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Mar. Drugs 2017, 15(7), 223; doi:10.3390/md15070223

Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP)

School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China
These authors contributed equally to this work.
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Received: 12 June 2017 / Revised: 5 July 2017 / Accepted: 9 July 2017 / Published: 14 July 2017
(This article belongs to the Special Issue Marine Biomimetics)
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Abstract

ROMP is an effective method for preparing functional polymers due to its having characteristics of “living” polymerization and rapid development of catalysts. In the present work, poly(norbornene-methylamine), a mimic of chitosan, was synthesized via ROMP reaction. The amino-protected product, 5-norbornene-2-(N-methyl)-phthalimide, was prepared by a reaction of 5-norbornene-2-methylamine with phthalic anhydride, which was then subjected to the ROMP reaction in the presence of Hoveyda-Grubbs 2nd catalyst to afford poly(norbornene-(N-methyl)-phthalimide). The target product, poly(norbornene-methylamine), was obtained by deprotection reaction of poly(norbornene-(N-methyl)-phthalimide). The products in each step were characterized by FTIR and 1H-NMR, and their thermal stabilities were determined by TG analysis. The effects of molar ratio between monomer ([M]/[I]) and catalyst on the average relative molecular weight ( M n ¯ ) and molecular weight distribution of the produced polymer products were determined by gel permeation chromatography (GPC). It was found that the M n ¯ of poly(norbornene-(N-methyl)-phthalimide) was controllable and exhibited a narrow polydispersity index (PDI) (~1.10). The synthesis condition of 5-norbornene-2-(N-methyl)-phthalimide was optimized by determining the yields at different reaction temperatures and reaction times. The highest yield was obtained at a reaction temperature of 130 °C and a reaction time of 20 min. Our work provides a new strategy to synthesize polymers with controllable structures and free –NH2 groups via ROMP. View Full-Text
Keywords: ROMP; poly(norbornene-methylamine); controllable; living polymerization; chitosan ROMP; poly(norbornene-methylamine); controllable; living polymerization; chitosan
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MDPI and ACS Style

Li, N.; Wang, H.; Qu, X.; Chen, Y. Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP). Mar. Drugs 2017, 15, 223.

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