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Spirooxazine type hydrogen ion fluorescent probe compound based on 1,8-naphthalimide unit, and synthesis method and application of compound

A naphthalimide and fluorescent probe technology, which is applied in chemical instruments and methods, fluorescence/phosphorescence, color-changing fluorescent materials, etc., to achieve the effect of simplifying the purification steps

Active Publication Date: 2019-05-17
CHIFENG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, a dual-functional photochromic material can be obtained by bonding photochromic spirooxazine to the naphthalimide unit. At present, there are few research reports in this field at home and abroad, so our work will expand the development of naphthalene imide. The scope of application of imine compounds

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  • Spirooxazine type hydrogen ion fluorescent probe compound based on 1,8-naphthalimide unit, and synthesis method and application of compound
  • Spirooxazine type hydrogen ion fluorescent probe compound based on 1,8-naphthalimide unit, and synthesis method and application of compound
  • Spirooxazine type hydrogen ion fluorescent probe compound based on 1,8-naphthalimide unit, and synthesis method and application of compound

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Embodiment

[0039] The concrete synthetic route of present embodiment compound comprises the following steps:

[0040] Synthesis of S1, 1-nitroso-2,7-binaphthol 1

[0041] Dissolve 4g of 2,7-binaphthol in 80mL of near-boiling distilled water, stir evenly, and quickly pour it into a three-necked bottle equipped with an electric stirrer, add an aqueous solution of sodium nitrite (1.84g of nitrous acid Sodium dissolved in 40mL distilled water), after mixing well, slowly add sulfuric acid solution dropwise (mix 1.44g concentrated sulfuric acid with 20mL water and cool), control the temperature below 0°C, continue stirring for 1h after the dropwise addition, add a small amount of ammonium sulfate to remove Excess nitrous acid was filtered under reduced pressure after the reaction was complete, the solid was washed with distilled water and then vacuum-dried to obtain 4.20 g of purple-red compound 1.

[0042] S2. Synthesis of compound 1,3,3-trimethylspiroindoline-2,3′[3H]-naphtho[2,1-b][1,4]oxa...

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Abstract

The invention provides a spirooxazine type hydrogen ion fluorescent probe compound based on a 1,8-naphthalimide unit, and a synthesis method and application of the compound. According to the invention, photochromic base spirooxazine is bonded to a naphthalimide unit to obtain a difunctional photochromic material; when naphthalimide is substituted, dimethylamino is introduced through a novel method; the final compound is yellow before illumination, is green after illumination and has an obvious photochromic effect; the compound emits bright green fluorescence by own, and after acid is added, color changes; and in addition, the value of the bright green fluorescence emitted by the compound is obviously lowered. The compound belongs to the spirooxazine compound which simultaneously has photochromic performance and can emit the fluorescence, and the compound also has a fluorescent probe function capable of identifying hydrogen ions.

Description

technical field [0001] The invention relates to a spirooxazine hydrogen ion fluorescent probe compound based on a 1,8-naphthalimide unit, a synthesis method and an application thereof. Background technique [0002] In recent years, the synthesis and application of organic photochromic compounds have attracted much attention. Spirooxazine compounds are widely used in photochromic glasses, optical filters, optical instruments, Glass partitions and decorative items also have broad application prospects in the fields of optical information storage and light regulation of biomolecular activity. Spirooxazine compounds not only have photochromic and thermochromic properties, but also have acid-chromic effects, that is, they can be stimulated to change their absorption spectrum through various ways. [0003] Due to the high scientific and commercial value of spirooxazine compounds, many research groups have been working on the theoretical and applied research of this kind of photof...

Claims

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Application Information

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IPC IPC(8): C07D498/10C09K11/06C09K9/02G01N21/64
Inventor 刘箫音张杨党江雁杨艳秋杨素华
Owner CHIFENG UNIV
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