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Bis-benzotriazole containing organic dyestuff with super thermal stability
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A technology of benzotriazole and organic dyes, which is applied in the fields of acetophenone-based hydroxyketone dyes and organic chemistry, and can solve problems such as easy breakage of chemical bonds
Inactive Publication Date: 2017-01-11
CHONGQING UNIV
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Because the chemical bonds of organic molecules are easy to break, it is difficult for organic materials to exist stably at 400°C, so there are not many organic small molecule materials with a thermal decomposition temperature of 400°C or above.
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[0017] 1-[3-(2H-Benzotriazol-2-yl)-4-hydroxyphenyl]ethanone (0.20mmol, 0.120g), and terephthalaldehyde (0.10mmol, 0.013g) in a three-necked flask Mix in 15mL ethanol as a solvent, 80 ~ 90 ℃ magnetic stirring for 20 hours to end the reaction, suction filtration, ethanol washing, vacuum drying, to obtain the target product, yield 76%, its 1 The H NMR spectrum is as figure 1 . 1 H-NMR (CDCl 3 ,400MHZ)δ(ppm):11.469(s,2H,-OH),8.599-8.596(t,J=1.2Hz,2H,Ar-H),8.307-8.289(m,2H,Ar-H),8.078 -8.045(m,7H,Ar-H),7.958(s,J=12.4Hz,3H,Ar-H),7.788-7.762(d,J=10.4Hz,2H,Ar-H),7.551-7.535( m, 4H, -CH=CH-), 7.304-7.289 (d, J=6Hz, 2H, Ar-H).
[0020] 1-[3-(2H-Benzotriazol-2-yl)-4-hydroxyphenyl]ethanone (0.20mmol, 0.120g), and o-phthalaldehyde (0.10mmol, 0.013g) in a three-necked flask mixed with 15 mL of ethanol as a solvent, stirred magnetically at 80-90°C for 20 hours, then ended the reaction, filtered with suction, washed with ethanol, and dried in vacuo to obtain the target product with a yield of 68%. 1 The H NMR spectrum is as figure 2 . 1 H-NMR (CDCl 3 ,400MHZ)δ(ppm):11.472(s,2H,-OH),8.584(s,2H,Ar-H),8.303-8.288(s,J=6Hz,2H,Ar-H),8.078-8.045( m,6H,Ar-H),7.958(s,4H,Ar-H),7.787-7.761(d,J=10.4Hz,2H,Ar-H),7.550-7.535(m,4H,-CH=CH -), 7.300-7.286 (d, J=5.6Hz, 2H, Ar-H).
Embodiment 3
[0022] For sample (2E,2'E)-3,3'-benzene-1,4-diylbis{1-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]propane -2-en-1-one} for thermogravimetric analysis, the parameters are: temperature range 0 ~ 600 ° C, heating rate 10 ° C / min. After the test is completed, the thermogravimetric map 3 is obtained. The thermal decomposition temperature is 407.35°C, indicating that it is a dye molecule with excellent thermal stability.
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Abstract
The invention discloses bis-benzotriazole containing organic dyestuff with super thermal stability. The chemical general formula of the organic dyestuff is shown in the description. The organic dyestuff with super thermal stability comprises the following synthesis steps that 1-[3-(2H-benzotriazole-2-yl)-4-hydroxylphenyl]aceton and a phthalic aldehyde derivative are added into a three-mouth flask according to the ratio of 2:1, ethyl alcohol with the volume 20-30 times that of 1-[3-(2H-benzotriazole-2-yl)-4-hydroxylphenyl]aceton is added to serve as a solvent, magnetic stirring is carried out at the temperature of 80-90 DEG C for 20 hours, suction filtration, ethyl alcohol washing and vacuum drying are carried out after the reaction is over, and the target compound is obtained. The bis-benzotriazole containing organic dyestuff with super thermal stability can exist stably even at the high temperature of 400 DEG C, which proves that the organic dyestuff is a thermal stabilizer with excellent performance.
Description
technical field [0001] The invention belongs to the field of organic superthermally stable organic materials, in particular to a class of superthermally stable bisbenzotriazole-containing organic dyes and their synthesis. Background technique [0002] Recently, organic small molecule materials have been widely used in materials science and chemical engineering. Because the chemical bonds of organic molecules are easy to break, it is difficult for organic materials to exist stably at 400°C. Therefore, there are few organic small molecule materials with a thermal decomposition temperature of 400°C or above. Contents of the invention [0003] The purpose of the present invention is in order to overcome the above-mentioned deficiencies in the background technology, and synthesize a class of bisbenzotriazole-containing organic dyes with superthermal stability. [0004] The compound with organic high thermal stability that the present invention relates to, its chemical formula ...
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