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    Organocatalysis by hydrogen-bonding: a new approach to controlled/living polymerization of α-amino acid N-carboxyanhydrides

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    Type
    Article
    Authors
    Zhao, Wei cc
    Gnanou, Yves cc
    Hadjichristidis, Nikos cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Polymer Synthesis Laboratory
    Date
    2015
    Permanent link to this record
    http://hdl.handle.net/10754/594074
    
    Metadata
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    Abstract
    A new method, based on hydrogen-bonding organocatalysis, was developed to achieve living ring-opening polymerization of N-carboxyanhydride of α-amino acids using aminoalcohols as initiators in the presence of N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea (TU-S). The thiourea provides, through hydrogen bonding, simultaneous activation of NCA monomers/reversible deactivation of polymer chain-ends/silencing of the tertiary amine and thus allows the polymerization to proceed in a highly controllable mode. For example, by using N,N-dimethyl ethanolamine (DMEA), as an initiator in the presence of TU-S, a series of well-defined linear polypeptides with differently designed Mns (3.01 × 104-18.10 × 104) and low PDI values (1.02-1.05) were successfully synthesized. This general strategy was also extended to the synthesis of well-defined di- and multi-armed polypeptides by using di-, tri-, or tetra-aminoalcohol initiators (methyldiethanolamine (MDEA), triethanolamine (TEA) or N,N,N′,N′-tetrakis(2-hydroxyethyl)ethylenediamine (THEED)) in the presence of TU-S. © The Royal Society of Chemistry 2015.
    Citation
    Zhao W, Gnanou Y, Hadjichristidis N (2015) Organocatalysis by hydrogen-bonding: a new approach to controlled/living polymerization of α-amino acid N-carboxyanhydrides. Polym Chem 6: 6193–6201. Available: http://dx.doi.org/10.1039/c5py00874c.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Polymer Chemistry
    DOI
    10.1039/c5py00874c
    ae974a485f413a2113503eed53cd6c53
    10.1039/c5py00874c
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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