One-Step Sixfold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors

Panagiota Kafourou, Byoungwook Park, Joel Luke, Luxi Tan, Julianna Panidi, Florian Glöcklhofer, Jehan Kim, Thomas D. Anthopoulos, Ji Seon Kim, Kwanghee Lee, Sooncheol Kwon*, Martin Heeney*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

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 μe≈0.15 cm2 V−1 s−1 with excellent ambient stability for 100 hours, highlighting the benefits of the cyanated end group and the synthetic approach.

Original languageEnglish (US)
Pages (from-to)5970-5977
Number of pages8
JournalAngewandte Chemie - International Edition
Volume60
Issue number11
DOIs
StatePublished - Mar 8 2021

Bibliographical note

Publisher Copyright:
© 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

Keywords

  • field effect transistors
  • fluorine
  • nucleophilic aromatic substitution
  • organic electronics
  • semiconductors

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

Fingerprint

Dive into the research topics of 'One-Step Sixfold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors'. Together they form a unique fingerprint.

Cite this