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

Yuki Morimoto; Yun Hee Koo; Kazuya Otsubo; Hidetsugu Kitakado; Shu Seki; Atsuhiro Osuka; Takayuki Tanaka

doi:10.1002/anie.202200341

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

Angew Chem Int Ed Engl. 2022 Mar 28;61(14):e202200341. doi: 10.1002/anie.202200341. Epub 2022 Feb 15.

Authors

Yuki Morimoto¹, Yun Hee Koo², Kazuya Otsubo¹, Hidetsugu Kitakado¹, Shu Seki², Atsuhiro Osuka¹, Takayuki Tanaka^{1

2}

Affiliations

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
² Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.

PMID: 35119187
DOI: 10.1002/anie.202200341

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.

Keywords: Antiaromaticity; Hole-Transporting Materials; Microwave Conductivity; Polycyclic Aromatic Hydrocarbons; Solid-State Emission.

Abstract

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