화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.104, 592-604, December, 2021
Collaborative fabrication of poly(L-proline)s with well-defined mesopores and hydrophobicity: Synergistic effect of mesoporous confinement and hydrophobic micro-environment on organic transformations
E-mail:
The preparation of materials with a well-defined mesoporous structure and hydrophobicity is of great significance for heterogeneous catalyst development, yet there still remains a challenge for fabricating the above materials without using templates. Herein, the polymerization of L-proline-functionalized monomer with crosslinkers containing variable alkyl-bridged length (n = 2,4,6,8) and vinyl-modified Fe3O4 nanoparticles to construct mesoporous poly(L-proline)s (MPLPs) has been reported for the first time. The resultant MPLPs were analyzed by characterization methods, suggesting that MPLPs with a well-defined mesoporous structure and unique hydrophobicity were successfully constructed by synergistic regulation of vinyl-modified Fe3O4 nanoparticles and crosslinkers with alkyl-bridged length of 6 carbon atoms, in which vinyl-modified Fe3O4 nanoparticles as structural reinforcer plays a vital role for the mesoporous formation. Moreover, the resultant MPLPs were found to be efficient catalysts for one-pot synthesis of functionalized spiroindolones and olefins. The kinetic study and the water contact angle indicate the mesoporous confinement and hydrophobic micro-environment in organic transformations. Hence, the high activity of MPLPs is ascribed to synergistic effect of mesoporous confinement and hydrophobic micro-environment, and the adsorption experiment results further confirm this synergistic catalysis. This work promotes a textural engineering approach to the development of multifunctional materials with well-defined mesopores and hydrophobicity.
  1. Zhang RQ, Liu ZQ, Luo ZL, Xu F, Chen YS, J. Ind. Eng. Chem., 80, 431 (2109)
  2. Kim JK, Kim DU, Ryu JH, Yoon SH, J. Ind. Eng. Chem., 71, 93 (2019)
  3. Xu TT, Xue CF, Zhang ZL, Hao XG, Chem., 26, 1924 (2014)
  4. Bradshaw D, El-Hankari S, Lupica-Spagnolo L, Chem. Soc. Rev., 43, 5431 (2014)
  5. Fang B, Kim JH, Kim MS, Yu JS, Accounts Chem. Res., 46, 1397 (2012)
  6. Yang XY, Le´onard A, Lemaire A, Tian G, Su BL, Chem. Commun., 47, 2763 (2011)
  7. Gerardin C, Reboul J, Bonneb M, Lebeau B, Chem. Soc. Rev., 42, 4217 (2013)
  8. Sun MH, Huang SZ, Chen LH, Li Y, Yang XY, Yuan ZY, Su BL, Chem. Soc. Rev., 45, 3479 (2016)
  9. Rostamnia S, Rahmani T, Xin H, J. Ind. Eng. Chem., 32, 218 (2015)
  10. Rostamnia S, Doustkhah E, Synlett., 26, 1345 (2015)
  11. Song N, Yang YW, Chem. Soc. Rev., 44, 3474 (2015)
  12. Pan L, He Q, Liu J, Chen Y, Ma M, Zhang L, Shi J, J. Am. Chem. Soc., 13, 5722 (2012)
  13. Walcarius A, Chem. Soc. Rev., 42, 4098 (2013)
  14. Rostamnia S, Hossieni HG, Doustkhah E, J. Organomet. Chem., 791, 18 (2015)
  15. Rostamnia S, Morsali A, Inorg. Chim. Acta., 411, 113 (2014)
  16. Wang J, Ma Q, Wang Y, Li Z, Li Z, Yuan Q, Chem. Soc. Rev., 47, 8766 (2018)
  17. Rostamnia S, Doustkhah E, J. Mol. Catal. A-Chem., 411, 317 (2016)
