Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization

Conjugated polymers, with excellent optical and electrical properties, have appeared as promising operative materials for a diverse range of applications. Donor-Acceptor (D-A) framework, which copolymerizes electron-donors and electron- acceptors alternatively in conjugated backbones, has proven to...

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Main Author:	Wong, Xin Lin
Format:	Thesis
Language:	English English
Published:	2020
Subjects:	QD241-441 Organic chemistry
Online Access:	https://eprints.ums.edu.my/id/eprint/40565/1/24%20PAGES.pdf https://eprints.ums.edu.my/id/eprint/40565/2/FULLTEXT.pdf
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spelling	my-ums-ep.405652024-09-30T04:33:22Z Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization 2020 Wong, Xin Lin QD241-441 Organic chemistry Conjugated polymers, with excellent optical and electrical properties, have appeared as promising operative materials for a diverse range of applications. Donor-Acceptor (D-A) framework, which copolymerizes electron-donors and electron- acceptors alternatively in conjugated backbones, has proven to be the most effective strategy for obtaining low bandgap polymers that desirable for optoelectronic applications. The synthesis of conjugated polymers is primarily relied on conventional cross-couplings, in particularly, Suzuki and Stille couplings, which involve the use of costly toxic organometallic reagents for monomers’ functionalization. Despite robust and effective, these protocols produce stoichiometric quantities of toxic byproducts. Direct arylation polymerization (DArP) is a newly established synthetic strategy that provides a clean and low cost pathway towards conjugated polymers. It allows direct coupling of aryl halides and aromatic compounds without preactivation of Carbon-Hydrogen (C-H) bonds. In this research, an alternating D-A type copolymer based on N-9-hexadecyl-2,7-dibromocarbazole and 4,7-di(2-thienyl)benzothiadiazole was synthesized by DArP. This structure is modified from the classical low bandgap copolymer poly[N-9’-heptadecanyl-2,7-carbazole-alt -5,5-(4’,7’-di-2-thienyl-2’,1’,3’-benzothiadiazole)] (PCDTBT) which exhibited excellent devices performance. One-pot DArP reaction was carried out under phosphine-free condition with palladium (II) acetate as the catalyst, pivalic acid as the additive, and potassium carbonates as the base. The resulting copolymer, poly[(9-hexadecyl-2,7-carabzole-alt-4,7-di(2-thienyl)-2,1,3-benzothiadiazole)] (P1) was obtained in 44%. It showed good solubility in organic solvents and has been satisfactorily characterized by FTIR and NMR. UV-Vis absorption spectra show the presence of inter-chain interaction and aggregation in the solid state. The optical bandgap of the copolymer was found to be in between 1.77 – 1.81 eV, which is slightly lower than that of the PCDTBT (1.88 eV). 2020 Thesis https://eprints.ums.edu.my/id/eprint/40565/ https://eprints.ums.edu.my/id/eprint/40565/1/24%20PAGES.pdf text en public https://eprints.ums.edu.my/id/eprint/40565/2/FULLTEXT.pdf text en validuser masters Universiti Malaysia Sabah Faculty of Science and Natural Resources
institution	Universiti Malaysia Sabah
collection	UMS Institutional Repository
language	English English
topic	QD241-441 Organic chemistry
spellingShingle	QD241-441 Organic chemistry Wong, Xin Lin Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
description	Conjugated polymers, with excellent optical and electrical properties, have appeared as promising operative materials for a diverse range of applications. Donor-Acceptor (D-A) framework, which copolymerizes electron-donors and electron- acceptors alternatively in conjugated backbones, has proven to be the most effective strategy for obtaining low bandgap polymers that desirable for optoelectronic applications. The synthesis of conjugated polymers is primarily relied on conventional cross-couplings, in particularly, Suzuki and Stille couplings, which involve the use of costly toxic organometallic reagents for monomers’ functionalization. Despite robust and effective, these protocols produce stoichiometric quantities of toxic byproducts. Direct arylation polymerization (DArP) is a newly established synthetic strategy that provides a clean and low cost pathway towards conjugated polymers. It allows direct coupling of aryl halides and aromatic compounds without preactivation of Carbon-Hydrogen (C-H) bonds. In this research, an alternating D-A type copolymer based on N-9-hexadecyl-2,7-dibromocarbazole and 4,7-di(2-thienyl)benzothiadiazole was synthesized by DArP. This structure is modified from the classical low bandgap copolymer poly[N-9’-heptadecanyl-2,7-carbazole-alt -5,5-(4’,7’-di-2-thienyl-2’,1’,3’-benzothiadiazole)] (PCDTBT) which exhibited excellent devices performance. One-pot DArP reaction was carried out under phosphine-free condition with palladium (II) acetate as the catalyst, pivalic acid as the additive, and potassium carbonates as the base. The resulting copolymer, poly[(9-hexadecyl-2,7-carabzole-alt-4,7-di(2-thienyl)-2,1,3-benzothiadiazole)] (P1) was obtained in 44%. It showed good solubility in organic solvents and has been satisfactorily characterized by FTIR and NMR. UV-Vis absorption spectra show the presence of inter-chain interaction and aggregation in the solid state. The optical bandgap of the copolymer was found to be in between 1.77 – 1.81 eV, which is slightly lower than that of the PCDTBT (1.88 eV).
format	Thesis
qualification_level	Master's degree
author	Wong, Xin Lin
author_facet	Wong, Xin Lin
author_sort	Wong, Xin Lin
title	Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
title_short	Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
title_full	Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
title_fullStr	Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
title_full_unstemmed	Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
title_sort	synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization
granting_institution	Universiti Malaysia Sabah
granting_department	Faculty of Science and Natural Resources
publishDate	2020
url	https://eprints.ums.edu.my/id/eprint/40565/1/24%20PAGES.pdf https://eprints.ums.edu.my/id/eprint/40565/2/FULLTEXT.pdf
_version_	1811770532340695040

Synthesis and characterization of carbazole-based conjugated polymer via direct arylation polymerization

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