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
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