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Novel Core-Expanded Rylenebis(dicarboximide) Dyes Bearing Pentacene Units: Facile Synthesis and Photophysical Properties

Novel Core-Expanded Rylenebis(dicarboximide) Dyes Bearing Pentacene Units: Facile Synthesis and Photophysical Properties

Yuri Avlasevich, Sibylle Müller, Peter Erk, Klaus Müllen

Chemistry. 2007;13(23):6555-61.

PMID: 17614307

Abstract:

Two synthetic routes for the benzannulation in the "bay"-region of rylenebis(dicarboximide)s leading to new pi-system-expanded chromophores are described. The first route follows a two-step approach: Suzuki coupling of bromo-substituted perylenebis(dicarboximide) with 2-bromophenylboronic acid, followed by palladium-catalysed dehydrobromination. The second route is best described as a palladium-assisted cycloaddition of benzyne, formed in situ, to the bay-region of the bromo-substituted rylene core. Two new types of core-expanded rylene dyes were synthesised: yellow dibenzocoronenebis(dicarboximide)s, absorbing at 490 nm, and a green dinaphthoquaterrylenebis(dicarboximide), which absorbs at 700 nm. These new chromophores are characterised by significant hypsochromic shifts of absorption, compared to their parent rylenebis(dicarboximide)s, excellent photostabilities and high fluorescence quantum yields.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP244205401	2-Bromophenylboronic acid		244205-40-1	Price

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