Citation: Shaogang Gong, Peng Du, Haiyan Ma. Binuclear Aluminum Complexes Supported by Linked Bis(β-diketiminate) Ligands for Ring-Opening Polymerization of Cyclic Esters[J]. Chinese Journal of Polymer Science, ;2018, 36(2): 190-201. doi: 10.1007/s10118-018-2053-7 shu

Binuclear Aluminum Complexes Supported by Linked Bis(β-diketiminate) Ligands for Ring-Opening Polymerization of Cyclic Esters

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

Corresponding author: Haiyan Ma, haiyanma@ecust.edu.cn
Received Date: 1 September 2017
Accepted Date: 30 September 2017
Available Online: 21 November 2017

Binuclear aluminum alkyl complexes 2a-4g supported by linked bis(β-diketiminate) ligands were synthesized via the reaction of AlEt₃ or AlMe₃ and the corresponding proligand in a 2:1 molar ratio with moderate yields. The isolated complexes were well-characterized by ¹H-NMR, ¹³C-NMR and elemental analysis. The binuclear nature of aluminum complex 2b was further confirmed by an X-ray diffraction study. All complexes 2a-4g could efficiently initiate the ring-opening polymerization (ROP) of ε-caprolactone in toluene. The substituents at the aromatic rings and the linker unit in the auxiliary ligands exerted significant influence on the catalytic behavior of the investigated aluminum complexes. Complex 4g (R¹=R²=Cl) containing propylenyl bridging unit exhibited the highest catalytic activity among these complexes, which might be attributed to the increased electrophilicity of the metal center as well as more opened coordination sphere. The molecular weights of obtained poly(ε-caprolactone)s deviating considerably from the theoretical values indicated that the ROP of ε-caprolactone by complexes 2a-4g was not well-controlled, which was also judged from the broad molecular weight distributions (MWD=1.47-2.47) of produced poly(ε-caprolactone)s. These complexes proved to be inactive toward the polymerization of rac-lactide alone. In the presence of alcohol the polymerization occurred, which was actually initiated by the decomposition species of the aluminum complex upon the treatment with isopropanol.
- Bis (β-diketiminate) ligand,
- Aluminum complex,
- Binuclear,
- Polymerization,
- Cyclic ester
1. [1]
  Mecking S.. Nature or petrochemistry?—Biologically degradable materials[J]. Angew. Chem. Int. Ed., 2004,43:1078-1085. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Ragauskas A. J., Williams C. K., Davison B. H., Britovsek G., Cairney J., Eckert C. A., Frederick W. J., Hallett J. P., Leak D. J., Liotta C. L., Mielenz J. R., Murphy R., Templer R., Tschaplinski T.. The path forward for biofuels and biomaterials[J]. Science, 2006,311:484-489. doi: 10.1126/science.1114736
3. [3]
  Williams C. K., Hillmyer M. A.. Polymers from renewable resources: a perspective for a special issue of polymer reviews[J]. Polym. Rev., 2008,48:1-10. doi: 10.1080/15583720701834133
4. [4]
  Dechy-Cabaret O., Martin-Vaca B., Bourissou D.. Controlled ring-opening polymerization of lactide and glycolide[J]. Chem. Rev., 2004,104:6147-6176. doi: 10.1021/cr040002s
5. [5]
  Wu J., Yu T. L., Chen C. T., Lin C. C.. Recent developments in main group metal complexes catalyzed/initiated polymerization of lactides and related cyclic esters[J]. Coord. Chem. Rev., 2006,250:602-626. doi: 10.1016/j.ccr.2005.07.010
6. [6]
  Platel R. H., Hodgson L. M., Williams C. K.. Biocompatible initiators for lactide polymerization[J]. Polym. Rev., 2008,48:11-63. doi: 10.1080/15583720701834166
7. [7]
  Thomas C. M.. Stereocontrolled ring-opening polymerization of cyclic esters: synthesis of new polyester microstructures[J]. Chem. Soc. Rev., 2010,39:165-173. doi: 10.1039/B810065A
8. [8]
  Stanford M. J., Dove A. P.. Stereocontrolled ring-opening polymerization of lactide[J]. Chem. Soc. Rev., 2010,39:486-494. doi: 10.1039/B815104K
9. [9]
  Cheng M., Attygalle A. B., Lobkovsky E. B., Coates G. W.. Single-site catalysts for ring-opening polymerization: synthesis of heterotactic poly(lactic acid) from rac-lactide[J]. J. Am. Chem. Soc., 1999,121:11583-11584. doi: 10.1021/ja992678o
10. [10]
  Chamberlain B. M., Cheng M., Moore D. R., Ovitt T. M., Lobkovsky E. B., Coates G. W.. Polymerization of lactide with zinc and magnesium β-diiminate complexes: stereocontrol and mechanism[J]. J. Am. Chem. Soc., 2001,123:3229-3238. doi: 10.1021/ja003851f
11. [11]
  Chisholm M. H., Gallucci J., Phomphrai K.. Coordination chemistry and reactivity of monomeric alkoxides and amides of magnesium and zinc supported by the diiminato ligand CH(CMeNC₆H₃-2, 6-ⁱPr₂)₂[J]. A comparative study. Inorg. Chem., 2002,41:2785-2794.
