Synthesis of low band gap polymers based on pyrrolo[3,2-d:4,5-d′]bisthiazole (PBTz) and thienylenevinylene (TV) for organic thin-film transistors (OTFTs)

Patra, Dhananjaya; Lee, Jae-Hyuk; Lee, Jongbok; Sredojević, Dušan N.; White, Andrew J. P.; Bazzi, Hassan S.; Heeney, Martin; Fang, Lei; Yoon, Myung Han; Al‐Hashimi, Mohammed

doi:10.1039/c6tc04763g

Cited by 25 publications

(24 citation statements)

References 65 publications

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“…66 in electron transport materials as part of co-polymers or centered between two NDIs. [72][73][74][75] Compared to DTPs such as 51 (Figure 7), the nitrogen bridge in 105 decreases the LUMO levels significantly (-0.8 eV) and shifts the absorption slightly to the red. 86 The addition of electron withdrawing cyano substituents in the bridge of 120 and the installation of peripheral sulfur redox switches provides access to sulfoxides 121 and sulfones 122.…”

Section: Core Substitutionmentioning

confidence: 96%

Dithienothiophenes at Work: Access to Mechanosensitive Fluorescent Probes, Chalcogen-Bonding Catalysis, and Beyond

et al. 2019

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In this review, the multifunctionality of dithieno[3,2-b:2',3'-d]thiophenes (DTTs) is covered comprehensively. This is of interest because all involved research is very recent, emphasizes timely topics such as mechanochemistry for bioimaging or chalcogen bonds for catalysis and solar cells, and because the newly emerging privileged scaffold is embedded in an inspiring structural space. At the beginning, DTTs are introduced with regard to nomenclature, constitutional isomers and optoelectronic properties. The structural space around DTTs is mapped out next with regard to heteroatom substitution in bridge and core, covering much of the periodic table, eccentric heteroatom doping and bridge expansions. After a brief summary of synthetic approaches to the DTT scaffold, chalcogen bonds are introduced as, together with redox switching and turn-on fluorescence, one of the three conceptual foundations of most multifunctionality. Realized functions cover anion binding, transport (ion carriers, ion channels), catalysis, and the first fluorescent probes to image physical forces in living cells.

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Section: Core Substitutionmentioning

confidence: 96%

Dithienothiophenes at Work: Access to Mechanosensitive Fluorescent Probes, Chalcogen-Bonding Catalysis, and Beyond

et al. 2019

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“…Due to the advantages such as low cost, easy modification, friendly environment, light weight, and mechanical flexibility, solution‐processable organic semiconductors gain the increasing attention. Both conjugated small molecules and polymers, which possess an enormously extended conjugated system, can be employed into the organic optoelectronic devices, such as organic light emitting diodes, organic thin‐film transistors, and organic solar cells (OSCs),. In fact, the first conceptual OSCs were reported by Kallmann and Pope in 1959 that consisted of a pristine single crystal anthracene material between two electrodes .…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Nonfullerene Acceptors for Organic Solar Cells

Liu

Hou

et al. 2017

Macromol. Rapid Commun.

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Recently, research on nonfullerene acceptors in organic solar cells has gradually become a hot topic due to such superior characteristics of light absorption and energy-level-convenient manipulation, multiformity of the photoactive material structures, as well as the extensive area in production compared to the fullerene derivatives. However, the nonfullerene acceptors evolved slowly before 2012 and, as a matter of fact, the power conversion efficiency values could only bear 2.0%. Strikingly, nonfullerene acceptors have developed at a fast pace since 2013, with the best device performance of 13.1% now. In this review, recent research progress on nonfullerene acceptors, including small molecules and polymers, are sorted and summarized on the basis of the different characteristics.

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“…The surface features, such as the surface roughness, skewness, kurtosis, and height, were determined using the software on the AFM instrument. Figure 7 shows the two-dimensional and three-dimensional AFM image of the oligo-pyrazole thin film 21 μm coated on a glass substrate [ 36 , 37 ]. In the AFM images, a few black regions and several yellow regions appeared over a large area.…”

Section: Resultsmentioning

confidence: 99%

A novel oligo-pyrazole-based thin film: synthesis, characterization, optical and morphological properties

2018

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Pyrazole-3,4-dicarboxylic acid 2 was synthesized via the hydrolysis of pyrazole-3-carboxylic acid 1 and subsequently heated with thionyl chloride to give the novel pyrazole-3,4-dicarbonyl dichloride 3, which was easily converted into oligo-pyrazole 4 upon its reaction with p-phenylene-diamine. These newly synthesized compounds were characterized by 1H-NMR, 13C-NMR, and FT-IR spectroscopy, and gel permission chromatography (GPC). Three novel oligo-pyrazole thin films were prepared using oligo-pyrazole 4 with these respective values of thickness: 20, 21, and 24 μm. The optical properties of the films, including the absorbance, transmittance, and optical band gap, were determined using UV-vis spectroscopy. The Eg values of the films were found to be 1.426, 1.537, and 1.648 eV for the 20, 21, and 24 μm thick organic films, respectively. Atomic force microscopy (AFM) was used to examine the surface morphology and properties of the organic films. In the AFM images, a few black regions were observed and several yellow regions appeared over a large area, and the surface of the oligo-pyrazole films had an extremely low roughness value. The as-synthesized oligo-pyrazole has great potential in optoelectronic applications according to the optical properties of the as-prepared films. Graphical abstract Electronic supplementary materialThe online version of this article (10.1007/s00396-018-4342-7) contains supplementary material, which is available to authorized users.

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Synthesis of low band gap polymers based on pyrrolo[3,2-d:4,5-d′]bisthiazole (PBTz) and thienylenevinylene (TV) for organic thin-film transistors (OTFTs)

Abstract: New low band gap copolymers P1–P4, based on thienylenevinylene (TV) and pyrrolo[3,2-d:4,5-d′]bisthiazole (PBTz).

Cited by 25 publications

References 65 publications

Dithienothiophenes at Work: Access to Mechanosensitive Fluorescent Probes, Chalcogen-Bonding Catalysis, and Beyond

Dithienothiophenes at Work: Access to Mechanosensitive Fluorescent Probes, Chalcogen-Bonding Catalysis, and Beyond

Recent Advances in Nonfullerene Acceptors for Organic Solar Cells

A novel oligo-pyrazole-based thin film: synthesis, characterization, optical and morphological properties

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