Pentacenones as Divergent Intermediates to Unsymmetrically Substituted Pentacenes: Synthesis and Crystallographic Analysis.
J Org Chem
; 87(24): 16236-16249, 2022 Dec 16.
Article
em En
| MEDLINE
| ID: mdl-36416781
We report a general method for the desymmetrization of 6,13-pentacenequinone to access ethynylated pentacene ketones, namely, 13-hydroxy-13-(ethynylated)pentacene-6(13H)-ones. These pentacene ketones ("pentacenones") serve as divergent intermediates to unsymmetrically 6,13-disubstituted pentacenes, commonly used for studying singlet fission processes and charge transport phenomena in organic field effect transistors. We report a synthetic method to access pentacenones, which utilizes a precipitation/crystallization from the crude mixture to enable facile purification on a multigram scale. X-ray crystallographic analysis of the pentacenones reveals key noncovalent interactions that contribute to the crystallization, specifically, hydrogen bonding between the ketone and alcohol functional groups as well as π-π-stacking and dipole-dipole interactions.
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MEDLINE
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2022
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Article