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A kind of water-soluble dye of indole half cyanine structure and its synthetic method
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A technology of water-soluble dyes and indole semicyanines, applied in organic dyes, chemical instruments and methods, methenyl/polymethenyl dyes, etc., can solve the problem of low yield, achieve high yield and simple product purification , the effect of mild reaction conditions
Active Publication Date: 2020-10-16
CHINA THREE GORGES UNIV
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Problems solved by technology
However, the current common semicyanine dyes use basic catalysts for heating and reflux reactions, and purification steps are required, resulting in low yields.
Method used
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Embodiment 1
[0036] Take 2,3,3-trimethylindole 1 (1.43g, 9.00mmol), weigh iodomethane (2.55g, 18.00mmol), measure toluene 20mL, mix and dissolve, heat and stir, and reflux at 120°C for 4 hours , filtered and washed with ethanol to obtain compound 3 as a red off-white solid. Take the above compound 3 (301.2mg, 1mmol), weigh it as 2-formylpyrrole (190.2g, 2.00mmol), measure 10mL of ethanol, mix and dissolve, heat and stir, reflux at 80°C for 2 hours, spin dry, and heat to dissolve with water. The filtrate was obtained by suction filtration, and then extracted with dichloromethane and spin-dried to obtain compound 5:
[0037]
Embodiment 2
[0039] Take 2,3,3-trimethylindole 1 (2.86g, 18.00mmol), weigh iodomethane (2.55g, 18.00mmol), measure toluene 20mL, mix and dissolve, heat and stir, and reflux at 120°C for 4 hours , filtered and washed with ethanol to obtain compound 3 as a red off-white solid. Take the above compound 3 (301.2mg, 1mmol), weigh it as 2-formylpyrrole (190.2g, 2.00mmol), measure 10mL of ethanol, mix and dissolve, heat and stir, reflux at 80°C for 2 hours, spin dry, and heat to dissolve with water. The filtrate was obtained by suction filtration, and then extracted with dichloromethane and spin-dried to obtain compound 5:
[0040]
Embodiment 3
[0042] Take 2,3,3-trimethylindole 1 (1.43g, 9.00mmol), weigh iodomethane (2.55g, 18.00mmol), measure toluene 20mL, mix and dissolve, heat and stir, and reflux at 120°C for 10 hours , filtered and washed with ethanol to obtain compound 3 as a red off-white solid. Take the above compound 3 (301.2mg, 1mmol), weigh it as 2-formylpyrrole (190.2g, 2.00mmol), measure 10mL of ethanol, mix and dissolve, heat and stir, reflux at 80°C for 2 hours, spin dry, and heat to dissolve with water. The filtrate was obtained by suction filtration, and then extracted with dichloromethane and spin-dried to obtain compound 5:
[0043]
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Abstract
The invention discloses a water-soluble dye of an indole hemicyanine structure and a synthesis method of the water-soluble dye. The compound structure is shown as a following formula: (please see thespecifications for the formula). According to the synthesis method, a 2,3,3-trimethylindolenine derivative and pyrrole-2-carboxaldehyde are taken as raw materials, a single condensation reaction is conducted, and the water-soluble dye of the indole hemicyanine structure is synthesized. According to the water-soluble dye of the indole hemicyanine structure, the synthesis method is simple, reactionconditions are easy to control, and the yield is high. The water-soluble dye has good water solubility and pH response and is applied to a biological body advantageously.
Description
technical field [0001] The invention discloses a water-soluble dye with an indole semicyanine structure and a synthesis method thereof. The dye can be widely used in the fields of environment, biology, material science and the like. Background technique [0002] Compounds with cyanine-like dye structures have superior spectral properties and have been widely used in many fields such as biomarkers, fluorescence imaging, and targeted therapy. At the same time, because the spectral properties of such molecules are extremely sensitive to changes in the surrounding environment, they are often used to study the polar properties of solvents. Based on the characteristic that cyanine dyes are sensitive to the surrounding chemical environment, there are few reports on the use of this structure and its application in the detection of solution pH. Obviously, the rational design of cyanine dyes and the study of their pH response process are of great significance to the study of the envi...
Claims
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Application Information
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