学, 2022, 50(3):433-451.

    2. [2]

      WARD T J, WARD K D. Anal. Chem., 2012, 84(2):626-635.WARD T J, WARD K D. Anal. Chem., 2012, 84(2):626-635.

    3. [3]

      LIU Yu-Jian, LIU Zhi-Min, XU Zhi-Gang. Chin. J. Anal. Chem., 2017, 45(3):369-373. 刘育坚, 刘智敏, 许志刚. 分析化学, 2017, 45(3):369-373.

    4. [4]

      DOBÓ M, FOROUGHBAKHSHFASAEI M, HORVÁTH P, SZABÓ Z I, TÓTH G. J. Chromatogr. A, 2022, 1662:462741.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.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.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.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.SCHURIG V. J. Chromatog. A, 1994, 666(1-2):111-129.

    9. [9]

      SCHURIG V. J. Chromatogr. A, 2001, 906(1-2):275-299.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.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.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.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.NIE M Y, ZHOU L M, WANG Q H, ZHU D Q. Chromatographia, 2000, 51(11-12):736-740.

    14. [14]

      SHI Jie-Hua, YE Yan. Chin. J. Anal. Chem., 2010, 38(10):1450-1456. 施介华, 叶燕. 分析化学, 2010, 38(10):1450-1456.

    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.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.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.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.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.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.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.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]

      REN Chao-Xing, AI Ping, LI Li, ZI Min, MENG Xia, DING Hui, YUAN Li-Ming. Chin. J. Anal. Chem., 2006, 34(11):1637-1640. 任朝兴, 艾萍, 李莉, 字敏, 孟霞, 丁惠, 袁黎明. 分析化学, 2006, 34(11):1637-1640.

    23. [23]

      HAN X, YUAN C, HOU B, LIU L, LI H, LIU Y, CUI Y. Chem. Soc. Rev., 2020, 49(17):6248-6272.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.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.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.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.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.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.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.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.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.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.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.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.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.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.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.WANG W, ZHANG Y, TANG B, HOU H, TANG S, LUO A. J. Chromatogr. A, 2022, 1675:463150.

  • 加载中
WeChat 扫一扫看文章
计量
  • PDF下载量:  15
  • 文章访问数:  1484
  • HTML全文浏览量:  97
文章相关
  • 收稿日期:  2022-06-23
  • 修回日期:  2023-02-22
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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章

All Rights Reserved by the Chinese Chemical Society   中国化学会 版权所有 京ICP备05002797号

本系统由北京仁和汇智信息技术有限公司开发    技术支持: info@rhhz.net