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...

Full description

Saved in:

Bibliographic Details
Main Author:	Sailan, Nurul Ashikin
Format:	Thesis
Language:	English
Published:	2019
Subjects:	QD Chemistry
Online Access:	http://eprints.utm.my/id/eprint/102073/1/NurulAshikinSailanMFS2019.pdf
Tags:	Add Tag No Tags, Be the first to tag this record!

id	my-utm-ep.102073
record_format	uketd_dc
spelling	my-utm-ep.1020732023-07-31T07:48:32Z Synthesis of methacrylate- acrylamide based copolymer via reverse addition-fragmentation chain transfer polymerization with thiol- conjugation and thermoresponsive studies 2019 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 http://eprints.utm.my/id/eprint/102073/ http://eprints.utm.my/id/eprint/102073/1/NurulAshikinSailanMFS2019.pdf application/pdf en public http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:145884 masters Universiti Teknologi Malaysia, Faculty of Science Faculty of Science
institution	Universiti Teknologi Malaysia
collection	UTM Institutional Repository
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
qualification_level	Master's degree
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
granting_institution	Universiti Teknologi Malaysia, Faculty of Science
granting_department	Faculty of Science
publishDate	2019
url	http://eprints.utm.my/id/eprint/102073/1/NurulAshikinSailanMFS2019.pdf
_version_	1776100839309443072

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

Similar Items