Stabilizing Pentacene By Cyclopentannulation |
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Authors: | Sambasiva R Bheemireddy Dr Pamela C Ubaldo Peter W Rose Dr Aaron D Finke Prof Junpeng Zhuang Prof Lichang Wang Prof Kyle N Plunkett |
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Institution: | 1. Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA);2. Swiss Light Source, Paul Scherrer Institute, Villigen PSI (Switzerland) |
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Abstract: | 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‐tetraaryldicyclopentafg,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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Keywords: | acenes conjugation organic electronics palladium polycyclic aromatic hydrocarbons |
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