12. [12]
  Williams C. K., Breyfogle L. E., Choi S. K., Nam W., Young V. G., Hillmyer M. A., Tolman W. B.. A highly active zinc catalyst for the controlled polymerization of lactide[J]. J. Am. Chem. Soc., 2003,125:11350-11359. doi: 10.1021/ja0359512
13. [13]
  Dove A., Gibson V. C., Marshall E., White A., Williams D.. Magnesium and zinc complexes of a potentially tridentate β-diketiminate ligand[J]. Dalton Trans.,, 2004:570-578.
14. [14]
  Silvernail C. M., Yao L. J., Hill L. M. R., Hillmyer M. A., Tolman W. B.. Structural and mechanistic studies of bis(phenolato)amine zinc(Ⅱ) catalysts for the polymerization of ε-caprolactone[J]. Inorg. Chem., 2007,46:6565-6574. doi: 10.1021/ic700581s
15. [15]
  Chuang H. J., Ch en, H. Li.; Huang B. H., Tsai T. E., Huang P. L., Liao T. T., Lin C. C.. Efficient zinc initiators supported by NNO-tridentate ketiminate ligands for cyclic esters polymerization[J]. J. Polym. Sci., Part A: Polym. Chem., 2013,51:1185-1196. doi: 10.1002/pola.26486
16. [16]
  Song S., Zhang X., Ma H., Yang Y.. Zinc complexes supported by claw-type aminophenolate ligands: synthesis, characterization and catalysis in the ring-opening polymerization of rac-lactide[J]. Dalton Trans., 2012,41:3266-3277. doi: 10.1039/c2dt11767c
17. [17]
  Honrado M., Otero A., Fernández-Baeza J., Sánchez-Barba L. F., Lara-Sánchez A., Tejeda J., Carrión M. P., Martínez-Ferrer J., Garcés A., Rodríguez A. M.. Efficient synthesis of an unprecedented enantiopure hybrid scorpionate/cyclopentadienyl by diastereoselective nucleophilic addition to a fulvene[J]. Organometallics, 2013,32:3437-3440. doi: 10.1021/om4003279
18. [18]
  Wang H., Ma H.. Highly Diastereoselective synthesis of chiral aminophenolate zinc complexes and isoselective polymerization of rac-lactide[J]. Chem. Commun., 2013,49:8686-8688. doi: 10.1039/c3cc44980g
19. [19]
  Wang H., Yang Y., Ma H.. Stereoselectivity switch between zinc and magnesium initiators in the polymerization of rac-lactide: different coordination chemistry, different stereocontrol mechanisms[J]. Macromolecules, 2014,47:7750-7764. doi: 10.1021/ma501896r
20. [20]
  Mou Z., Liu B., Wang M., Xie H., Li P., Li L., Li S., Cui D.. Isoselective ring-opening polymerization of rac-lactide initiated by achiral heteroscorpionate zwitterionic zinc complexes[J]. Chem. Commun., 2014,50:11411-11413. doi: 10.1039/C4CC05033A
21. [21]
  Abbina S., Du G.. Zinc-catalyzed highly isoselective ring opening polymerization of rac-lactide[J]. ACS Macro Lett., 2014,3:689-692. doi: 10.1021/mz5002959
22. [22]
  Yang Y., Wang H., Ma H.. Stereoselective polymerization of rac-lactide catalyzed by zinc complexes with tetradentate aminophenolate ligands in different coordination patterns: kinetics and mechanism[J]. Inorg. Chem., 2015,54:5839-5854. doi: 10.1021/acs.inorgchem.5b00558
23. [23]
  Wang H., Yang Y., Ma H.. Exploring steric effects in diastereoselective synthesis of chiral aminophenolate zinc complexes and stereoselective ring-opening polymerization of rac-lactide[J]. Inorg. Chem., 2016,55:7356-7372. doi: 10.1021/acs.inorgchem.6b00378
24. [24]
  Rosen T., Popowski Y., Goldberg I., Kol M.. Zinc complexes of sequential tetradentate monoanionic ligands in the isoselective polymerization of rac-lactide[J]. Chem. Eur. J., 2016,22:11533-11536. doi: 10.1002/chem.201601979
