Dithienylmethanone‐Based Cross‐Conjugated Polymer Semiconductors: Synthesis, Characterization, and Application in Field‐Effect Transistors

Shi, Kai; Zhang, Weifeng; Wei, Congyuan; Lin, Zuzhang; Liu, Xiaotong; Yu, Gui

doi:10.1002/pola.28976

Cited by 6 publications

(4 citation statements)

References 53 publications

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“…19 The intermediate compound 3 was prepared by using lithium diisopropylamide (LDA) and pinacol borate according to the literature. [12][13][14][15][16][17][18] Finally, the key intermediates 2a-2c were respectively coupled with compound 3 using the Suzuki coupling method with the catalyst Pd(PPh 3 ) 4 to prepare the three target conjugated compounds DPP-BVCNT, DPP-2FBVCNT, and DPP-3FBVCNT. The synthetic routes of the target conjugated compounds and intermediates are shown in Scheme 1.…”

Section: Synthesis and Thermal Propertiesmentioning

confidence: 99%

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Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Wang

et al. 2019

Organic Materials

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Based on diketopyrrolopyrrole (DPP) and (E)-3-phenyl-2-(thiophen-2-yl)acrylonitrile (BVCNT)-linked conjugated backbones, three donor–acceptor type conjugated organic small-molecule compounds DPP-BVCNT, DPP-2FBVCNT, and DPP-3FBVCNT were designed and synthesized. Among them, the 2-decyltetradecyl side chain on the DPP acceptor unit was used to ensure the solubility of the material. The fluorine (F) atoms combined with the nitrile on the BVCNT donor unit were used to adjust electronic structures and charge carrier transport properties of the conjugated system. All the three small molecules exhibited good solution dispersibility and thermal stability, providing an important guarantee for the solution processing and annealing optimization of organic field-effect transistors (OFETs). The top-gate-bottom-contact OFET devices based on these compounds showed good ambipolar or p-type performances. The relationship between molecular structures and OFET performances indicated that the F-substitution and its position significantly affected their charge carrier transport properties. The F-substitution could remarkably change the performance from p-type to ambipolar especially for the outer-side-F-substituted compound DPP-2FBVCNT, which showed the best OFET performances with the maximum hole/electron mobilities of 0.023/0.220 cm2 V−1 s−1. These results provided a promising idea for developing small-molecule OFET materials with good solution processability, good thermal stability, and high ambipolar performances.

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Section: Synthesis and Thermal Propertiesmentioning

confidence: 99%

“…Intermediate compounds 2a-2c and 3 were prepared according to the reported methods. [12][13][14][15][16][17][18][19] General Preparation Method of the Key BVCNT-Based Intermediates (2a-2c)…”

Section: Synthetic Proceduresmentioning

confidence: 99%

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Wang

et al. 2019

Organic Materials

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“…The design, synthesis, and applications of conjugated polymers (CPs) has been the focus of many research groups due to the growing uses for these polymers as biomarkers, , fluorescent sensors, − and semiconductors. − One class of CPs, termed donor–acceptor polymers, is comprised of two monomers, one of which acts as an energy donor and the other as an energy acceptor. Such donor–acceptor polymers have unique photophysical properties that can be targeted for solar cells, , LEDs, , and deep tissue imaging , applications, with the photophysical properties tunable via judicious choice of starting monomers. , Moreover, the morphology of donor–acceptor polymers has significant additional effects on the emission profile, with polymers that are aggregated in thin films or nanoparticles generally having both decreased fluorescence emission and shifts in the emission maxima compared to the nonaggregated, well-solubilized polymer in solution. − …”

Section: Introductionmentioning

confidence: 99%

Effects of Structural Variation in Conjugated Side Chains on the Photophysics of Conjugated Polymers in Nanoparticles

2019

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Conjugated polymers (CPs) are widely used for a variety of applications as a result of their high quantum yields, strong extinction coefficients, and good stability to a variety of experimental conditions. In many cases, the use of conjugated polymer nanoparticles (CPNs) provides additional practical advantages. The ability to understand how the structure of the CP affects its photophysical properties has the potential to significantly accelerate research in this area. In this work we examine 3 CPs, including two novel polymer architectures, and evaluate how the structures of the conjugated side chains affect the photophysical properties of the free polymer chains as well as the properties of aggregated CPNs. Both the linker identity and the terminal aromatic rings of the side chains were found to affect the photophysical properties of the CPs, with the terminal groups leading to the most substantial changes in photophysical properties in all of the polymeric forms (well-solubilized in organic solvent and aggregated in nanoparticles).

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“…Introduction: The design, synthesis, and applications of conjugated polymers (CPs) have been the focus of many research groups due to the growing uses for these polymers as biomarkers, 78,79 fluorescent sensors, 80,81,82 and semiconductors. 83,84,85 One class of CPs, termed donor-acceptor polymers, are comprised of two monomers, one of which acts as an energy donor and the other as an energy acceptor. Such donor-acceptor polymers have unique photophysical properties that can be targeted for solar cells, 86,87 LEDs, 88,89 and deep tissue imaging 90,91 applications, with the photophysical properties tunable via judicious choice of starting monomers.…”

Section: Uv-visible and Fluorescence Emission Spectra Of All Polymersmentioning

confidence: 99%

Synthesis and Characterization of Novel Materials for the Detection and Removal of Toxicants

Jones¹

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The goal of this graduate research has been to develop novel materials for the detection and removal of small molecule toxicants that have been introduced into natural water sources as a result of human industries. Traditional methods for detection of small molecule toxicants rely on laboratory grade equipment, such as gas chromatography (GC), mass spectroscopy (MS), GC-MS, and high-performance liquid chromatography (HPLC). These traditional methods have high sensitivity; however, they suffer from a lack of portability, a high degree of training needed to use them, expensive instrumentation, and extended times for data processing and analysis. To address this problem, several novel conjugated fluorescent polymers have been developed for the rapid detection of multiple small molecule toxicants. Fluorescence as a means of detection was chosen due to the high sensitivity, ease of use, vi AKNOWLEDGEMENTS I would first like to thank my advisor, Dr. Mindy Levine, for all of her help and support throughout my time at URI. Mindy is an excellent scientist, great inspiration, and a dedicated advisor who has helped me learn and grow in ways I had not imagined before starting on my Ph.D. journey. Her "let's do it" attitude and thoughtful insights made her a pleasure and inspiration to work with.

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Dithienylmethanone‐Based Cross‐Conjugated Polymer Semiconductors: Synthesis, Characterization, and Application in Field‐Effect Transistors

Cited by 6 publications

References 53 publications

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Synthesis and Performance of (E)-3-Phenyl-2-(thiophen-2-yl)acrylonitrile-Based Small-Molecule Semiconductors

Effects of Structural Variation in Conjugated Side Chains on the Photophysics of Conjugated Polymers in Nanoparticles

Synthesis and Characterization of Novel Materials for the Detection and Removal of Toxicants

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