Stabilizing Pentacene By Cyclopentannulation.

Bheemireddy SR; Ubaldo PC; Rose PW; Finke AD; Zhuang J; Wang L; Plunkett KN

doi:10.1002/anie.201508650

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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

polycyclic aromatic hydrocarbons

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).

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