25. [25]
  Shueh M. L., Wang Y. S., Huang B. H., Kuo C. Y., L in, C. C.. Reactions of 2, 2-methylene bis(4-chloro-6-isopropyl-3-methylphenol) and 2, 2-ethylidene bis(4, 6-di-tert-butylphenol) with MgⁿBu₂: efficient catalysts for ring-opening polymerization of ε-caprolactone and L-lactide.[J]. Macromolecules, 2004,37:5155-5162. doi: 10.1021/ma049778l
26. [26]
  Yu T. L., Wu C. C., Chen C. C., Huang B. H., Wu J., Lin C. C.. Catalysts for the ring-opening polymerization of ε-caprolactone and L-lactide and the mechanistic study[J]. Polymer, 2005,46:5909-5917. doi: 10.1016/j.polymer.2005.04.079
27. [27]
  Wang L., Ma H.. Highly active magnesium initiators for ring-opening polymerization of rac-LA[J]. Macromolecules, 2010,43:6535-6537. doi: 10.1021/ma101263g
28. [28]
  Song S., Ma H., Yang Y.. Magnesium complexes supported by salan-like ligands, synthesis, characterization and their application in the ring-opening polymerization of rac-lactide[J]. Dalton Trans., 2013,42:14200-14211. doi: 10.1039/c3dt51344k
29. [29]
  Xie H., Mou Z., Liu B., Li P., Rong W., Li S., Cui D.. Phosphinimino-amino magnesium complexes, synthesis and catalysis of heteroselective ROP of rac-lactide[J]. Organometallics, 2014,33:722-730. doi: 10.1021/om401056s
30. [30]
  Chisholm M. H., Gallucci J. C., Phomphrai K.. Well-defined calcium initiators for lactide polymerization[J]. Inorg. Chem., 2004,43:6717-6725. doi: 10.1021/ic0490730
31. [31]
  Chisholm M. H., Gallucci J. C., Phomphrai K.. Lactide polymerization by well-defined calcium coordination complexes, comparisons with related magnesium and zinc chemistry[J]. Chem. Commun., 2003:48-49.
32. [32]
  Darensbourg D. J., Choi W., Karroonnirun O., Bhuvanesh N.. Ring-opening polymerization of cyclic monomers by complexes derived from biocompatible metals[J]. Production of poly(lactide), poly(trimethylene carbonate), and their copolymers. Macromolecules, 2008,41:3493-3502.
33. [33]
  Bhattacharjee J., Harinath A., Nayek H. P., Sarkar A., Panda T. K.. Highly active and iso-selective catalysts for the ring-opening polymerization of cyclic esters using group 2 metal initiators[J]. Chem. Eur. J., 2017,23:9319-9331. doi: 10.1002/chem.v23.39
34. [34]
  Fuoco T., Pappalardo D.. Aluminum alkyl complexes bearing salicylaldiminato ligands: versatile initiators in the ring-opening polymerization of cyclic esters[J]. Catalysts, 2017. doi: 10.3390/catal7020064
35. [35]
  Huang C. H., Wang F. C., Ko B. T., Yu T. L., Lin C. C.. Ring-opening polymerization of ε-caprolactone and L-lactide using aluminum thiolates as initiator[J]. Macromolecules, 2001,34:356-361. doi: 10.1021/ma0014719
36. [36]
  Alcazar-Roman L. M., O'Keefe B. J., Hillmyer M. A., Tolman W. B.. Electronic influence of ligand substituents on the rate of polymerization of ε-caprolactone by single-site aluminium alkoxide catalysts[J]. Dalton Trans., 2003:3082-3087.
37. [37]
  Chen C. T., Huang C. A., Huang B. H.. Aluminium metal complexes supported by amine bis-phenolate ligands as catalysts for ring-opening polymerization of ε-caprolactone[J]. Dalton Trans., 2003:3799-3803.
38. [38]
  Chen C. T., Huang C. A., Huang B. H.. Aluminum complexes supported by tridentate aminophenoxide ligand as efficient catalysts for ring-opening polymerization of ε-caprolactone[J]. Macromolecules, 2004,33:7968-7973.
