Synthesis And Photophysical Property Of Tripod BODIPY Fluorescent Compounds Bearing Carboxyl Group

During the past two decade, Boron dipyrromethene dyes(BODIPY) have got rapid development. Because they have many excellent properties, such as stable optical properties, higher fluorescence quantum yields etc. Many detection means have been applied to the research of modern biotechnology and life sciences, such as good sensitivity, low detectability and good selectivity. One kind of novel tripod BODIPY fluorescent dye containing ester group was synthesized from an aldehyde-containing intermediate prepared via stepwise nucleophilic substitution of cyanuric chloride. Afterwards, we got a new dye with carboxyl group by means of catalytic hydrogenolysis. All the four compounds haven’t been reported so far and were characterized by HRMS, 1H NMR, 13 C NMR, and IR.First, the appropriate reaction conditions were found through exploring the transformation from ester to carboxyl group and the results were showed as follow:(1) It failed to get the target dye via hydrolysis of methyl ester under basic conditions.(2) Benzyl ester group was introduced and the target dye containing carboxyl group was successfully generated via the palladium-carbon catalytic hydrogenolysis.(3) The stability of the tripod structure was explored under the palladium-carbon catalytic hydrogenolysis.(4) The conditions of catalytic transfer hydrogenolysis were explored under the palladium-carbon.Second, the UV-Vis and fluorescence spectra of the two dyes containing benzyl ester and carboxyl group obtained in this paper were showed as follow:(1) The maximum absorption wavelength of the two kinds of dyes were identical. The maximum absorption wavelength in methylene chloride was 501 nm.(2) High molar extinction coefficient and fluorescence quantum yields were received respectively from the two kinds of fluorescent dyes.