Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors

Panagiota Kafourou; Mohamad Insan Nugraha; Aggelos Nikitaras; Luxi Tan; Yuliar Firdaus; Filip Aniés; Flurin D. Eisner; Bowen Ding; Jonas Wenzel; Martin Holicky; Leonidas Tsetseris; Thomas D. Anthopoulos; Martin Heeney

doi:10.1021/acsmaterialslett.1c00635

Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors

Panagiota Kafourou, Mohamad Insan Nugraha, Aggelos Nikitaras, Luxi Tan, Yuliar Firdaus, Filip Aniés, Flurin D. Eisner, Bowen Ding, Jonas Wenzel, Martin Holicky, Leonidas Tsetseris, Thomas D. Anthopoulos, Martin Heeney

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15 Scopus citations

Abstract

Small band gap molecular semiconductors are of interest for the development of transparent electronics. Here we report two near-infrared (NIR), n-type small molecule semiconductors, based upon an acceptor-donor-acceptor (A-D-A) approach. We show that the inclusion of molecular spacers between the strong-electron-accepting end group, 2,1,3-benzothiadiazole-4,5,6-tricarbonitrile, and the donor core affords semiconductors with very low band gaps down to 1 eV. Both materials were synthesized by a one-pot, 6-fold nucleophilic displacement of a fluorinated precursor by cyanide. Significant differences in solid-state ordering and charge carrier mobility are observed depending on the nature of the spacer, with a thiophene spacer resulting in solution processed organic field-effect transistors (OFETs) exhibiting excellent electron mobility up to 1.1 cm2 V-1 s-1. The use of silver nanowires as the gate electrode enables the fabrication of a semitransparent OFET device with an average visible transmission of 71% in the optical spectrum.

Original language	English (US)
Pages (from-to)	165-174
Number of pages	10
Journal	ACS Materials Letters
DOIs	https://doi.org/10.1021/acsmaterialslett.1c00635
State	Published - Dec 17 2021

Bibliographical note

KAUST Repository Item: Exported on 2022-01-18
Acknowledged KAUST grant number(s): OSR-2020-CRG8-4095, OSR-2018-CARF/CCF-3079
Acknowledgements: The authors thank the Engineering and Physical Sciences Research Council (EPSRC) (EP/L016702/1 and EP/T028513/1), Global Research Laboratory Program of the National Research Foundation (NRF-2017K1A1A2013153), the Royal Society, and the Wolfson Foundation (Royal Society Wolfson Fellowship) for funding. M.I.N., M.H., and T.D.A. acknowledge funding from the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Award Nos. OSR-2018-CARF/CCF-3079 and OSR-2020-CRG8-4095. F.E. thanks EPSRC for support via a Doctoral Prize Fellowship.

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10.1021/acsmaterialslett.1c00635

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Kafourou, P., Nugraha, M. I., Nikitaras, A., Tan, L., Firdaus, Y., Aniés, F., Eisner, F. D., Ding, B., Wenzel, J., Holicky, M., Tsetseris, L., Anthopoulos, T. D., & Heeney, M. (2021). Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors. ACS Materials Letters, 165-174. https://doi.org/10.1021/acsmaterialslett.1c00635

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title = "Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors",

abstract = "Small band gap molecular semiconductors are of interest for the development of transparent electronics. Here we report two near-infrared (NIR), n-type small molecule semiconductors, based upon an acceptor-donor-acceptor (A-D-A) approach. We show that the inclusion of molecular spacers between the strong-electron-accepting end group, 2,1,3-benzothiadiazole-4,5,6-tricarbonitrile, and the donor core affords semiconductors with very low band gaps down to 1 eV. Both materials were synthesized by a one-pot, 6-fold nucleophilic displacement of a fluorinated precursor by cyanide. Significant differences in solid-state ordering and charge carrier mobility are observed depending on the nature of the spacer, with a thiophene spacer resulting in solution processed organic field-effect transistors (OFETs) exhibiting excellent electron mobility up to 1.1 cm2 V-1 s-1. The use of silver nanowires as the gate electrode enables the fabrication of a semitransparent OFET device with an average visible transmission of 71% in the optical spectrum.",

author = "Panagiota Kafourou and Nugraha, {Mohamad Insan} and Aggelos Nikitaras and Luxi Tan and Yuliar Firdaus and Filip Ani{\'e}s and Eisner, {Flurin D.} and Bowen Ding and Jonas Wenzel and Martin Holicky and Leonidas Tsetseris and Anthopoulos, {Thomas D.} and Martin Heeney",

note = "KAUST Repository Item: Exported on 2022-01-18 Acknowledged KAUST grant number(s): OSR-2020-CRG8-4095, OSR-2018-CARF/CCF-3079 Acknowledgements: The authors thank the Engineering and Physical Sciences Research Council (EPSRC) (EP/L016702/1 and EP/T028513/1), Global Research Laboratory Program of the National Research Foundation (NRF-2017K1A1A2013153), the Royal Society, and the Wolfson Foundation (Royal Society Wolfson Fellowship) for funding. M.I.N., M.H., and T.D.A. acknowledge funding from the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Award Nos. OSR-2018-CARF/CCF-3079 and OSR-2020-CRG8-4095. F.E. thanks EPSRC for support via a Doctoral Prize Fellowship.",

year = "2021",

month = dec,

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doi = "10.1021/acsmaterialslett.1c00635",

language = "English (US)",

pages = "165--174",

journal = "ACS Materials Letters",

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publisher = "American Chemical Society",

