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Stereo-control on Lanthanide Triple-stranded Helicates Toward Enhanced Enantioselective Sensing

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Chemical Research in Chinese Universities Aims and scope

Abstract

Chiral metal-organic cages (MOCs) serve as a representative model for enzyme simulation, offering a robust platform for reproducing and expanding enzyme functions at the molecular level. In this study, we present a family of lanthanide triple-stranded helicates with finely-tuned stereoconfigurations, self-assembled from ligands featuring both point and axial chiral centers. Circular dichroism (CD) and circularly polarized luminescence (CPL) spectroscopy demonstrated that peripheral point chirality induces the stereoconfiguration (Δ/Λ) of the metal center, while bridging axial chirality defines the cavity chiral microenvironment, resulting in the formation of both homochiral and mesomeric helicates. In comparison to mesocate, the homochiral helicates exhibited heightened enantioselectivity in the luminescent detection of D/L-leucinol.

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References

  1. Xuan W., Zhang M., Liu Y., Chen Z., Cui Y., J. Am. Chem. Soc., 2012, 134, 6904

    Article  CAS  PubMed  Google Scholar 

  2. Schulte T. R., Holstein J. J., Clever G. H., Angew. Chem. Int. Ed., 2019, 58, 5562

    Article  CAS  Google Scholar 

  3. Guo X. Q., Zhou L. P., Hu S. J., Cai L. X., Cheng P. M., Sun Q. F., J. Am. Chem. Soc., 2021, 143, 6202

    Article  CAS  PubMed  Google Scholar 

  4. Wu K., Li K., Hou Y.-J., Pan M., Zhang L.-Y., Chen L., Su C.-Y., Nat. Commun., 2016, 7, 10487

    Article  ADS  CAS  PubMed  PubMed Central  Google Scholar 

  5. Zhu C., Tang H., Yang K., Fang Y., Wang K.-Y., Xiao Z., Wu X., Li Y., Powell J. A., Zhou H.-C., J. Am. Chem. Soc., 2021, 143, 12560

    Article  CAS  PubMed  Google Scholar 

  6. Wu G. C., Chen Y. X., Fang S., Tong L., Shen L. B., Ge C. Q., Pan Y. J., Shi X. L., Li H., Angew. Chem. Int. Ed., 2021, 60, 16594

    Article  CAS  Google Scholar 

  7. Jiao J., Dong J., Li Y., Cui Y., Angew. Chem. Int. Ed., 2021, 60, 16568

    Article  CAS  Google Scholar 

  8. Ueda Y., Ito H., Fujita D., Fujita M., J. Am. Chem. Soc., 2017, 139, 6090

    Article  CAS  PubMed  Google Scholar 

  9. Jiao J. J., Tan C. X., Li Z. J., Liu Y., Han X., Cui Y., J. Am. Chem. Soc., 2018, 140, 2251

    Article  CAS  PubMed  Google Scholar 

  10. Li X. Z., Wu J. G., He C., Meng Q. T., Duan C. Y., Small, 2019, 15, 1804770

    Article  Google Scholar 

  11. Guo J., Fan Y.-Z., Lu Y.-L., Zheng S.-P., Su C.-Y., Angew. Chem. Int. Ed., 2020, 59, 8661

    Article  CAS  Google Scholar 

  12. Chu D., Gong W., Jiang H., Tang X., Cui Y., Liu Y., CCS Chem., 2022, 4, 1180

    Article  CAS  Google Scholar 

  13. Zhao C., Toste F. D., Raymond K. N., Bergman R. G., J. Am. Chem. Soc., 2014, 136, 14409

    Article  CAS  PubMed  Google Scholar 

  14. Zhu H. T. Z., Li Q., Shi B. B., Xing H., Sun Y., Lu S., Shangguan L. Q., Li X. P., Huang F. H., Stang P. J., J. Am. Chem. Soc., 2020, 142, 17340

    Article  CAS  PubMed  Google Scholar 

  15. He Y. P., Chen G. H., Li D. J., Li Q. H., Zhang L., Zhang J., Angew. Chem. Int. Ed., 2021, 60, 2920

    Article  CAS  Google Scholar 

  16. Lu Z. F., Ronson T. K., Heard A. W., Feldmann S., Vanthuyne N., Martinez A., Nitschke J. R., Nat. Chem., 2023, 15, 405

