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Title: Amidine-Mediated Zwitterionic Ring-Opening Polymerization of N-Alkyl N-Carboxyanhydride: Mechanism, Kinetics, and Architecture Elucidation

Abstract

Zwitterionic ring-opening polymerization (ZROP) of N-butyl N-carboxyanhydrides (Bu-NCAs) has been investigated using 1,8-diazabicycloundec-7-ene (DBU), a bicyclic amidine initiator. It was found that poly(N-butylglycine)s (PNBGs) with molecular weight (Mn) in the 3.5–32.4 kg mol–1 range and polydispersity index (PDI) in the 1.02–1.12 range can be readily obtained by systematically varying the initial monomer to initiator feed ratio. The polymerization exhibits characteristics of a controlled polymerization, as evidenced by the linear increase of polymer molecular weight with conversion and the successful enchainment experiments. Kinetic studies revealed that the reaction is first-order dependent on the monomer and the DBU concentration. The rate of initiation is comparable to that of the propagation. Random copolypeptoids of poly[(N-propargylglycine)-r-(N-butylglycine)]s [P(NPgG-r-NBG)s] were also synthesized by DBU-mediated copolymerization of Bu-NCA and N-propargyl N-carboxyanhydride (Pg-NCA). Subsequent grafting with azido-terminated poly(ethylene glycol) (PEG) produces bottlebrush copolymers. Analysis of bottlebrush copolymer samples using atomic force microscopy (AFM) revealed a surface morphology of toroid-shaped nanostructures, consistent with the polypeptoid backbone having cyclic architecture. Here, small-angle neutron scattering (SANS) characterization of the bottlebrush polymer ensemble in solution also confirms the cyclic architecture of the polypeptoid backbones.

Authors:
 [1];  [1];  [1];  [2];  [2];  [1];  [1]
+ Show Author Affiliations
  1. Louisiana State University, Baton Rouge, LA (United States)
  2. Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Louisiana State Univ., Baton Rouge, LA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
OSTI Identifier:
1672151
Grant/Contract Number:  
SC0012432; CHE 0955820
Resource Type:
Accepted Manuscript
Journal Name:
Macromolecules
Additional Journal Information:
Journal Volume: 49; Journal Issue: 4; Journal ID: ISSN 0024-9297
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; Chemical structure; Living polymerization; Monomers; Polymerization; Polymers

Citation Formats

Li, Ang, Lu, Lu, Li, Xin, He, LiLin, Do, Changwoo, Garno, Jayne C., and Zhang, Donghui. Amidine-Mediated Zwitterionic Ring-Opening Polymerization of N-Alkyl N-Carboxyanhydride: Mechanism, Kinetics, and Architecture Elucidation. United States: N. p., 2016. Web. doi:10.1021/acs.macromol.5b02611.
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Li, Ang, Lu, Lu, Li, Xin, He, LiLin, Do, Changwoo, Garno, Jayne C., & Zhang, Donghui. Amidine-Mediated Zwitterionic Ring-Opening Polymerization of N-Alkyl N-Carboxyanhydride: Mechanism, Kinetics, and Architecture Elucidation. United States. https://doi.org/10.1021/acs.macromol.5b02611
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Li, Ang, Lu, Lu, Li, Xin, He, LiLin, Do, Changwoo, Garno, Jayne C., and Zhang, Donghui. Fri . "Amidine-Mediated Zwitterionic Ring-Opening Polymerization of N-Alkyl N-Carboxyanhydride: Mechanism, Kinetics, and Architecture Elucidation". United States. https://doi.org/10.1021/acs.macromol.5b02611. https://www.osti.gov/servlets/purl/1672151.
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@article{osti_1672151,
title = {Amidine-Mediated Zwitterionic Ring-Opening Polymerization of N-Alkyl N-Carboxyanhydride: Mechanism, Kinetics, and Architecture Elucidation},
author = {Li, Ang and Lu, Lu and Li, Xin and He, LiLin and Do, Changwoo and Garno, Jayne C. and Zhang, Donghui},
abstractNote = {Zwitterionic ring-opening polymerization (ZROP) of N-butyl N-carboxyanhydrides (Bu-NCAs) has been investigated using 1,8-diazabicycloundec-7-ene (DBU), a bicyclic amidine initiator. It was found that poly(N-butylglycine)s (PNBGs) with molecular weight (Mn) in the 3.5–32.4 kg mol–1 range and polydispersity index (PDI) in the 1.02–1.12 range can be readily obtained by systematically varying the initial monomer to initiator feed ratio. The polymerization exhibits characteristics of a controlled polymerization, as evidenced by the linear increase of polymer molecular weight with conversion and the successful enchainment experiments. Kinetic studies revealed that the reaction is first-order dependent on the monomer and the DBU concentration. The rate of initiation is comparable to that of the propagation. Random copolypeptoids of poly[(N-propargylglycine)-r-(N-butylglycine)]s [P(NPgG-r-NBG)s] were also synthesized by DBU-mediated copolymerization of Bu-NCA and N-propargyl N-carboxyanhydride (Pg-NCA). Subsequent grafting with azido-terminated poly(ethylene glycol) (PEG) produces bottlebrush copolymers. Analysis of bottlebrush copolymer samples using atomic force microscopy (AFM) revealed a surface morphology of toroid-shaped nanostructures, consistent with the polypeptoid backbone having cyclic architecture. Here, small-angle neutron scattering (SANS) characterization of the bottlebrush polymer ensemble in solution also confirms the cyclic architecture of the polypeptoid backbones.},
doi = {10.1021/acs.macromol.5b02611},
journal = {Macromolecules},
number = 4,
volume = 49,
place = {United States},
year = {Fri Feb 05 00:00:00 EST 2016},
month = {Fri Feb 05 00:00:00 EST 2016}
}
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Journal Article:
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https://doi.org/10.1021/acs.macromol.5b02611
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Figures / Tables:

Scheme 1 Scheme 1: MALDI-TOF MS analysis of a low molecular weight polymer revealed the dominant presence of molecular ions that are consistent with the structures of cyclic PNBG polymers bearing one DBU moiety (a, b, c and h, Figure S2) and the cyclic zwitterionic PNBG species bearing one DBU moiety andmore » one carbamate end-group (d and e, Figure S2)« less
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