Light trigger molecule based on triphenylamine and application thereof
An optical trigger and triphenylamine technology, which is applied to the optical trigger molecule and its application field, can solve the problems of slow photolysis speed, low photolysis efficiency, and low fluorescence intensity increase multiple.
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Embodiment 1
[0062]Synthesis of the light trigger molecule TPA-1
[0063]
[0064] 1-1) Synthesis of the intermediate Beenzoin-1.
[0065] Benzaldehyde (0.53g, 5mmol), 4-(N,N-diphenylamino)benzaldehyde (2.73g, 10mmol), triethylamine (505mg, 5mmol) and 20mL ethanol were added to the reaction bottle, stirred at 60 °C for 24 hours. After the reaction was completed, the reaction mixture was quenched with 30 mL of water and extracted with dichloromethane. The organic layer is dried with anhydrous sodium sulfate and the organic solvent is evaporated to dry. The crude product was purified by silica gel column chromatography to give the intermediate Beenzoin-1, an orange solid. 1 H NMR(400MHz,CD 2 Cl 2 ):δ7.63(m,2H),7.42(m,4H),7.31(m,8H),7.13(m,2H),6.94(m,2H),5.89(s,1H).
[0066] 1-2) Synthesis of the light trigger molecule TPA-1
[0067] The above-formula benzoin intermediate (381 mg, 1 mmol) was dissolved in 15 mL toluene, trimethylchlorosilane (0.5 mL) and glycol (0.5 mL) were added to the soluti...
Embodiment 2
[0069] Synthesis of the light trigger molecule TPA-2
[0070]
[0071] 2-1) Synthesis of the intermediate Beenzoin-2.
[0072]4-Fluorobenzaldehyde (0.62g, 5 mmol), 4-(N,N-diphenylamino)benzaldehyde (2.73g, 10 mmol), triethylamine (505 mg, 5 mmol) and 20 mL ethanol were added to the reaction bottle, stirred at 60 °C for 24 hours. After the reaction was completed, the reaction mixture was quenched with 30 mL of water and extracted with dichloromethane. The organic layer is dried with anhydrous sodium sulfate and the organic solvent is evaporated to dry. The crude product was purified by silica gel column chromatography to give the intermediate Benzoin-2, orange solid. 1 H NMR(400MHz,CD 2 Cl 2 ):δ7.83(m,2H),7.40(m,4H),7.31(m,8H),7.10(m,2H),6.93(m,2H),5.88(s,1H).
[0073] 2-2) Synthesis of the light trigger molecule TPA-2
[0074] The above-formula benzoin intermediate (381 mg, 1 mmol) was dissolved in 15 mL toluene, trimethylchlorosilane (0.5 mL) and glycol (0.5 mL) were added to t...
Embodiment 3
[0076] Synthesis of the light trigger molecule TPA-3
[0077]
[0078] 3-1) Synthesis of the intermediate Beenzoin-3.
[0079]4-Bromobenzaldehyde (0.93g, 5 mmol), 4-(N,N-diphenylamino)benzaldehyde (2.73 g, 10 mmol), triethylamine (505 mg, 5 mmol) and 20 mL ethanol were added to the reaction bottle, stirred at 60 °C for 24 hours. After the reaction was completed, the reaction mixture was quenched with 30 mL of water and extracted with dichloromethane. The organic layer is dried with anhydrous sodium sulfate and the organic solvent is evaporated to dry. The crude product was purified by silica gel column chromatography to give the intermediate Benzoin-2, orange solid. 1 H NMR(400MHz,CD 2 Cl 2 ):δ7.83(m,2H),7.41(m,4H),7.29(m,8H),7.10(m,2H),6.93(m,2H),5.86(s,1H).
[0080] 3-2) Synthesis of the light trigger molecule TPA-3
[0081] The above-formula benzoin intermediate (381 mg, 1 mmol) was dissolved in 15 mL toluene, trimethylchlorosilane (0.5 mL) and glycol (0.5 mL) were added to t...
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