Abstract
Ultra‐electron‐deficient azaacenes were synthesized via Buchwald‐Hartwig coupling of ortho‐diaminoarenes with chlorinated mellophanic diimide followed by oxidation of the intermediate N,N’‐dihydro compounds with MnO2 or PbO2. The resulting cata‐annulated bisimide azaacenes have ultrahigh electron affinities with first reduction potentials as low as −0.35 V recorded for a tetraazapentacene. Attempts to prepare a tetrakis(dicarboximide)tetraazaheptacene resulted in the formation of a symmetric butterfly dimer.
Highlights
There is a constant push in materials science to prepare organic materials with extreme and attractive properties for uses that range from solar cells and n-channel materials to spintronics
We couple MDI-Cl2[7] with aromatic diamines[8] to explore novel electron-deficient azaacenes
Cata-condensed bisimides are more powerful than CN-substituents, as evidenced by a comparison of the first reduction potentials of 3 a (À 0.62 V) to that of a dicyanodiazaacene (À 0.7 V).[12]
Summary
The addition of bisimides to the terminal ring of azaacenes using a simple coupling-oxidation sequence results in near-IR absorbers with high electron affinities up to À 4.35 eV. Or quadruply bisimide-substituted azapentacenes are stable, processable, yet amorphous materials that should be almost ideal materials for solar cells, and, upon shortening the hexyl chains, may give attractive n-channel semiconductors for thin film transistors, which we will report upon in the future
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
