Skip to main content
Log in

Selective construction of molecular Solomon links and figure-eight knots by fine-tuning unsymmetrical ligands

  • Articles
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Using the strategy of ligand fine-tuning by steric hindrance, we successfully obtained Solomon links (\(4_1^2\)) and figure-eight knots (41) with half-sandwich organometallic unit and amino-acid embedded ligands. The two curved bidentate ligands exhibit subtle differences, whereas they result in totally distinct entanglement modes. An alcoholysis reaction with the ligands leads to the formation of a molecular tweezer. Notably, unsymmetrical ligands were utilized in the self-assembly process to explore the formation of directional molecules, and the reactions exhibited selectivity due to comprehensive π interactions and multiple hydrogen bonds. The topologies and behavior of the above structures were confirmed through single-crystal X-ray diffraction, nuclear magnetic resonance techniques and mass spectrometry.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Dietrich-Buchecker CO, Sauvage JP, Kintzinger JP. Tetrahedron Lett, 1983, 24: 5095–5098

    Article  CAS  Google Scholar 

  2. Gil-Ramírez G, Leigh DA, Stephens AJ. Angew Chem Int Ed, 2015, 54: 6110–6150

    Article  Google Scholar 

  3. Sawada T, Yamagami M, Ohara K, Yamaguchi K, Fujita M. Angew Chem Int Ed, 2016, 55: 4519–4522

    Article  CAS  Google Scholar 

  4. Xu L, Zhang WB. Sci China Chem, 2018, 61: 3–16

    Article  CAS  Google Scholar 

  5. Oka Y, Masai H, Terao J. Angew Chem Int Ed, 2023, 62: e202217002

    Article  CAS  Google Scholar 

  6. Qiu XT, Yao R, Zhou WF, Liu MD, Liu Q, Song YL, Young DJ, Zhang WH, Lang JP. Chem Commun, 2018, 54: 4168–4171

    Article  CAS  Google Scholar 

  7. Shen YR, Gao X, Cui Z, Jin GX. Chin J Chem, 2021, 39: 3303–3308

    Article  CAS  Google Scholar 

  8. Pentecost CD, Chichak KS, Peters AJ, Cave GW, Cantrill SJ, Stoddart JF. Angew Chem Int Ed, 2007, 46: 218–222

    Article  CAS  Google Scholar 

  9. Ponnuswamy N, Cougnon FBL, Pantoş GD, Sanders JKM. J Am Chem Soc, 2014, 136: 8243–8251

    Article  CAS  PubMed  Google Scholar 

  10. Beves JE, Danon JJ, Leigh DA, Lemonnier JF, Vitorica-Yrezabal IJ. Angew Chem Int Ed, 2015, 54: 7555–7559

    Article  CAS  Google Scholar 

  11. Song YH, Singh N, Jung J, Kim H, Kim EH, Cheong HK, Kim Y, Chi KW. Angew Chem Int Ed, 2016, 55: 2007–2011

    Article  CAS  Google Scholar 

  12. Chichak KS, Cantrill SJ, Pease AR, Chiu SH, Cave GWV, Atwood JL, Stoddart JF. Science, 2004, 304: 1308–1312

    Article  CAS  PubMed  Google Scholar 

  13. Guo X, Lin E, Gao J, Mao T, Yan D, Cheng P, Ma S, Chen Y, Zhang Z. Angew Chem Int Ed, 2021, 60: 2974–2979

    Article  CAS  Google Scholar 

  14. Castle T, Evans ME, Hyde ST. New J Chem, 2008, 32: 1484–1492

    Article  CAS  Google Scholar 

  15. Zhao X, Wang H, Li B, Zhang W, Li X, Zhao W, Janiak C, Heard AW, Yang XJ, Wu B. Angew Chem Int Ed, 2022, 61: e202115042

    Article  CAS  Google Scholar 

  16. Dang LL, Zhang TT, Chen T, Zhao Y, Gao X, Aznarez F, Ma LF, Jin GX. Angew Chem Int Ed, 2023, 62: e202301516

    Article  CAS  Google Scholar 

  17. Liu XR, Cui PF, Guo ST, Lin YJ, Jin GX. J Am Chem Soc, 2023, 51: 7779–7809

    Google Scholar 

  18. Horner KE, Miller MA, Steed JW, Sutcliffe PM. Chem Soc Rev, 2016, 45: 6432–6448

    Article  CAS  PubMed  Google Scholar 

  19. Ashbridge Z, Fielden SDP, Leigh DA, Pirvu L, Schaufelberger F, Zhang L. Chem Soc Rev, 2022, 51: 7779–7809

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Jamieson EMG, Modicom F, Goldup SM. Chem Soc Rev, 2018, 47: 5266–5311

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Caprice K, Pál D, Besnard C, Galmés B, Frontera A, Cougnon FBL. J Am Chem Soc, 2021, 143: 11957–11962

