Citation: Maryam Keram, Ma Haiyan. Non-symmetric β-Diketiminate Magnesium Complexes as Initiators for Ring-Opening Polymerization/Copolymerization of Lactide, ε-Caprolactone[J]. Acta Chimica Sinica, ;2018, 76(2): 121-132. doi: 10.6023/A17090442 shu

Non-symmetric β-Diketiminate Magnesium Complexes as Initiators for Ring-Opening Polymerization/Copolymerization of Lactide, ε-Caprolactone

Maryam Keram ,
Ma Haiyan ^,

Laboratory of Organometallic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237

Corresponding author: Ma Haiyan, haiyanma@ecust.edu.cn
Received Date: 28 September 2017
Available Online: 2 February 2018
Fund Project: the National Natural Science Foundation of China 21474028the National Natural Science Foundation of China 21074032Project supported by the National Natural Science Foundation of China (Nos. 21074032, 21474028)

Figures(7)

Magnesium silylamido complexes 1~7 bearing non-symmetric β-diketiminate ligands were synthesized via the reactions of corresponding proligands HL^1~7 with one equivalent of Mg[N(SiMe₃)₂]₂ at 80℃ in toluene. All complexes were characterized by ¹H NMR, ¹³C NMR and elemental analysis. The monomeric nature of complexes 1 and 5 in the solid state was further confirmed by X-ray diffraction studies. In both complexes, the metal center is tri-coordinated by the β-diketiminate ligand and one silylamido group. The very close bond lengths of two Mg-N bonds as well as close C-N distances of the chelate ring indicate significant delocalization. The apparent deviation of the magnesium center from the ligand backbone plane suggests a certain ηⁿ-coordination nature of the ligand to the metal center. These magnesium silylamido complexes showed good catalytic activities for the ring-opening polymerization of rac-lactide under ambient conditions, and could polymerize 300 equivalents of rac-lactide to high molecular weight polymers within short time in THF. The solvent effect played a critical role during the polymerization process. All complexes showed higher catalytic activity in THF than in toluene. Taking complex 2 as an example, a monomer conversion of 96% could be achieved within 10 min in THF, whereas a conversion of 80% could only be achieved within extended polymerization time of 210 min in toluene (Table 1, Entries 6 and 9, [LA]₀/[Mg]₀=100). Upon the addition of isopropanol, the activities of magnesium silylamido complexes 1~7 increased significantly. For instance, when the polymerization runs were carried in THF in the presence of isopropanol, the reaction time could be reduced to 10~20 min even with a high molar ratio of[LA]₀/[Mg]₀=300. Moreover, the type and location of the substituent(s) on the N-aryl group of the β-diketiminate ligand exerts a significant influence on the catalytic activity of the corresponding complex toward the polymerization of rac-lactide. In the absence of excess isopropanol, the introduction of sterically demanding substituent to the ortho-position of N-aryl ring leads to a decrease of the polymerization activity; but the influence of electron-withdrawing group is different in different solvents (toluene or THF). These magnesium complexes could produce heterotactic polymers in THF (P_r=0.64~0.80) and atactic polymers in toluene (P_r=0.45~0.58). Magnesium complexes 1~7 also displayed high catalytic activities for the ring-opening polymerization (ROP) of ε-caprolactone, among them complexes bearing β-diketiminate ligand with bulky ortho-substituted N-aryl rings showed higher activities. Generally, the ROPs of ε-caprolactone initiated by these magnesium silylamido complexes were not well-controlled, giving moderately distributed polymers (M_w/M_n=1.37~1.67). Additionally, diblock copolymers of L-lactide and ε-caprolactone were obtained by using 2 as the initiator via both sequential feeding of two monomers (in either order) and the one-pot method. The formation of diblock copolymers were verified by ¹H NMR, ¹³C NMR, DSC and GPC analysis.
