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A catalytic approach of blending CO2-activating MOF struts for cycloaddition reaction in a helically interlaced Cu(II) amino acid imidazolate framework: DFT-corroborated investigation

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Abstract

In CO2 transformation catalysis, the synthesis of cyclic carbonates using two classes of MOF catalysts viz., zeolitic imidazolate frameworks (ZIF) and MOFs with carboxylate-capped SBUs have gained large attention. Herein we propose the strategy of employing a unified multifunctional framework formed in the metal-centered assembly of imidazole and amino-carboxylates for CO2 transformation, such as propylene carbonate (PC) by the cycloaddition of CO2 with propylene oxide. The framework {[Cu(L-asp)(1,4-bix)0.5]·3H2O}n (CuAspBix) comprises of the amino acid building units, L-aspartic acid (L-Asp) and the flexible ligand, 1,4-bis(imidazole-1-yl methyl)benzene [1,4-Bix]. The 1,4-Bix ligand with imidazole terminals renders elongated M-M distances and flexibility in comparison with pristine ZIF materials. The cumbersome synthesis procedure poor phase purity of the bulk catalyst in solvothermal conditions were improved by a microwave-assisted synthesis, preserving the structural and physicochemical properties. Minimal energy input or room temperatures for the catalysis occurred via the synergistic participation of CuAspBix and quaternary ammonium bromide salt, demonstrated by density-functional theory computational studies to propose mechanistic pathway of the reaction. Reaction conditions were optimized by altering the parameters. The heterogeneous catalyst was reused four times without a significant change in activity.

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References

  1. H.C. Zhou, J.R. Long, O.M. Yaghi, Chem. Rev. 112, 673 (2012)

    Article  CAS  PubMed  Google Scholar 

  2. N. Stock, S. Biswas, Chem. Rev. 112, 933 (2012)

    Article  CAS  PubMed  Google Scholar 

  3. H.C. Zhou, S. Kitagawa, Chem. Soc. Rev. 43, 5415 (2014)

    Article  CAS  PubMed  Google Scholar 

  4. M. Rimoldi, A.J. Howarth, M.R. De Stefano, L. Lin, S. Goswami, P. Li, J.T. Hupp, O.K. Farha, ACS Catal. 7, 997–1014 (2017)

