Skip to main content
SpringerLink
Log in

Chiral covalent organic frameworks for asymmetric catalysis and chiral separation

  • Mini Reviews
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Covalent organic frameworks (COFs), covalently assembled from the condensation reactions of organic building blocks, are a fascinating class of functional porous materials with two- or three-dimensional crystalline organic structures. Generally, it is preferable to use symmetric and rigid building blocks to construct highly crystalline COFs with desired topology. On the other hand, the incorporation of chiral functional moieties in the building blocks would open up new applications such as asymmetric catalysis and chiral separation. This mini review highlights the principle strategies in the design and synthesis of chiral COFs. The interesting and potential applications of these chiral COFs for asymmetric catalysis and chiral separation are also summarized. This mini review aims to provide an up-to-date advancement of chiral COFs for asymmetric catalysis and chiral separation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Côté AP, Benin AI, Ockwig NW, O’Keeffe M, Matzger AJ, Yaghi OM. Science, 2005, 310: 1166–1170

    Article  Google Scholar 

  2. Hunt JR, Doonan CJ, Le Vangie JD, Côté AP, Yaghi OM. J Am Chem Soc, 2008, 130: 11872–11873

    Article  CAS  Google Scholar 

  3. Wan S, Guo J, Kim J, Ihee H, Jiang D. Angew Chem Int Ed, 2008, 47: 8826–8830

    Article  CAS  Google Scholar 

  4. Liu Y, Ma Y, Zhao Y, Sun X, Gándara F, Furukawa H, Liu Z, Zhu H, Zhu C, Suenaga K, Oleynikov P, Alshammari AS, Zhang X, Terasaki O, Yaghi OM. Science, 2016, 351: 365–369

    Article  CAS  Google Scholar 

  5. El-Kaderi HM, Hunt JR, Mendoza-Cortés JL, Côté AP, Taylor RE, O’Keeffe M, Yaghi OM. Science, 2007, 316: 268–272

    Article  CAS  Google Scholar 

  6. Han SS, Mendoza-Cortés JL, Goddard III WA. Chem Soc Rev, 2009, 38: 1460–1476

    Article  CAS  Google Scholar 

  7. Feng X, Ding X, Jiang D. Chem Soc Rev, 2012, 41: 6010–6022

    Article  CAS  Google Scholar 

  8. Ding SY, Wang W. Chem Soc Rev, 2013, 42: 548–568

    Article  CAS  Google Scholar 

  9. Waller PJ, Gándara F, Yaghi OM. Acc Chem Res, 2015, 48: 3053–3063

    Article  CAS  Google Scholar 

  10. Sakaushi K, Antonietti M. Acc Chem Res, 2015, 48: 1591–1600

    Article  CAS  Google Scholar 

  11. Das S, Heasman P, Ben T, Qiu S. Chem Rev, 2017, 117: 1515–1563

    Article  CAS  Google Scholar 

  12. Diercks CS, Yaghi OM. Science, 2017, 355: eaal1585

    Google Scholar 

  13. Xiang Z, Cao D, Dai L. Polym Chem, 2015, 6: 1896–1911

    Article  CAS  Google Scholar 

  14. Huang N, Wang P, Jiang D. Nat Rev Mater, 2016, 1: 16068

    Article  CAS  Google Scholar 

  15. Segura JL, Mancheño MJ, Zamora F. Chem Soc Rev, 2016, 45: 5635–5671

    Article  CAS  Google Scholar 

  16. Li Z, Feng X, Zou Y, Zhang Y, Xia H, Liu X, Mu Y. Chem Commun, 2014, 50: 13825–13828

    Article  CAS  Google Scholar 

  17. Huang N, Chen X, Krishna R, Jiang D. Angew Chem Int Ed, 2015, 54: 2986–2990

    Article  CAS  Google Scholar 

  18. Xiang Z, Mercado R, Huck JM, Wang H, Guo Z, Wang W, Cao D, Haranczyk M, Smit B. J Am Chem Soc, 2015, 137: 13301–13307