- β-diketiminate ligand,
- magnesium complex,
- cyclic ester,
- ring-opening polymerization,
- copolymerization
1. [1]
  Mecking, S. Angew. Chem., Int. Ed. 2004, 43, 1078. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Tsuji, H. Macromol. Biosci. 2005, 5, 569. doi: 10.1002/(ISSN)1616-5195
3. [3]
  Fukushima, K.; Kimura, Y. Polym. Int. 2006, 55, 626. doi: 10.1002/(ISSN)1097-0126
4. [4]
  Woodruff, M. A.; Hutmacher, D. W. Prog. Polym. Sci. 2010, 35(10), 1217. doi: 10.1016/j.progpolymsci.2010.04.002
5. [5]
  Ye, W.-P.; Chien, Y. W. J. Control. Release 1996, 41(3), 259. doi: 10.1016/0168-3659(96)01330-2
6. [6]
  Huang, M.-H.; Li, S.; Vert, M. Polymer 2004, 45(26), 8675. doi: 10.1016/j.polymer.2004.10.054
7. [7]
  Guo, B.; Glavas, L.; Albertsson, A.-C. Prog. Polym. Sci. 2013, 38(9), 1263. doi: 10.1016/j.progpolymsci.2013.06.003
8. [8]
  Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147. doi: 10.1021/cr040002s
9. [9]
  Platel, R. H.; Hodgson, L. M.; Williams, C. K. Polym. Rev. 2008, 48, 11. doi: 10.1080/15583720701834166
10. [10]
  Thomas, C. M. Chem. Soc. Rev. 2010, 39, 165. doi: 10.1039/B810065A
11. [11]
  Stanford, M. J.; Dove, A. P. Chem. Soc. Rev. 2010, 39, 486. doi: 10.1039/B815104K
12. [12]
  Dijkstra, P. J.; Du, H.; Feijen, J. Polym. Chem. 2011, 2, 520. doi: 10.1039/C0PY00204F
13. [13]
  Wei, Y.; Wang, S.; Zhou, S. Dalton Trans. 2016, 45, 4471. doi: 10.1039/C5DT04240B
14. [14]
  Pappalardo, D.; Annunziata, L.; Pellecchia, C. Macromolecules 2009, 42, 6056. doi: 10.1021/ma9010439
15. [15]
  Nomura, N.; Akita, A.; Ishii, R.; Mizuno, M. J. Am. Chem. Soc. 2010, 132, 1750. doi: 10.1021/ja9089395
16. [16]
  Qian, F.; Liu, K.; Ma, H. Chin. J. Catal. 2011, 32, 189 (in Chinese).
17. [17]
  Wang, Y.; Ma, H. Chem. Commun. 2012, 48, 6729. doi: 10.1039/c2cc31716h
18. [18]
  Li, G.; Lamberti, M.; Pappalardo, D.; Pellecchia, C. Macromolecules 2012, 45, 8614. doi: 10.1021/ma3019848
19. [19]
  Cross, E. D.; Allan, L. E. N.; Decken, A.; Shaver, M. P. J. Polym. Sci. Part A: Polym. Chem. 2013, 51, 1137. doi: 10.1002/pola.26476
20. [20]
  Liu, Y.; Dong, W.-S. Liu, J.-Y.; Li, Y.-S. Dalton Trans. 2014, 43, 2244. doi: 10.1039/C3DT52712C
21. [21]
  Kan, C.; Ma, H. RSC Adv. 2016, 6, 47402. doi: 10.1039/C6RA07374C
22. [22]
  Meléndez, D. O.; Castro-Osma, J. A.; Lara-Sánchez, A.; Rojas, R. S.; Otero, A. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2397. doi: 10.1002/pola.v55.14
23. [23]
  Darensbourg, D. J.; Karroonnirum, O. Macromolecules 2010, 43, 8880. doi: 10.1021/ma101784y
