Near-infrared two-window fluorescence probe based on Aza-BODIPY, as well as preparation and application thereof
A fluorescent probe and near-infrared technology, applied in the field of organic fluorescent probes, can solve the problems of low resolution, shallow penetration depth, poor signal-to-noise ratio, etc., and achieve good photostability and no toxic side effects
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[0049] Example 1
[0050] The preparation method of a series of near-infrared two-window fluorescent probe FBL3 based on Aza-BODIPY is as follows:
[0051] 1.1 1: Add phosphorus oxychloride (1.17g, 7.62mmol) slowly to a round bottom flask containing DMF (1.67g, 22.87mmol) in an ice-salt bath, and remove the ice bath after the addition is complete. Under the protection of nitrogen, continue stirring for half an hour at room temperature to prepare the Vilsmeier-Haack reagent. Then, the DMF solution in which julonidine (1.2 g, 6.93 mmol) was dissolved was slowly added dropwise, and after the dropwise addition was completed, it was refluxed at 90° C. for 4 hours. Pour the reacted material into ice water to stop the reaction, continue to stir for at least 2 h, a yellow solid precipitated, and finally a light yellow solid 1 was obtained by suction filtration. 1 H NMR (300MHz, CDCl3) δ 9.59 (s, 1H), 7.28 (s, 2H), 3.28 (t, J = 6.0, 4H), 2.76 (t, J = 6.0, 4H), 1.95 (m, 4H ). The reaction...
Example Embodiment
[0059] Example 2
[0060] The preparation method of a series of near-infrared two-window fluorescent probe FBL3 based on Aza-BODIPY is as follows:
[0061] 2.1 1: Add phosphorus oxychloride (2.34g, 15.24mmol) slowly to a round bottom flask containing DMF (3.34g, 45.74mmol) in an ice-salt bath, and remove the ice bath after the addition is complete. Under the protection of nitrogen, continue stirring for half an hour at room temperature to prepare Vilsmeier-Haack reagent. Then the DMF solution in which julonidine (2g, 11.55 mmol) was dissolved was slowly added dropwise, and after the dropwise addition was completed, it was refluxed at 90°C for 4h. Pour the reacted material into ice water to stop the reaction, continue to stir for at least 2 h, a yellow solid precipitated, and finally a light yellow solid 1 was obtained by suction filtration.
[0062] 2.2 10: Add methoxyacetophenone (751mg, 5mmol), compound 1 (800mg, 3.94mmol), ethanol (60mL), KOH (20% aqueous solution, 20mL) in a ro...
Example Embodiment
[0065] Example 3
[0066] The preparation method of a series of near-infrared two-window fluorescent probe FBL3 based on Aza-BODIPY is as follows:
[0067] 3.1 1: Phosphorus oxychloride (0.585g, 3.81mmol) was slowly added dropwise to a round bottom flask containing DMF (1g, 13.72mmol) in an ice-salt bath, and the ice bath was removed after the addition was completed. Under the protection of nitrogen, continue stirring for half an hour at room temperature to prepare the Vilsmeier-Haack reagent. Then, the DMF solution in which julonidine (0.6 g, 3.46 mmol) was dissolved was slowly added dropwise, and after the dropwise addition, the solution was refluxed at 90° C. for 4 hours. Pour the reacted material into ice water to stop the reaction, continue to stir for at least 2 h, a yellow solid precipitated, and finally a light yellow solid 1 was obtained by suction filtration.
[0068] 3.2 10: Add methoxyacetophenone (375.5mg, 2.5mmol), compound 1 (300mg, 1.476mmol), ethanol (30mL), KOH (2...
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