39. [39]
  Spassky N., Wisniewski M., Pluta C., LeBorgne A.. Highly stereoelective polymerization of rac-(D, L)-lactide with a chiral Schiff's base/aluminium alkoxide initiator[J]. Macromol. Chem. Phys., 1996,197:2627-2637. doi: 10.1002/macp.1996.021970902
40. [40]
  Radano C. P., Baker G. L., Smith M. R.. Ⅲ[J]. Stereoselective polymerization of a racemic monomer with a racemic catalyst: direct preparation of the polylactic acid stereocomplex from racemic lactide. J. Am. Chem. Soc., 2000,122:1552-1553.
41. [41]
  Nomura N., Ishii R., Akakura M., Aoi K.. Stereoselective ring-opening polymerization of racemic lactide using aluminum-achiral ligand complexes: exploration of a chain-end control mechanism[J]. J. Am. Chem. Soc., 2002,124:5938-5939. doi: 10.1021/ja0175789
42. [42]
  Ovitt T. M., Coates G. W.. Stereochemistry of lactide polymerization with chiral catalysts: new opportunities for stereocontrol using polymer exchange mechanisms[J]. J. Am. Chem. Soc., 2002,124:1316-1326. doi: 10.1021/ja012052+
43. [43]
  Zhong Z., Dijkstra P. J., Feijen J.. [(Salen)Al]-mediated, controlled and stereoselective ring-opening polymerization of lactide in solution and without solvent: synthesis of highly isotactic polylactide stereocopolymers from racemic D, L-lactide[J]. Angew. Chem. Int. Ed., 2002,114:4692-4695. doi: 10.1002/1521-3757(20021202)114:23<4692::AID-ANGE4692>3.0.CO;2-5
44. [44]
  Zhong Z., Dijkstra P. J., Feijen J.. Controlled and stereoselective polymerization of lactide: kinetics, selectivity, and microstructures[J]. J. Am. Chem. Soc., 2003,125:11291-11298. doi: 10.1021/ja0347585
45. [45]
  Tang Z., Chen X., Pang X., Yang Y., Zhang X., Jing X.. Stereoselective polymerization of rac-lactide using a monoethylaluminum Schiff base complex[J]. Biomacromolecules, 2004,5:965-970. doi: 10.1021/bm034467o
46. [46]
  Hormnirun P., Marshall E. L., Gibson V. C., White A. J. P., Williams D. J.. Remarkable stereocontrol in the polymerization of racemic lactide using aluminum initiators supported by tetradentate aminophenoxide ligands[J]. J. Am. Chem. Soc., 2004,126:2688-2689. doi: 10.1021/ja038757o
47. [47]
  Majerska K., Duda A.. Stereocontrolled polymerization of racemic lactide with chiral initiator: combining stereoselection and chiral ligand-exchang mechanism[J]. J. Am. Chem. Soc., 2004,126:1026-1027. doi: 10.1021/ja0388966
48. [48]
  Chisholm M. H., Patmore N. J., Zhou Z.. Concerning the relative importance of enantiomorphic site versus chain end control in the stereoselective polymerization of lactides: reactions of (R, R-salen)-and (S, S-salen)-aluminium alkoxides LAlOCH₂R complexes (R = CH₃ and S-CHMeCl)[J]. Chem. Commun., 2005:127-129.
