Low-bandgap conjugated polymers based on benzodipyrrolidone with reliable unipolar electron mobility exceeding 1 cm2 V−1 s−1

Yang, Mingqun; Du, Tian; Zhao, Xuxia; Huang, Xuelong; Pan, Langheng; Pang, Shuting; Tang, Haoran; Peng, Zhongxiang; Ye, Long; Deng, Yunfeng; Sun, Mingliang; Duan, Chunhui; Huang, Fei; Cao, Yong

doi:10.1007/s11426-021-9991-0

Cited by 25 publications

(13 citation statements)

References 75 publications

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“…In view of these features, quinoidal compounds with dicyanomethylene end groups have been widely used as electron-accepting molecules in conductive charge-transfer salts and have been studied as n-type organic semiconductors in OTFTs and OTEs. ,− However, such compounds are unsuitable for the construction of CPs because the potential polymerization sites are occupied by CN groups. Other quinoidal units, such as oxindole-terminated , and carbonyl-terminated quinoids, , pyrollidone-fused quinoids, − and p -azaquinodimethane, , that can be incorporated into polymer backbones have been developed. Unfortunately, CPs based on these units usually exhibit relatively high-lying E LUMO s, making n-type behavior difficult to achieve (Figure S1).…”

Section: Introductionmentioning

confidence: 99%

n-Type Conjugated Polymers Based on an Indandione-Terminated Quinoidal Building Block

Liu

Wang

et al. 2022

Macromolecules

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Conjugated polymers (CPs) with deep LUMO energy levels (E LUMO s) are essential for developing n-type organic electronics. However, few approaches can markedly lower the E LUMO s of CPs. Herein, this issue is addressed by the introduction of a quinoidal building block into the polymer chain. Two CPs, PIQ-A and PIQ-O, are synthesized based on an indandioneterminated quinoidal unit, with alkyl or oligo(ethylene glycol) side chains on the comonomer, respectively. The CPs show ultralow E LUMO s of ca. −4.30 eV, which is lower by 0.75 eV compared to the analogous polymer with aromatic conjugated structure. The deep LUMO energy levels endow the CPs with unipolar n-type transport behavior in organic thin-film transistors and efficient n-type doping in organic thermoelectrics, with doped PIQ-O showing an optimized electrical conductivity of 0.43 S cm −1 and a power factor of 4.24 μW m −1 K −2 . Importantly, the electrical conductivity of doped polymer thin films (∼50 nm) barely changes after a 7 day exposure to air, and the doped PIQ-O film shows an electrical conductivity of 0.39 S cm −1 even after a 15 day exposure to air. This work provides a new approach to develop CPs with ultralow LUMO energy levels, toward high-performance and potentially airstable n-type organic electronics.

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Section: Introductionmentioning

confidence: 99%

n-Type Conjugated Polymers Based on an Indandione-Terminated Quinoidal Building Block

Liu

Wang

et al. 2022

Macromolecules

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“…The reduction in the band-gap of the material is mainly attributed to the rising HOMO levels as the π-conjugation increases. All these materials showed unipolar electron transport behaviors, exhibiting a maximum μ e of 0.38 cm 2 V −1 s −1 [ 28 ].…”

Section: Synthetic Tactics Of π-Extended Quinoidal Acceptorsmentioning

confidence: 99%

Recent Research Progress in Indophenine-Based-Functional Materials: Design, Synthesis, and Optoelectronic Applications

Ren

Yassar

2023

Materials

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This review highlights selected examples, published in the last three to four years, of recent advance in the design, synthesis, properties, and device performance of quinoidal π-conjugated materials. A particular emphasis is placed on emerging materials, such as indophenine dyes that have the potential to enable high-performance devices. We specifically discuss the recent advances and design guidelines of π-conjugated quinoidal molecules from a chemical standpoint. To the best of the authors’ knowledge, this review is the first compilation of literature on indophenine-based semiconducting materials covering their scope, limitations, and applications. In the first section, we briefly introduce some of the organic electronic devices that are the basic building blocks for certain applications involving organic semiconductors (OSCs). We introduce the definition of key performance parameters of three organic devices: organic field effect transistors (OFET), organic photovoltaics (OPV), and organic thermoelectric generators (TE). In section two, we review recent progress towards the synthesis of quinoidal semiconducting materials. Our focus will be on indophenine family that has never been reviewed. We discuss the relationship between structural properties and energy levels in this family of molecules. The last section reports the effect of structural modifications on the performance of devices: OFET, OPV and TE. In this review, we provide a general insight into the association between the molecular structure and electronic properties in quinoidal materials, encompassing both small molecules and polymers. We also believe that this review offers benefits to the organic electronics and photovoltaic communities, by shedding light on current trends in the synthesis and progression of promising novel building blocks. This can provide guidance for synthesizing new generations of quinoidal or diradical materials with tunable optoelectronic properties and more outstanding charge carrier mobility.

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“…[10][11][12][13][14] The introduction of quinoidal units into the polymer backbones can effectively tune the physicochemical properties of the resulting polymers. [15][16][17] Recently, Liu and co-workers have developed a promising para-azaquinodimethane (p-AQM) building block, which features an N-heteroaromatic quinoidal skeleton and has the ability to stabilize the quinoidal character of the conjugated system. 18 The reported thiophene-flanked p-AQMs, which possess a coplanar structure and rigid conformation with limited rotational freedom due to non-covalent intramolecular S • • • N interactions, have generated significant interest in functional polymeric materials.…”

Section: Introductionmentioning

confidence: 99%

“…10–14 The introduction of quinoidal units into the polymer backbones can effectively tune the physicochemical properties of the resulting polymers. 15–17…”

Section: Introductionmentioning

confidence: 99%

6H-[1,2,5]Thiadiazolo[3,4-e]thieno[3,2-b]indole-flanked para-azaquinodimethane based aromatic-quinoidal polymer semiconductors with high molecular weights synthesized via direct arylation polycondensation

Xiao

et al. 2023

Mater. Adv.

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Low-bandgap conjugated polymers based on benzodipyrrolidone with reliable unipolar electron mobility exceeding 1 cm2 V−1 s−1

Cited by 25 publications

References 75 publications

n-Type Conjugated Polymers Based on an Indandione-Terminated Quinoidal Building Block

n-Type Conjugated Polymers Based on an Indandione-Terminated Quinoidal Building Block

Recent Research Progress in Indophenine-Based-Functional Materials: Design, Synthesis, and Optoelectronic Applications

6H-[1,2,5]Thiadiazolo[3,4-e]thieno[3,2-b]indole-flanked para-azaquinodimethane based aromatic-quinoidal polymer semiconductors with high molecular weights synthesized via direct arylation polycondensation

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