24. [24]
  Wei, Z.; Liu, L.; Wang, P.; Gao, J.; Qi, M. Acta Polym. Sinica 2008, 10, 947 (in Chinese). doi: 10.3321/j.issn:1000-3304.2008.10.004
25. [25]
  Pappuru, S.; Chakraborty, D.; Sundar, J. V.; Roymuhury, S. K.; Ramkumar, V.; Subramanian, V.; Chand, D. K. Polymer 2016, 102, 231. doi: 10.1016/j.polymer.2016.08.007
26. [26]
  Olsén, P.; Borke, T.; Odelius, K.; Albertsson, A.-C. Biomacromolecules 2013, 14, 2883. doi: 10.1021/bm400733e
27. [27]
  Radano, C. P.; Baker, G. L.; Smith, M. R. Ⅲ. J. Am. Chem. Soc. 2000, 122, 1552. doi: 10.1021/ja9930519
28. [28]
  Zhong, Z.-Y.; Dijkstra, P. J.; Feijen, J. Angew. Chem., Int. Ed. 2002, 41, 4510. doi: 10.1002/1521-3773(20021202)41:23<4510::AID-ANIE4510>3.0.CO;2-L
29. [29]
  Zhong, Z.-Y.; Dijkstra P. J.; Feijen, J. J. Am. Chem. Soc. 2003, 125, 11291. doi: 10.1021/ja0347585
30. [30]
  Nomura, N.; Ishii, R.; Akakura, M.; Aoi, K. J. Am. Chem. Soc. 2002, 124, 5938. doi: 10.1021/ja0175789
31. [31]
  Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1316. doi: 10.1021/ja012052+
32. [32]
  Tang, Z.-H.; Chen, X.-S.; Pang, X.; Yang, Y.-K.; Zhang, X.-F.; Jing, X.-B. Biomacromolecules 2004, 5, 965. doi: 10.1021/bm034467o
33. [33]
  Hormnientry, P.; Marshall, E. L.; Gibson, V. C.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 2004, 126, 2688. doi: 10.1021/ja038757o
34. [34]
  Dagorne, S.; Le-Bideau, F.; Welter, R.; Bellemin-Laponnaz, S.; Maisse-Francoise, A. Chem.-Eur. J. 2007, 13, 3202. doi: 10.1002/(ISSN)1521-3765
35. [35]
  Nomura, N.; Ishii, R.; Yamamoto, Y.; Kondo, T. Chem.-Eur. J. 2007, 13, 4433. doi: 10.1002/(ISSN)1521-3765
36. [36]
  Du, H.; Pang, X.; Yu, H.; Zhuang, X.; Chen, X.; Cui, D.; Wang, X.; Jing, X. Macromolecules 2007, 40, 1904. doi: 10.1021/ma062194u
37. [37]
  Gong, S.; Ma, H. Dalton Trans. 2008, 25, 3345.
38. [38]
  Qian, F.; Liu, K.-Y.; Ma, H. Dalton Trans. 2010, 39, 8071. doi: 10.1039/c0dt00272k
39. [39]
  Chen, H.-L.; Dutta, S.; Huang, P.-H.; Lin, C.-C. Organometallics 2012, 31, 2016. doi: 10.1021/om201281w
40. [40]
  Hild, F.; Neehaul, N.; Bier, F.; Wirsum, M.; Gourlaouen, C.; Dagorne, S. Organometallics 2013, 32, 587. doi: 10.1021/om3011068
41. [41]
  Altaf, C. T.; Wang, H.; Keram, M.; Yang, Y.; Ma, H. Polyhedron 2014, 81, 11. doi: 10.1016/j.poly.2014.05.055
42. [42]
  Pilone, A.; Press, K.; Goldberg, I.; Kol, M.; Mazzeo, M.; Lamberti, M. J. Am. Chem. Soc. 2014, 136, 2940. doi: 10.1021/ja412798x
43. [43]
  Qu, Z.; Li, X.; Pang, X.; Duan, R.; Gao, B.; Chen, X. Chem. J. Chin. Univ. 2014, 35(3), 626 (in Chinese).