49. [49]
  Nomura N., Ishii R., Yamamoto Y., Kondo T.. Stereoselective ring-opening polymerization of a racemic lactide by using achiral salen-and homosalen-aluminum complexes[J]. Chem. Eur. J., 2007,13:4433-4451. doi: 10.1002/(ISSN)1521-3765
50. [50]
  Du H., Pang X., Yu H., Zhuang X., Chen X., Cui D., Wang X., Jing X.. Polymerization of rac-lactide using Schiff base aluminum catalysts: structure, activity, and stereoselectivity[J]. Macromolecules, 2007,40:1904-1913. doi: 10.1021/ma062194u
51. [51]
  Chen H. L., Dutta S., Huang P. Y., Lin C. C.. Preparation and characterization of aluminum alkoxides coordinated on salen-type ligands: highly stereoselective ring-opening polymerization of rac-Lactide[J]. Organometallics, 2012,31:2016-2025. doi: 10.1021/om201281w
52. [52]
  Maudoux N., Roisnel T., Dorcet V., Carpentier J. F., Sarazin , Y .. Chiral (1, 2)-diphenylethylene-salen complexes of triel metals: coordination patterns and mechanistic considerations in the isoselective ROP of lactide[J]. Chem. Eur. J., 2014,20:6131-6147. doi: 10.1002/chem.201304788
53. [53]
  Pilone A., Press K., Goldberg I., Kol M., Mazzeo M., Lamberti M.. Gradient isotactic multiblock polylactides from aluminum complexes of chiral salalen ligands[J]. J. Am. Chem. Soc., 2014,136:2940-2943. doi: 10.1021/ja412798x
54. [54]
  Press K., Goldberg I., Kol M.. Mechanistic insight into the stereochemical control of lactide polymerization by salan-aluminum catalysts[J]. Angew. Chem. Int. Ed., 2015,54:14858-14861. doi: 10.1002/anie.201503111
55. [55]
  Douglas A. F., Patrick B. O., Mehrkhodavandi P.. A highly active chiral indium catalyst for living lactide polymerization[J]. Angew. Chem. Int. Ed., 2008,120:2322-2325. doi: 10.1002/(ISSN)1521-3757
56. [56]
  Yu I., Acosta-Ramírez A., Mehrkhodavandi P.. Mechanism of living lactide polymerization by dinuclear indium catalysts and its Impact on isoselectivity[J]. J. Am. Chem. Soc., 2012,134:12758-12773. doi: 10.1021/ja3048046
57. [57]
  Aluthge D. C., Patrick B. O., Mehrkhodavandi P.. A Highly active and site selective indium catalyst for lactide polymerization[J]. Chem. Commun., 2013,49:4295-4297. doi: 10.1039/C2CC33519K
58. [58]
  Aluthge D. C., Ahn J. M., Mehrkhodavandi P.. Overcoming aggregation in indium salen catalysts for isoselective lactide polymerization[J]. Chem. Sci., 2015,6:5284-5292. doi: 10.1039/C5SC01584G
59. [59]
  Myers D., White A. J. P., Forsyth C. M., Bown M., Williams C. K.. Phosphasalen indium complexes showing high rates and isoselectivities in rac-lactide polymerizations[J]. Angew. Chem. Int. Ed., 2017,56:5277-5282. doi: 10.1002/anie.201701745
60. [60]
  Zhang J., Xiong J., Sun Y., Tang N., Wu J.. Highly iso-selective and active catalysts of sodium and potassium monophenoxides capped by a crown ether for the ring-opening polymerization of rac-lactide[J]. Macromolecules, 2014,47:7789-7796. doi: 10.1021/ma502000y
61. [61]
  Dai Z., Sun Y., Xiong J., Pan X., Wu J.. Alkali-metal monophenolates with a sandwich-type catalytic center as catalysts for highly isoselective polymerization of rac-lactide[J]. ACS Macro Lett., 2015,4:556-560. doi: 10.1021/acsmacrolett.5b00209
62. [62]
  Sun Y., Xiong J., Dai Z., Pan X., Tang N., Wu J.. Stereoselective alkali-metal catalysts for highly isotactic poly(rac-lactide) synthesis[J]. Inorg. Chem., 2016,55:136-143. doi: 10.1021/acs.inorgchem.5b02709
63. [63]
  Russell S. K., Gamble C. L., Gibbins K. J., Juhl K. C. S., Mitchell , Ⅲ , W. S.; Tumas A. J., Hofmeister E. G.. Stereoselective controlled polymerization of D, L-lactide with[J]. Macromolecules, 2005,38:10336-10340. doi: 10.1021/ma051811w
64. [64]
  Chmura A. J., Davidson M. G., Frankis C. J., Jones M. D., Lunn M. D.. Highly active and stereoselective zirconium and hafnium alkoxide initiators for solvent-free ring-opening polymerization of rac-lactide[J]. Chem. Commun., 2008:1293-1295.
65. [65]
  Zelikoff A. L., Kopilov J., Goldberg I., Coates G. W., Kol M.. New facets of an old ligand, titanium and zirconium complexes of phenylenediamine bis(phenolate) in lactide polymerisation catalysis[J]. Chem. Commun., 2009:6804-6806.
