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A technology of fluorescent fluoroboron dipyrrole and fluoroboron dipyrrole, which is applied in the directions of organic dyes, azo dyes, luminescent materials, etc., can solve the problems of difficulty, difficulty in laser dyes, and reduction of laser efficiency.
Inactive Publication Date: 2009-10-28
DALIAN UNIV OF TECH
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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.
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Embodiment 1
[0038]
[0039]In a 100mL two-necked bottle, add 0.50mmol of fluoroborate dipyrrole raw material, 3 times the molar amount of N-butylcarbazole aldehyde, and 0.1mmol of piperidine as catalyst, 3 capsules Molecular sieves were ground into powder and added to the system, 20mL o-dichlorobenzene, under the protection of nitrogen, magnetically stirred, kept the system at 120°C, reacted for 8h, passed through a silica gel column, and obtained a blue-purple solid with a yield of 70%, HRMS [M] + : 557.2817(m / z); 1 H-NMR (400Mz, CDCl3): δ=1.36(s, 3H), 1.70(s, 3H), 2.56(s, 3H), 3.4(t, 2H), 5.5(s, 1H), 5.6(s, 1H), 6.84 (d, 2H) 7.21-7.30 (m, 12H).
Embodiment 2
[0041]
[0042] In a 100mL two-necked bottle, add 0.50mmol of fluoroborate dipyrrole raw material, 6 times the molar amount of N-ethylcarbazole aldehyde, and 0.1mmol of piperidine as catalyst, 3 capsules Molecular sieves were ground into powder and added to the system, 20mL of N-methylpyrrolidone, under nitrogen protection, magnetically stirred, kept the system at 120°C, reacted for 16h, passed through a silica gel column, and obtained a dark green solid with a yield of 35%, HRMS [M] + : 780.3926(m / z); 1 H-NMR (400Mz, CDCl 3 ): δ = 1.36 (s, 6H), 1.70-2.54 (m, 15H), 3.4 (m, 4H), 6.84 (d, 4H), 7.21-7.30 (m, 14H).
Embodiment 3
[0044]
[0045] Add 0.50mmol fluoroborate dipyrrole raw material, 3.5 times the molar amount of N-isopropylcarbazole aldehyde, and 0.08mmol piperidine as catalyst in 100mL two-necked bottle, 3 capsules Molecular sieves were ground into powder and added to the system, 15mL of chlorobenzene, under the protection of nitrogen, magnetically stirred, kept the system at 130°C, reacted for 12h, passed through a silica gel column, and obtained a blue-purple solid with a yield of 65%, HRMS [M] + : 671.3491(m / z) 1 H-NMR (400Mz, CDCl 3 ): δ=1.36(s, 3H), 1.70(s, 3H), 1.85(t, 6H), 2.56(s, 3H), 3.4(m, 1H), 6.84(d, 2H) 7.21-7.30(m , 11H), 9.56 (s, 1H).
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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 ...
Claims
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