@article{oai:nagoya.repo.nii.ac.jp:02001677, author = {Tajima, Keita and Matsuo, Kyohei and Yamada, Hiroko and Seki, Shu and Fukui, Norihito and Shinokubo, Hiroshi}, issue = {25}, journal = {Angewandte Chemie International Edition}, month = {Jun}, note = {We report the synthesis and properties of acridino[2,1,9,8-klmna]acridine bisimide (AABI), a nitrogen-doped anthanthrene with two imide functionalities. AABI exhibits excellent electron affinity as evident by its low-lying LUMO level (−4.1 eV vs. vacuum). Single-electron reduction of one AABI derivative afforded the corresponding radical anion, which was stable under ambient conditions. Photoconductivity measurements suggest that the intrinsic electron mobility of an N-phenethyl AABI derivative obeys a band-transport model. Accordingly, an electron mobility of 0.90 cm^2 V^−1 s^−1 was attained with the corresponding single-crystal organic field-effect transistor (OFET) device. The vacuum-deposited OFET device consisting of a polycrystalline sample exhibited high electron mobility of up to 0.27 cm^2 V^−1 s^−1 even in air. This study demonstrates that dual incorporation of both imide substituents and imine-type nitrogen atoms is an effective strategy to create novel electron-deficient π-systems.}, pages = {14060--14067}, title = {Acridino[2,1,9,8-klmna]acridine Bisimides: An Electron-Deficient π-System for Robust Radical Anions and n-Type Organic Semiconductors}, volume = {60}, year = {2021} }