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Kafourou, P, Nugraha, MI, Nikitaras, A, Tan, L, Firdaus, Y, Aniés, F, Eisner, FD, Ding, B, Wenzel, J, Holicky, M, Tsetseris, L, Anthopoulos, TD & Heeney, M 2021, 'Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors', ACS Materials Letters, pp. 165-174. https://doi.org/10.1021/acsmaterialslett.1c00635

TY - JOUR

T1 - Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors

AU - Kafourou, Panagiota

AU - Nugraha, Mohamad Insan

AU - Nikitaras, Aggelos

AU - Tan, Luxi

AU - Firdaus, Yuliar

AU - Aniés, Filip

AU - Eisner, Flurin D.

AU - Ding, Bowen

AU - Wenzel, Jonas

AU - Holicky, Martin

AU - Tsetseris, Leonidas

AU - Anthopoulos, Thomas D.

AU - Heeney, Martin

N1 - KAUST Repository Item: Exported on 2022-01-18 Acknowledged KAUST grant number(s): OSR-2020-CRG8-4095, OSR-2018-CARF/CCF-3079 Acknowledgements: The authors thank the Engineering and Physical Sciences Research Council (EPSRC) (EP/L016702/1 and EP/T028513/1), Global Research Laboratory Program of the National Research Foundation (NRF-2017K1A1A2013153), the Royal Society, and the Wolfson Foundation (Royal Society Wolfson Fellowship) for funding. M.I.N., M.H., and T.D.A. acknowledge funding from the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under Award Nos. OSR-2018-CARF/CCF-3079 and OSR-2020-CRG8-4095. F.E. thanks EPSRC for support via a Doctoral Prize Fellowship.

PY - 2021/12/17

Y1 - 2021/12/17

N2 - Small band gap molecular semiconductors are of interest for the development of transparent electronics. Here we report two near-infrared (NIR), n-type small molecule semiconductors, based upon an acceptor-donor-acceptor (A-D-A) approach. We show that the inclusion of molecular spacers between the strong-electron-accepting end group, 2,1,3-benzothiadiazole-4,5,6-tricarbonitrile, and the donor core affords semiconductors with very low band gaps down to 1 eV. Both materials were synthesized by a one-pot, 6-fold nucleophilic displacement of a fluorinated precursor by cyanide. Significant differences in solid-state ordering and charge carrier mobility are observed depending on the nature of the spacer, with a thiophene spacer resulting in solution processed organic field-effect transistors (OFETs) exhibiting excellent electron mobility up to 1.1 cm2 V-1 s-1. The use of silver nanowires as the gate electrode enables the fabrication of a semitransparent OFET device with an average visible transmission of 71% in the optical spectrum.

AB - Small band gap molecular semiconductors are of interest for the development of transparent electronics. Here we report two near-infrared (NIR), n-type small molecule semiconductors, based upon an acceptor-donor-acceptor (A-D-A) approach. We show that the inclusion of molecular spacers between the strong-electron-accepting end group, 2,1,3-benzothiadiazole-4,5,6-tricarbonitrile, and the donor core affords semiconductors with very low band gaps down to 1 eV. Both materials were synthesized by a one-pot, 6-fold nucleophilic displacement of a fluorinated precursor by cyanide. Significant differences in solid-state ordering and charge carrier mobility are observed depending on the nature of the spacer, with a thiophene spacer resulting in solution processed organic field-effect transistors (OFETs) exhibiting excellent electron mobility up to 1.1 cm2 V-1 s-1. The use of silver nanowires as the gate electrode enables the fabrication of a semitransparent OFET device with an average visible transmission of 71% in the optical spectrum.

UR - http://hdl.handle.net/10754/675005

UR - https://pubs.acs.org/doi/10.1021/acsmaterialslett.1c00635

UR - http://www.scopus.com/inward/record.url?scp=85121904369&partnerID=8YFLogxK

U2 - 10.1021/acsmaterialslett.1c00635

DO - 10.1021/acsmaterialslett.1c00635

M3 - Article

SN - 2639-4979

SP - 165

EP - 174

JO - ACS Materials Letters

JF - ACS Materials Letters

ER -

Near-IR Absorbing Molecular Semiconductors Incorporating Cyanated Benzothiadiazole Acceptors for High-Performance Semitransparent n-Type Organic Field-Effect Transistors

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