    Article  CAS  Google Scholar 

  19. Wei H, Chai S, Hu N, Yang Z, Wei L, Wang L. Chem Commun, 2015, 51: 12178–12181

    Article  CAS  Google Scholar 

  20. Stegbauer L, Hahn MW, Jentys A, Savasci G, Ochsenfeld C, Lercher JA, Lotsch BV. Chem Mater, 2015, 27: 7874–7881

    Article  CAS  Google Scholar 

  21. Pyles DA, Crowe JW, Baldwin LA, McGrier PL. ACS Macro Lett, 2016, 5: 1055–1058

    Article  CAS  Google Scholar 

  22. Baldwin LA, Crowe JW, Pyles DA, McGrier PL. J Am Chem Soc, 2016, 138: 15134–15137

    Article  CAS  Google Scholar 

  23. Zeng Y, Zou R, Zhao Y. Adv Mater, 2016, 28: 2855–2873

    Article  CAS  Google Scholar 

  24. Kang Z, Peng Y, Qian Y, Yuan D, Addicoat MA, Heine T, Hu Z, Tee L, Guo Z, Zhao D. Chem Mater, 2016, 28: 1277–1285

    Article  CAS  Google Scholar 

  25. Fu J, Das S, Xing G, Ben T, Valtchev V, Qiu S. J Am Chem Soc, 2016, 138: 7673–7680

    Article  CAS  Google Scholar 

  26. Biswal BP, Chaudhari HD, Banerjee R, Kharul UK. Chem Eur J, 2016, 22: 4695–4699

    Article  CAS  Google Scholar 

  27. Pachfule P, Kandambeth S, Díaz Díaz D, Banerjee R. Chem Commun, 2014, 50: 3169–3172

    Article  CAS  Google Scholar 

  28. Fang Q, Gu S, Zheng J, Zhuang Z, Qiu S, Yan Y. Angew Chem Int Ed, 2014, 53: 2878–2882

    Article  CAS  Google Scholar 

  29. Shinde DB, Kandambeth S, Pachfule P, Kumar RR, Banerjee R. Chem Commun, 2015, 51: 310–313

    Article  CAS  Google Scholar 

  30. Xu F, Xu H, Chen X, Wu D, Wu Y, Liu H, Gu C, Fu R, Jiang D. Angew Chem Int Ed, 2015, 54: 6814–6818

    Article  CAS  Google Scholar 

  31. DeBlase CR, Hernández-Burgos K, Rotter JM, Fortman DJ, dos S. Abreu D, Timm RA, Diógenes ICN, Kubota LT, Abruña HD, Dichtel WR. Angew Chem Int Ed, 2015, 54: 13225–13229

    Article  CAS  Google Scholar 

  32. Liao H, Wang H, Ding H, Meng X, Xu H, Wang B, Ai X, Wang C. J Mater Chem A, 2016, 4: 7416–7421

    Article  CAS  Google Scholar 

  33. Yoo JT, Cho SJ, Jung GY, Kim SH, Choi KH, Kim JH, Lee CK, Kwak SK, Lee SY. Nano Lett, 2016, 16: 3292–3300

    Article  CAS  Google Scholar 

  34. Vazquez-Molina DA, Mohammad-Pour GS, Lee C, Logan MW, Duan X, Harper JK, Uribe-Romo FJ. J Am Chem Soc, 2016, 138: 9767–9770

    Article  CAS  Google Scholar 

  35. Patra BC, Khilari S, Satyanarayana L, Pradhan D, Bhaumik A. Chem Commun, 2016, 52: 7592–7595

    Article  CAS  Google Scholar 

  36. Bai L, Gao Q, Zhao Y. J Mater Chem A, 2016, 4: 14106–14110

    Article  CAS  Google Scholar 

  37. Chandra S, Roy Chowdhury D, Addicoat M, Heine T, Paul A, Banerjee R. Chem Mater, 2017, 29: 2074–2080

    Article  CAS  Google Scholar 

  38. Ding SY, Dong M, Wang YW, Chen YT, Wang HZ, Su CY, Wang W. J Am Chem Soc, 2016, 138: 3031–3037

    Article  CAS  Google Scholar 

  39. Aiyappa HB, Thote J, Shinde DB, Banerjee R, Kurungot S. Chem Mater, 2016, 28: 4375–4379

    Article  CAS  Google Scholar 

  40. Huang N, Zhai L, Xu H, Jiang D. J Am Chem Soc, 2017, 139: 2428–2434

    Article  CAS  Google Scholar 

  41. Sun Q, Aguila B, Perman J, Earl LD, Abney CW, Cheng Y, Wei H, Nguyen N, Wojtas L, Ma S. J Am Chem Soc, 2017, 139: 2786–2793

