The Research On Synthetic Methodology And Spectral Properties Based On BODIPY Dyes

Organic optical materials are hence suitable for use in many fields, for example, photolumicescence and electroluminescence, which have attracted considerable attentions. In the last decades, boron dipyrromethene dyes (BODIPY) have draw much attention of the researchers for their exceptional photochemistry and photophysical properties. In this paper, new series of BODIPY dyes have been synthesized and identified. The optical and electrochemistry properties have been studied to explore the applications of these compouds in fluorescent sensing and optical functional materials (electroluminescent materials, two-photon absorption activity materials and laser dyes).1. The new fluorophores were synthesized by Suzuki coupling recation onβ-position of the BODIPY core. Compounds 6a and 6b were designed for detecting proton based on PET (Photoinduced Electron Transfer) mechanism. The electron transfer processes were proved by crystal data and electrochemistry research. Compounds 7 and 8 contained conjugated double bonds, which resulted in the notable long maximum absorption wavelength, the fluorescence emission wavelength, and the large Stokes shift (more than 80 nm).2. Four novel fluorescent dyes were obtained by introducing conjugated groups onβ-position of the BODIPY through Sonogashira coupling reaction. Systemic research on the compounds was carried out, and compound T2 was used as the reference compound because of its simple structure. Compounds T3 and T4 were two D-π-D type two-photon activity materials with long absorption and emission wavelengths (650 nm), also with good linear optical properties. The preliminary fluorescence imaging experiments indicated their cell-permeability and nontoxicity. This suggested that the novel BODIPY dyes were highly applicable as fluorescent reporters, particularly in assays which were based on two-photon excited fluorescence. Compound T5, bulky 4-tritylphenylethynyl substituted BODIPY with pure red emission, relatively large Stokes shift, high fluorescence quantum yield, less self-quenching was efficiently synthesized. The electroluminescent properties were also preliminary investigated.3. Compounds K1-K8 were synthesized by introducing conjugated groups on a-position of BODIPY through Knoevenagel reaction. Contrastive research was carried on K1-K5 in detail. Through comparison and combination of two strategies, extension ofπ-conjugation and adjustment of ICT effects, we obtained a new carbazole-containing BODIPY derivative K5 which was an excellent fluorophore with relatively long emission, large molar extinction coefficient, narrow spectra shapes, high fluorescence quantum yields in polar and apolar solvents. These advantageous characteristics together with the laser properties make it potentially useful as a new biological tool. K6 and K7 were two red emission laser dyes with excellent luminescent yields and photostabilities, which can compete with the commercial dyes in red region. Compound K8 was a good NIR fluorescent dye with maximum absorption at 675 nm, fluorescence emission at 700 nm and fluorescence quantum yield 0.7 in polar solvents.4. Compounds E1 and E2 were obtained by simple and convenient methods which designed based on fluorescence resonance energy transfer mechanism, and BODIPY acted as the energy donor. The optical and laser properties were investigated. Comparing reference compound T2 and E1, excited by different lamps (500 nm,532 nm and 570 nm), it also proved the FRET process in E1. It provided a route to novel laser dyes.