Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 52, Pages 15762-15766Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508650
Keywords
acenes; conjugation; organic electronics; palladium; polycyclic aromatic hydrocarbons
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Funding
- National Science Foundation [CHE-1352431]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1352431] Funding Source: National Science Foundation
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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).
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