Organic dye containing polycarbazole and preparation method and application thereof
A technology of organic dyes and bicarbazoles, applied in the field of organic dyes, can solve problems such as the absence of polycarbazoles, and achieve the effects of easy preparation, stable performance, and low price
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Embodiment 1
[0034] Reflux 16.7g carbazole and 16.5g t-BuOK in 100ml THF for 8 hours, then slowly drop into 13ml bromobutane, continue to reflux for 10 hours, cool, remove THF under reduced pressure, extract with chloroform, wash with water, anhydrous Dried over sodium sulfate, separated by column chromatography to obtain N-butylcarbazole; 11.1g of N-butylcarbazole was dissolved in 40ml of DMF, 1.8g of NBS was added twice under ice bath, and reacted in the dark for 12 hours. Poured into water for extraction with chloroform, washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 3-bromo-N-n-butylcarbazole; after anhydrous and oxygen-free treatment, 40ml THF was added to the In a three-necked flask of bromo-N-n-butylcarbazole, cool down to -78°C in a dry ice-acetone bath, then slowly add 6.5ml of 1.6M n-BuLi dropwise, stir for 2 hours, then add dropwise 2ml of 2-iso Propoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborinane, add a small amount of water ...
Embodiment 2
[0040] The difference between this embodiment and Example 1 is only that: 5-bromothiophene-2-aldehyde is replaced by 5-bromo-3,4-ethylenedioxythiophene-2-aldehyde, and the rest of the content is the same as that of the embodiment Same as described in 1, the chemical structural formula of the organic dye obtained is as follows:
[0041]
[0042] Its structural characterization data are as follows: 1 H NMR (400MHz, DMSO-d6) δ: 8.697(s, 1H), 8.649(s, 1H), 8.591(s, 1H), 8.268-8.295(d, 1H), 8.232(s, 1H), 7.884- 7.912(m, 3H), 7.662-7.743(m, 3H), 7.587-7.614(d, 1H), 7.424-7.472(t, 1H), 7.180-7.230(t, 1H), 4.399-4.535(m, 8H ), 1.755-1.797 (m, 4H), 1.251-1.374 (m, 4H), 0.858-0.907 (t, 6H).
[0043] The normalized ultraviolet absorption spectrum of the organic dyes prepared in this embodiment in THF solution is shown in figure 2 shown.
[0044] The dye-sensitized solar cell sensitized by the organic dye prepared according to the method described in Example 1 has a light intensit...
Embodiment 3
[0046] Dissolve 0.55g of compound d in Example 1 in 10ml of DMF, add 0.18g of NBS twice under ice bath, and react in the dark for 12 hours, pour into water for extraction with chloroform, wash with water, dry over anhydrous sodium sulfate, and perform column chromatography Separated to obtain compound f; under argon protection, 10ml H 2 O and 20ml THF were added to the 3 ) 4 and 0.53g Na 2 CO 3 In a three-necked flask, heated to reflux for 24 hours; THF was removed under reduced pressure, extracted with chloroform, washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain compound h; under the protection of argon, 0.15g compound h, 0.050g Dissolve cyanoacetic acid in 10ml of acetonitrile, add 0.1ml of piperidine, reflux for 5 hours, remove acetonitrile under reduced pressure after cooling, extract with chloroform, wash with water, dry over anhydrous sodium sulfate, and separate by column chromatography to obtain the organic com...
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