Dibenzodiazapyracylenes: Doubly N-Doped Cyclopenta-Fused Polycyclic Molecules That Exhibit High Carrier Mobility
Yuki Morimoto
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorYun Hee Koo
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Kazuya Otsubo
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorHidetsugu Kitakado
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Shu Seki
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorProf. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Takayuki Tanaka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorYuki Morimoto
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorYun Hee Koo
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Kazuya Otsubo
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorHidetsugu Kitakado
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Shu Seki
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorProf. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Takayuki Tanaka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorAbstract
Pyracylene is a unique cyclopenta-fused polycyclic aromatic hydrocarbon (CP-PAH) that exhibits dual aromatic characteristics. Herein we report the synthesis of doubly N-doped benzannulated pyracylenes, namely dibenzodiazapyracylenes, by oxidative N−N linking reaction of [2.2](2,5)pyrrolophane-type precursors. Dibenzodiazapyracylenes displayed well-ordered π-stacked molecular packing in the solid state, which were feasible for effective hole-transporting along the stacking direction. High carrier mobility was estimated by microwave conductivity measurements as compared to dibenzoullazine. The high HOMO level of dibenzodiazapyracylene was verified by electrochemistry and its persistent radical cation species has been detected.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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