Light trigger molecule based on BODIPY and application thereof
An optical trigger and molecular technology, applied in applications, material analysis through optical means, nanotechnology for materials and surface science, etc., can solve problems such as low photolysis efficiency, slow photolysis speed, and less BODIPY
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Embodiment 1
[0080] Synthesis of phototrigger molecule PPG-1
[0081]
[0082] 1-1) Synthesis of intermediate MA-1-1.
[0083] Dissolve p-bromobenzaldehyde (300 mg, 1.22 mmol) and 2,4-dimethylpyrrole (255 mg, 2.46 mmol) in dry CH 2 Cl 2 (100 mL), and 5 μL of trifluoroacetic acid was added, and reacted overnight at room temperature. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (290mg, 1.26mmol) was slowly added to the solution and stirred for two hours, triethylamine (1.5mL) was added dropwise and stirred After 30 minutes, boron trifluoride diethyl ether (1.5 mL) was slowly added dropwise and stirred for another 6 hours. Add 50mL 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.
[0084] 1 H NMR (400MHz, CDCl 3 ): δ7.68(d, J=12.0Hz, 2H), 7.21(d, J=8.0Hz, 2H), 6.01(s, 2H), 2.57(s...
Embodiment 2
[0092] Synthesis of phototrigger molecule PPG-2
[0093]
[0094] 2-1) Synthesis of intermediate MA-1-2
[0095] Dissolve p-bromobenzaldehyde (300 mg, 1.22 mmol) and 2,4-dimethyl-3-ethylpyrrole (302 mg, 2.46 mmol) in dry CH 2 Cl 2 (100 mL), and 5 μL of trifluoroacetic acid was added, 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 50mL 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.
[0096] 1 H NMR (400MHz, CDCl 3 ): δ7.67(d, J=8.0Hz, 2H), 7.21(d, J=8.0Hz, 2H), 2.55(s, 6H), 2.34(q, J=8.0Hz, 4H), 1.34(s ,6H),1.01(t,J=8.0Hz,6H)...
Embodiment 3
[0101] Synthesis of phototrigger molecule PPG-3
[0102]
[0103] 3-1) Synthesis of intermediate MA-1-3
[0104] Dissolve p-bromobenzaldehyde (300mg, 1.22mmol) and 2-thienpyrrole (367mg, 2.46mmol) in dry CH 2 Cl 2 (100 mL), and 5 μL of trifluoroacetic acid was added, 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 50mL 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.
[0105] 1 H NMR (400MHz, CDCl 3 ): δ8.24(d, J=4.0Hz, 2H), 7.69(d, J=8.0Hz, 2H), 7.54(d, J=8.0Hz, 2H), 7.44(d, J=8.0Hz, 2H ),7.24(d,J=4.0Hz,2H),6.85(d,J=4.0Hz,2H...
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