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Chlorination <i>vs.</i> fluorination: a study of halogenated benzo[ <i>c</i> ][1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging
摘要： Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor-acceptor (D-A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are designed and synthesized. The photophysical, theoretical calculations, and electrochemical properties explored in this study have proved that the introducing of chlorine atoms will lead to a lower HOMO level, stronger steric hindrance, and a relative lower quantum yield in solutions. When the organic dots are fabricated, the chlorinated dots demonstrate much higher fluorescence quantum yield, larger Stokes shift, and better photostability than that of the fluorinated dots. After labeling A549 cells, all the chlorinated/fluorinated dots exhibit high red emission intensities. All these results indicated that the subtle change in the halogen atom of the benzo[c][1,2,5]thiadiazole unit is a unique method to tune the photophysical properties of those materials, which also provides good guidelines to design highly efficient red/near-infrared molecules for cellular imaging applications.
关键词： 5]thiadiazole,organic semiconducting dots,chlorination,benzo[c][1,fluorination,near-infrared cellular imaging,2
更新于2025-09-23 15:19:57
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[IEEE 2018 4th IEEE International Conference on Emerging Electronics (ICEE) - Bengaluru, India (2018.12.17-2018.12.19)] 2018 4th IEEE International Conference on Emerging Electronics (ICEE) - Effect of Fluorination on the D-A-D type Hole Transporting Materials for Perovskite Solar Cells
摘要： To study the effect of fluorination on hole transporting materials (BTD-Th and BTD-F-Th) for the efficient perovskite solar cells, we designed and synthesized a novel D-A-D type hole transporting molecule having benzo[1,2-c][1,2,5]thiadiazole (BTD) as electron acceptor unit and thiophene (Th) as a simple electron donor unit. The D-A-D molecules BTD-Th and BTD-F-Th were synthesized by palladium(0) catalyzed Stille coupling reaction. The electrochemical band gap of synthesized compounds varies from -1.5 eV to -1.7 eV, Which were ideal for hole transport material (with perovskite active layer) and effective electron blocking layer. The architecture of the perovskite device is glass/ITO/SnO2/CH3NH3PbI3(Perovskite)/Hole Transport Material/Ag.
关键词： Perovskite,benzo[1,2-c][1,2,5]thiadiazole,thiophene,hole transporting materials
更新于2025-09-16 10:30:52
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Synthesis of new simple hole-transport materials bearing benzodithiazole based core for perovskite solar cells
摘要： Benzo[c][1,2,5]thiadiazole(BT) core-based novel organic hole-transport materials (HTMs) BTT-PMe and BTT-2F are successfully synthesized for perovskite solar cells. The new HTMs are prepared by the simpler synthetic route with cost-effective purification steps. These HTMs are structurally confirmed by NMR, FT-IR and mass spectroscopy. The optical parameters are analysed using the UV–Vis spectrophotometer and cyclic voltammetry. To further confirmation of these properties we conducted the theoretical studies, which are fully matched with the experimental data. We have studied the effect of fluorine atom for its photo physical properties.
关键词： Photophysical properties,Perovskite solar cells,Benzo[c][1,2,5]thiadiazole,Hole-transport materials (HTMs)
更新于2025-09-12 10:27:22
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New Class of Supramolecular Bowl-Shaped Columnar Mesogens Derived from Thiacalix[4]arene Exhibiting Gelation and Organic Light-Emitting Diodes Applications
摘要： A new class of blue light-emitting bowl-shaped mesogens with the thiacalix[4]arene core appended with 1,3,4-thiadiazole derivatives having peripheral alkoxy side chains have been synthesized and well characterized. The liquid crystalline behavior of present synthesized derivatives was examined by optical polarizing microscopy, di?erential scanning calorimetry, and X-ray di?raction studies. It was observed that these thiacalix[4]arene derivatives were capable of stabilizing the observed Colh phase with a higher temperature range. The cone-shaped thiacalix[4]-arene-based liquid crystals with peripheral alkoxy side chains able to pack into the interactions and thermal behavior. All derivatives showed blue luminescence in solution, solid thin-?lm, and gelation state. The hexagonal columnar phase and emissive nature of thiadiazole-based thiacalixarene compounds having xerogel behavior make them favorable in the application of emissive electronic display devices. The electrochemical properties of these thiacalixarene-based compounds demonstrate the e?ect of alkyl side chain on the highest occupied molecular orbital?lowest unoccupied molecular orbital energy levels and also exhibited lower electron band gaps. The electroluminescence behavior of the compound 10c was examined as emissive layers in the fabrication of organic light-emitting diodes.
关键词： thiacalix[4]arene,bowl-shaped mesogens,blue light-emitting,organic light-emitting diodes,1,3,4-thiadiazole derivatives,liquid crystalline behavior
更新于2025-09-12 10:27:22