1,8-naphthalimide-based light-controlled fluorescent molecular switch compound bonded with bis-spilenpyran unit and synthesis method and application of compound

A technology of bonding bispiropyran and naphthalimide, which is applied in the fields of chemical instruments and methods, fluorescence/phosphorescence, and material analysis by optical means, can solve the problems of weak photosensitivity and low efficiency of fluorescence fluorescence resonance energy transfer. Advanced problems, to achieve the effect of simple purification method, improved fluorescence resonance energy transfer efficiency, and high purity

Active Publication Date: 2019-04-19
CHIFENG UNIV
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  • Abstract
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Problems solved by technology

[0007] The invention provides a 1,8-naphthalimide light-controlled fluorescent molecular switch compound bonded with a double spiropyran unit and a synthesis method thereof, and solves the problem of 1,8-

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  • 1,8-naphthalimide-based light-controlled fluorescent molecular switch compound bonded with bis-spilenpyran unit and synthesis method and application of compound
  • 1,8-naphthalimide-based light-controlled fluorescent molecular switch compound bonded with bis-spilenpyran unit and synthesis method and application of compound
  • 1,8-naphthalimide-based light-controlled fluorescent molecular switch compound bonded with bis-spilenpyran unit and synthesis method and application of compound

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Embodiment

[0043] The concrete synthetic route of present embodiment compound comprises the following steps:

[0044] Synthesis of S1, 2,3,3-trimethylindoline 1

[0045] Dissolve 39.3g of phenylhydrazine hydrochloride in 300mL of glacial acetic acid and heat with stirring. After reflux, add 44mL of methyl isopropyl ketone dropwise. The sodium aqueous solution was neutralized to about pH=7, and extracted three times with ether. The organic layer was dried overnight with anhydrous magnesium sulfate, diethyl ether was distilled off under normal pressure, and the fraction at 80-82°C was collected by distillation under reduced pressure to obtain 10.11 g of compound 1 as a light yellow liquid.

[0046] Synthesis of S2, 3-iodopropionic acid 2

[0047] Under the protection of nitrogen, add 16.65g of anhydrous sodium iodide and 10.84g of 3-chloropropionic acid into a 250mL three-necked flask, then add 100mL of methyl ethyl ketone, heat and reflux for 10 hours with magnetic stirring, filter afte...

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Abstract

The invention provides a 1,8-naphthalimide-based light-controlled fluorescent molecular switch compound bonded with a bis-spilenpyran unit and a synthesis method and application of the compound. Firstly, bis-spiropyran is modified to a 1,8-naphthylimide molecule through a covalent bond, the compound shows a good photochromic effect and light-controlled two-color fluorescent molecular switch performance in an organic solvent and a solid medium, the fluorescence resonance energy transfer efficiency of the compound is greatly improved, and the thermodynamic stability and photosensitivity of the compound are also high. The 1,8-naphthalimide-based light-controlled fluorescent molecular switch compound bonded with the bis-spilenpyran unit and the synthesis method and application of the compoundcan be used in the field of ion detection and photochemical imaging of biological systems.

Description

technical field [0001] The invention relates to a 1,8-naphthoimide light-controlled fluorescent molecular switch compound bonded with double spiropyran units and a synthesis method thereof. Background technique [0002] Naphthalimide compounds have a large conjugated structure and strong fluorescence properties. Their good photochemical stability and thermal stability make them used as chromophores in the fields of dyes, fluorescent sensors and fluorescent molecular probes. and fluorescent functional groups. [0003] As one of the most extensively researched photochromic compounds, spiropyran compounds have high fatigue resistance and photostability, so their synthesis and application have attracted much attention. The changes in physical properties make it widely used as molecular optical switch materials in the fields of chemical sensing, temperature-sensitive materials, and analytical chemistry. [0004] For compounds that can emit fluorescence, if their emission spectr...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06C09K2211/1029C09K2211/1088G01N21/643
Inventor 杨素华院雪梅靳晓娟厚华颖孟祥磊
Owner CHIFENG UNIV
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