44. [44]
  Marlier, E. E.; Macaranas, J. A.; Marell, D. J.; Dunbar, C. R.; Johnson, M. A.; DePorre, Y.; Miranda, M. O.; Neisen, B. D.; Cramer, C. J.; Hillmyer, M. A.; Tolman, W. B. ACS Catal. 2016, 6, 1215. doi: 10.1021/acscatal.5b02607
45. [45]
  Xi, Y.; Rajendran, N. M.; Zhang, W.-J.; Sun, Y.; Lei, M.; Sun, W.-H. ChemistrySelect 2016, 1, 5660. doi: 10.1002/slct.201601517
46. [46]
  Rajendran, N. M.; Xi, Y.; Zhang, W.-J.; Braunstein, P.; Liang, T. L.; Sun, W.-H. Inorg. Chem. Front. 2016, 3, 1317. doi: 10.1039/C6QI00177G
47. [47]
  Jia, B.; Hao, J.-S.; Tong, H.-B.; Wei, X.-H.; Zhou, M.-S.; Liu, D.-S. Chin. J. Inorg. Chem. 2017, 33(10), 1876. doi: 10.11862/CJIC.2017.221
48. [48]
  Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583. doi: 10.1021/ja992678o
49. [49]
  Chamberlain, B.; Cheng, M.; Moore, D.; Ovitt, T.; Lobkovsky, E.; Coates. G. J. Am. Chem. Soc. 2001, 123, 3229. doi: 10.1021/ja003851f
50. [50]
  Chisholm, M. H.; Gallucci, J.; Phomphrai, K. Inorg. Chem. 2002, 41, 2785. doi: 10.1021/ic020148e
51. [51]
  Williams, C. K.; Breyfogle, L. E.; Choi, S. K.; Nam, W.; Young, V. G.; Hillmyer, M. A.; Tolman, W. B. J. Am. Chem. Soc. 2003, 125, 11350. doi: 10.1021/ja0359512
52. [52]
  Dove, A. P.; Gibson, V. C.; Marshall, E. L.; White, A. J. P.; Williams, D. J. Dalton Trans. 2004, 570.
53. [53]
  Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Inorg. Chem. 2005, 44, 8004. doi: 10.1021/ic048363d
54. [54]
  Hua, J.; Yang, J.; Hu, Y.; Wei, J.; Li, S. Acta Chim. Sinica 2008, 66, 2730 (in Chinese). doi: 10.3321/j.issn:0567-7351.2008.24.012
55. [55]
  Huang, Y.; Hung, W.-C.; Liao, M.-Y.; Tsai, T.-E.; Peng, Y.-L.; Lin, C.-C. J. Polym. Sci., Part A, Polym. Chem. 2009, 47, 2318. doi: 10.1002/pola.v47:9
56. [56]
  Xu, X.; Chen, Y.; Zou, G.; Ma, Z.; Li, G. J. Organomet. Chem. 2010, 695, 1155. doi: 10.1016/j.jorganchem.2010.01.023
57. [57]
  Wang, L.; Ma, H. Dalton Trans. 2010, 39, 7897. doi: 10.1039/c0dt00250j
58. [58]
  Song, S.; Zhang, X.; Ma, H.; Yang, Y. Dalton Trans. 2012, 41, 3266. doi: 10.1039/c2dt11767c
59. [59]
  Chuang, H.-J.; Chen, H.-L.; Huang, B.-H.; Tsai, T.-E.; Huang, P.-L.; Liao, T.-T.; Lin, C.-C. J. Polym. Sci., Part A, Polym. Chem. 2013, 51, 1185. doi: 10.1002/pola.26486
60. [60]
  Whitehorne, T. J. J.; Vabre, B.; Schaper, F. Dalton Trans. 2014, 43, 6339. doi: 10.1039/C3DT53278J
61. [61]
  Wang, H.; Ma, H. Chem. Commun. 2013, 49, 8686. doi: 10.1039/c3cc44980g
62. [62]
  Wang, H.; Yang, Y.; Ma, H. Macromolecules 2014, 47, 7750. doi: 10.1021/ma501896r
63. [63]
  Mou, Z.; Liu, B.; Wang, M.; Xie, H.; Li, P.; Li, L.; Li, S.; Cui, D. Chem. Commun. 2014, 50, 11411. doi: 10.1039/C4CC05033A
64. [64]
  Abbina, S.; Du, G. ACS Macro Lett. 2014, 3, 689. doi: 10.1021/mz5002959
65. [65]
  Yang, Y.; Wang, H.; Ma, H. Inorg. Chem. 2015, 54, 5839. doi: 10.1021/acs.inorgchem.5b00558
66. [66]
  Wang, H.; Yang, Y.; Ma, H. Inorg. Chem. 2016, 55, 7356. doi: 10.1021/acs.inorgchem.6b00378
67. [67]
  Rosen, T.; Popowski, Y.; Goldberg, I.; Kol, M. Chem.-Eur. J. 2016, 22, 11533. doi: 10.1002/chem.201601979
68. [68]
  Huang, M.; Ma, H. Dalton Trans. 2015, 44, 12420. doi: 10.1039/C5DT00158G
69. [69]
  Huang, M.; Ma, H. Eur. J. Inorg. Chem. 2016, 3791.