    Article  CAS  Google Scholar 

  42. Thote J, Aiyappa HB, Deshpande A, Díaz Díaz D, Kurungot S, Banerjee R. Chem Eur J, 2014, 20: 15961–15965

    Article  CAS  Google Scholar 

  43. Stegbauer L, Schwinghammer K, Lotsch BV. Chem Sci, 2014, 5: 2789–2793

    Article  CAS  Google Scholar 

  44. Vyas VS, Haase F, Stegbauer L, Savasci G, Podjaski F, Ochsenfeld C, Lotsch BV. Nat Commun, 2015, 6: 8508

    Article  CAS  Google Scholar 

  45. Dalapati S, Jin E, Addicoat M, Heine T, Jiang D. J Am Chem Soc, 2016, 138: 5797–5800

    Article  CAS  Google Scholar 

  46. Lin G, Ding H, Yuan D, Wang B, Wang C. J Am Chem Soc, 2016, 138: 3302–3305

    Article  CAS  Google Scholar 

  47. Wang P, Kang M, Sun S, Liu Q, Zhang Z, Fang S. Chin J Chem, 2014, 32: 838–843

    Article  CAS  Google Scholar 

  48. Das G, Biswal BP, Kandambeth S, Venkatesh V, Kaur G, Addicoat M, Heine T, Verma S, Banerjee R. Chem Sci, 2015, 6: 3931–3939

    Article  CAS  Google Scholar 

  49. Li Z, Zhang Y, Xia H, Mu Y, Liu X. Chem Commun, 2016, 52: 6613–6616

    Article  CAS  Google Scholar 

  50. Karmakar A, Kumar A, Chaudhari AK, Samanta P, Desai AV, Krishna R, Ghosh SK. Chem Eur J, 2016, 22: 4931–4937

    Article  CAS  Google Scholar 

  51. Zhang Y, Shen X, Feng X, Xia H, Mu Y, Liu X. Chem Commun, 2016, 52: 11088–11091

    Article  CAS  Google Scholar 

  52. Chen L, Furukawa K, Gao J, Nagai A, Nakamura T, Dong Y, Jiang D. J Am Chem Soc, 2014, 136: 9806–9809

    Article  CAS  Google Scholar 

  53. Dogru M, Bein T. Chem Commun, 2014, 50: 5531–5546

    Article  CAS  Google Scholar 

  54. Ding H, Li Y, Hu H, Sun Y, Wang J, Wang C, Wang C, Zhang G, Wang B, Xu W, Zhang D. Chem Eur J, 2014, 20: 14614–14618

    Article  CAS  Google Scholar 

  55. Chandra S, Kundu T, Kandambeth S, Babarao R, Marathe Y, Kunjir SM, Banerjee R. J Am Chem Soc, 2014, 136: 6570–6573

    Article  CAS  Google Scholar 

  56. Calik M, Auras F, Salonen LM, Bader K, Grill I, Handloser M, Medina DD, Dogru M, Löbermann F, Trauner D, Hartschuh A, Bein T. J Am Chem Soc, 2014, 136: 17802–17807

    Article  CAS  Google Scholar 

  57. Cai SL, Zhang YB, Pun AB, He B, Yang J, Toma FM, Sharp ID, Yaghi OM, Fan J, Zheng SR, Zhang WG, Liu Y. Chem Sci, 2014, 5: 4693–4700

    Article  CAS  Google Scholar 

  58. Jin S, Supur M, Addicoat M, Furukawa K, Chen L, Nakamura T, Fukuzumi S, Irle S, Jiang D. J Am Chem Soc, 2015, 137: 7817–7827

    Article  CAS  Google Scholar 

  59. Ma H, Liu B, Li B, Zhang L, Li YG, Tan HQ, Zang HY, Zhu G. J Am Chem Soc, 2016, 138: 5897–5903

    Article  CAS  Google Scholar 

  60. Xu H, Tao S, Jiang D. Nat Mater, 2016, 15: 722–726

    Article  CAS  Google Scholar 

  61. Chandra S, Kundu T, Dey K, Addicoat M, Heine T, Banerjee R. Chem Mater, 2016, 28: 1489–1494

    Article  CAS  Google Scholar 

  62. Medina DD, Petrus ML, Jumabekov AN, Margraf JT, Weinberger S, Rotter JM, Clark T, Bein T. ACS Nano, 2017, 11: 2706–2713