    Article  CAS  Google Scholar 

  5. H. Furukawa, K.E. Cordova, M. O’Keeffe, O.M. Yaghi, Science 341, 1230444 (2013)

    Article  PubMed  CAS  Google Scholar 

  6. J. An, O.K. Farha, J.T. Hupp, E. Pohl, J.I. Yeh, N.L. Rosi, Nature Commun. 3, 604 (2012)

    Article  CAS  Google Scholar 

  7. M. Farrag, Res. Chem. Intermed. 7, 1 (2021)

    Google Scholar 

  8. W.G. Cui, T.L. Hu, Small 5, 2003971 (2020)

    Google Scholar 

  9. T. Sakakura, J.C. Choi, H. Yasuda, Chem. Rev. 107, 2365 (2007)

    Article  CAS  PubMed  Google Scholar 

  10. Y. Xie, T.T. Wang, X.H. Liu, K. Zou, W.Q. Deng, Nature Commun. 4, 1960 (2013)

    Article  CAS  Google Scholar 

  11. Z. Yuan, M.R. Eden, Ind. Eng. Chem. Res. 55, 3383 (2016)

    Article  CAS  Google Scholar 

  12. A.J. Kamphuis, F. Picchioni, P.P. Pescarmona, Green Chem. 21, 406 (2019)

    Article  CAS  Google Scholar 

  13. M. Ding, R.W. Flaig, H.L. Jiang, O.M. Yaghi, Chem. Soc. Rev. 48, 2783 (2019)

    Article  CAS  PubMed  Google Scholar 

  14. Y. Wang, N. Li, Y. Wang, Res. Chem. Intermed. 43, 5229 (2017)

    Article  CAS  Google Scholar 

  15. R. Das, C.M. Nagaraja, Inorg. Chem. 59, 9765 (2020)

    Article  CAS  PubMed  Google Scholar 

  16. M. North, R. Pasquale, C. Young, Green Chem. 12, 1514 (2010)

    Article  CAS  Google Scholar 

  17. P.P. Pescarmona, M. Taherimehr, Catal. Sci. Technol. 2, 2169 (2012)

    CAS  Google Scholar 

  18. M. North, R. Pasquale, Angew. Chem. Int. Ed. 48, 2946 (2009)

    Article  CAS  Google Scholar 

  19. K. Sumida, D.L. Rogow, J.A. Mason, T.M. McDonald, E.D. Bloch, Z.R. Herm, T.H. Bae, J.R. Long, Chem. Rev. 112, 724 (2012)

    Article  CAS  PubMed  Google Scholar 

  20. T.K. Pal, D. De, P.K. Bharadwaj, Coord. Chem. Rev. 408, 213173 (2020)

    Article  CAS  Google Scholar 

  21. N. Kielland, C.J. Whiteoak, A.W. Kleij, Adv. Synth. Catal. 355, 2115 (2013)

    Article  CAS  Google Scholar 

  22. T. Sakakura, K. Kohno, Chem. Commun. 45, 1312 (2009)

    Article  CAS  Google Scholar 

  23. I.S. Metcalfe, M. North, R. Pasquale, A. Thursfiel, Energy Environ. Sci. 3, 212 (2010)

    Article  CAS  Google Scholar 

  24. W.J. Peppel, Ind. Eng. Chem. 50, 767 (1958)

    Article  CAS  Google Scholar 

  25. D.J. Darensbourg, M.W. Holtcamp, Coord. Chem. Rev. 153, 155 (1996)

    Article  CAS  Google Scholar 

  26. J.N. Appaturi, R.J. Ramalingam, M.K. Gnanamani, G. Periyasami, P. Arunachalam, R. Adnan, F. Adam, M.D. Wasmiah, H.A. Al-Lohedan, Catalysts 11, 4 (2021)

    Article  CAS  Google Scholar 

  27. S.M. Sadeghzadeh, Res. Chem. Intermed. 42, 2317 (2016)

    Article  CAS  Google Scholar 

  28. S.W. Park, B.S. Choi, D.W. Park, J.W. Lee, Res. Chem. Intermed. 34, 881 (2008)

    Article  CAS  Google Scholar 

  29. J. Liu, P.K. Thallapally, B.P. McGrail, D.R. Brown, J. Liu, Chem. Soc. Rev. 41, 2308 (2012)

    Article  CAS  PubMed  Google Scholar 

  30. A.L. Dzubak, L.C. Lin, J. Kim, J.A. Swisher, R. Poloni, S.N. Maximoff, B. Smit, L. Gagliardi, Nature Chem. 4, 810 (2012)

    Article  CAS  Google Scholar 

  31. A.C. Kathalikkattil, R. Babu, J. Tharun, R. Roshan, D.W. Park, Catal. Surv Asia 19, 223 (2015)

    Article  CAS  Google Scholar 

  32. R. Babu, R. Roshan, A.C. Kathalikkattil, D.W. Kim, D.W. Park, A.C.S. Appl, Mater. Interfaces 8, 33723 (2016)

    Article  CAS  Google Scholar 

  33. R. Babu, A.C. Kathalikkattil, R. Roshan, J. Tharun, D.W. Kim, D.W. Park, Green Chem. 18, 232 (2016)

    Article  Google Scholar 

  34. J.F. Kurisingal, Y. Rachuri, Y. Gu, Y. Choe, D.W. Park, Chem. Eng. J. 386, 121700 (2020)

    Article  CAS  Google Scholar 

  35. J.F. Kurisingal, Y. Rachuri, A.S. Palakkal, R.S. Pillai, Y. Gu, Y. Choe, D.W. Park, A.C.S. Appl, Mater. Interfaces 11, 41458 (2019)

