Premium
Acridino[2,1,9,8‐ klmna ]acridine Bisimides: An Electron‐Deficient π‐System for Robust Radical Anions and n‐Type Organic Semiconductors
Author(s) -
Tajima Keita,
Matsuo Kyohei,
Yamada Hiroko,
Seki Shu,
Fukui Norihito,
Shinokubo Hiroshi
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202102708
Subject(s) - imide , organic field effect transistor , homo/lumo , electron mobility , electron affinity (data page) , chemistry , photochemistry , imine , electron , derivative (finance) , electron transport chain , electron donor , single crystal , materials science , crystallography , transistor , field effect transistor , optoelectronics , organic chemistry , molecule , biochemistry , physics , quantum mechanics , voltage , financial economics , economics , catalysis
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.