Premium
One‐Step Sixfold Cyanation of Benzothiadiazole Acceptor Units for Air‐Stable High‐Performance n‐Type Organic Field‐Effect Transistors
Author(s) -
Kafourou Panagiota,
Park Byoungwook,
Luke Joel,
Tan Luxi,
Panidi Julianna,
Glöcklhofer Florian,
Kim Jehan,
Anthopoulos Thomas D.,
Kim JiSeon,
Lee Kwanghee,
Kwon Sooncheol,
Heeney Martin
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202013625
Subject(s) - ambipolar diffusion , homo/lumo , organic semiconductor , acceptor , semiconductor , field effect transistor , materials science , chemistry , electron mobility , transistor , photochemistry , optoelectronics , organic chemistry , molecule , electron , physics , quantum mechanics , voltage , condensed matter physics
Reported here is a new high electron affinity acceptor end group for organic semiconductors, 2,1,3‐benzothiadiazole‐4,5,6‐tricarbonitrile (TCNBT). An n‐type organic semiconductor with an indacenodithiophene (IDT) core and TCNBT end groups was synthesized by a sixfold nucleophilic substitution with cyanide on a fluorinated precursor, itself prepared by a direct arylation approach. This one‐step chemical modification significantly impacted the molecular properties: the fluorinated precursor, TFBT IDT, a poor ambipolar semiconductor, was converted into TCNBT IDT, a good n‐type semiconductor. The electron‐deficient end group TCNBT dramatically decreased the energy of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO) compared to the fluorinated analogue and improved the molecular orientation when utilized in n‐type organic field‐effect transistors (OFETs). Solution‐processed OFETs based on TCNBT IDT exhibited a charge‐carrier mobility of up to μ e ≈0.15 cm 2 V −1 s −1 with excellent ambient stability for 100 hours, highlighting the benefits of the cyanated end group and the synthetic approach.