  18. Rostamnia S, Rahmani T, Appl. Organomet. Chem., 29, 471 (2015)
  19. Rostamnia S, Liu X, Zheng D, J. Colloid Interface Sci., 432, 86 (2014)
  20. Cao H, Zhu XH, Wang D, Sun Z, Deng Y, Hou XF, Zhao D, ACS Catal., 5, 27 (2015)
  21. Petkova D, Borlinghaus N, Sharma S, et al., ACS Sustain. Chem. Eng., 8, 12612 (2020)
  22. Sokkalingam P, Shraberg J, Rick SW, Gibb BC, J. Am. Chem. Soc., 138(1), 48 (2016)
  23. Zapata PA, Huang Y, Gonzalez-Borja MA, Resasco DE, J. Catal., 308, 82 (2013)
  24. Gounder R, Davis ME, J. Catal., 308, 176 (2013)
  25. Al-Zuraiji SM, Benko T, Illes L, Nemeth M, Frey K, Sulyok A, Pap JS, J. Catal., 381, 615 (2020)
  26. Sun X, Xia L, Yang Q, Zhang Z, Bao Z, Ren Q, Yang Y, Xing H, J. Mater. Chem. A, 5, 14114 (2017)
  27. Wang Q, Ling X, Ye T, Zhou Y, Wang J, J. Mater. Chem. A, 7, 19140 (2019)
  28. Zhang J, Qiao ZA, Mahurin SM, Jiang X, Chai SH, Lu H, Nelson K, Dai S, Angew. Chem.-Int. Edit., 127, 4665 (2015)
  29. Soll S, Zhang P, Zhao Q, Wang Y, Yuan J, Polym. Chem., 4, 5048 (2013)
  30. Zhao Q, Dunlop JW, Qiu X, Huang F, Zhang Z, Heyda J, Dzubiella J, Antonietti M, Yuan J, Nat. Commun., 5, 4293 (2014)
  31. Jeon C, Han JJ, Seo M, ACS Appl. Mater. Interfaces., 10, 40854 (2018)
  32. Yue Y, Mayes RT, Kim J, Fulvio PF, Sun XG, Tsouris C, Chen J, Brown S, Dai S, Angew. Chem.-Int. Edit., 52, 13458 (2013)
  33. Liu F, Kong W, Qi C, Zhu L, Xiao FS, ACS Catal., 2, 565 (2012)
  34. Verwey EJW, Nature, 44, 327 (1939)
  35. Natour S, Abu-Reziq R, ChemCatChem, 7, 2230 (2015)
  36. Zhang Q, Su H, Luo J, Wei Y, Catal. Sci. Technol., 3, 235 (2013)
  37. Ying A, Hou H, Liu S, Chen G, Yang J, Xu S, ACS Sustain. Chem. Eng., 4, 625 (2016)
  38. Manna PK, Nickel R, Lie J, Wroczynskyj Y, Liu S, Lierop J, Dalton Trans., 48, 6588 (2019)
  39. Ying A, Li S, Liu X, Wang J, Liu Y, Liu Z, J. Catal., 391, 312 (2020)
  40. Bae SJ, Kim SW, Hyeon T, Kim BM, Chem. Commun., 31 (2000).
  41. Calderon F, Fernndez R, Snchez F, Fernndez-Mayoralas A, Adv. Synth. Catal., 347, 1395 (2005)
  42. Doyaguez EG, Calderon F, Sanchez F, Fernndez-Mayoralas A, J. Org. Chem., 72, 9353 (2007)
  43. Zhao M, Yang L, Liu B, Liu T, Int. Jagric. Biol., 21, 449 (2019)
  44. Hojati SF, Moosavifar M, Moeinieghbali N, J. Chem. Sci., 132, 38 (2020)
  45. Varga G, Kukovecz A, Konya Z, Sipos P, Palinko I, J. Catal., 381, 308 (2020)
  46. Rostamnia S, Doustkhah E, J. Mang. Magn. Mater., 386, 111 (2015)
  47. Alizadeh A, Zohreh N, Rostamnia S, Tetrahedron, 63, 8083 (2007)
  48. Alizadeh A, Rostamnia S, Zhu LG, Tetrahedron Lett., 51, 4750 (2010)
  49. Alizadeh A, Oskueyan Q, Rostamnia S, Synth, 2007, 2637 (2007)
  50. Song H, Wang Y, Xiao M, Liu L, Liu Y, Liu X, Gai H, ACS Sustainable Chem. Eng., 7, 9489 (2019)
  51. Zhang X, Jing L, Wei L, Zhang F, Yang H, ACS Catal., 7, 6711 (2017)
  52. Abbaspourrad A, Carroll NJ, Kim SH, Weitz DA, Adv. Mater., 25(23), 3215 (2013)
  53. Yang Y, Ambrogi M, Kirmse H, Men YJ, Antonietti M, Yuan JY, Chem. Mater., 27, 127 (2015)
  54. Yang HQ, Jiao X, Li SR, Chem. Commun., 48, 11217 (2012)
  55. Zhang XM, Zhao YP, Peng J, Yang QH, Green Chem., 17, 1899 (2015)