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Issue 20, 2014
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A base–conjugate-acid pair for living/controlled ring-opening polymerization of trimethylene carbonate through hydrogen-bonding bifunctional synergistic catalysis

Xin Wang,a  Saide Cui,a  Zhenjiang Li,a  Suli Kan,a  Qiguo Zhang,a  Chengxu Zhao,a  Hao Wu,a  Jingjing Liu,a  Wenzhuo Wua  and  Kai Guo*a 
Author affiliations

* Corresponding authors

a State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd South, Nanjing 211816, China
E-mail: guok@njtech.edu.cn

Abstract

The ring-opening polymerization (ROP) of trimethylene carbonate (TMC) using a base–acid binary organocatalyst system of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) and Brønsted acid trifluoromethanesulfonic acid (TFA) with benzyl alcohol (BnOH) as the initiator has been investigated. The MTBD and its conjugate-acid pair H-bonding bifunctional synergistic activation mechanism was demonstrated by NMR measurements, and the living/controlled nature of MTBD/TFA catalyzed ROP of TMC was confirmed by the kinetic and chain extension experiments. The controlled ROP of TMC with the optimal molar ratio of MTBD/TFA = 2/1 proceeded to afford well-defined PTMC with narrow molecular weight distributions (Mw/Mn ∼ 1.1). The molecular weights determined by 1H NMR are in precise agreement with the theoretical values. 1H NMR, SEC, and MALDI-ToF MS measurements confirmed the structure of the obtained homopolymer PTMC. In addition, a diblock copolymer consisting of poly(trimethylene carbonate) and poly(L-lactide) (PTMC-b-PLLA) was synthesized successfully by the MTBD/TFA binary catalyst system.

Graphical abstract: A base–conjugate-acid pair for living/controlled ring-opening polymerization of trimethylene carbonate through hydrogen-bonding bifunctional synergistic catalysis

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Publication details

The article was received on 03 Jun 2014, accepted on 25 Jun 2014 and first published on 27 Jun 2014


Article type: Paper
DOI: 10.1039/C4PY00773E
Citation: Polym. Chem., 2014,5, 6051-6059
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    A base–conjugate-acid pair for living/controlled ring-opening polymerization of trimethylene carbonate through hydrogen-bonding bifunctional synergistic catalysis

    X. Wang, S. Cui, Z. Li, S. Kan, Q. Zhang, C. Zhao, H. Wu, J. Liu, W. Wu and K. Guo, Polym. Chem., 2014, 5, 6051
    DOI: 10.1039/C4PY00773E

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