Thiophene‐<i>S</i>,<i>S</i>‐dioxidized Indophenine: A Quinoid‐Type Building Block with High Electron Affinity for Constructing n‐Type Polymer Semiconductors with Narrow Band Gaps

Deng, Yunfeng; Sun, Bin; He, Yinghui; Quinn, Jesse; Guo, Chang; Li, Yuning

doi:10.1002/anie.201508781

Cited by 83 publications

(72 citation statements)

References 44 publications

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“…4b). Notable examples include poly(thieno [3,4-b] pyrazine), [41][42][43][44] poly(thieno [3,4-b]thiophene), [45][46][47][48] poly(naphtho [2,3-c]thiophene), 49,50 poly(dithieno [3,4- 51 poly(thieno [3,4-b]quinoxaline), 50 etc. Many of these polythiophene-derived homopolymers were polymerized by electrochemical or chemical oxidation (Fig.…”

Section: Proquinoidal Polymersmentioning

confidence: 99%

Quinoidal conjugated polymers with open-shell character

Fang

2021

Polym. Chem.

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Section: Proquinoidal Polymersmentioning

confidence: 99%

Quinoidal conjugated polymers with open-shell character

Fang

2021

Polym. Chem.

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“…Separating the mixture of E / Z ‐isomers by silica gel column chromatography was difficult due to their rapid isomerization at room temperature, which is consistent with the previous studies. [ 24‐27 ]…”

Section: Resultsmentioning

confidence: 99%

Quinoidal bisthienoisatin based semiconductors: Synthesis, characterization, and carrier transport property

et al. 2020

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Novel quinoidal bisthienoisatin (QBTI) derivatives end‐capped with phenyl and thienyl groups were designed and synthesized. Single‐crystal X‐ray structure analysis of phenyl group flanked QBTI molecule confirmed that the quinoidal structure contributed to the high planarity of the molecular skeleton and the construction of one‐dimensional stacks. The quinoidal form of bisthienoisatin derivatives displayed ambipolar carrier transport properties with mobilities of approximately 10−4 cm2 V−1 s−1. Different flanking aromatic rings considerably affected the thin‐film microstructure and hence the charge carrier transport properties of the material. The QBTI‐based narrow energy gap polymers were theoretically designed and synthesized. Delocalized quinoidal resonance of QBTI unit along the polymer backbone is of particular importance to achieve relatively high conductive state (10−3 S cm−1). We demonstrate that QBTI cores should be promising building blocks for constructing narrow energy gap semiconducting and conductive polymers.

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“…Li and co‐workers oxidized the sulfur atoms of the quinoidal thiophene in M11 . [ 111 ] Three isomers of the resulting M12 were readily isolated, and the optimal isomer could be converted from the other two isomers via heat treatment. More favorably, M12 showed increased electron affinity.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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Thiophene‐S,S‐dioxidized Indophenine: A Quinoid‐Type Building Block with High Electron Affinity for Constructing n‐Type Polymer Semiconductors with Narrow Band Gaps

Cited by 83 publications

References 44 publications

Quinoidal conjugated polymers with open-shell character

Quinoidal conjugated polymers with open-shell character

Quinoidal bisthienoisatin based semiconductors: Synthesis, characterization, and carrier transport property

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

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