Naphthindole계 Cyanine 염료의 합성 및 응용에 관한 연구

Abstract

Functional cyanine dyes have been widely applied to display material, organic photo conductor material and laser material and being actively applied to various fields, such as information record, organic solar cell and counterfeit material in recent. The functional dyes, which is suitable for photo conductor material, are diphenylmethine, methine, polymethine, porphyrine, quinone, ditol, cyanine, which have strong nonlinear tendency. Photo conductor material should be great in selective absorption capacity according to the radiation of laser light source. As the characteristics, which should be possessed by organic dye compounds, for this use, optical property, light resistance in the short wavelength of visible light zone and solubility in solvents should be good. And it gives optical characteristic controls selective wavelength by service. This study is for synthesis and physical properties of cyanine dye, which gives no effect to visible light transmittance and which can absorbs specific wavelength for using on information recording material and plasma display panel material. Cyanine dyes are researched widely as functional dyes. Especially, indole cyanine dyes are expected from their superior solubility and their strong absorption in various wavelengths. Cyanine dyes have relatively good stability, high molar absorption coefficients (～10^(-5) M^(-1) cm^(-1)), medium fluorescence intensity, narrow spectrum width and the ability to form H- or J-aggregate. The maximium absorption wavelength of cyanine can be tuned precisely from near-UV to near-IR by chemical structural modification. With these unique photo physical and photo chemical properties, cyanine dyes are recently being used in many applications such as nonlinear optics, optical data storage, biomolecular labeling, dye laser, photo refractive materials and photo dynamic therapy. Therefore, this study was carried out to research the spectroscopic properties of functional cyanine dyes which lead to change middle-chain, indole and N-terminal group. And then, the synthesized cyanine dyes were studied thermal property as ^(-)I. The spectroscopic properties of sixteen cyanine dyes were measured with UV/VIS/NIR spectrometer (Shimadzu 3150PC) for characters of half band width, maximum absorption wavelength and shape of wavelength. In addition, differential scanning calorimeter was employed to measure durability for heating the results were as follows. These cyanine dyes bearing with three kind of methine, five methine and four indole synthesized in above 60%, respectively. Synthesized cyanine dyes represented maximum absorption wavelength at near 546.5～820nm and had molar extinction coefficient above 7×10⁴. The maximum absorption wavelength was red shift about 100nm with the increase of two methine groups such as CAD-1(546.5nm), CAD-5(642nm). The other hand, half band width of cyanine dyes decreased according to increase middle chains ; CAD-1(52nm), CAD-5(38nm). Cyanine dye bearing with methyl 4-methylbenzoate at N-terminal group showed the best melting point ; CAD-4, CAD-8, CAD-12, CAD-16, CAD-20 and CAD-24.