NDLI: Introduction of methyl groups on vinylene segments of phenylene vinylene systems: synthesis and properties

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Introduction of methyl groups on vinylene segments of phenylene vinylene systems: synthesis and properties

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Introduction of methyl groups on vinylene segments of phenylene vinylene systems: synthesis and properties

Content Provider	Royal Society of Chemistry (RSC)
Author	Sellinger, Alan Chan, Khai Leok
Copyright Year	2009
Abstract	A facile synthetic route towards phenylene vinylene systems with methyl substituents at the vinyl linkages is demonstrated through palladium catalyzed Heck coupling of 1,4-diisopropenylbenzene with aryl bromides. The coupling leads to a series of model compounds that feature, in some cases, direct access to a trans-configuration at the double bonds. The oxidative stability of these systems is surprisingly unaffected by the presence of allylic C-H bonds in the methyl substituents. The methyl substituents modulate the electronic properties of the phenylene vinylene systems by inducing a significant twist to the conjugated backbone. The study suggests that the introduction of methyl groups at vinylene sites is a viable alternative to functionalising and tuning the properties of phenylene vinylene systems.
Starting Page	3976
Ending Page	3981
Page Count	6
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b909500d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Vinylene group Aryl
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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