    Article  CAS  PubMed  Google Scholar 

  17. Pan M., Wu K., Zhang J.-H., Su C.-Y., Coord. Chem. Rev., 2019, 378, 333

    Article  CAS  Google Scholar 

  18. Chen W., Tang X., Dou W., Wang B., Guo L., Ju Z., Liu W., Chem. Eur. J., 2017, 23, 9804

    Article  CAS  PubMed  Google Scholar 

  19. Tateishi T., Kojima T., Hiraoka S., Commun. Chem., 2018, 1, 20

    Article  Google Scholar 

  20. Raee E., Liu B. Q., Yang Y. Q., Namani T., Cui Y. P., Sahai N., Li X. P., Liu T. B., Nano Lett., 2022, 22, 4421

    Article  ADS  CAS  PubMed  Google Scholar 

  21. Huang C., Li J. J., Zhu X. Y., Wang Y. F., Nanoscale, 2023, 15, 19475

    Article  CAS  PubMed  Google Scholar 

  22. Zhou Y., Li H., Zhu T., Gao T., Yan P., J. Am. Chem. Soc., 2019, 141, 19634

    Article  CAS  PubMed  Google Scholar 

  23. Tan Y. B., Okayasu Y., Katao S., Nishikawa Y., Asanoma F., Yamada M., Yuasa J., Kawai T., J. Am. Chem. Soc., 2020, 142, 17653

    Article  CAS  PubMed  Google Scholar 

  24. Howlader P., Mondal S., Ahmed S., Mukherjee P. S., J. Am. Chem. Soc., 2020, 142, 20968

    Article  CAS  PubMed  Google Scholar 

  25. Hu S. J., Guo X. Q., Zhou L. P., Yan D. N., Cheng P. M., Cai L. X., Li X. Z., Sun Q. F., J. Am. Chem. Soc., 2022, 144, 4244

    Article  CAS  PubMed  Google Scholar 

  26. He Y.-P., Yuan L.-B., Song J.-S., Chen G.-H., Ling Q., Li C., Zhang L., Zhang J., Chem. Mater., 2018, 30, 7769

    Article  CAS  Google Scholar 

  27. Hamilton T. D., MacGillivray L. R., Cryst. Growth Des., 2004, 4, 419

    Article  CAS  Google Scholar 

  28. Jin R. Z., Bian Z., He Y. B., Gao L. X., Chem. Res. Chinese Universities, 2010, 26 (6), 857

    CAS  Google Scholar 

  29. Chen L.-J., Yang H.-B., Shionoya M., Chem. Soc. Rev., 2017, 46, 2555

    Article  CAS  PubMed  Google Scholar 

  30. Sen S. K., Natarajan R., Inorg. Chem., 2019, 58, 7180

    Article  CAS  PubMed  Google Scholar 

  31. Luo X.-Y., Pan M., Coord. Chem. Rev., 2022, 468, 214640

    Article  CAS  Google Scholar 

  32. Dou W.-T., Yang C.-Y., Hu L.-R., Song B., Jin T., Jia P.-P., Ji X., Zheng F., Yang H.-B., Xu L., ACS Materials Lett., 2023, 5, 1061

    Article  CAS  Google Scholar 

  33. Han Z., Wang K., Wang M., Sun T., Xu J., Zhou H.-C., Cheng P., Shi W., Chem, 2023, 9, 2561

    Article  CAS  Google Scholar 

  34. Bunzen J., Bruhn T., Bringmann G., Lutzen A., J. Am. Chem. Soc., 2009, 131, 3621

    Article  CAS  PubMed  Google Scholar 

  35. Malik A. U., Gan F. W., Shen C. S., Yu N., Wang R. B., Crassous J., Shu M. H., Qiu H. B., J. Am. Chem. Soc., 2018, 140, 2769

    Article  CAS  PubMed  Google Scholar 

  36. Zhou Y. Y., Li H. F., Zhu T. Y., Gao T., Yan P. F., J. Am. Chem. Soc., 2019, 141, 19634

    Article  CAS  PubMed  Google Scholar 

  37. Ramakrishna E., Tang J. D., Tao J. J., Fang Q., Zhang Z. B., Huang J. Y., Li S. J., Chem. Commun., 2021, 57, 9088

    Article  CAS  Google Scholar 

  38. Zhang L. Y., Liu H. P., Yuan G. Z., Han Y. F., Chin. J. Chem., 2021, 39, 2273

    Article  CAS  Google Scholar 

  39. Domoto Y., Yamamoto K., Horie S., Yu Z. S., Fujita M., Chem. Sci., 2022, 13, 4372

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Stang P. J., Olenyuk B., Muddiman D. C., Smith R. D., Organometallics, 1997, 16, 3094

    Article  CAS  Google Scholar 

  41. Nishioka Y., Yamaguchi T., Kawano M., Fujita M., J. Am. Chem. Soc., 2008, 130, 8160

    Article  CAS  PubMed  Google Scholar 

  42. Chepelin O., Ujma J., Wu X., Slawin A. M. Z., Pitak M. B., Coles S. J., Michel J., Jones A. C., Barran P. E., Lusby P. J., J. Am. Chem. Soc., 2012, 134, 19334

