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One-pot Two Polymers: ABB′ Melt Polycondensation For Linear Polyesters And Hyperbranched Poly(ester-urethane)s Based On Natural L -amino Acids

Rajendra Aluri, M. Jayakannan
Published 2015 · Chemistry

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We report a novel one-pot ABB′ synthetic route for linear polyester and hyperbranched poly(ester-urethane)s based on multi-functional L-amino acid monomers via a temperature selective melt polycondensation approach. L-Serine, D-serine and L-threonine amino acids were converted into multi-functional ABB′ monomers (A = hydroxyl, B = carboxylic ester and B′ = urethane). At 120 °C, the ABB′ monomer underwent thermo-selective transesterification polycondensation (A reacted with B) to produce linear polyesters with B′ functionality as the pendent functionality in each repeating units. At 150 °C, the ABB′ monomer underwent dual ester-urethane self-polycondensation to produce new classes of hyperbranched poly(ester-urethane)s (A reacted with B and B′). Interestingly, the secondary hydroxyl group in the L-threonine monomer did not react at 120 °C; however, it became active at 150 °C to yield exclusively linear polyesters. The temperature selective polycondensation process was confirmed by appropriate model reactions and 1H and 13C NMR spectroscopic analysis. The role of the macrocyclic formation in the polycondensation process was also investigated by MALDI-TOF MS. The amino acid based new polymers were found to exhibit diverse molecular self-assembly. The linear polyesters adopted a β-sheet conformation which produced a helical nano-fibrous morphology. The hyperbranched polymers underwent a globular coil-like conformation for spherical nano-particular assemblies. Both the secondary structure formation as well as their morphological features were confirmed by circular dichroism spectroscopy and electron and atomic microscopy analyses. The new one-pot synthetic pathway is versatile in making diverse linear and branched polymers based on natural L-amino acids with a nano-fibrous or a spherical morphology for future applications in biomedical and thermoplastic industries.
This paper references
10.1016/J.POLYMER.2011.11.016
Synthesis of novel hyperbranched poly(ester-amide)s based on acidic and basic amino acids via “AD + CBB′” couple-monomer approach
Youmei Bao (2012)
10.1039/B312826A
Synthesis of new thermotropic liquid crystalline polyurethanes containing biphenyl mesogens using a novel AB-type self-polycondensation.
T. Ranganathan (2004)
10.1039/B005552M
A novel hyperbranched polyether by melt transetherification
M. Jayakannan (2000)
10.1021/MA2004663
Hyperbranched Polyacetals with Tunable Degradation Rates
S. Chatterjee (2011)
10.1039/c2cs35130g
Biocompatible or biodegradable hyperbranched polymers: from self-assembly to cytomimetic applications.
Haibao Jin (2012)
10.1002/1521-3927(20011201)22:18<1463::AID-MARC1463>3.0.CO;2-F
Recent Developments in Polyether Synthesis
M. Jayakannan (2001)
10.1039/c1cc13443d
Novel application of a Fe-Zn double-metal cyanide catalyst in the synthesis of biodegradable, hyperbranched polymers.
J. Sebastian (2011)
10.1021/bm301489s
pH-triggered aggregate shape of different generations lysine-dendronized maleimide copolymers with maltose shell.
S. Boye (2012)
10.1021/bm501903t
Amyloid-like hierarchical helical fibrils and conformational reversibility in functional polyesters based on L-amino acids.
S. Anantharaj (2015)
10.1002/ACTP.1997.010480105
Degree of branching in hyperbranched polymers
Dirk Holter (1997)
10.1002/POLA.10527
SEC-MALDI-TOF mass spectral characterization of a hyperbranched polyether prepared via melt transetherification
M. Jayakannan (2002)
10.1002/POLA.22578
Solvent‐free and nonisocyanate melt transurethane reaction for aliphatic polyurethanes and mechanistic aspects
P. Deepa (2008)
10.1002/POLA.22295
The thermal polymerization of amino acids revisited; Synthesis and structural characterization of hyperbranched polymers from L‐lysine
M. Scholl (2007)
10.1039/c5cc00644a
One-pot synthesis of doxorubicin-loaded multiresponsive nanogels based on hyperbranched polyglycerol.
Ana Sousa-Herves (2015)
10.1021/MA070494L
Controlling polymer architecture in the thermal hyperbranched polymerization of L-lysine
M. Scholl (2007)
10.1002/POLA.24340
Synthesis of novel hyperbranched poly(ester‐amide)s based on neutral α‐amino acids via “AD + CBB′” couple‐monomer approach
Youmei Bao (2010)
10.1016/J.POLYMER.2012.12.040
Fabrication of gold nanoparticles through autoreduction of chloroaurate ions by thermo- and pH-responsive amino acid-based star-shaped copolymers
Youmei Bao (2013)
10.1021/JA00012A030
One-step synthesis of hyperbranched dendritic polyesters
C. Hawker (1991)
10.1021/MA0489218
Synthesis of water soluble hyperbranched polyurethanes using selective activation of AB2 monomers
S. Rannard (2004)
10.1039/c3cc45101a
A Pd-diimine catalytic inimer for synthesis of polyethylenes of hyperbranched-on-hyperbranched and star architectures.
Li-xin Xu (2013)
10.1021/MA900946P
Single Step Synthesis of Peripherally “Clickable” Hyperbranched Polyethers
Animesh Saha (2009)
10.1039/b814560c
Supramolecular self-assembly of amphiphilic hyperbranched polymers at all scales and dimensions: progress, characteristics and perspectives.
Y. Zhou (2009)
10.1016/J.PROGPOLYMSCI.2008.09.001
Dendritic and hyperbranched polyamides
M. Scholl (2009)
10.1016/J.EURPOLYMJ.2004.02.007
Synthesis and applications of hyperbranched polymers
C. R. Yates (2004)
10.1039/c2cc30239j
Thiol-promoted catalytic synthesis of diphenolic acid with sulfonated hyperbranched poly(arylene oxindole)s.
S. Van de Vyver (2012)
10.1021/bm900724c
Bioreducible hyperbranched poly(amido amine)s for gene delivery.
J. Chen (2009)
10.1021/bm300697h
Polymers from amino acids: development of dual ester-urethane melt condensation approach and mechanistic aspects.
S. Anantharaj (2012)
10.1016/J.PROGPOLYMSCI.2003.12.002
Hyperbranched polymers: from synthesis to applications
C. Gao (2004)
10.1039/c0cc04096g
Clickable polyglycerol hyperbranched polymers and their application to gold nanoparticles and acid-labile nanocarriers.
Andrew T. Zill (2011)
10.1021/MA0301348
Cyclic Polycarbonates by Polycondensation of Bisphenol A with Triphosgene
H. Kricheldorf (2004)
10.1021/BM700491Q
Poly(acrylic acid)-block-poly(L-valine): evaluation of beta-sheet formation and its stability using circular dichroism technique.
A. Sinaga (2007)
10.1002/POLA.22058
Solvent‐induced self‐organization approach for polymeric architectures of micropores, hexagons and spheres based on polyurethanes prepared via novel melt transurethane methodology
P. Deepa (2007)



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