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Diindenopyrazines: Electron‐Deficient Arenes
Author(s) -
Brosius Victor,
Weigold Svenja,
Hippchen Nikolai,
Rominger Frank,
Freudenberg Jan,
Bunz Uwe H. F.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100372
Subject(s) - aryl , electron , semiconductor , electron transport chain , chemistry , redox , electron acceptor , electron mobility , solubility , electron affinity (data page) , materials science , combinatorial chemistry , chemical physics , photochemistry , organic chemistry , optoelectronics , physics , molecule , biochemistry , quantum mechanics , alkyl
The syntheses, properties and application of the air‐stable electron acceptors, diindenopyrazines 4 a – g are reported demonstrating the introduction of functional aryl groups in the 6‐ and 12‐positions. The targets are accessible on the hundred milligram to gram scale. The structure of the aryl groups in 4 a – g modulates their solubility, redox potentials and optical properties. The introduction of electron‐poor aryl groups to the electron‐poor diindenopyrazine backbone reduces the electron affinity to −4 eV, making the compounds attractive as n‐semiconductors. A simple organic field‐effect transistor of 4 e –without optimization– shows electron transport with a mobility of up to 0.037 cm 2 V −1 s −1 .