66. [66]
  Whitelaw E., Davidson M., Jones M.. Group 4 salalen complexes for the production and degradation of polylactide[J]. Chem. Comm., 2011,47:10004-10006. doi: 10.1039/c1cc13910j
67. [67]
  Stopper A., Okuda J., Kol M.. Ring-opening polymerization of lactide with Zr complexes of {ONSO} ligands: from heterotactically inclined to isotactically inclined poly(lactic acid)[J]. Macromolecules, 2012,45:698-704. doi: 10.1021/ma2023364
68. [68]
  Jones M. D., Hancock S. L., McKeown P., Sch fer P. M., Buchard A., Thomas L. H., Mahon M. F., Lowe J. P.. Zirconium complexes of bipyrrolidine derived salan ligands for the isoselective polymerisation of rac-lactide[J]. Chem. Commun., 2014,50:15967-15970. doi: 10.1039/C4CC07871C
69. [69]
  Jones M. D., Brady L., McKeown P., Buchard A., Schäfer P. M., Thomas L. H., Mahon M. F., Woodman T. J., Lowe J. P.. Metal influence on the iso- and hetero-selectivity of complexes of bipyrrolidine derived salan ligands for the polymerisation of rac-lactide[J]. Chem. Sci., 2015,6:5034-5039. doi: 10.1039/C5SC01819F
70. [70]
  Cai C. X., Amgoune A., Lehmann C. W., Carpentier J. F.. Stereoselective ring-opening polymerization of racemic lactide using alkoxy-amino-bis(phenolate) group 3 metal complexes[J]. Chem. Commun., 2004:330-331.
71. [71]
  Ma H., Spaniol T., Okuda J.. Highly heteroselective ring-opening polymerization of rac-lactide initiated by bis(phenolato) scandium complexes[J]. Angew. Chem. Int. Ed., 2006,45:7818-7821. doi: 10.1002/(ISSN)1521-3773
72. [72]
  Amgoune A., Thomas C. M., Roisnel T., Carpentier J. F.. Ring-opening polymerization of lactide with group 3 metal complexes supported by dianionic alkoxy-amino-bisphenolate ligands, combining high activity, productivity and selectivity[J]. Chem. Eur. J., 2006,12:169-179. doi: 10.1002/(ISSN)1521-3765
73. [73]
  Amgoune A., Thomas C. M., Carpentier J. F.. Yttrium complexes as catalysts for living and immortal polymerization of lactide to highly heterotactic PLA[J]. Macromol. Rapid Commun., 2007,28:693-697. doi: 10.1002/(ISSN)1521-3927
74. [74]
  Liu X., Shang X., Tang T., Cui D., Chen X., Jing X.. Achiral lanthanide alkyl complexes bearing N, O multidentate ligands, synthesis and catalysis of highly heteroselective ring-opening polymerization of rac-lactide[J]. Organometallics, 2007,26:2747-2757. doi: 10.1021/om0700359
75. [75]
  Arnold P. L., Buffet J. C., Blaudeck R. P., Sujecki S., Blake A. J., Wilson C. A.. C₃-Symmetric lanthanide tris(alkoxide) complexes formed by preferential complexation and their stereoselective polymerization of rac-lactide[J]. Angew. Chem. Int. Ed., 2008,47:6033-6036. doi: 10.1002/anie.v47:32
76. [76]
  Clark , L; Cushion M., Dyer H., Schwarz A., Duchateau R., Mountford P.. Dicationic and zwitterionic catalysts for the amine-initiated, immortal ring-opening polymerization of rac-lactide: facile synthesis of amine-terminated, highly heterotactic PLA[J]. Chem. Commun., 2010,46:273-275. doi: 10.1039/B919162C
77. [77]
  Yang S., Zhu Du, Zhang Y., Shen Q.. Highly Heteroselective ring-opening polymerization of racemic lactide initiated by divalent ytterbium complexes bearing amino bis(phenolate) ligands[J]. Chem. Commun., 2012,48:9780-9782. doi: 10.1039/c2cc34451c
78. [78]
  Cao T. P. A., Buchard A., Goff X. F. L., Auffrant A., Williams C. K.. Phosphasalen yttrium complexes, highly active and stereoselective initiators for lactide polymerization[J]. Inorg. Chem., 2012,51:2157-2169. doi: 10.1021/ic202015z
79. [79]
  Bakewell C., Cao T. P. A., Long N., Le Goff X. F., Auffrant A., Williams C. K.. Yttrium phosphasalen initiators for rac-lactide polymerization: excellent rates and high iso-selectivities[J]. J. Am. Chem. Soc., 2012,134:20577-20580. doi: 10.1021/ja310003v
80. [80]