    Article  CAS  Google Scholar 

  63. Meng X, Wang HN, Song SY, Zhang HJ. Chem Soc Rev, 2017, 46: 464–480

    Article  CAS  Google Scholar 

  64. Feldblyum JI, McCreery CH, Andrews SC, Kurosawa T, Santos EJG, Duong V, Fang L, Ayzner AL, Bao Z. Chem Commun, 2015, 51: 13894–13897

    Article  CAS  Google Scholar 

  65. Fang Q, Wang J, Gu S, Kaspar RB, Zhuang Z, Zheng J, Guo H, Qiu S, Yan Y. J Am Chem Soc, 2015, 137: 8352–8355

    Article  CAS  Google Scholar 

  66. Bai L, Phua SZF, Lim WQ, Jana A, Luo Z, Tham HP, Zhao L, Gao Q, Zhao Y. Chem Commun, 2016, 52: 4128–4131

    Article  CAS  Google Scholar 

  67. Vyas VS, Vishwakarma M, Moudrakovski I, Haase F, Savasci G, Ochsenfeld C, Spatz JP, Lotsch BV. Adv Mater, 2016, 28: 8749–8754

    Article  CAS  Google Scholar 

  68. Tan J, Namuangruk S, Kong W, Kungwan N, Guo J, Wang C. Angew Chem Int Ed, 2016, 55: 13979–13984

    Article  CAS  Google Scholar 

  69. Ding SY, Gao J, Wang Q, Zhang Y, Song WG, Su CY, Wang W. J Am Chem Soc, 2011, 133: 19816–19822

    Article  CAS  Google Scholar 

  70. Nagai A, Guo Z, Feng X, Jin S, Chen X, Ding X, Jiang D. Nat Commun, 2011, 2: 536

    Article  Google Scholar 

  71. Xu H, Chen X, Gao J, Lin J, Addicoat M, Irle S, Jiang D. Chem Commun, 2014, 50: 1292–1294

    Article  CAS  Google Scholar 

  72. Qian HL, Yang CX, Yan XP. Nat Commun, 2016, 7: 12104

    Article  CAS  Google Scholar 

  73. Xu HS, Ding SY, An WK, Wu H, Wang W. J Am Chem Soc, 2016, 138: 11489–11492

    Article  CAS  Google Scholar 

  74. Wang X, Han X, Zhang J, Wu X, Liu Y, Cui Y. J Am Chem Soc, 2016, 138: 12332–12335

    Article  CAS  Google Scholar 

  75. Ascherl L, Sick T, Margraf JT, Lapidus SH, Calik M, Hettstedt C, Karaghiosoff K, Döblinger M, Clark T, Chapman KW, Auras F, Bein T. Nat Chem, 2016, 8: 310–316

    Article  CAS  Google Scholar 

  76. Xu H, Gao J, Jiang D. Nat Chem, 2015, 7: 905–912

    Article  CAS  Google Scholar 

  77. Yang CX, Liu C, Cao YM, Yan XP. Chem Commun, 2015, 51: 12254–12257

    Article  CAS  Google Scholar 

  78. Liu LH, Yang CX, Yan XP. J Chromatogr A, 2017, 1479: 137–144

    Article  CAS  Google Scholar 

  79. Liu GF, Zhang D, Feng CL. Angew Chem Int Ed, 2014, 53: 7789–7793

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Singapore Academic Research Fund (RG112/15, RG19/16).

Author information

Authors and Affiliations

  1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore

    Guofeng Liu, Jianhui Sheng & Yanli Zhao

  2. School of Materials Science and Engineering, Nanyang Technological University, Singapore, 639798, Singapore

    Yanli Zhao

  3. Department of Macromolecular Science, Fudan University, Shanghai, 200433, China

    Jianhui Sheng

Authors
  1. Guofeng Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jianhui Sheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yanli Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yanli Zhao.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, G., Sheng, J. & Zhao, Y. Chiral covalent organic frameworks for asymmetric catalysis and chiral separation. Sci. China Chem. 60, 1015–1022 (2017). https://doi.org/10.1007/s11426-017-9070-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-017-9070-1

Keywords

Search

Navigation