| Autor: |
Schroeder ZW; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada., McDonald R; X-ray Crystallography Lab, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada., Ferguson MJ; X-ray Crystallography Lab, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada., Chalifoux WA; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada., Tykwinski RR; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada., Lehnherr D; Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada. |
| Abstrakt: |
We report a general method for the desymmetrization of 6,13-pentacenequinone to access ethynylated pentacene ketones, namely, 13-hydroxy-13-(ethynylated)pentacene-6(13 H )-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. |
