Journal article
Stabilizing Pentacene By Cyclopentannulation.
- Bheemireddy SR Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA).
- Ubaldo PC Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA).
- Rose PW Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA).
- Finke AD Swiss Light Source, Paul Scherrer Institute, Villigen PSI (Switzerland).
- Zhuang J Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA).
- Wang L Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA).
- Plunkett KN Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University, Carbondale, IL 62901 (USA). kplunkett@chem.siu.edu.
- 2016-01-16
Published in:
- Angewandte Chemie (International ed. in English). - 2015
English
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).
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/anie.201508650
- PMID 26768696
- Persistent URL
- https://sonar.ch/global/documents/13353
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