    Article  CAS  Google Scholar 

  36. L. He, J.K. Nath, Q. Lin, Chem. Commun. 55, 412 (2019)

    Article  CAS  Google Scholar 

  37. W. Xiang, J. Ren, S. Chen, C. Shen, Y. Chen, M. Zhang, C.J. Liu, Appl. Energy 277, 115560 (2020)

    Article  CAS  Google Scholar 

  38. S. Suleman, H.A. Younus, N. Ahmad, Z.A.K. Khattak, H. Ullah, J. Park, T. Han, B. Yu, F. Verpoort, Appl. Catal. A. Gen. 591, 117384 (2020)

    Article  CAS  Google Scholar 

  39. R.R. Kuruppathparambil, R. Babu, H. Jeong, Y.H. Jang, M.H. Lee, D.W. Park, Korean J. Chem. Eng. 36, 643 (2019)

    Article  CAS  Google Scholar 

  40. J.F. Kurisingal, Y. Rachuri, Y. Gu, Y. Choe, D.W. Park, Inorg. Chem. Front. 6, 3613 (2019)

    Article  CAS  Google Scholar 

  41. J.F. Kurisingal, Y. Rachuri, Y. Gu, R.K. Chitumalla, S. Vuppala, K.K. Bisht, J. Jang, E. Suresh, D.W. Park, ACS Sustain. Chem. Eng. 8, 10822 (2020)

    CAS  Google Scholar 

  42. J.F. Kurisingal, Y. Li, Y. Sagynbayeva, R.K. Chitumalla, S. Vuppala, Y. Rachuri, Y. Gu, J. Jang, D.W. Park, Catal. Today 352, 227 (2020)

    Article  Google Scholar 

  43. Q.D. Yan, H.J. Xu, X.C. Jing, H. Hu, S.L. Wang, C.Y. Zeng, Y.N. Gao, RSC Adv. 10, 17396 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. X. Wang, L. Yang, Y. Chen, C. Yang, J. Lan, J. Sun, Ind. Eng. Chem. Res. 59, 21018 (2020)

    Article  CAS  Google Scholar 

  45. W. Xiang, J. Ren, S. Chen, C. Shen, Y. Chen, M. Zhang, C. Liu, Appl. Energy 277, 115560 (2020)

    Article  CAS  Google Scholar 

  46. S. Zhang, M.S. Jang, J. Lee, P. Puthiaraj, W.S. Ahn, ACS Sustain. Chem. Eng. 8, 7078 (2020)

    Article  CAS  Google Scholar 

  47. W. Dai, P. Mao, Y. Liu, S. Zhang, B. Li, L. Yang, X. Luo, J. Zou, J. CO2 Util. 36, 295 (2020)

  48. W.G. Cui, G.Y. Zhang, T.L. Hu, X.H. Bu, Coord. Chem. Rev. 387, 79 (2019)

    Article  CAS  Google Scholar 

  49. X. Liu, J. Li, N. Li, B. Li, X.H. Bu, Chin. J. Chem. 39, 440 (2021)

    Article  CAS  Google Scholar 

  50. R. Abazari, S. Sanati, A. Morsali, A.M. Kirillov, A.M.Z. Slawin, C.L. Capenter-Warren, Inorg. Chem. 60, 2056 (2021)

    Article  CAS  PubMed  Google Scholar 

  51. Q.Q. Zhu, W.W. Zhang, H.W. Zhang, Y. Yuan, R. Yuan, F. Sun, H. He, Inorg. Chem. 58, 15637 (2019)

    Article  CAS  PubMed  Google Scholar 

  52. H. He, J.A. Perman, G. Zhu, S. Ma, Small 12, 6309 (2016)

    Article  CAS  PubMed  Google Scholar 

  53. H. He, Q. Sun, W. Gao, J.A. Perman, F. Sun, G. Zhu, B. Aguila, K. Forrest, B. Space, S. Ma, Angew. Chem. Int. Ed. 57, 4657 (2018)

