Strong-fluorescence boron dipyrromethene dye containing carbazole structure

Abstract

The invention belongs to strong-fluorescence boron dipyrromethene dyes containing a carbazole structure in the technical field of organic chemical industry and fine chemical industry. Because a method for preparing the strong-fluorescence boron dipyrromethene dye containing the carbazole structure and derivatives thereof adopts boron dipyrromethene and carbazole aldehyde with substituent as raw materials, the molar ratio of the boron dipyrromethene to the carbazole aldehyde is 1:2-5, piperidine is a catalyst, a 4-angstrom molecular sieve is a dehydrating agent, and the molar ratio of the borondipyrromethene to the catalyst is 1:0.01-0.20; in an organic solvent, at the temperature of between 100 and 150 DEG C and under the protection of argon or nitrogen, the mixture reacts for 8 to 50 hours by stirring, the carbazole aldehyde and the active methylene of the boron dipyrromethene are dehydrated to generate the boron dipyrromethene derivatives; and after the carbazole structure with different substituents is introduced into the boron dipyrromethene, the optical property of the boron dipyrromethene compound is changed, the red shift of the absorption spectrum thereof is 80 nanometers, the red shift of the emission spectrum is 90 nanometers, higher fluorescence quantum yield is kept at 0.67, the laser efficiency reaches more than 30 percent, and the strong-fluorescence boron dipyrromethene derivatives containing the carbazole structure are obtained.

Description

technical field [0001] The invention relates to a preparation method of a class of strong fluorescent fluoroboron dipyrrole dyes containing a carbazole structure and derivatives thereof, and belongs to the technical fields of organic chemical industry and fine chemical industry. Background technique [0002] Fluoroboron dipyrrole dyes are a kind of commonly used dye precursors, and their basic structure is shown in the figure below. [0003] [0004] It is a very important compound in organic dyes. At the same time, the large π-π conjugated system in its molecular structure endows it with excellent fluorescence and photoelectric properties, such as high molar extinction coefficient, high quantum yield, and better Photochemical stability and other properties make its derivatives have applications in biological probes, solar cells, lasers and other fields. Especially in the application of laser dyes, the dominant position of fluoroboron dipyrrole dyes has been established ...

AI Technical Summary

Problems solved by technology

However, it is difficult to obtain high-efficiency laser dyes with excellent optical properties and moderate wavelengths. The main problem is that the yield of target compounds is not high, and the laser efficiency is low. Therefore, many scientists still study, for example: R.Sastre from Spain Adv.Funct.Mater.2007, 3088-3098 published by et al. in 2007 and J.Photochem.and Photobiol.A:Chem.2008, 192-197 published in 2008

But there are few reports about fluoroboron dipyrrole dyes as red laser dyes

The reason is that there are few fluoroboron-dipyrrole dyes that emit red light, and the general synthesis is relatively complicated. More importantly, the luminous efficiency is not high, resulting in a decrease in laser efficiency, and it is difficult to become a commercial laser dye.

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