Two-photon fluorescent material benzoxazolyl pyridinium salt and its preparation method and application
A technology of benzoxazolyl pyridinium salt and two-photon fluorescence, applied in the field of fluorescent materials, can solve problems such as two-photon absorption limitation, and achieve the effects of low cost, easy operation and easy availability of raw materials
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Embodiment 1
[0041] The preparation method of two-photon fluorescent material benzoxazolyl pyridinium salt, see figure 1 , including the following steps:
[0042] A, the preparation of intermediate M1
[0043] Weigh 20.4g (0.15mol) of p-toluic acid and 35.97g (0.33mol) of o-aminophenol, put them in a 250mL three-neck flask, add 1500mL of polyphosphoric acid, under nitrogen protection, reflux at 220°C for 6h, and then the obtained reaction Cool the liquid to 80°C, pour it into a large beaker with ice water, add an appropriate amount of saturated NaOH aqueous solution dropwise to adjust the pH of the solution to 7-8, use 300mL of ethyl acetate for multiple extractions, then spin dry the ethyl acetate, and then Ethanol recrystallization was carried out to obtain 9.84 g of solid, namely intermediate M1, with a yield of 31%.
[0044] Intermediate M1 1 H NMR: (400MHz, CD 2 Cl 2): δ(ppm)8.17(s,2H),7.77(s,1H),7.63(s,1H),7.38(s,4H),2.48(s,2H). 13 C NMR: (100MHz, CD 2 Cl 2 ):δ(ppm)163.58,151...
Embodiment 2
[0061] Preparation method of two-photon fluorescent material benzoxazolylpyridinium salt
[0062] This embodiment is similar to Embodiment 1, and for the sake of concise description, only the differences will be described. Their difference is: in step A of this example, reflux was carried out at 210°C for 7 hours, and the yield of M1 was 30.5%. The yield is 58%. In step C, the yield of M3 is 75% under reflux at 40°C for 8h. In step D, the yield of M4 is 59% under reflux at 140°C for 10h. In step E, it is The temperature was raised to 50° C. and reacted at this temperature for 3 hours, the yield of M5 was 70%. In step F, the reaction was carried out at 60° C. for 7 hours, and the yield of the target product L was 61%.
Embodiment 3
[0064] Preparation method of two-photon fluorescent material benzoxazolylpyridinium salt
[0065] This embodiment is similar to Embodiment 1, and for the sake of concise description, only the differences will be described. Their differences are: in step A of this example, reflux was carried out at 240°C for 4 hours, and the yield of M1 was 30%. The yield is 56%. In step C, the yield of M3 is 76% under reflux at 60°C for 7h. In step D, the yield of M4 is 58% under reflux at 140°C for 14h. In step E, it is Raise the temperature to 40° C. and react at this temperature for 6 h, the yield of M5 is 69%. In step F, the reaction is carried out at 90° C. for 4 h, and the yield of the target product L is 59%.
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