Gutenberg Open Science: End group functionality of 95–99% : epoxide functionalization of polystyryl-lithium evaluated via solvent gradient interaction chromatography

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-8698

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DC Field	Value	Language
dc.contributor.author	Dreier, Philip	-
dc.contributor.author	Ahn, Junyoung	-
dc.contributor.author	Chang, Taihyun	-
dc.contributor.author	Frey, Holger	-
dc.date.accessioned	2023-01-30T09:06:29Z	-
dc.date.available	2023-01-30T09:06:29Z	-
dc.date.issued	2022	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/8714	-
dc.description.abstract	End group functionality is a key parameter of functional polymer chains. The end-capping efficiency of living polystyryl lithium with various epoxides, namely ethylene oxide (EO), ethoxy ethyl glycidyl ether (EEGE) and isopropylidene glyceryl glycidyl ether (IGG), is investigated with solvent gradient interaction chromatography (SGIC). Generally, end-capping efficiencies >95% are observed. Hydroxy functional polystyrene (PS–OH, PS–EEGE–OH, and PS–IGG–OH) with molar masses ranging from 13.8 to 15.0 kg mol−1 are obtained, with dispersities of 1.05–1.06. Deprotection of the acetal (PS–EEGE–OH) and ketal protective group (PS–IGG–OH) is investigated. Nearly quantitative deprotection (>99%) resulting in the corresponding multihydroxy functional PS (PS–(OH)2 and PS–(OH)3) are observed via SGIC. Esterification of PS–OH with succinic anhydride shows a conversion of 98% to the corresponding ester. A detailed picture of side reactions during the carbanionic polymer synthesis subsequent epoxide termination is obtained, demonstrating 95–99% terminal functionality. Depending on the polarity of the end group, an elution order of PS–OH < PS–(OH)2 < PS–(OH)3 < PS–COOH is obtained in SGIC. The study demonstrates both the analytical power of SGIC and the exceptionally high terminal functionalization efficiency of anionic polymerization methods.	en_GB
dc.description.sponsorship	Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - Projektnummer 491381577	de
dc.language.iso	eng	de
dc.rights	CC BY	*
dc.rights.uri	https://creativecommons.org/licenses/by/4.0/	*
dc.subject.ddc	540 Chemie	de_DE
dc.subject.ddc	540 Chemistry and allied sciences	en_GB
dc.title	End group functionality of 95–99% : epoxide functionalization of polystyryl-lithium evaluated via solvent gradient interaction chromatography	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-8698	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 09 Chemie, Pharmazie u. Geowissensch.	de
jgu.organisation.number	7950	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	Macromolecular rapid communications	de
jgu.journal.volume	43	de
jgu.journal.issue	23	de
jgu.pages.alternative	2200560	de
jgu.publisher.year	2022	-
jgu.publisher.name	Wiley-VCH	de
jgu.publisher.place	Weinheim	-
jgu.publisher.issn	1521-3927	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	540	de
jgu.publisher.doi	10.1002/marc.202200560	de
jgu.organisation.ror	https://ror.org/023b0x485	-
jgu.subject.dfg	Naturwissenschaften	de
Appears in collections:	DFG-491381577-H

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