Benzophenothiazine derivative and preparation method thereof
A technology of benzophenothiazine and derivatives, which is applied in the field of organic photoelectric functional materials, can solve the problems of resource scarcity, limited development and application, and high price, and achieve the goal of broadening the spectral response range, improving charge transfer, and low production cost. Effect
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[0038] Example 1:
[0039]
[0040] Synthetic route is shown below:
[0041]
[0042] 2-Amino-benzenethiol (0.75g, 6mmol) and 1-tetralone (0.584g, 4mmol), a mixed solution (16.0 mL) is stirred for 24 hours in air in DMSO at 110 ℃. After completion, the reaction mixture was diluted with ethyl acetate (64.0mL), and filtered. The volatiles were removed in vacuo to give the crude product. Further column chromatography on silica gel (EtOAc / petroleum ether) to obtain separated and purified 1-benzo phenothiazine. Yield: 87%. 1 H NMR (400MHz, Chloroform-d) δ9.58 (s, 2H), 7.89-7.80 (m, 2H), 7.76-7.69 (m, 2H), 7.64 (dd, J = 7.4,1.5Hz, 2H), 7.53-7.42 (m, 4H), 7.29 (dd, J = 7.4,0.5Hz, 2H), 7.19-7.15 (m, 1H), 7.15-7.01 (m, 7H).
[0043]
[0044] Benzo phenothiazine was added in a round bottom flask 1 (1.246g, 5mmo1), 4- bromoxynil (1.092g, 6mmo1), sodium tert-butoxide (2.76g, 15mmo1), tris (dibenzylideneacetone) dipalladium dipalladium (92mg, 0.1mmo1), tri-tert-butylphosphine tetrafluo...
Example Embodiment
[0045] Example 2:
[0046]
[0047] Synthetic route is shown below:
[0048]
[0049]2-Amino-benzenethiol (0.75g, 6mmol) and 1-tetralone (0.584g, 4mmol), a mixed solution (16.0 mL) is stirred for 24 hours in air in DMSO at 110 ℃. After completion, the reaction mixture was diluted with ethyl acetate (64.0mL), and filtered. The volatiles were removed in vacuo to give the crude product. Further column chromatography on silica gel (EtOAc / petroleum ether) to obtain separated and purified 1-benzo phenothiazine. Yield: 87%. 1 H NMR (400MHz, Chloroform-d) δ9.58 (s, 2H), 7.89-7.80 (m, 2H), 7.76-7.69 (m, 2H), 7.64 (dd, J = 7.4,1.5Hz, 2H), 7.53-7.42 (m, 4H), 7.29 (dd, J = 7.4,0.5Hz, 2H), 7.19-7.15 (m, 1H), 7.15-7.01 (m, 7H).
[0050]
[0051] Benzo phenothiazine was added 1 (1.246g, 5mmo1) in a round bottom flask (4-bromophenyl) [bis (2,4,6-trimethylphenyl)] borane (2.424g, 6mmo1) , sodium tert-butoxide (2.76g, 15mmo1), tris (dibenzylideneacetone) dipalladium (92mg, 0.1mmo1), tri-ter...
Example Embodiment
[0052] Example 3:
[0053]
[0054] Synthetic route is shown below:
[0055]
[0056] 2-Amino-benzenethiol (0.75g, 6mmol) and 1-tetralone (0.584g, 4mmol), a mixed solution (16.0 mL) is stirred for 24 hours in air in DMSO at 110 ℃. After completion, the reaction mixture was diluted with ethyl acetate (64.0mL), and filtered. The volatiles were removed in vacuo to give the crude product. Further column chromatography on silica gel (EtOAc / petroleum ether) to obtain separated and purified 1-benzo phenothiazine. Yield: 87%. 1 H NMR (400MHz, Chloroform-d) δ9.58 (s, 2H), 7.89-7.80 (m, 2H), 7.76-7.69 (m, 2H), 7.64 (dd, J = 7.4,1.5Hz, 2H), 7.53-7.42 (m, 4H), 7.29 (dd, J = 7.4,0.5Hz, 2H), 7.19-7.15 (m, 1H), 7.15-7.01 (m, 7H).
[0057]
[0058] Benzo phenothiazine was added in a round bottom flask 1 (1.246g, 5mmo1), 5- bromo-1,3-isophthalonitrile (1.246g, 6mmo1), sodium tert-butoxide (2.76g, 15mmo1), tris ( dibenzylideneacetone) dipalladium (92mg, 0.1mmo1), tri-tert-butylphosphine tet...
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