70. [70]
  Thevenon, A.; Romain, C.; Bennington, M. S.; White, A. J. P.; Davidson, H. J.; Brooker, S.; Williams, C. K. Angew. Chem., Int. Ed. 2016, 55, 8680. doi: 10.1002/anie.201602930
71. [71]
  Akpan, E. D.; Ojwach, S. O.; Omondi, B.; Nyamoria, V. O. New J. Chem. 2016, 40, 3499. doi: 10.1039/C5NJ03159A
72. [72]
  Keram, M.; Ma, H. Appl. Organomet. Chem. 2017, 3893.
73. [73]
  Jędrzkiewicz, D.; Adamus, G.; Kwiecień, M.; John, Ł.; Ejfler. J. Inorg. Chem. 2017, 56, 1349. doi: 10.1021/acs.inorgchem.6b02439
74. [74]
  Bai, J.; Xiao, X.; Zhang, Y.; Chao, J.; Chen, X. Dalton Trans. 2017, 46, 9846. doi: 10.1039/C7DT01877K
75. [75]
  Wang, L.; Ma, H. Macromolecules 2010, 43, 6535. doi: 10.1021/ma101263g
76. [76]
  Chisholm, M.; Choojun, K.; Gallucci, J.; Wambua, P. Chem. Sci. 2012, 3, 3445. doi: 10.1039/c2sc21017g
77. [77]
  Wang, Y.; Zhao, W.; Liu, X.; Cui, D.; Chen, Y.-X. E. Macromolecules 2012, 45, 6957. doi: 10.1021/ma3007625
78. [78]
  Song, S.; Ma, H.; Yang, Y. Dalton Trans. 2013, 42, 14200. doi: 10.1039/c3dt51344k
79. [79]
  Xie, H.; Mou, Z.; Liu, B.; Li, P.; Rong, W.; Li, S.; Cui, D. Organometallics 2014, 33, 722. doi: 10.1021/om401056s
80. [80]
  Walton, M. J.; Lancaster, S. J.; Redshaw, C. ChemCatChem 2014, 6, 1892. doi: 10.1002/cctc.v6.7
81. [81]
  Yang, Y.; Wang, H.; Ma, H. Polyhedron 2016, 117, 569. doi: 10.1016/j.poly.2016.06.036
82. [82]
  Wang, H.; Guo, J.; Yang, Y.; Ma, H. Dalton Trans. 2016, 45, 10942. doi: 10.1039/C6DT01126H
83. [83]
  Rosen, T.; Goldberg, I.; Venditto, V.; Kol, M. J. Am. Chem. Soc. 2016, 138, 12041. doi: 10.1021/jacs.6b07287
84. [84]
  Rosen, T.; Goldberg, I.; Navarra, W.; Venditto, V.; Kol, M. Chem. Sci. 2017, 8, 5476. doi: 10.1039/C7SC01514C
85. [85]
  Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Chem. Commun. 2003, 48.
86. [86]
  Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Inorg. Chem. 2004, 43, 6717. doi: 10.1021/ic0490730
87. [87]
  Darensbourg, D. J.; Choi, W.; Karroonnirun, O.; Bhuvanesh, N. Macromolecules 2008, 41, 3493. doi: 10.1021/ma800078t
88. [88]
  Chen, H.-Y.; Tang, H.-Y.; Lin, C.-C. Polymer 2007, 48, 2257. doi: 10.1016/j.polymer.2007.02.030
89. [89]
  Bhattacharjee, J.; Harinath, A.; Nayek, H. P.; Sarkar, A.; Panda, T. K. Chem.-Eur. J. 2017, 24, 9319.
