Engineering the packing structure of thioether‐ and sulfone‐substituted dibenzo[a,e]pentalenes by pentafluorophenyl substitution

Abstract: Dibenzo[a,e]pentalene derivatives as nonalternant conjugated hydrocarbons are attractive for use as ambipolar or n-type semiconductors in field-effect transistors. For organic semiconductors, not only the energy levels of the frontier molecular orbitals but also their solid-state packing is crucial for good charge transport abilities. The introduction of fluorine atoms into organic semiconductors can lead to a closer packing in the solid state, enabled through F⋯F, F⋯H, and F⋯π-interactions. We herein introduce pentafluorophenyl substituents into thioether- and sulfone-DBPs and demonstrate how these substituents not only further lower their LUMO energies to values down to −3.6 eV for the thioethers and −4.1 eV for the sulfone but also lead to a denser packing in the solid state due to fluorine-based interactions between the molecules

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch
• Notes: Journal of physical organic chemistry. - 36, 6 (2023) , e4491, ISSN: 1099-1395

Contributors, Places and Time

• Event: Veröffentlichung
• (where): Freiburg
• (who): Universität
• (when): 2023
• Creator: Hermann, Mathias ; Grenz, David ; Esser, Birgit

Further information

• DOI: 10.1002/poc.4491
• URN: urn:nbn:de:bsz:25-freidok-2377844
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 10:45 AM CEST