Synthesis and characterization of naphthalenediimide-thienothiophene-conjugated polymers for OFET and OPT applications

Dilara Gunturkun; Recep Isci; Sheida Faraji; Berkay Sütay; Leszek A. Majewski; Turan Ozturk

doi:10.1039/d3tc02109b

Synthesis and characterization of naphthalenediimide-thienothiophene-conjugated polymers for OFET and OPT applications

Dilara Gunturkun, Recep Isci, Sheida Faraji, Berkay Sütay, Leszek A. Majewski, Turan Ozturk^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

Three novel donor-acceptor-based conjugated polymers with a naphthalenedimide-thienothiophene backbone, possessing electron acceptor nitrile (CN) and electron donor methoxy (OMe) groups and an acetylene spacer were designed and synthesized. They were successfully obtained via Stille and Sonogashira couplings and were characterized using UV-Vis spectrometry, cyclic voltammetry and DFT studies. They were used to fabricate organic field-effect transistors (OFETs) and organic phototransistors (OPTs) devices. All the polymers exhibited n-type behavior in bottom-gate and top-contact organic thin-film transistors. Regarding the OPT devices, while the polymer with the CN moiety showed the highest photosensitivity P value (209), the copolymer containing the acetylene spacer and electron donor methoxy group exhibited the largest photoresponsivity R-value (2.2 × 10⁶ A W⁻¹). Our findings demonstrated that the introduction of various functional groups and a triple bond spacer is an effective approach for manipulating the optical and electronic properties, as well as enhancing the overall performance of the devices.

Original language	English
Pages (from-to)	13129-13141
Number of pages	13
Journal	Journal of Materials Chemistry C
Volume	11
Issue number	38
DOIs	https://doi.org/10.1039/d3tc02109b
Publication status	Published - 4 Sept 2023

Bibliographical note

Publisher Copyright:
© 2023 The Royal Society of Chemistry.

Funding

We thank the Higher Education Council of Turkey (YOK) and TUBITAK grants to Recep Isci (PhD, 100/2000 YOK, 2214A and 2211A BIDEP/TUBITAK), 118C365 numbered TUBITAK BIDEB 2232 Project and Unsped Global Lojistik, Turkey, for financial support. Computing resources used in this work were provided by the National Center for High Performance Computing (UHeM) under grant number 1010722021.

Funders	Funder number
Higher Education Council of Turkey
YOK	118C365, 2211A BIDEP/TUBITAK, 2214A
Ulusal Yüksek Başarımlı Hesaplama Merkezi, Istanbul Teknik Üniversitesi	1010722021
Sheikh Bahaei National High Performance Computing Center, Isfahan University of Technology

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abstract = "Three novel donor-acceptor-based conjugated polymers with a naphthalenedimide-thienothiophene backbone, possessing electron acceptor nitrile (CN) and electron donor methoxy (OMe) groups and an acetylene spacer were designed and synthesized. They were successfully obtained via Stille and Sonogashira couplings and were characterized using UV-Vis spectrometry, cyclic voltammetry and DFT studies. They were used to fabricate organic field-effect transistors (OFETs) and organic phototransistors (OPTs) devices. All the polymers exhibited n-type behavior in bottom-gate and top-contact organic thin-film transistors. Regarding the OPT devices, while the polymer with the CN moiety showed the highest photosensitivity P value (209), the copolymer containing the acetylene spacer and electron donor methoxy group exhibited the largest photoresponsivity R-value (2.2 × 106 A W−1). Our findings demonstrated that the introduction of various functional groups and a triple bond spacer is an effective approach for manipulating the optical and electronic properties, as well as enhancing the overall performance of the devices.",

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AU - Gunturkun, Dilara

AU - Isci, Recep

AU - Faraji, Sheida

AU - Sütay, Berkay

AU - Majewski, Leszek A.

AU - Ozturk, Turan

PY - 2023/9/4

Y1 - 2023/9/4

N2 - Three novel donor-acceptor-based conjugated polymers with a naphthalenedimide-thienothiophene backbone, possessing electron acceptor nitrile (CN) and electron donor methoxy (OMe) groups and an acetylene spacer were designed and synthesized. They were successfully obtained via Stille and Sonogashira couplings and were characterized using UV-Vis spectrometry, cyclic voltammetry and DFT studies. They were used to fabricate organic field-effect transistors (OFETs) and organic phototransistors (OPTs) devices. All the polymers exhibited n-type behavior in bottom-gate and top-contact organic thin-film transistors. Regarding the OPT devices, while the polymer with the CN moiety showed the highest photosensitivity P value (209), the copolymer containing the acetylene spacer and electron donor methoxy group exhibited the largest photoresponsivity R-value (2.2 × 106 A W−1). Our findings demonstrated that the introduction of various functional groups and a triple bond spacer is an effective approach for manipulating the optical and electronic properties, as well as enhancing the overall performance of the devices.

AB - Three novel donor-acceptor-based conjugated polymers with a naphthalenedimide-thienothiophene backbone, possessing electron acceptor nitrile (CN) and electron donor methoxy (OMe) groups and an acetylene spacer were designed and synthesized. They were successfully obtained via Stille and Sonogashira couplings and were characterized using UV-Vis spectrometry, cyclic voltammetry and DFT studies. They were used to fabricate organic field-effect transistors (OFETs) and organic phototransistors (OPTs) devices. All the polymers exhibited n-type behavior in bottom-gate and top-contact organic thin-film transistors. Regarding the OPT devices, while the polymer with the CN moiety showed the highest photosensitivity P value (209), the copolymer containing the acetylene spacer and electron donor methoxy group exhibited the largest photoresponsivity R-value (2.2 × 106 A W−1). Our findings demonstrated that the introduction of various functional groups and a triple bond spacer is an effective approach for manipulating the optical and electronic properties, as well as enhancing the overall performance of the devices.

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Synthesis and characterization of naphthalenediimide-thienothiophene-conjugated polymers for OFET and OPT applications

Abstract

Bibliographical note

Funding

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