    Article  CAS  Google Scholar 

  54. R. Das, D. Muthukumar, R.S. Pillai, C.M. Nagaraja, Chem. Eur. J. 26, 17445 (2020)

    Article  CAS  PubMed  Google Scholar 

  55. L.H. Hu, Z.C. Yan, X.H. Mo, X. Peng, L. Chen, Micro. Meso. Mater. 294, 109917 (2020)

    Article  CAS  Google Scholar 

  56. J. Tharun, G. Mathai, A.C. Kathalikkattil, R. Roshan, Y.S. Won, S.J. Cho, J.S. Chang, D.W. Park, ChemPlusChem 80, 715 (2015)

    Article  CAS  PubMed  Google Scholar 

  57. K.R. Roshan, J. Tharun, K.Y. Hwang, A.C. Kathalikkattil, D.W. Kim, D.W. Park, Appl. Catal. B. Environ. 182, 562 (2016)

    Article  CAS  Google Scholar 

  58. G.Y. Hwang, K.R. Roshith, H.M. Jeong, S. Ravi, M.I. Kim, D.W. Park, J. CO2 Util. 15, 123 (2016)

  59. K.R. Roshith, H.M. Jeong, R. Babu, G.Y. Hwang, G.S. Jeong, M.I. Kim, D.W. Kim, D.W. Park, Green Chem. 18, 6349 (2016)

    Article  CAS  Google Scholar 

  60. R. Babu, J.F. Kurisingal, S.H. Kim, H.J. Kim, G.K. Choi, D.W. Park, J. CO2 Util. 25, 6 (2018)

  61. J.M. Joo, B.B. Touré, D. Sames, J. Org. Chem. 75, 4911 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. A.C. Kathalikkattil, K.K. Bisht, N. Aliaga-Alcalde, E. Suresh, Cryst. Growth. Des. 11, 1631 (2011)

    Article  CAS  Google Scholar 

  63. S.L. Anderson, K.C. Stylianou, Coord. Chem. Rev. 349, 102 (2017)

    Article  CAS  Google Scholar 

  64. I. Imaz, M. Rubio-Martinez, J. An, I. Sole-Font, N.L. Rosi, D. Maspoch, Chem. Commun. 47, 7287 (2011)

    Article  CAS  Google Scholar 

  65. M.J. Ingleson, J.P. Barrio, J. Basca, C. Dickinson, H. Park, M.J. Rosseinsky, Chem. Commun. 47, 4899 (2008)

    Google Scholar 

  66. R. Vaidhyanathan, D. Bradshaw, J.-N. Rebilly, J.P. Barrio, J.A. Gould, N.G. Berry, M.J. Rosseinsky, Angew. Chemie Int. Ed. 45, 6495 (2006)

    Article  CAS  Google Scholar 

  67. A.C. Kathalikkattil, R. Roshan, J. Tharun, H.G. Soek, H.S. Ryu, D.W. Park, ChemCatChem 6, 284 (2014)

    Article  CAS  Google Scholar 

  68. A.C. Kathalikkattil, R. Roshan, J. Tharun, R. Babu, G.S. Jeong, D.W. Kim, S.J. Cho, D.W. Park, Chem. Commun. 52, 280 (2016)

    Article  CAS  Google Scholar 

  69. A.C. Kathalikkattil, R. Babu, R.K. Roshan, H. Lee, H. Kim, J. Tharun, E. Suresh, D.W. Park, J. Mater. Chem. A. 3, 22636 (2015)

    Article  CAS  Google Scholar 

  70. G.S. Jeong, A.C. Kathalikkattil, R. Babu, Y.G. Chung, D.W. Park, Chinese. J. Catal. 39, 63 (2018)

    CAS  Google Scholar 

  71. H. Pan, J.A. Ritter, P.B. Balbuena, Langmuir 14, 6323 (1998)

    Article  CAS  Google Scholar 

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Acknowledgements

This study was supported by the National Research Foundation of Korea through the Basic Research Project (2019R1I1A-01057644).

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Kathalikkattil, A.C., Gu, Y., Kurisingal, J.F. et al. A catalytic approach of blending CO2-activating MOF struts for cycloaddition reaction in a helically interlaced Cu(II) amino acid imidazolate framework: DFT-corroborated investigation. Res Chem Intermed 47, 3979–3997 (2021). https://doi.org/10.1007/s11164-021-04507-6

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