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Fluorescent probe for detecting formaldehyde as well as preparation method and application of fluorescent probe

A fluorescent probe, formaldehyde technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex molecular structure of formaldehyde probe, slow reaction speed, lengthy synthesis steps, etc., and achieve easy popularization and application. , Easy to operate, the effect of improving sensitivity

Active Publication Date: 2016-05-04
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the two reported formaldehyde probes have disadvantages such as complex molecular structure, lengthy synthesis steps, expensive reagents, and slow reaction speed, which are not conducive to their detection in complex organisms or environments.

Method used

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  • Fluorescent probe for detecting formaldehyde as well as preparation method and application of fluorescent probe
  • Fluorescent probe for detecting formaldehyde as well as preparation method and application of fluorescent probe
  • Fluorescent probe for detecting formaldehyde as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]Embodiment 1, the preparation of fluorescent probe Nap-AD

[0052] Step a): under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalic anhydride to 100mL of absolute ethanol, and then inject 2.95g of 3,6,9-trioxa-1-aminodecane, Reflux for 5 hours. After the reaction is complete, leave it overnight to precipitate needle-like crystals, filter and wash with cold ethanol three times to obtain the intermediate N-3,6,9-trioxadecanyl-4-bromo-1,8-naphthalimide 6.10 g (80% yield).

[0053] Step b): Under an inert atmosphere, add 5.00g of N-3,6,9-trioxadecanyl-4-bromo-1,8-naphthalimide and 3.79g of hydrazine hydrate into 100mL of acetone and reflux React for 12 hours. After the reaction was complete, the reaction solution was spin-dried, separated and purified by column chromatography to obtain 4.10 g (93% yield) of the final product Nap-AD, a yellow solid.

[0054] 1 HNMR (400MHz, Chloroform-d) δ8.07 (t, J = 8.3Hz, 2H), 7.74 (d, J = 8.3Hz, 1H), 7.29–7.11 (m, 2H), 6.93 (d...

Embodiment 2

[0055] Embodiment 2, the preparation of fluorescent probe Nap-AD

[0056] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalene dicarboxylic anhydride into 100mL of anhydrous methanol, and then inject 1.96g of 3,6,9-trioxa-1-aminodecane, Reflux for 10 hours. After the reaction is complete, leave it overnight to precipitate needle-like crystals, filter and wash with cold ethanol three times to obtain the intermediate N-3,6,9-trioxadecanyl-4-bromo-1,8-naphthalimide 4.90 g (96% yield).

[0057] Step b): Under an inert atmosphere, add 5.00g of N-3,6,9-trioxadecanyl-4-bromo-1,8-naphthalimide and 1.52g of hydrazine hydrate into 100mL of acetonitrile and reflux React for 20 hours. After the reaction was complete, the reaction solution was spin-dried, separated and purified by column chromatography to obtain 4.10 g (93% yield) of the final product Nap-AD, a yellow solid.

[0058] 1 HNMR (400MHz, Chloroform-d) δ8.07 (t, J = 8.3Hz, 2H), 7.74 (d, J = 8.3Hz, 1H), 7...

Embodiment 3

[0059] Embodiment 3, the preparation of fluorescent probe Nap-AD

[0060] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalic anhydride to 100mL of anhydrous ethylene glycol monomethyl ether, and then inject 1.47g of 3,6,9-trioxa-1 -Aminodecane, reflux reaction for 6 hours. After the reaction is complete, leave it overnight to precipitate needle-like crystals, filter and wash with cold ethanol three times to obtain the intermediate N-3,6,9-trioxadecanyl-4-bromo-1,8-naphthalimide 3.60 g (95% yield).

[0061] Step b): Under an inert atmosphere, add 5.00g of N-3,6,9-trioxadecanyl-4-bromo-1,8-naphthalimide and 0.76g of hydrazine hydrate into 100mL DMF for reflux reaction 1 hour. After the reaction was complete, the reaction solution was spin-dried, separated and purified by column chromatography to obtain 4.30 g (97% yield) of the final product Nap-AD as a yellow solid.

[0062] 1 HNMR (400MHz, Chloroform-d) δ8.07 (t, J = 8.3Hz, 2H), 7.74 (d, J = 8.3Hz, 1H...

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Abstract

The invention discloses a fluorescent probe for detecting formaldehyde as well as a preparation method and an application of the fluorescent probe. The structure of the fluorescent probe is presented by a formula I (shown in the specification). A kit for detecting formaldehyde comprises a compound represented by the formula I and a solvent. The ''off-on'' type formaldehyde probe for naphthalimide dyes and the specific detection kit have good responses to a formaldehyde solution, can be used for detecting formaldehyde in cells and have the characteristics of being simple and convenient to operate, low in cost, sensitive in response and easy to popularize and apply.

Description

technical field [0001] The invention belongs to the technical field of biological and environmental detection, and specifically relates to a naphthalimide-hydrazine derivative used as a formaldehyde fluorescent probe material and a preparation method and application thereof. Background technique [0002] Formaldehyde (HCHO) is an important chemical raw material and organic solvent, which is widely used in anticorrosion and disinfection, and is often used in resin, plastic, rubber, dye and other manufacturing industries. Formaldehyde (HCHO) has a pungent odor, can strongly stimulate the respiratory tract and digestive tract, and is highly toxic. In addition, long-term inhalation of formaldehyde will cause diseases such as nasal cancer, digestive tract cancer, lung cancer, brain cancer, leukemia and senile dementia (see R.G.Liteplo, R.Beauchamp, M.E.Meek, R.Chenier, Formaldehyde (Concise International Chemical Assessment Documents), World Health Organization: Geneva ,2002). ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D221/14G01N21/64
CPCG01N21/6402C09K11/06C07D221/14C09K2211/1029
Inventor 韩益丰陈波魏婷
Owner ZHEJIANG SCI-TECH UNIV
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