Green fluorescence cyanine dye and preparation method as well as application thereof
A technology of fluorescent dyes and green cyanines, which is applied in a class of green fluorescent cyanine dyes, preparation and application fields, can solve problems such as complex structures, large molecules, and impermeability of living cells, and achieve high fluorescent quantum production The effect of suitable rate and spectral range
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[0057] In another aspect, the present invention also provides a preparation method of the above-mentioned compound, the method comprising:
[0058] Prepare the first quaternary ammonium salt intermediate and the second quaternary ammonium salt intermediate respectively, wherein the first quaternary ammonium salt comprises quinoline substituted compounds and 4-chloroquinoline substitutes as raw materials to prepare respective quaternary ammonium salts, and then the first quaternary ammonium salt The ammonium salt reacts with the second quaternary ammonium salt intermediate in the presence of an organic base to obtain the final compound. The specific synthesis scheme is described below.
[0059] First is to prepare the first quaternary ammonium salt intermediate, that is, the compound of formula IIa or IIb and R 4 Z reaction, prepare the first quaternary ammonium salt intermediate IIIa or IIIb respectively, wherein Z is halogen or OTs, Z - Halogen anions or OTs generated for t...
Embodiment 1
[0104] Synthesis of the first quaternary ammonium salt intermediate 1-ethyl-4-iodoquinoline quaternary ammonium salt:
[0105] Add 10mmol of 4-chloroquinoline and 20mmol of ethyl iodide into a 100ml round bottom flask containing 20ml of toluene. Under the protection of nitrogen, the reaction was stopped after heating to reflux for 10 h. After the mixture was cooled to room temperature, the precipitate was filtered and the filter cake was washed with ethyl acetate. After drying, a yellow solid powder was obtained with a crude yield of 98%.
Embodiment 2
[0107] Synthesis of the second quaternary ammonium salt intermediate 1-diethylaminobutyl-2-methylbenzothiazole quaternary ammonium salt:
[0108] 10mmol of 2-methylbenzothiazole and 20mmol of 1-diethylamino-4-bromobutane were added to a 100ml round bottom flask containing 20ml of toluene. Under the protection of nitrogen, the reaction was stopped after heating to reflux for 18h. After the mixture was cooled to room temperature, the precipitate was filtered and the filter cake was washed with ether. After drying, a white solid powder was obtained with a crude yield of 75%.
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