Synthesis of Some Fluorescent Dyes Based on Stilbene Derivatives with Various Substituents and Their Effects on the Absorption Maxima

The six stilbene-based dyes containing benzoxazole substituents to improve solubility of dyes as well as the efficiency of fluorescence at blue emission were synthesized. In this work, absorption and fluorescent properties of the synthesized dyes were investigated. For the derivatization of benzoxazolyl stilbene dye, -NO2 and -NH2 groups were introduced in sequence onto benzoxazolyl rings. The emission maxima of the six dyes prepared were observed in the range of 435 nm~471 nm. In addition, the solubility of the dyes in dichloromethane was examined for application to the nonpolar polymer films such as PE, PP, PVC and so on. N-alkyl groups were determined to have a greater solubility of alkylated stilbene-based dyes than analogue containing and unsubstituted group. Furthermore, investigation of the optical effects of tortional strain according to conformation of side group was also performed. For identifying these properties, the geometry, dihedral angle, and other parameters of synthesized dyes were calculated by the density functional theory and time-dependent function using a gaussian 09 program.