Stabilizing Pentacene By Cyclopentannulation

A new class of stabilized pentacene derivatives with externally fused five‐membered rings are prepared by means of a key palladium‐catalyzed cyclopentannulation step. The target compounds are synthesized by chemical manipulation of a partially saturated 6,13‐dibromopentacene precursor that can be fu...

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Bibliographic Details
Published in:Angewandte Chemie 2015-12, Vol.127 (52), p.15988-15992
Main Authors: Bheemireddy, Sambasiva R., Ubaldo, Pamela C., Rose, Peter W., Finke, Aaron D., Zhuang, Junpeng, Wang, Lichang, Plunkett, Kyle N.
Format: Article
Language:English
Subjects:
Acene
Benzoquinone
Chemical compounds
Chemical reactions
Chemical synthesis
Chemistry
Dehydrogenation
Derivatives
Energy gap
Konjugation
Molecular orbitals
Organische Elektronik
Palladium
Pentacene
Photodegradation
Polycyclische aromatische Kohlenwasserstoffe
Precursors
Water treatment
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Summary:A new class of stabilized pentacene derivatives with externally fused five‐membered rings are prepared by means of a key palladium‐catalyzed cyclopentannulation step. The target compounds are synthesized by chemical manipulation of a partially saturated 6,13‐dibromopentacene precursor that can be fully aromatized in a final step through a DDQ‐mediated dehydrogenation reaction (DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone). The new 1,2,8,9‐tetraaryldicyclopenta[fg,qr]pentacene derivatives have narrow energy gaps of circa 1.2 eV and behave as strong electron acceptors with lowest unoccupied molecular orbital energies between −3.81 and −3.90 eV. Photodegradation studies reveal the new compounds are more photostable than 6,13‐bis(triisopropylsilylethynyl)pentacene (TIPS‐pentacene). Fünferreihe: Eine palladiumkatalysierte Cyclopentanellierung mit anschließender DDQ‐vermittelter Dehydrierung überführt partiell hydrierte Pentacen‐ Vorstufen in stabilisierte Pentacene. Die Produkte sind hervorragende Elektronenakzeptoren mit kleinen Energielücken.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201508650