Dithienonaphthobisthiadiazole synthesized by thienannulation of electron-deficient rings: an acceptor building unit for high-performance π-conjugated polymers

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2024-11-18 DOI:10.1039/d4sc05793g

Tsubasa Mikie, Tomokazu Morioku, Shota Suruga, Momoka Hada, Yuki Sato, Hideo Ohkita, Itaru Osaka

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Abstract

The development of building units for π-conjugated polymers is a driving force in advancing the field of organic electronics. In this study, we designed and synthesized dithienonaphthobisthiadiazole (TNT) as a thiophene-fused acceptor (A) building unit and two TNT-based π-conjugated polymers named PTNT2T and PTNT1-F. We found that the microwave-assisted thiophene annulation reaction (thienannulation) of arylethynylated naphthobisthiadiazole (NTz) via C–H functionalization effectively produced TNT moieties. With the π-extended structure of TNT, the polymers had rigid backbones that benefited in-plane and out-of-plane charge carrier transport. Organic field-effect transistors (OFETs) based on PTNT2T exhibited hole mobilities as high as 1.10 cm² V⁻¹ s⁻¹. Furthermore, organic photovoltaic cells (OPVs) based on PTNT1-F showed high power conversion efficiencies of up to 17.4% when combined with a nonfullerene acceptor. This work provides an efficient method for the thienannulation of electron-deficient rings to access thiophene-fused A building units and shows the great promise of TNT as a building unit for high-performance π-conjugated polymers for organic electronic devices.

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通过缺电子环的噻吩化合成的二噻吩基萘双噻二唑：高性能 π 共轭聚合物的受体构建单元

开发π共轭聚合物的构建单元是推动有机电子学领域发展的动力。在本研究中，我们设计并合成了作为噻吩融合受体（A）构建单元的二噻吩基萘二噻二唑（TNT）以及两种基于 TNT 的 π 共轭聚合物，分别命名为 PTNT2T 和 PTNT1-F。我们发现，通过 C-H 功能化对芳基乙炔化的萘二噻二唑（NTz）进行微波辅助噻吩环化反应（噻吩环化），可有效生成 TNT 分子。由于 TNT 具有 π 扩展结构，聚合物具有刚性骨架，有利于平面内和平面外的电荷载流子传输。基于 PTNT2T 的有机场效应晶体管（OFET）的空穴迁移率高达 1.10 cm2 V-1 s-1。此外，基于 PTNT1-F 的有机光伏电池（OPV）在与非富勒烯受体结合时显示出高达 17.4% 的功率转换效率。这项工作为缺电子环的噻吩化提供了一种高效的方法，从而获得噻吩融合 A 构建单元，并表明 TNT 作为高性能 π 共轭聚合物的构建单元在有机电子设备中大有可为。

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来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.