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Diels-Alder Additions to 2,2’-Biaceanthrylene

preprint
submitted on 24.04.2021, 20:40 and posted on 28.04.2021, 04:46 by Yachu Du, Kyle Plunkett
A series of Diels-Alder reactions between the diene 2,2’-biaceanthylene and several dienophiles is presented. The diene is a cyclopenta-fused polycyclic aromatic hydrocarbon with anthracene units linked by two cyclopentene rings. Depending on the dienophile, the major product was the result of a single addition (dimethyl acetylenedicarboxylate) or double addition (quinone, benzyne) to the diene. Single crystal X-ray analysis of the quinone-derivative shows a propeller-like structure composed of mixed enantiomers. The synthesis and photophysical properties of these compounds is presented.

Funding

CAREER: Electron Acceptor Materials Based on Cyclopenta-fused Polycyclic Aromatic Hydrocarbons

Directorate for Mathematical & Physical Sciences

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History

Email Address of Submitting Author

kplunkett@chem.siu.edu

Institution

Southern Illinois University

Country

United States of America

ORCID For Submitting Author

0000-0002-5691-7876

Declaration of Conflict of Interest

None

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