Synthesis Characterrization And Properties Of New Aza-Bodipy Fluorescent Dyes

Aza-BODIPY fluorescent dyes, which are a new fluorescent compounds emerged in recent years and had excellent photophysical properties, such as long maximum absorption and emission wavelengths, high quantum yields, high absorpt-ion extinction coefficients, sharp fluorescence emission characteristics, high photostability, etc. It's a potentially useful photosensitizer for photodynamic therapy.In this thesis, ten new aza-BODIPY fluorescent dyes 1a~1j were synthesized, including five new aza-BODIPY fluorescent dyes 1a~1e and five new ferrocene aza-BODIPY dyes 1f~1j. The aza-BODIPY dyes were synthesized in four steps. Condensation of aryl-ethylketone and formald- ehyde afforded chalcones 2a~2j in 65~94% yields, then Michael addition with nitromethane gave the 1-phenyl-3-aryl-4-nitro-butanone 3a~3j in 70~81% yields, condensation with ammonium acetate afforded the aza- dipyrromethene 4a~4j in 24~41% yields, finally, complexation with boron trifluoride gave dyes 1a-1j in 63~90% yields. All the new compo- unds had been identified by IR, 1~H-NMR, (13)~C-NMR, MS and Elemental analysis techniques. We also optimized it's reaction conditions. The spectra of UV absorption and fluorescence emission of 1a~1j had been studied. A conclusion can be drawn that aza-BODIPY fluorescent dyes 1a~1e have high molar extinction coefficient, their maximum UV absorption wavelength and fluorescence emission wavelength would red-shift when the electron-donating group onto the para-position of the aryl rings locating 3,5 or 1,7 positions in the aza-BODIPY core. The introduction of ferrocene to aza-BODIPY core cause the UV absorption spectrum shows two strong absorption peak in 600~700nm and 800~900nm. But the fluorescence emission spectra without emission peak between 0~900nm. At the same time, elctrochemical properties of 1a~1d had been tested, and their structural stability was discussed by oxidation potential of CV. the electrochemical data showed that, substituent of the para-position of the aryl rings locating 3,5 or 1,7 positions in the aza-BODIPY core have a greater impact to the oxidation potential, electron-donating group will reduce the oxidation potential, and electron withdrawing group will increase the redox potential of the dyes which result in a better stability in turn. the ferrocene aza-BODIPY fluorescent dyes show no oxidation peak, indicating that these dyes more difficult to be oxidized.