Tripodal hydrogen bond donor binding with sulfonic acid enables ring-opening polymerization

Xiaopei Li; Qiguo Zhang; Zhenjiang Li; Songquan Xu; Chengxu Zhao; Cheng Chen; Xu Zhi; Huiying Wang; Ning Zhu; Kai Guo

doi:10.1039/c5py01931a

Tripodal hydrogen bond donor binding with sulfonic acid enables ring-opening polymerization

Xiaopei Li, Qiguo Zhang, Zhenjiang Li, Songquan Xu, Chengxu Zhao, Cheng Chen, Xu Zhi, Huiying Wang, Ning Zhu, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

H-bond donor (HBD) and Brønsted acid (BA) co-catalysis (HBD-BA) performed ring-opening polymerization (ROP) of cyclic esters in solution at room temperature. The HBD-BA strategy using thiophosphoric triamide (TPTA) binding with methanesulfonic acid (MSA) enabled the ROP of l-lactide (LA) to polylactide (PLA) with predicted molecular weights (M_n = 2.9-13.8 kDa) and low dispersities (D = 1.18-1.22). Associations of TPTA with MSA through triple hydrogen bonds stabilized the sulfonate anion and enhanced the catalytic performance of TPTA-MSA. Homopolymers of LA, trimethylene carbonate (TMC), δ-valerolactone, and ε-caprolactone (CL), and diblock copolymers PLA-b-PTMC and PLA-b-PCL with predicted M_n and narrow D were synthesized. NMR measurements, kinetics investigations, and chain extension experiments indicated that the TPTA-MSA catalyzed ROPs were controlled/living in nature. This is the first Brønsted acidic catalysis platform workable in all of the three major types of cyclic ester monomers including lactides, cyclic carbonates, and lactones.

Original language	English
Pages (from-to)	1368-1374
Number of pages	7
Journal	Polymer Chemistry
Volume	7
Issue number	7
DOIs	https://doi.org/10.1039/c5py01931a
State	Published - 21 Feb 2016

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title = "Tripodal hydrogen bond donor binding with sulfonic acid enables ring-opening polymerization",

abstract = "H-bond donor (HBD) and Br{\o}nsted acid (BA) co-catalysis (HBD-BA) performed ring-opening polymerization (ROP) of cyclic esters in solution at room temperature. The HBD-BA strategy using thiophosphoric triamide (TPTA) binding with methanesulfonic acid (MSA) enabled the ROP of l-lactide (LA) to polylactide (PLA) with predicted molecular weights (Mn = 2.9-13.8 kDa) and low dispersities (D = 1.18-1.22). Associations of TPTA with MSA through triple hydrogen bonds stabilized the sulfonate anion and enhanced the catalytic performance of TPTA-MSA. Homopolymers of LA, trimethylene carbonate (TMC), δ-valerolactone, and ε-caprolactone (CL), and diblock copolymers PLA-b-PTMC and PLA-b-PCL with predicted Mn and narrow D were synthesized. NMR measurements, kinetics investigations, and chain extension experiments indicated that the TPTA-MSA catalyzed ROPs were controlled/living in nature. This is the first Br{\o}nsted acidic catalysis platform workable in all of the three major types of cyclic ester monomers including lactides, cyclic carbonates, and lactones.",

author = "Xiaopei Li and Qiguo Zhang and Zhenjiang Li and Songquan Xu and Chengxu Zhao and Cheng Chen and Xu Zhi and Huiying Wang and Ning Zhu and Kai Guo",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

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doi = "10.1039/c5py01931a",

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T1 - Tripodal hydrogen bond donor binding with sulfonic acid enables ring-opening polymerization

AU - Li, Xiaopei

AU - Zhang, Qiguo

AU - Li, Zhenjiang

AU - Xu, Songquan

AU - Zhao, Chengxu

AU - Chen, Cheng

AU - Zhi, Xu

AU - Wang, Huiying

AU - Zhu, Ning

AU - Guo, Kai

PY - 2016/2/21

Y1 - 2016/2/21

N2 - H-bond donor (HBD) and Brønsted acid (BA) co-catalysis (HBD-BA) performed ring-opening polymerization (ROP) of cyclic esters in solution at room temperature. The HBD-BA strategy using thiophosphoric triamide (TPTA) binding with methanesulfonic acid (MSA) enabled the ROP of l-lactide (LA) to polylactide (PLA) with predicted molecular weights (Mn = 2.9-13.8 kDa) and low dispersities (D = 1.18-1.22). Associations of TPTA with MSA through triple hydrogen bonds stabilized the sulfonate anion and enhanced the catalytic performance of TPTA-MSA. Homopolymers of LA, trimethylene carbonate (TMC), δ-valerolactone, and ε-caprolactone (CL), and diblock copolymers PLA-b-PTMC and PLA-b-PCL with predicted Mn and narrow D were synthesized. NMR measurements, kinetics investigations, and chain extension experiments indicated that the TPTA-MSA catalyzed ROPs were controlled/living in nature. This is the first Brønsted acidic catalysis platform workable in all of the three major types of cyclic ester monomers including lactides, cyclic carbonates, and lactones.

AB - H-bond donor (HBD) and Brønsted acid (BA) co-catalysis (HBD-BA) performed ring-opening polymerization (ROP) of cyclic esters in solution at room temperature. The HBD-BA strategy using thiophosphoric triamide (TPTA) binding with methanesulfonic acid (MSA) enabled the ROP of l-lactide (LA) to polylactide (PLA) with predicted molecular weights (Mn = 2.9-13.8 kDa) and low dispersities (D = 1.18-1.22). Associations of TPTA with MSA through triple hydrogen bonds stabilized the sulfonate anion and enhanced the catalytic performance of TPTA-MSA. Homopolymers of LA, trimethylene carbonate (TMC), δ-valerolactone, and ε-caprolactone (CL), and diblock copolymers PLA-b-PTMC and PLA-b-PCL with predicted Mn and narrow D were synthesized. NMR measurements, kinetics investigations, and chain extension experiments indicated that the TPTA-MSA catalyzed ROPs were controlled/living in nature. This is the first Brønsted acidic catalysis platform workable in all of the three major types of cyclic ester monomers including lactides, cyclic carbonates, and lactones.

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U2 - 10.1039/c5py01931a

DO - 10.1039/c5py01931a

M3 - 文章

AN - SCOPUS:84957970500

SN - 1759-9954

VL - 7

SP - 1368

EP - 1374

JO - Polymer Chemistry

JF - Polymer Chemistry

IS - 7

ER -

Tripodal hydrogen bond donor binding with sulfonic acid enables ring-opening polymerization

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