Affiliation:
1. Institute of Organic Chemistry University of Freiburg Freiburg Germany
Abstract
AbstractDibenzo[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.
Funder
Deutsche Forschungsgemeinschaft
Subject
Organic Chemistry,Physical and Theoretical Chemistry
Cited by
2 articles.
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