1, 5, 9-triazanaphthalene coronene compound and synthetic method thereof
A compound, a technology of heterocones, applied in the field of polycyclic aromatic hydrocarbons and their preparation, can solve the problems of unfavorable conjugated system derivative expansion, harsh conditions, rare raw materials, etc., and achieve good thermal stability and chemical stability, and reaction conditions. Mild effect with little environmental pollution
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Embodiment 2
[0042] Example 2: Taking the synthesis of 4,8,12-tri-(p-methylphenyl)-1,5,9-triazepine as an example, its structural formula is as follows:
[0043]
[0044] The raw materials used and the synthesis method are:
[0045] In step 3 of this embodiment, benzoyl chloride is replaced with equimolar p-toluyl chloride, and the other steps of this step are the same as in Example 1. The other steps are the same as in Example 1, and the yellow solid 4,8,12-tri-(p-methylphenyl)-1,5,9-triazepine is prepared with a yield of 73% and a melting point of: > 300 o c.
[0046] The spectral data of the resulting product are as follows: 1 H NMR (500 MHz, CDCl 3 : CF 3 COOD = 0.5 mL : 10 μL): δ 9.64 (d, J = 9.1 Hz, 3H), 9.58 (d, J = 9.1 Hz, 3H), 8.12 (d, J = 7.7 Hz, 6H), 7.70 (d, J = 7.65 Hz, 6H), 2.66 (s, 9H). 13 C NMR (125 MHz, CDCl 3 : CF 3 COOD = 0.5 mL : 10 μL): δ 163.5, 144.0, 141.0, 133.4, 131.7, 130.7, 130.0, 127.3, 126.1, 121.1, 115.1, 21.9. HRMS: m / z calcd for C 4...
Embodiment 3
[0047] Example 3: Taking the synthesis of 4,8,12-tri-(p-methoxyphenyl)-1,5,9-triazepine as an example, its structural formula is as follows:
[0048]
[0049] The raw materials used and the synthesis method are:
[0050] In step 3 of this embodiment, benzoyl chloride is replaced with equimolar p-methoxybenzoyl chloride, and other steps of this step are the same as in embodiment 1. The other steps are the same as in Example 1, and a yellow solid 4,8,12-tri-(p-methoxyphenyl)-1,5,9-triazepine is prepared with a yield of 67% and a melting point of :> 300 o c.
[0051] The spectral data of the resulting product are as follows:
[0052] 1 H NMR (500 MHz, CF 3 COOD): δ 9.82 (d, J = 9.1 Hz, 3H), 9.58 (d, J = 9.1 Hz, 3H), 8.27 (d, J = 8.2 Hz, 6H), 7.49 (d, J = 8.3 Hz, 6H), 4.06 (s, 9H). 13 C NMR (125 MHz, CDCl 3 : CF 3 COOD = 0.5 mL : 0.1 mL): δ 166.5, 164.0, 138.6, 136.9, 134.9, 128.6, 123.8, 121.8, 121.0, 117.0, 115.4, 56.4.
[0053] HRMS: m / z calcd for...
Embodiment 4
[0054] Example 4: Taking the synthesis of 4,8,12-tri-(p-chlorophenyl)-1,5,9-triazepine as an example, its structural formula is as follows:
[0055]
[0056] The raw materials used and the synthesis method are:
[0057] In step 3 of this embodiment, benzoyl chloride is replaced with equimolar p-chlorobenzoyl chloride, and in step 4, it is washed with dichloromethane, and other steps of this step are the same as in embodiment 1. The other steps were the same as in Example 1, and the khaki solid 4,8,12-tri-(p-chlorophenyl)-1,5,9-triazepine was prepared with a yield of 74% and a melting point of: > 300 o c.
[0058] The spectral data of the resulting product are as follows: 1 H NMR (500 MHz, CDCl 3 : CF 3 COOD = 0.4 mL : 30 μL): δ 9.73 (d, J = 8.8 Hz, 3H), 9.69 (d, J = 8.6 Hz, 3H), 8.17 (d, J = 7.5 Hz, 6H), 7.70 (d, J = 7.7 Hz, 6H). 13 C NMR (125 MHz, CDCl 3 : CF 3 COOD = 0.6 mL : 40 μL): δ 163.0, 141.7, 139.6, 134.8, 132.8, 130.7, 128.5, 127.6, 125.2, ...
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