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Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons
Author(s) -
Lütke Eversloh Christian,
Avlasevich Yuri,
Li Chen,
Müllen Klaus
Publication year - 2011
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.201101126
Subject(s) - annulation , anthracene , perylene , palladium , pyrene , catalysis , chemistry , chromophore , absorption (acoustics) , photochemistry , ring (chemistry) , combinatorial chemistry , molecule , organic chemistry , materials science , composite material
Abstract We present a new and versatile one‐step synthesis of a series of small molecular chromophores based on cyclopentannulated polycyclic aromatic hydrocarbons (PAH). Easily available pyrene, anthracene, and perylene bromides serve as starting materials for the reactions. The formation of the five‐membered ring is achieved by the straightforward palladium(0)‐catalyzed carbannulation with various substituted acetylenes. This approach is applicable either to single or multiple annulation procedures leading to hitherto inaccessible PAH topologies. According to the resulting products of the diverse reactions, a mechanistic explanation is proposed. UV/Vis absorption as well as cyclovoltammetric measurements were performed for characterization demonstrating the value of this annulation technique. Optical absorptions of up to 780 nm and absorption coefficients ranging from 8000 to 34 000 M −1 cm −1 were detected.