  Bakewell C., White A. J. P., Long N. J., Auffrant A., Williams C. K.. Metal-size influence in iso-selective lactide polymerization[J]. Angew. Chem. Int. Ed., 2014,53:9226-9230. doi: 10.1002/anie.201403643
81. [81]
  Xu T. Q., Yang G. W., Liu C., Lu X. B.. Highly robust yttrium bis(phenolate) ether catalysts for excellent isoselective ring-opening polymerization of racemic lactide[J]. Macromolecules, 2017,50:515-522. doi: 10.1021/acs.macromol.6b02439
82. [82]
  Chakraborty D., Ch en, E. Y. X.. Neutral, three-coordinate, chelating diamide aluminum complexes: catalysts/initiators for synthesis of telechelic oligomers and high polymers.[J]. Organometallics, 2002,21:1438-1442. doi: 10.1021/om011051n
83. [83]
  Chai Z. Y., Zhang C., Wa ng, Z. X.. Synthesis, characterization, and catalysis in ε-caprolactone polymerization of aluminum and zinc complexes supported by N, N, N-chelate ligands.[J]. Organometallics, 2008,27:1626-1633. doi: 10.1021/om701112m
84. [84]
  Yao W., Mu Y., Gao A. H., Su Q., Liu; Y. J.; Zhang Y. Y.. Efficient ring-opening polymerization of ε-caprolactone using anilido-imine-aluminum complexes in the presence of benzyl alcohol[J]. Polymer, 2008,49:2486-2491. doi: 10.1016/j.polymer.2008.03.035
85. [85]
  Yao W., Mu Y., Gao A., Wei W., Ye L.. Bimetallic anilido-aldimine Al or Zn complexes for efficient ring-opening polymerization of ε-caprolactone[J]. Dalton Trans., 2008:3199-3206.
86. [86]
  Liu J., Ma H.. Aluminum complexes with bidentate amido ligands: synthesis, structure and performance on ligand-initiated ring-opening polymerization of rac-lactide[J]. Dalton Trans., 2014,43:9098-9110. doi: 10.1039/c4dt00353e
87. [87]
  Liu J., Ma H.. Well-controlled ring-opening polymerization of cyclic esters catalyzed by aluminum amido complexes: kinetics and mechanism[J]. J. Polym. Sci., A: Polym. Chem., 2014,52:3096-3106. doi: 10.1002/pola.v52.21
88. [88]
  Kosuru S. R., Sun T. H., Wang L. F., Vandavasi J. K., Lu W. Y., Lai Y. C., Hsu S. C. N., Chiang M. Y., Chen H. Y.. Enhanced catalytic activity of aluminum complexes for the ring-opening polymerization of ε-caprolactone[J]. Inorg. Chem., 2017,56:7998-8006. doi: 10.1021/acs.inorgchem.7b00763
89. [89]
  Gong S., Ma H.. β-Diketiminate aluminum complexes: synthesis, characterization and ring-opening polymerization of cyclic esters[J]. Dalton Trans., 2008:3345-3357.
90. [90]
  Pilz M., Limberg C., Ziemer B.. Xanthene-based ligand with two adjacent β-diiminato binding sites[J]. J. Org. Chem., 2006,71:4559-4564. doi: 10.1021/jo060394y
91. [91]
  Hebden T., Brennessel W., Flaschenriem C., Holland P.. A dinucleating ligand related to the β-diketiminates[J]. Dalton Trans., 2006:3855-3857.
92. [92]
  Vela J., Zhu L., Flaschenriem C., Brennessel W.. Macrocyclic binucleating β-diketiminate ligands and their lithium, aluminum, and zinc complexes[J]. Organometallics, 2007,26:3416-3423. doi: 10.1021/om0700258
93. [93]
  Vitanova D., Hampel F., Hultzsch K.. Synthesis and structural characterisation of novel linked bis(β-diketiminato) rare earth metal complexes[J]. Dalton Trans., 2005:1565-1566.
94. [94]
  Vitanova D., Hampel F., Hultzsch K.. Rare earth complexes based on β-diketiminato and novel linked bis(β-diketiminato) ligands: synthesis, structures characterization and catalytic application in epoxide/CO₂-copolymerization[J]. J. Organomet. Chem., 2005,690:5182-5197. doi: 10.1016/j.jorganchem.2005.03.066
95. [95]
  Gong S., Ma H., Huang J.. Zirconium and hafnium complexes supported by linked bis(β-diketiminate) ligands: synthesis, characterization and catalytic application in ethylene polymerization[J]. Dalton Trans., 2009:8237-8247.
96. [96]
  SADABS, Bruker Nonius area detector scaling and absorption correction-V2. 05; Bruker AXS Inc. : Madison, WI, 1996.
97. [97]
  Sheldrick, G. M. SHELXTL 5. 10 for windows NT, Structure Determination Software Programs; Bruker Analytical X-ray Systems, Inc. : Madison, WI, 1997.