    Article  CAS  PubMed  Google Scholar 

  43. Yang Y., Jia J.-H., Pei X.-L., Zheng H., Nan Z.-A., Wang Q.-M., Chem. Commun., 2015, 51, 3804

    Article  CAS  Google Scholar 

  44. Wu H. B., Wang Q. M., Angew. Chem. Int. Ed., 2009, 48, 7343

    Article  CAS  Google Scholar 

  45. Bolliger J. L., Belenguer A. M., Nitschke J. R., Angew. Chem. Int. Ed., 2013, 52, 7958

    Article  CAS  Google Scholar 

  46. Zhao C., Sun Q.-F., Hart-Cooper W. M., DiPasquale A. G., Toste F. D., Bergman R. G., Raymond K. N., J. Am. Chem. Soc., 2013, 135, 18802

    Article  CAS  PubMed  Google Scholar 

  47. Liu T., Liu Y., Xuan W., Cui Y., Angew. Chem. Int. Ed., 2010, 49, 4121

    Article  CAS  Google Scholar 

  48. Klein C., Gütz C., Bogner M., Topić F., Rissanen K., Lützen A., Angew. Chem. Int. Ed., 2014, 53, 3739

    Article  CAS  Google Scholar 

  49. Chen L., Kang J., Cui H., Wang Y., Liu L., Zhang L., Su C.-Y., Dalton Trans., 2015, 44, 12180

    Article  CAS  PubMed  Google Scholar 

  50. Yeung C. T., Yim K. H., Wong H. Y., Pal R., Lo W. S., Yan S. C., Yee-Man Wong M., Yufit D., Smiles D. E., McCormick L. J., Teat S. J., Shuh D. K., Wong W. T., Law G. L., Nat. Commun., 2017, 8, 1128

    Article  ADS  PubMed  PubMed Central  Google Scholar 

  51. Li K., Zhang L.-Y., Yan C., Wei S.-C., Pan M., Zhang L., Su C.-Y., J. Am. Chem. Soc., 2014, 136, 4456

    Article  CAS  PubMed  Google Scholar 

  52. Yan L.-L., Tan C.-H., Zhang G.-L., Zhou L.-P., Bünzli J.-C., Sun Q.-F., J. Am. Chem. Soc., 2015, 137, 8550

    Article  CAS  PubMed  Google Scholar 

  53. Howlader P., Mukherjee P. S., Chem. Sci., 2016, 7, 5893

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. Nemoto T., Ohshima T., Yamaguchi K., Shibasaki M., J. Am. Chem. Soc., 2001, 123, 2725

    Article  CAS  PubMed  Google Scholar 

  55. Brunel J. M., Chem. Rev., 2005, 105, 857

    Article  CAS  PubMed  Google Scholar 

  56. Parmar D., Sugiono E., Raja S., Rueping M., Chem. Rev., 2014, 114, 9047

    Article  CAS  PubMed  Google Scholar 

  57. Yan L. L., Tan C. H., Zhang G. L., Zhou L. P., Bunzli J. C., Sun Q. F., J. Am. Chem. Soc., 2015, 137, 8550

    Article  CAS  PubMed  Google Scholar 

  58. Yeung C.-T., Chan W. T. K., Yan S.-C., Yu K.-L., Yim K.-H., Wong W.-T., Law G.-L., Chem. Commun., 2015, 51, 592

    Article  CAS  Google Scholar 

  59. Parmar D., Sugiono E., Raja S., Rueping M., Chem. Rev., 2017, 117, 10608

    Article  CAS  PubMed  Google Scholar 

  60. Tang X. H., Chu D. D., Gong W., Cui Y., Liu Y., Angew. Chem. Int. Ed., 2021, 60, 9099

    Article  CAS  Google Scholar 

  61. Zou Y. Q., Zhang D. W., Ronson T. K., Tarzia A., Lu Z. F., Jelfs K. E., Nitschke J. R., J. Am. Chem. Soc., 2021, 143, 9009

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. Franchino A., Marti A., Echavarren A. M., J. Am. Chem. Soc., 2022, 144, 3497

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  63. Chen G.-H., He Y.-P., Yu Y., Lv H., Li S., Wang F., Gu Z.-G., Zhang J., Angew. Chem. Int. Ed., 2023, 62, e202300726

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the National Key Research and Development Program of China (Nos. 2021YFA1500400 and 2022YFA1503300) and the National Natural Science Foundation of China (Nos. 22201285, 21825107, and 22171264).

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Authors and Affiliations

  1. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, P. R. China

    Xiaoqing Guo, Xinyuan Zhang, Shaojun Hu, Lipeng Zhou & Qingfu Sun

  2. University of Chinese Academy of Sciences, Beijing, 100049, P. R. China

    Xinyuan Zhang & Qingfu Sun

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  1. Xiaoqing Guo
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  2. Xinyuan Zhang
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  3. Shaojun Hu
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  4. Lipeng Zhou
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  5. Qingfu Sun
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Correspondence to Xiaoqing Guo or Qingfu Sun.

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Guo, X., Zhang, X., Hu, S. et al. Stereo-control on Lanthanide Triple-stranded Helicates Toward Enhanced Enantioselective Sensing. Chem. Res. Chin. Univ. (2024). https://doi.org/10.1007/s40242-024-3287-2

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