Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies

The potential of poly(2-hydroxyethyl methacrylate)-random-poly(2-chloroethyl methacrylate)-block-poly(N-isopropylacryl-amide) (PHEMA-r-PCEMA-b-PNIPAM) for biological purpose was investigated. In this study, the synthetic strategies to prepare this copolymer were developed. Initially, PHEMA and PNIPA...

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Main Author: Sailan, Nurul Ashikin
Format: Thesis
Language:English
Published: 2019
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Online Access:http://eprints.utm.my/id/eprint/102073/1/NurulAshikinSailanMFS2019.pdf
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spelling my.utm.1020732023-07-31T07:48:32Z http://eprints.utm.my/id/eprint/102073/ Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies Sailan, Nurul Ashikin QD Chemistry The potential of poly(2-hydroxyethyl methacrylate)-random-poly(2-chloroethyl methacrylate)-block-poly(N-isopropylacryl-amide) (PHEMA-r-PCEMA-b-PNIPAM) for biological purpose was investigated. In this study, the synthetic strategies to prepare this copolymer were developed. Initially, PHEMA and PNIPAM were synthesized via reversible addition-fragmentation chain transfer (RAFT) radical polymerization to obtain a controlled molecular weight of the polymer. 4-Cyanopentanoic acid dithiobenzoate (CPADB) and 4,4’-azobis(4-cyanopentanoic acid) (ACPA) were chosen as the RAFT agent and initiator due to its compatibility with both monomers. In order to replace hydroxyl group (-OH) in PHEMA macroRAFT with chlorine (-Cl), thionyl chloride (SOCl2) was used as chlorinating agent and copolymer of PHEMA-r-PCEMA was successfully synthesized. The targeted copolymer, PHEMA-r-PCEMA-b-PNIPAM, was successfully synthesized by polymerizing PHEMA-r-PCEMA with N-isopropylacrylamide (NIPAM) monomer. The change of lower critical solution temperature (LCST) points for PNIPAM macroRAFT, PHEMA-b-PNIPAM and PHEMA-r-PCEMA-b-PNIPAM were observed. A decreasing trend of temperature was spotted as the copolymer hydrophobicity in aqueous solution was increased. Both PHEMA-r-PCEMA and PHEMA-r-PCEMA-b-PNIPAM were reacted with thiolglycerol to form a thioester via thiol-halogen SN2 nucleophilic substitution. PHEMA-r-PCEMA-b-PNIPAM potential as protein- polymer modification material was investigated by reacting PHEMA-r-PCEMA-b-PNIPAM with cysteine. Based on the 1H NMR result, chlorine (-Cl) was successfully substituted with cysteine. Thus, PHEMA-r-PCEMA-b-PNIPAM can potentially be used for biological applications. 2019 Thesis NonPeerReviewed application/pdf en http://eprints.utm.my/id/eprint/102073/1/NurulAshikinSailanMFS2019.pdf Sailan, Nurul Ashikin (2019) Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies. Masters thesis, Universiti Teknologi Malaysia, Faculty of Science. http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:145884
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Sailan, Nurul Ashikin
Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
description The potential of poly(2-hydroxyethyl methacrylate)-random-poly(2-chloroethyl methacrylate)-block-poly(N-isopropylacryl-amide) (PHEMA-r-PCEMA-b-PNIPAM) for biological purpose was investigated. In this study, the synthetic strategies to prepare this copolymer were developed. Initially, PHEMA and PNIPAM were synthesized via reversible addition-fragmentation chain transfer (RAFT) radical polymerization to obtain a controlled molecular weight of the polymer. 4-Cyanopentanoic acid dithiobenzoate (CPADB) and 4,4’-azobis(4-cyanopentanoic acid) (ACPA) were chosen as the RAFT agent and initiator due to its compatibility with both monomers. In order to replace hydroxyl group (-OH) in PHEMA macroRAFT with chlorine (-Cl), thionyl chloride (SOCl2) was used as chlorinating agent and copolymer of PHEMA-r-PCEMA was successfully synthesized. The targeted copolymer, PHEMA-r-PCEMA-b-PNIPAM, was successfully synthesized by polymerizing PHEMA-r-PCEMA with N-isopropylacrylamide (NIPAM) monomer. The change of lower critical solution temperature (LCST) points for PNIPAM macroRAFT, PHEMA-b-PNIPAM and PHEMA-r-PCEMA-b-PNIPAM were observed. A decreasing trend of temperature was spotted as the copolymer hydrophobicity in aqueous solution was increased. Both PHEMA-r-PCEMA and PHEMA-r-PCEMA-b-PNIPAM were reacted with thiolglycerol to form a thioester via thiol-halogen SN2 nucleophilic substitution. PHEMA-r-PCEMA-b-PNIPAM potential as protein- polymer modification material was investigated by reacting PHEMA-r-PCEMA-b-PNIPAM with cysteine. Based on the 1H NMR result, chlorine (-Cl) was successfully substituted with cysteine. Thus, PHEMA-r-PCEMA-b-PNIPAM can potentially be used for biological applications.
format Thesis
author Sailan, Nurul Ashikin
author_facet Sailan, Nurul Ashikin
author_sort Sailan, Nurul Ashikin
title Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
title_short Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
title_full Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
title_fullStr Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
title_full_unstemmed Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
title_sort synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies
publishDate 2019
url http://eprints.utm.my/id/eprint/102073/1/NurulAshikinSailanMFS2019.pdf
http://eprints.utm.my/id/eprint/102073/
http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:145884
_version_ 1773543500864815104
score 13.209306