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One-Step Sixfold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors.
Kafourou, Panagiota; Park, Byoungwook; Luke, Joel; Tan, Luxi; Panidi, Julianna; Glöcklhofer, Florian; Kim, Jehan; Anthopoulos, Thomas D; Kim, Ji-Seon; Lee, Kwanghee; Kwon, Sooncheol; Heeney, Martin.
Afiliação
  • Kafourou P; Department of Chemistry and Centre for Processable Electronics, Imperial College London, London, W12 0BZ, UK.
  • Park B; Heeger Center for Advanced Materials and Research Institute for Solar and Sustainable Energies, Gwangju Institute of Science and Technology, Gwangju, Republic of Korea.
  • Luke J; Department of Physics and Centre for Processable Electronics, Imperial College London, London, SW7 2AZ, UK.
  • Tan L; School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331, China.
  • Panidi J; Department of Physics and Centre for Processable Electronics, Imperial College London, London, SW7 2AZ, UK.
  • Glöcklhofer F; Department of Chemistry and Centre for Processable Electronics, Imperial College London, London, W12 0BZ, UK.
  • Kim J; Pohang Accelerator Laboratory, Pohang University of Science and Technology, Pohang, Republic of Korea.
  • Anthopoulos TD; Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology (KAUST), KAUST Solar Centre, Thuwal, 23955-6900, Saudi Arabia.
  • Kim JS; Department of Physics and Centre for Processable Electronics, Imperial College London, London, SW7 2AZ, UK.
  • Lee K; Heeger Center for Advanced Materials and Research Institute for Solar and Sustainable Energies, Gwangju Institute of Science and Technology, Gwangju, Republic of Korea.
  • Kwon S; Heeger Center for Advanced Materials and Research Institute for Solar and Sustainable Energies, Gwangju Institute of Science and Technology, Gwangju, Republic of Korea.
  • Heeney M; Department of Chemistry and Centre for Processable Electronics, Imperial College London, London, W12 0BZ, UK.
Angew Chem Int Ed Engl ; 60(11): 5970-5977, 2021 Mar 08.
Article em En | MEDLINE | ID: mdl-33315288
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.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article