Optical trigger molecule and application based on bodipy
An optical trigger and molecular technology, applied in applications, material analysis through optical means, nanotechnology for materials and surface science, etc., can solve the problems of slow photolysis speed, less BODIPY, and low photolysis efficiency
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Embodiment 1
[0082] Synthesis of phototrigger molecule PPG-1
[0083]
[0084] 1-1) Synthesis of intermediate MA-1-1.
[0085] p-Bromobenzaldehyde (300 mg, 1.22 mmol) and 2,4-dimethylpyrrole (255 mg, 2.46 mmol) were dissolved in dry CH 2 Cl 2 (100 mL), and added 5 μL of trifluoroacetic acid, and reacted overnight at room temperature. To the solution was slowly added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (290 mg, 1.26 mmol) and stirred for two hours, triethylamine (1.5 mL) was added dropwise After stirring for 30 minutes, boron trifluoride diethyl ether (1.5 mL) was slowly added dropwise and stirred for another 6 hours. Add 50 mL of water to the reaction solution to quench the reaction, take out the organic layer and wash with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried by a rotary evaporator, and the pure product was obtained by silica gel column chromatography.
[0086] 1 H NMR (400 MHz, CDCl 3 ): δ 7.68 (d, J= 12.0 Hz, 2H), 7.21 (d, J= 8.0Hz, 2H), 6....
Embodiment 2
[0094] Synthesis of phototrigger molecule PPG-2
[0095]
[0096] 2-1) Synthesis of intermediate MA-1-2
[0097] p-Bromobenzaldehyde (300 mg, 1.22 mmol) and 2,4-dimethyl-3-ethylpyrrole (302 mg, 2.46 mmol) were dissolved in dry CH 2 Cl 2 (100 mL), and added 5 μL of trifluoroacetic acid, and reacted overnight at room temperature. DDQ (290 mg, 1.26 mmol) was slowly added to the solution and stirred for two hours, triethylamine (1.5 mL) was added dropwise and stirred for 30 minutes, boron trifluoride diethyl ether (1.5 mL) was added dropwise and stirred for another 6 hours. Add 50 mL of water to the reaction solution to quench the reaction, take out the organic layer and wash with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried by a rotary evaporator, and the pure product was obtained by silica gel column chromatography.
[0098] 1 H NMR (400 MHz, CDCl 3 ): δ 7.67 (d, J= 8.0 Hz, 2H), 7.21 (d, J= 8.0Hz, 2H), 2.55 (s, 6H), 2.34 (q, J = 8.0 Hz, 4H), 1.34 (s, 6...
Embodiment 3
[0103] Synthesis of phototrigger molecule PPG-3
[0104]
[0105] 3-1) Synthesis of intermediate MA-1-3
[0106] p-Bromobenzaldehyde (300 mg, 1.22 mmol) and 2-thiophenepyrrole (367 mg, 2.46 mmol) were dissolved in dry CH 2 Cl 2 (100 mL), and added 5 μL of trifluoroacetic acid, and reacted overnight at room temperature. DDQ (290 mg, 1.26 mmol) was slowly added to the solution and stirred for two hours, triethylamine (1.5 mL) was added dropwise and stirred for 30 minutes, boron trifluoride diethyl ether (1.5 mL) was added dropwise and stirred for another 6 hours. Add 50 mL of water to the reaction solution to quench the reaction, take out the organic layer and wash with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried by a rotary evaporator, and the pure product was obtained by silica gel column chromatography.
[0107] 1 H NMR (400 MHz, CDCl 3 ): δ 8.24 (d, J= 4.0 Hz, 2H), 7.69 (d, J= 8.0Hz, 2H), 7.54 (d, J= 8.0 Hz, 2H), 7.44 (d, J= 8.0 Hz, 2H) , 7.24 (d,...
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