Organocatalysis by hydrogen-bonding: a new approach to controlled/living polymerization of α-amino acid N-carboxyanhydrides
KAUST DepartmentKAUST Catalysis Center (KCC)
Physical Sciences and Engineering (PSE) Division
Polymer Synthesis Laboratory
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AbstractA 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.
CitationZhao 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.
PublisherRoyal Society of Chemistry (RSC)