Guaiacolate derivatives‐containing sodium complexes as catalysts for l ‐lactide polymerization

Applied Organometallic Chemistry, vol. 37

Abstract

In this study, guaiacolate derivatives‐containing tetranuclear sodium catalysts were synthesized, and their catalytic activity in l‐lactide (LA) polymerization was evaluated. Using LBF‐Na (sodium complex bearing 2,3‐dihydro‐2,2‐dimethyl‐7‐benzofuranolate) as a catalyst, the polymerization of LA was studied in various solvents. LBF‐Na polymerized LA in dichloromethane, tetrahydrofuran, and toluene, and the catalytic activity of LBF‐Na was similar in these solvents. Among the sodium complexes, LOH‐Na (sodium complex bearing guaiacolate) exhibited higher catalytic activity (5 min, conversion = 93%; MnGPC = 7200) than the other tetranuclear sodium complexes. Furthermore, LOH‐Na exhibited an “immortal” property after 20 equivalents of benzyl alcohol loading during LA polymerization and good controllability in polylactide production. Thus, guaiacolate ligands increase the catalytic activity of sodium catalysts in LA polymerization in both coordinating and halogen‐containing solvents and under the condition of extra alcohol loading.

Authors 8

1. Tzu‐Yi Wu

   Kaohsiung Medical University

   Affiliation as printed

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC

2. Feng‐Jie Lai

   Chi Mei Medical Center · Southern Taiwan University of Science and Technology

   Affiliation as printed

   Center for General Education Southern Taiwan University of Science and Technology Tainan Taiwan, ROC

   Department of Dermatology Chi Mei Medical Center Tainan Taiwan, ROC

   Center for General Education, Southern Taiwan University of Science and Technology, Tainan, Taiwan, ROC

   Department of Dermatology, Chi Mei Medical Center, Tainan, Taiwan, ROC

3. Wei Lee

   Kaohsiung Medical University

   Affiliation as printed

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC

4. Chun‐Juei Chang

   National Sun Yat-sen University · Kaohsiung Medical University

   Affiliation as printed

   Department of Chemistry National Sun Yat‐Sen University Kaohsiung Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC

5. Yu‐Lun Chang Aachen Leiden Institute of Chemistry Faculty of Science Leiden University Leiden The Netherlands

   Leiden University · Kaohsiung Medical University

   Affiliation as printed

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Leiden Institute of Chemistry, Faculty of Science Leiden University Leiden The Netherlands

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC

6. Shangwu Ding

   National Sun Yat-sen University · Kaohsiung Medical University

   Affiliation as printed

   Department of Chemistry National Sun Yat‐Sen University Kaohsiung Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC

7. Hsuan‐Ying Chen corresponding

   National Sun Yat-sen University · Kaohsiung Medical University · Kaohsiung Medical University Chung-Ho Memorial Hospital

   Affiliation as printed

   Department of Chemistry National Sun Yat‐Sen University Kaohsiung Taiwan, ROC

   Department of Medical Research Kaohsiung Medical University Hospital Kaohsiung Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan, ROC

   Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan, ROC

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC

8. Yung‐Chi Chang Aachen Leiden Institute of Chemistry Faculty of Science Leiden University Leiden The Netherlands Faculty of Science, Leiden University

   Leiden University · Kaohsiung Medical University

   Affiliation as printed

   Department of Medicinal and Applied Chemistry, Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan, ROC

   Leiden Institute of Chemistry, Faculty of Science Leiden University Leiden The Netherlands

   Leiden Institute of Chemistry, Faculty of Science, Leiden University, Leiden, The Netherlands