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Novel Core‐Expanded Rylenebis(Dicarboximide) Dyes Bearing Pentacene Units: Facile Synthesis and Photophysical Properties
Author(s) -
Avlasevich Yuri,
Müller Sibylle,
Erk Peter,
Müllen Klaus
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700523
Subject(s) - chromophore , photochemistry , aryne , hypsochromic shift , fluorescence , palladium , cycloaddition , chemistry , solvatochromism , absorption (acoustics) , materials science , solvent , organic chemistry , catalysis , optics , composite material , physics
Two synthetic routes for the benzannulation in the “bay”‐region of rylenebis(dicarboximide)s leading to new π‐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.