Compound of substituted benzo heterocyclic by electrophosphorescence and luminous ligand thereof
A technology of electrophosphorescence and compounds, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc.
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Embodiment 1
[0014] Synthesis of 4-Benzothiazolyl-2-(N,N-Dimethyl)aniline
[0015]
[0016] In the flask, add 2.0 g of 4-dimethylaminobenzaldehyde, 3 ml of o-aminothiophenol, and 15 ml of methanol:benzene=1:2 mixed solution. After stirring, the reaction system was a dark brown-red transparent solution. After reacting at room temperature for 36h, a yellow precipitate was formed. Suction filtration, rinse the filter cake with methanol. Recrystallized from acetone to obtain light yellow needle-like crystals. Suction filtration and drying, the weight is 1.95g, the yield is 51%, and the melting point is 157-159°C.
[0017] 1 H-NMR (CDCl 3 ): 3.06(s, 6H), 6.75(d, J=8.88Hz, 2H), 7.31(t, J=0.8Hz, J=0.86Hz, 1H), 7.44(t, J=0.96Hz, J=0.93 Hz, 1H), 7.84 (d, J = 7.89 Hz, 1H), 7.97 (d, 2H), 7.99 (d, 1H). EI m / e: 254 (100%).
[0018] The maximum ultraviolet-visible absorption wavelength is 356nm (tetrahydrofuran solution), and the logε is 4.66. Blue fluorescence, the maximum fluorescence emiss...
Embodiment 2
[0020] Synthesis of 4-Benzothiazolyl-2-[N,N-bis(4-methyl)phenyl]aniline
[0021]
[0022] In the flask, add 1.0g 4-(2-p-methylphenyl)aminobenzaldehyde, 0.5g o-aminothiophenol, 15ml methanol: benzene=1:2 mixed solution, stir, the reaction system is light yellow transparent solution . Reaction at room temperature for 72h. The solvent was evaporated by rotary evaporation, and the product (dark yellow solid) was obtained after separation by column chromatography. Drying, the weight is 0.76g, the yield is 57%, and the melting point is 135-139°C.
[0023] 1 H-NMR (CDCl 3 ): 2.34(s, 6H), 7.03(d, J=8.64Hz, 2H), 7.06(d, J=8.24Hz, 4H), 7.12(d, J=8.15Hz, 4H), 7.33(t, 1H ), 7.45 (t, 1H), 7.86 (d, 1H), 7.88 (d, J = 8.8 Hz, 2H), 8.00 (d, 1H). EI m / e: 406 (100%).
[0024] The maximum ultraviolet-visible absorption wavelength is 379nm (tetrahydrofuran solution), and the logε is 3.82. Blue fluorescence, the maximum fluorescence emission wavelength is 476nm.
Embodiment 3
[0026] Synthesis of 4-Benzothiazolyl-2-(N,N-diphenyl)aniline
[0027]
[0028] In the flask, add 0.5g of 4-diphenylaminobenzaldehyde, 0.2g of o-aminothiophenol, and 15ml of a mixed solution of methanol:benzene=1:2, and stir at room temperature. The reaction system is a brownish-yellow transparent solution. Reaction 48h. The solvent was evaporated by rotary evaporation, and the product was separated by column chromatography to obtain a yellow flaky solid. Drying, the weight is 0.24g, the yield is 43%, and the melting point is 124-126°C.
[0029] 1 H-NMR (CDCl 3 ): 7.11(d, J=8.58Hz, 2H), 7.12(t, 2H), 7.17(d, J=7.68Hz, 4H), 7.31(t, 4H), 7.34(t, 1H), 7.46(t , 1H), 7.87 (d, J=7.88 Hz, 1H), 7.92 (d, 2H), 8.02 (d, J=8.13 Hz, 1H). EI m / e: 378 (100%).
[0030] The maximum ultraviolet-visible absorption wavelength is 372nm (tetrahydrofuran solution), and the logε is 3.80. Blue fluorescence, the maximum fluorescence emission wavelength is 456nm.
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