90. [90]
  Douglas, A. F.; Patrick, B. O.; Mehrkhodavandi, P. Angew. Chem., Int. Ed. 2008, 120, 2322. doi: 10.1002/(ISSN)1521-3757
91. [91]
  Yu, I.; Acosta-Ramírez, A.; Mehrkhodavandi, P. J. Am. Chem. Soc. 2012, 134, 12758. doi: 10.1021/ja3048046
92. [92]
  Aluthge, D. C.; Patrick, B. O.; Mehrkhodavandi, P. Chem. Commun. 2013, 49, 4295. doi: 10.1039/C2CC33519K
93. [93]
  Aluthge, D. C.; Ahn, J. M.; Mehrkhodavandi, P. Chem. Sci. 2015, 6, 5284. doi: 10.1039/C5SC01584G
94. [94]
  Myers, D.; White, A. J. P.; Forsyth, C. M.; Bown, M.; Williams, C. K. Angew. Chem., Int. Ed. 2017, 56, 5277. doi: 10.1002/anie.201701745
95. [95]
  Ebrahimi, T.; Aluthge, D. C.; Patrick, B. O.; Hatzikiriakos, S. G.; Mehrkhodavandi, P. ACS Catal. 2017, 7, 6413. doi: 10.1021/acscatal.7b01939
96. [96]
  Zhang, J.; Xiong, J.; Sun, Y.; Tang, N.; Wu, J. Macromolecules 2014, 47, 7789. doi: 10.1021/ma502000y
97. [97]
  Dai, Z.; Sun, Y.; Xiong, J.; Pan, X.; Wu, J. ACS Macro Lett. 2015, 4, 556. doi: 10.1021/acsmacrolett.5b00209
98. [98]
  Sun, Y.; Xiong, J.; Dai, Z.; Pan, X.; Tang, N.; Wu, J. Inorg. Chem. 2016, 55, 136. doi: 10.1021/acs.inorgchem.5b02709
99. [99]
  Chen, C.; Cui, Y.; Mao, X.; Pan, X.; Wu, J. Macromolecules 2017, 50, 83. doi: 10.1021/acs.macromol.6b02271
100. [100]
  Romain, C.; Brelot, L.; Bellemin-Laponnaz, S.; Dagorne, S. Organometallics 2010, 29, 1191.
101. [101]
  Whitelaw, E.; Jones, M.; Mahon, M. Inorg. Chem. 2010, 49, 7176. doi: 10.1021/ic1010488
102. [102]
  Whitelaw, E.; Davidson, M.; Jones, M. Chem. Commun. 2011, 47, 10004. doi: 10.1039/c1cc13910j
103. [103]
  Stopper, A.; Okuda, J.; Kol, M. Macromolecules 2012, 45, 698. doi: 10.1021/ma2023364
104. [104]
  Jones, M. D.; Hancock, S. L.; McKeown, P.; Schafer, P. M.; Buchard, A.; Thomas, L. H.; Mahon, M. F.; Lowe, J. P. Chem. Commun. 2014, 50, 15967. doi: 10.1039/C4CC07871C
105. [105]
  Mandal, M.; Chakraborty, D.; Ramkumar, V. RSC Adv. 2015, 5, 28536. doi: 10.1039/C4RA17201A
106. [106]
  Jones, M. D.; Brady, L.; McKeown, P.; Buchard, A.; Schafer, P. M.; Thomas, L. H.; Mahon, M. F.; Woodman, T. J.; Lowe, J. P. Chem. Sci. 2015, 6, 5034. doi: 10.1039/C5SC01819F
107. [107]
  Pappuru, S.; Chakraborty, D.; Ramkumar, V.; Chand, D. K. Polymer 2017, 123, 267. doi: 10.1016/j.polymer.2017.06.073
108. [108]
  Cai, C.-X.; Amgoune, A.; Lehmann, C. W.; Carpentier, J.-F. Chem. Commun. 2004, 330.
