Volume 134, Issue 14 e202200341
Forschungsartikel

Dibenzodiazapyracylenes: Doubly N-Doped Cyclopenta-Fused Polycyclic Molecules That Exhibit High Carrier Mobility

Yuki Morimoto

Yuki Morimoto

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan

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Yun Hee Koo

Yun Hee Koo

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan

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Dr. Kazuya Otsubo

Dr. Kazuya Otsubo

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan

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Hidetsugu Kitakado

Hidetsugu Kitakado

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan

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Prof. Dr. Shu Seki

Corresponding Author

Prof. Dr. Shu Seki

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan

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Prof. Dr. Atsuhiro Osuka

Prof. Dr. Atsuhiro Osuka

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan

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Prof. Dr. Takayuki Tanaka

Corresponding 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

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First published: 04 February 2022

Abstract

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.

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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