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Rodríguez-Rubio A, Savoini A, Modicom F, Butler P, Goldup SM. J Am Chem Soc, 2022, 144: 11927–11932

    Article  PubMed  PubMed Central  Google Scholar 

  23. McConnell AJ, Wood CS, Neelakandan PP, Nitschke JR. Chem Rev, 2015, 115: 7729–7793

    Article  CAS  PubMed  Google Scholar 

  24. Wang Y, Gong J, Wang X, Li WJ, Wang XQ, He X, Wang W, Yang HB. Angew Chem Int Ed, 2022, 61: e202210542

    Article  CAS  Google Scholar 

  25. Liu JX, Chen K, Redshaw C. Chem Soc Rev, 2023, 52: 1428–1455

    Article  CAS  PubMed  Google Scholar 

  26. Goldup SM. Nat Chem, 2016, 8: 404–406

    Article  CAS  PubMed  Google Scholar 

  27. Marcos V, Stephens AJ, Jaramillo-Garcia J, Nussbaumer AL, Woltering SL, Valero A, Lemonnier JF, Vitorica-Yrezabal IJ, Leigh DA. Science, 2016, 352: 1555–1559

    Article  CAS  PubMed  Google Scholar 

  28. Mitra R, Zhu H, Grimme S, Niemeyer J. Angew Chem Int Ed, 2017, 56: 11456–11459

    Article  CAS  Google Scholar 

  29. Martinez-Cuezva A, Saura-Sanmartin A, Alajarin M, Berna J. ACS Catal, 2020, 10: 7719–7733

    Article  CAS  Google Scholar 

  30. Mo X, Deng Y, Lai SKM, Gao X, Yu HL, Low KH, Guo Z, Wu HL, Au-Yeung HY, Tse ECM. J Am Chem Soc, 2023, 145: 6087–6099

    Article  CAS  PubMed  Google Scholar 

  31. Zhang L, Qiu Y, Liu WG, Chen H, Shen D, Song B, Cai K, Wu H, Jiao Y, Feng Y, Seale JSW, Pezzato C, Tian J, Tan Y, Chen XY, Guo QH, Stern CL, Philp D, Astumian RD, Goddard Iii WA, Stoddart JF. Nature, 2023, 613: 280–286

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Jiao Y, Stoddart JF. Matter, 2021, 4: 2582–2584

    Article  CAS  Google Scholar 

  33. Zhang ZH, Andreassen BJ, August DP, Leigh DA, Zhang L. Nat Mater, 2022, 21: 275–283

    Article  CAS  PubMed  Google Scholar 

  34. Spence GT, Beer PD. Acc Chem Res, 2013, 46: 571–586

    Article  CAS  PubMed  Google Scholar 

  35. Lewis JEM, Beer PD, Loeb SJ, Goldup SM. Chem Soc Rev, 2017, 46: 2577–2591

    Article  CAS  PubMed  Google Scholar 

  36. Inthasot A, Tung ST, Chiu SH. Acc Chem Res, 2018, 51: 1324–1337

    Article  CAS  PubMed  Google Scholar 

  37. Gao WX, Feng HJ, Guo BB, Lu Y, Jin GX. Chem Rev, 2020, 120: 6288–6325

    Article  CAS  PubMed  Google Scholar 

  38. Alexander JW, Briggs GB. Ann Math, 1926, 28: 562–586

    Article  Google Scholar 

  39. Zhang HN, Lin YJ, Jin GX. Chem Asian J, 2021, 16: 1918–1924

    Article  CAS  PubMed  Google Scholar 

  40. Inomata Y, Sawada T, Fujita M. Chem, 2020, 6: 294–303

    Article  CAS  Google Scholar 

  41. Inomata Y, Sawada T, Fujita M. J Am Chem Soc, 2021, 143: 16734–16739

    Article  CAS  PubMed  Google Scholar 

  42. Cui Z, Mu QS, Gao X, Jin GX. J Am Chem Soc, 2023, 145: 725–731

    Article  CAS  PubMed  Google Scholar 

  43. Itabashi H, Datta S, Tsukuda R, Hollamby MJ, Yagai S. Chem Sci, 2023, 14: 3270–3276

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. Gao WX, Feng HJ, Lin YJ, Jin GX. J Am Chem Soc, 2019, 141: 9160–9164

    Article  CAS  PubMed  Google Scholar 

  45. Zhang HN, Yu WB, Lin YJ, Jin GX. Angew Chem Int Ed, 2021, 60: 15466–15471

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (22031003, 21720102004) and Shanghai Science Technology Committee (19DZ2270100).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Guo-Xin Jin.

Ethics declarations

Conflict of interest The authors declare no conflict of interest.

Additional information

Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

Supporting Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mu, QS., Gao, X., Cui, Z. et al. Selective construction of molecular Solomon links and figure-eight knots by fine-tuning unsymmetrical ligands. Sci. China Chem. 66, 2885–2891 (2023). https://doi.org/10.1007/s11426-023-1675-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-023-1675-0

Navigation