3-Octadecyl-2-[3-(3-octadecyl-2(3H)-benzoxazolylmethylidene)-1-propen-1-yl]benzoxazole perchlorate is a synthetic organic compound known for its unique photophysical properties. This compound, often abbreviated for convenience, was developed through efforts to create new organic dyes with enhanced optical properties for use in electronic and optoelectronic applications. Its discovery was part of a broader study of benzoxazolyl salts, which are known for their conjugated systems that impart desirable electronic properties.
The synthesis of 3-octadecyl-2-[3-(3-octadecyl-2(3H)-benzoxazolidin-1-yl)-1-propen-1-yl]benzoxazole perchlorate involves multiple steps: the benzoxazole core is formed by condensation of 2-aminophenol with a suitable aldehyde or acid; the octadecyl group is introduced by alkylation, usually using an octadecyl halide, to form a long aliphatic chain connected to the benzoxazole ring; the two benzoxazole units are connected by a propenylidene bridge to form a conjugated system, which enhances the electronic and optical properties of the compound; the last step is to convert the benzoxazole intermediate into the perchlorate form by reaction with perchloric acid, which enhances the solubility and stability of the compound in various solvents.
The compound exhibits strong absorption and fluorescence in the visible and near-infrared regions. Its extended conjugated system allows for high molar absorption coefficients and fluorescence quantum yields, making it suitable for optical applications. The perchlorate form has enhanced stability compared to other counterions, allowing the compound to retain its properties under various environmental conditions. The long octadecyl chain increases the compound's solubility in nonpolar solvents, facilitating its incorporation into organic materials and devices.
The main application of this benzoxazole salt is in organic electronics, including organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs). Its excellent photophysical properties make it an effective component in these devices, improving their efficiency and performance. In OLEDs, the compound is used as a fluorescent dye, which enables high brightness and color purity. Its ability to emit in the near-infrared region also makes it suitable for applications in communications and night vision technology. In OPVs, it acts as a light-absorbing material, which helps in the efficient conversion of light into electrical energy. Its broad absorption spectrum allows for better utilization of the solar spectrum. The stable electronic properties of the compound make it a candidate material for OFETs, which can enhance the charge transport properties of the organic semiconductor layer.
The strong fluorescence of 3-octadecyl-2-[3-(3-octadecyl-2(3H)-benzoxazolidin-1-yl)-1-propen-1-yl]benzoxazole perchlorate makes it useful in the development of fluorescent sensors. These sensors can detect a variety of analytes, including metal ions and biomolecules, through changes in fluorescence intensity or wavelength.
In bioimaging, the compound's near-infrared fluorescence enables deeper tissue penetration and reduces background interference, making it useful for imaging applications in biological systems.
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