A kind of method for preparing conjugated bridge chain meso-substituted cyanine dye
A technology of cyanine dyes and cyanine dyes, applied in organic dyes, chemical instruments and methods, methine/polymethine dyes, etc., can solve the problems of difficult separation and purification, many by-products, complicated methods, etc., and achieve simplified operation process, The effect of short time consumption and simple reaction steps
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Embodiment 1
[0062] Preparation of Wujiachuan condensing agent (α-mercaptopropionic acid-β-aniline acrolein):
[0063] The reaction equation is:
[0064]
[0065] Add 2.016g (0.024mol) NaHCO 3 , 5mL water and 3.18g (0.03mol) mercaptopropionic acid were added to a 50mL round bottom flask, stirred at 60℃ for 15 minutes, 1.806g (0.006mol) α-bromo-β-aniline acrolein was dissolved in 15mL methanol and added to In the reaction flask, react at 60°C for 5 hours and monitor the liquid quality. After the experiment, it was in a yellow turbid liquid, concentrated, and the residue was completely dissolved in methanol and concentrated twice, the remaining water was taken as much as possible, and then dissolved in 3 mL of methanol to form a reddish brown solution. Slowly add anhydrous ether, a solid precipitated out, which was brown and viscous at first, and turned into a yellow turbid liquid after standing for a while, filtered, and the filter cake was dried. The yield was about 45%.
Embodiment 2
[0067] Preparation of water-soluble cyanine dye CyIC-2:
[0068]
[0069] Combine iodized N-ethyl-2,3,3-trimethyl-5-sulfonate-3H indole quaternary ammonium salt with Wujiachuan condensing agent (α-mercaptopropionic acid-β-aniline acrolein) Put into a round bottom flask, the molar ratio of the indole quaternary ammonium salt to the condensing agent is 2:1, then add acetic anhydride, and heat and reflux at 120°C for 0.5 to 1 hour. After the reaction solution is cooled to room temperature, the acetic anhydride is spin-dried, and the crude product is separated and purified by column chromatography using ethanol: water: dichloromethane = 1.6: 0.3: 1.9 to 2.2 as the eluent.
Embodiment 3
[0071] Preparation of fat-soluble cyanine dye CyBC-2:
[0072]
[0073] The prepared iodinated N-ethyl-2,3,3-trimethyl-benzindole quaternary ammonium salt and the Wujiachuan condensing agent (α-mercaptopropionic acid-β-aniline acrolein) are in a molar ratio Add acetic anhydride as a catalyst at a ratio of 2:1, and react under reflux at 120°C for 0.5 to 1 hour to obtain a dark green solution. Rotary steam at 65°C. When it becomes viscous, stop, immediately add in advance Preheated to 65 ℃ methanol: water is a 5:1 mixed solution, it can be seen that granular solids precipitate immediately on the bottle wall; let stand to cool and filter to obtain a crude product; use methanol: ethyl acetate=1:1 for elution The crude product was separated and purified by column chromatography.
[0074] The method of the present invention can shorten the production cycle, simplify the operation process, reduce the cost of such fluorescent dyes, and further promote the development of fluorescent cyanin...
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