A quinazolinone compound-based aggregation-induced luminescent probe and its preparation method and application
A quinazolinone and compound technology, which is applied in the application field of quinazolinone compounds and ammonia gas detection, can solve the problems of difficulty in synthesis, inconvenience to be made portable, complex structure of compounds and the like
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Embodiment 1
[0116] According to the synthetic route of the present invention, synthesize the compound of formula II with the following specific structure:
[0117] (1) Synthesis of Compound II-1: 2-[2-hydroxyphenyl]-4-(3H)-quinazolone (R 1 = H, R 2 =H)
[0118]
[0119] Anthranilamide (272mg, 2mmol), salicylaldehyde (244mg, 2mmol) and iodine (508mg, 2mmol) were placed in 15mL of ethanol and reacted under reflux for 6 hours. After the reaction was completed, 5% by mass fraction of sodium thiosulfate solution was added to remove unreacted iodine. A large amount of white precipitate precipitated out of the reaction solution, which was filtered, washed with water (10 mL×2) and ethanol (10 mL×2), and dried in vacuo to obtain a white solid with a mass of 390 mg (yield 82%).
[0120] 1 H NMR (d 6 -DMSO,500MHz):δ13.78(br s,1H),12.48(br s,1H),8.23(dd,J 1 =8.0Hz,J 2 =1.5Hz,1H),8.16(dd,J 1 =8.0Hz,J 2 =1.5Hz,1H),7.86(td,J 1 =8.5Hz,J 2 =1.5Hz, 1H), 7.77(d, J=8.0Hz, 2H), 7.56(td, J 1 =8....
Embodiment 2
[0138] According to the synthetic route of the present invention, the formula I compound of following specific structure is synthesized on the basis of the compound of Example 1:
[0139] (1) Synthetic (R 1 = H, R 2 = H, R 3 = methyl)
[0140]
[0141] 2-[2-Hydroxyphenyl]-4-(3H)-quinazolinone (280mg, 1.0mmol) was added to 5mL methanol solution dissolved with sodium methoxide (108mg, 2.0mmol), and reacted at room temperature under nitrogen protection 5 minutes. After the reaction solution became clear, methanol was removed by rotary evaporation. Subsequently, 10 mL of THF and acetic anhydride (408 mg, 4.0 mmol) were added and reacted at room temperature for 2 hours under nitrogen protection. After the reaction was completed, THF was removed by rotary evaporation, the residue was washed with water, and then dried in vacuo to obtain a white solid with a mass of 266 mg (yield: 95%).
[0142] 1 H NMR (CDCl 3 ,500MHz):δ10.42(br s,1H),8.29(dd,J 1 =7.5Hz,J 2 =1.0Hz,1H),8....
Embodiment 3
[0150] Fluorescence property test of formula I compound and formula II compound
[0151] 1. Fluorescence quantum yield is measured by C11347 Quantaurus_QY instrument.
[0152] 2. Research method of fluorescence emission spectrum in tetrahydrofuran / water:
[0153] tetrahydrofuran and water according to different volume ratios (THF: water = 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, 1:99) to form mixed solutions with different water contents, compound I-1 and compounds II-1~II-5 were dissolved in these mixed solutions respectively, so that the concentration of the compound was 10 -5 mol L -1 , using appropriate excitation light to detect the fluorescence emission of compound I-1 and compounds II-1-II-5 in these solvent systems.
[0154] see attached results Figure 1-6 . When the water content in the mixed solution system is continuously increased, the solubility of compounds II-1-II-5 gradually decreases and thus aggregates, and the fluorescence ...
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