Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP)
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-nor...
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doaj-45c42ce589da4363b7d080c19087002e2020-11-24T21:34:42ZengMDPI AGMarine Drugs1660-33972017-07-0115722310.3390/md15070223md15070223Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP)Na Li0Huanhuan Wang1Xiaosai Qu2Yu Chen3School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSchool of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSchool of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSchool of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, ChinaROMP 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.https://www.mdpi.com/1660-3397/15/7/223ROMPpoly(norbornene-methylamine)controllableliving polymerizationchitosan |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Na Li Huanhuan Wang Xiaosai Qu Yu Chen |
spellingShingle |
Na Li Huanhuan Wang Xiaosai Qu Yu Chen Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP) Marine Drugs ROMP poly(norbornene-methylamine) controllable living polymerization chitosan |
author_facet |
Na Li Huanhuan Wang Xiaosai Qu Yu Chen |
author_sort |
Na Li |
title |
Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP) |
title_short |
Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP) |
title_full |
Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP) |
title_fullStr |
Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP) |
title_full_unstemmed |
Synthesis of Poly(norbornene-methylamine), a Biomimetic of Chitosan, by Ring-Opening Metathesis Polymerization (ROMP) |
title_sort |
synthesis of poly(norbornene-methylamine), a biomimetic of chitosan, by ring-opening metathesis polymerization (romp) |
publisher |
MDPI AG |
series |
Marine Drugs |
issn |
1660-3397 |
publishDate |
2017-07-01 |
description |
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. |
topic |
ROMP poly(norbornene-methylamine) controllable living polymerization chitosan |
url |
https://www.mdpi.com/1660-3397/15/7/223 |
work_keys_str_mv |
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