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One-step Six-fold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors

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Title: One-step Six-fold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors
Authors: Heeney, M
Kafourou, P
Park, B
Luke, J
Luxi, T
Panidi, J
Glöcklhofer, F
Kim, J
Anthopoulos, TD
Kim, J-S
Lee, K
Kwon, S
Item Type: Journal Article
Abstract: We report 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 six-fold nucleophilic substitution with cyanides on a fluorinated precursor, itself prepared by a direct arylation approach. This one-step chemical modification was found to significantly impact the molecular properties: the fluorinated precursor, TFBT IDT, a poor ambipolar semiconductor, was converted into TCNBT IDT, a good n-type semiconductor. The highly 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.
Issue Date: 14-Dec-2020
Date of Acceptance: 12-Dec-2020
URI: http://hdl.handle.net/10044/1/85031
DOI: 10.1002/anie.202013625
ISSN: 1433-7851
Publisher: Wiley
Journal / Book Title: Angewandte Chemie International Edition
Copyright Statement: © 2020 Wiley-VCH GmbH.
Sponsor/Funder: EPSRC
The Royal Society
Kaust
EPRSC
National Research Foundation of Korea (NRF)
Funder's Grant Number: EP/L016702/1
RSWF\R1\180001
OSR-2019-CRG8-4095.2
EP/T028513/1
NRF-2017K1A1A2013153
Keywords: Organic semiconductor Acceptor endgroup n-type material Nucleophillic aromatic substitution Field-effect transistor
Organic semiconductor Acceptor endgroup n-type material Nucleophillic aromatic substitution Field-effect transistor
Organic Chemistry
03 Chemical Sciences
Publication Status: Published online
Conference Place: Germany
Open Access location: https://onlinelibrary.wiley.com/doi/10.1002/anie.202013625
Online Publication Date: 2020-12-14
Appears in Collections:Physics
Chemistry
Experimental Solid State