Isoindole bora fluorescent dye and its preparation method and application
A fluorescent dye, isoindole boron technology, applied in the field of fluorescent dyes, can solve the problems of cumbersome preparation process, poor spectral selectivity of isoindole bora near-infrared fluorescent dyes, complicated methods, etc.
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[0048] The present invention also provides a method for preparing the above-mentioned isoindolebora fluorescent dye, wherein the preparation method comprises the following steps:
[0049] In the presence of a solvent, the halogenated hydrocarbon (R13-X) and the compound of the formula (II) are stirred at 20-25 ° C in the dark for 12-15 h according to the molar ratio of 1:5-10, and purified, That is, the isoindole borofluorescent dye shown in formula (I) is obtained;
[0050]
[0051] Wherein, R1, R2, R3, R4 are each independently hydrogen, C1-C12 alkyl, halogen or C1-C12 alkoxy;
[0052] R5, R6, R7, R8 are each independently hydrogen, C1-C12 alkyl, halogen, C1-C12 alkoxy, cycloalkyl or aryl;
[0053] R9 is hydrogen, alkenyl or C1-C12 alkyl;
[0054] R10 and R11 are each independently hydrogen, C1-C12 alkyl, halogen or alkenyl;
[0055] R12 is hydrogen, C1-C12 alkyl, halogen, alkenyl or C1-C12 alkoxy;
[0056] The R13 is a C1-C12 alkyl group, and X is a halogen.
[0057...
preparation example 1
[0077] Preparation of raw material 1-(3-bromo-1H-isoindole-1-ylidene)-N,N-dimethylmethylamine: 1.5g (5.24mmol) POBr 3 Put it in a 250ml round-bottomed flask, add 50ml of dichloromethane, cool to 0°C, add 0.27ml (3.49mmol) of DMF dropwise to the solution under stirring, and finish dropping within 5min, then place the reaction at 20°C and stir After 0.5 hours, it was cooled to 0° C., 1.0 g (7.5 mmol) of isoindol-1-one was weighed and dissolved in dichloromethane, and then placed in a constant pressure dropping funnel and added dropwise to the above mixture. After the dropwise addition was completed, it was transferred to a 60°C oil bath, heated to reflux, and TLC spotted. The reaction was completed in 2.5h, and after cooling to room temperature, 100ml of ice water was added, and the pH value was adjusted to 8 with sodium carbonate, extracted, concentrated, passed through a column, and recrystallized to obtain a pale yellow solid.
preparation example 2
[0079] Preparation of raw material (2-hydroxyphenyl)-2H-isoindole-1-carbaldehyde: Weigh 1-(3-bromo-1H-isoindole-1-ylidene)-N,N-dimethylformaldehyde Amine 400mg (1.66mmol), 2-hydroxyphenylboronic acid 331mg (3.5mmol) Na 2 CO 3 (1M, 5mL) in a 100ml Schlenk reactor, after three flushes and three releases, Pd (PPh) was added under the condition of argon 3 ) 4 60 mg, (0.05 mmol), after three times of flushing and three releases, it was moved to a 75°C oil bath with heating and stirring for 12 hours. After cooling to room temperature, it was extracted with water, the organic phase was collected, dried over anhydrous sodium sulfate, and rotary evaporated on a rotary evaporator to obtain a yellow solid. After dissolving with absolute ethanol, saturated sodium hydroxide solution was added and heated to reflux for 3h. After removing the ethanol, extract with water and ethyl acetate, neutralize with dilute HCl (3M) to pH 7, collect the organic phase, dry over anhydrous sodium sulfat...
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