98. [98]
  SAINT, Version 6. 02; Bruker AXS Inc. : Madison, WI, 1999.
99. [99]
  Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures; University of Gottingen: Germany, 1990.
100. [100]
  Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997.
101. [101]
  Johnson, C. K. ORTEP-II: A FORTRAN Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1976.
102. [102]
  Nomura N., Aoyama T., Ishii R., Kondo T.. Salicylaldimine-aluminum complexes for the facile and efficient ring-opening polymerization of ε-caprolactone[J]. Macromolecules, 2005,38:5363-5366. doi: 10.1021/ma050606d
103. [103]
  Radzewich C. E., Coles M. P., Jordan R. F.. Reversible ethylene cycloaddition reactions of cationic aluminum β-diketiminate complexes[J]. J. Am. Chem. Soc., 1998,120:9384-9385. doi: 10.1021/ja9818405
104. [104]
  Li D., Peng Y., Geng C., Liu K., Kong D.. Well-controlled ring-opening polymerization of cyclic esters initiated by dialkylaluminum β-diketiminates[J]. Dalton Trans., 2013,42:11295-11303. doi: 10.1039/c3dt50372k
105. [105]
  Hao P., Yang Z., Li W., Ma X., Roesky H. W., Yang Y., Li J.. Aluminum complexes containing the C―O―Al―O―C framework as efficient initiators for ring-opening polymerization of ε-caprolactone[J]. Organometallics, 2015,34:105-108. doi: 10.1021/om500950p
106. [106]
  Lu N., Jiang Z., Pei H., Liu W., Li Y., Dong Y.. Ring-opening polymerization of ε-caprolactone initiated by aluminium complexes based on pyridine-substituted asymmetric β-diketiminate ligands[J]. Eur. J. Inorg. Chem., 2017:1320-1327.
107. [107]
  Lewiński J., Horeglad P., Wojcik K., Justyniak I.. Chelation effect in polymerization of cyclic esters by metal alkoxides: structure characterization of the intermediate formed by primary insertion of lactide into the Al―OR bond of an organometallic initiator[J]. Organometallics, 2005,24:4588-4593. doi: 10.1021/om050295v
108. [108]
  Yu R., Hung C., Huang J., Lee H., Chen J.. Four-and five-coordinate aluminum ketiminate complexes: synthesis, characterization, and ring-opening polymerization[J]. Inorg. Chem., 2002,41:6450-6455. doi: 10.1021/ic025785j
1. [1]
  Laiying Zhang , Yinghuan Wu , Yazi Yu , Yecheng Xu , Haojie Zhang , Weitai Wu . Innovation and Practice of Polymer Chemistry Experiment Teaching for Non-Polymer Major Students of Chemistry: Taking the Synthesis, Solution Property, Optical Performance and Application of Thermo-Sensitive Polymers as an Example. University Chemistry, 2024, 39(4): 213-220. doi: 10.3866/PKU.DXHX202310126
2. [2]
  Xue Zhao , Mengshan Chen , Dan Wang , Haoran Zhang , Guangzhi Hu , Yingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327
3. [3]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
4. [4]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
5. [5]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
6. [6]
  Xinzhi Ding , Chong Liu , Jing Niu , Nan Chen , Shutao Xu , Yingxu Wei , Zhongmin Liu . Solid-state NMR study of the stability of MOR framework aluminum. Chinese Journal of Structural Chemistry, 2024, 43(4): 100247-100247. doi: 10.1016/j.cjsc.2024.100247
7. [7]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
8. [8]
  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
9. [9]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
10. [10]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2023.100277
11. [11]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
12. [12]
  Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
13. [13]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
14. [14]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
15. [15]
  Zhenjie Yang , Chenyang Hu , Xuan Pang , Xuesi Chen . Sequence design in terpolymerization of ε-caprolactone, CO₂ and cyclohexane oxide: Random ester-carbonate distributions lead to large-span tunability. Chinese Chemical Letters, 2024, 35(5): 109340-. doi: 10.1016/j.cclet.2023.109340
16. [16]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
17. [17]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
18. [18]
  Lumin Zheng , Ying Bai , Chuan Wu . Multi-electron reaction and fast Al ion diffusion of δ-MnO₂ cathode materials in rechargeable aluminum batteries via first-principle calculations. Chinese Chemical Letters, 2024, 35(4): 108589-. doi: 10.1016/j.cclet.2023.108589
19. [19]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
20. [20]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(947)
HTML views(41)

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