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Phenoxy-benzothiadiazole dyes: Synthesis, photophysical properties and preliminary application in OLEDs

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Abstract The synthesis of a phenoxy-benzothiadiazole (BTD) derivative is reported for the first time. This derivative was employed as an intermediate in the obtention of two novel highly fluorescent aryl-phenoxy-BTD… Click to show full abstract

Abstract The synthesis of a phenoxy-benzothiadiazole (BTD) derivative is reported for the first time. This derivative was employed as an intermediate in the obtention of two novel highly fluorescent aryl-phenoxy-BTD dyes. Their photophysical properties were evaluated in solution and the results indicate a strong intramolecular charge transfer (ICT) character in the excited state. The luminophore 3a , possessing a donor-BTD-phenoxide architecture, exhibits superior fluorescence quantum yield (0.67) than the designed acceptor-BTD-phenoxide dye (0.06). After electrochemical and photoluminescence characterization of thin films of 3a , an OLED with the configuration ITO/PEDOT:PSS/ 3a /TPBi/LiF/Al was constructed. This device displayed a green emission centered at 547 nm, with CIE coordinates of (0.40, 0.55). For comparison, an OLED using a previously reported luminescent BTD-pyridyl derivative was also constructed. The OLED made with the phenoxy-BTD derivative operated using less current density and led to higher irradiance and electrical stability, indicating the high potential of ArO-BTD dyes for future application in electroluminescent devices.

Keywords: phenoxy benzothiadiazole; benzothiadiazole dyes; dyes synthesis; application; btd; photophysical properties

Journal Title: Tetrahedron Letters
Year Published: 2018

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