109. [109]
  Ma, H.; Spaniol, T.; Okuda, J. Angew. Chem., Int. Ed. 2006, 45, 7818. doi: 10.1002/(ISSN)1521-3773
110. [110]
  Amgoune, A.; Thomas, C. M.; Roisnel, T.; Carpentier, J.-F. Chem.-Eur. J. 2006, 12, 169. doi: 10.1002/(ISSN)1521-3765
111. [111]
  Liu, X.; Shang, X.; Tang, T.; Cui, D.; Chen, X.; Jing, X. Organometallics 2007, 26, 2747. doi: 10.1021/om0700359
112. [112]
  Arnold, P. L.; Buffet, J. C.; Blaudeck, R.; Sujecki, S.; Blake, A. J.; Wilson, C. Angew. Chem., Int. Ed. 2008, 47, 6033. doi: 10.1002/anie.v47:32
113. [113]
  Zhang, Z.; Xu, X.; Sun, S.; Yao, Y.; Zhang, Y.; Shen, Q. Chem. Commun. 2009, 7414.
114. [114]
  Dyer, H. E.; Huijser, S.; Susperregui, N.; Bonnet, F.; Schwarz, A. D.; Duchateau, R.; Maron, L.; Mountford, P. Organometallics 2010, 29, 3602. doi: 10.1021/om100513j
115. [115]
  Clark, L.; Cushion, M.; Dyer, H.; Schwarz, A.; Duchateau, R.; Mountford, P. Chem. Commun. 2010, 46, 273. doi: 10.1039/B919162C
116. [116]
  Bing, X.; Yao, Y.-M. Chin. J. Inorg. Chem. 2011, 27, 1805 (in Chinese).
117. [117]
  Yang, S.; Du, Z.; Zhang, Y.; Shen, Q. Chem. Commun. 2012, 48, 9780. doi: 10.1039/c2cc34451c
118. [118]
  Cao, T.-P.-A.; Buchard, A.; Goff, X.-F.-L.; Auffrant, A.; Williams, C. K. Inorg. Chem. 2012, 51, 2157. doi: 10.1021/ic202015z
119. [119]
  Bakewell, C.; Cao, T.-P.-A.; Long, N.-J.; Goff, X.-F.-L.; Auffrant, A.; Williams, C. K. J. Am. Chem. Soc. 2012, 134, 20577. doi: 10.1021/ja310003v
120. [120]
  Bie, Z.-Y.; Zheng, H.; Pan, Y.-W.; Ye, Y. J. Zhejiang Univ. (Sci. Ed.) 2013, 40(6), 650 (in Chinese).
121. [121]
  Bakewell, C.; White, A. J. P.; Long, N.-J.; Williams, C. K. Angew. Chem., Int. Ed. 2014, 53, 9226. doi: 10.1002/anie.201403643
122. [122]
  Bakewell, C.; White, A. J. P.; Long, N.-J.; Williams, C. K. Inorg. Chem. 2015, 54, 2204. doi: 10.1021/ic5027015
123. [123]
  Xu, T.-Q.; Yang, G.-W.; Liu, C.; Lu, X.-B. Macromolecules 2017, 50, 515. doi: 10.1021/acs.macromol.6b02439
124. [124]
  Wei, Z.-Y.; Liu, L.; Yu, F.-Y.; Wang, P.; Qu, C.; Qi, M. Polym. Bull. 2008, 61, 407. doi: 10.1007/s00289-008-0964-0
125. [125]
  Wang, S.; Lu, L.; Gruetzmacher, J.; Currier, B.; Yaszemski, M. Macromolecules 2005, 38, 7358. doi: 10.1021/ma050884c
1. [1]
  Hongling Yuan , Jialin Xie , Jiawei Wang , Jixiang Zhao , Jiayan Liu , Qing Feng , Wei Qi , Min Liu . Cyclic Olefin Copolymer (COC): The Agile Vanguard in the Realm of Materials. University Chemistry, 2024, 39(7): 294-298. doi: 10.12461/PKU.DXHX202311041
2. [2]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
3. [3]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
4. [4]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
5. [5]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
6. [6]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
7. [7]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
8. [8]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
9. [9]
  Yuanyi Lu , Jun Zhao , Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088
10. [10]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
11. [11]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
12. [12]
  Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
13. [13]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
14. [14]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
15. [15]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
16. [16]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
17. [17]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
18. [18]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
19. [19]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
20. [20]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(3278)
HTML views(791)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142