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Effect of the phenyl ring substituent on stereoselectivity in the ring-opening polymerization of the rac-lactide initiated by salen aluminum complexes

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Abstract

A number of unreported salen aluminum complexes bearing Schiff base ligands starting from (R,R)-1,2-diammoniumcyclohexane mono-(+)-tartrate salt were synthesized. These complexes were characterized by 1H, 13C NMR, and elemental analysis. These complexes were employed as initiators for the ring-opening polymerization (ROP) of L-lactide and rac-lactide. Complex 3 (R = Br) showed the highest activity for the ROP of L-lactide among these complexes, and complex 2 (R = iPr) possessed the highest stereoselectivity for the ROP of rac-lactide among these aluminum isopropoxides. The kinetics studies of the polymerization employed complex 2 as initiator indicated that the polymerization rate was first-ordered in lactide and initiator.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (grant number 21204082); the Project for Science and Technology Development of Jilin Science & Technology Department, Jilin province, China (grant number 20140204017GX); the Science and Technology Bureau of Changchun City, China (grant number 2013060); and Training Programs of Innovation and Entrepreneurship for Undergraduates (No. 2015X094).

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    1. School of Materials Science and Engineering, Changchun University of Science and Technology, Changchun, 130022, China

      Zuwang Wen, Dongni Li, Juquan Qi, Xuedi Chen, Yue Jiang, Li Chen, Bo Gao, Yuan Cui & Qian Duan

    2. China–Japan Union Hospital of Jilin University, Jilin University, 126 Xiantai Street, Changchun, 130033, China

      Dongni Li

    3. Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry Chinese Academy of Sciences, Changchun, 130022, China

      Bo Gao

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    Zuwang Wen and Dongni Li contributed equally to this work.

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    Wen, Z., Li, D., Qi, J. et al. Effect of the phenyl ring substituent on stereoselectivity in the ring-opening polymerization of the rac-lactide initiated by salen aluminum complexes. Colloid Polym Sci 293, 3449–3457 (2015). https://doi.org/10.1007/s00396-015-3720-7

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