Dipyrrol borane (BODIPY) and preparation method and application thereof

A compound and compound technology, applied in the field of dipyrrole borane compound and its preparation, can solve problems such as inconvenient operation, increased cost for consumers, weak absorption of detection reagents, etc.

Active Publication Date: 2013-08-07
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This kind of kit usually needs to be enriched for more than 10 hours, which takes a long time; this kind of detection reagent itself has weak absorption, the color change is not obvious, the detection error is large, and the operation is inconvenient
Human eyes have great individual differences in color judgment, and a single indicator is not conducive to accurate judgment
The other is the use of spectral detection technology, which requires expensive instruments and greatly increases the cost of use for consumers.

Method used

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  • Dipyrrol borane (BODIPY) and preparation method and application thereof
  • Dipyrrol borane (BODIPY) and preparation method and application thereof
  • Dipyrrol borane (BODIPY) and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Preparation of compound Ia (1,7-bis(3-methoxy-3-propionyl)-3,5-diethoxycarbonyl-2,6-dimethyl-dipyrrole borane), the relevant reaction scheme is as follows :

[0096]

[0097] 20.3 g (80 mmol) of dipyrrolyl ester (compound 1) was dissolved in 100 ml of ethyl acetate. 12.8g of liquid bromine (1eq.) was added dropwise within 15min, and after stirring for 1 hour, a pale yellow precipitate was precipitated. The above reaction mixture was spin-dried, and the solid was dissolved in 100ml of methanol, and 2ml of HCl was added to reflux for 1 hour, then cooled to 0°C and washed with 10%NH 3 ·H 2O adjusted the pH=7, and a large amount of solids were precipitated. The above solid was filtered off and recrystallized from 70:30 methanol:water solution. Pure compound (2) was obtained. 9.8g (20mmol) of compound (2) was dissolved in 60ml of dry dichloromethane, and 4.5g (1eq.) DDQ (English name of dichlorodicyanobenzoquinone: 2,3-Dichloro-5,6-dicyano -1,4-benzoquinone) was add...

Embodiment 2

[0099] Preparation of compound Ib (1,7-bis(3-methoxy-3-propionyl)-3,5-diethyl-2,6-dimethyl-dipyrrole borane), the relevant reaction scheme is as follows:

[0100]

[0101] 15.6 g (80 mmol) of dipyrrolyl ester (compound 1) was dissolved in 100 ml of ethyl acetate. 12.8g of liquid bromine (1eq.) was added dropwise within 15min, and after stirring for 1 hour, a pale yellow precipitate was precipitated. The above reaction mixture was spin-dried, and the solid was dissolved in 100ml of methanol, and 2ml of HCl was added to reflux for 1 hour, then cooled to 0°C, and washed with 10%NH 3 ·H 2 O adjusted the pH=7, and a large amount of solids were precipitated. The above solid was filtered off and recrystallized with 70:30 methanol:water solution to obtain pure compound (2). 7.5g (20mmol) of compound (2) was dissolved in 60ml of dry dichloromethane, and 4.5g (1eq.) DDQ (dichlorodicyanobenzoquinone English name:

[0102] 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone) was added to the...

Embodiment 3

[0104] Prepare the formaldehyde detection solution containing complex IIaa from compound Ia and hydrazine hydrate:

[0105]

[0106] The compound Ia prepared in Example 1 was dissolved in an ethanol solution to form a 1mmol / L solution; after 80% hydrazine hydrate was diluted 10% with ethanol, it was made into an 8% dilute solution, and was added dropwise to In the above compound Ia solution, the solution changed from red to light red; after the above solution was placed in a dark room or refrigerator (4°C) for 24 hours, the solution became colorless, and the formaldehyde detection solution was obtained. Complex IIaa: 1 H NMR (400MHz,THF)δ5.23(s,1H),4.32–4.08(m,4H),3.57(s,6H),2.98–2.82(m,2H),2.82–2.69(m,2H), 2.63–2.50(m,2H),2.50–2.35(m,2H),2.24(s,6H),1.32(t,J=7.1Hz,6H).

[0107] The high-resolution mass spectrometry data of the colorless solution after adding hydrazine are shown in the following table:

[0108]

[0109]

[0110] The crystal structure of complex IIaa...

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PUM

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Abstract

The invention discloses a formaldehyde detection probe compound and a detection method. The compound is a high fluorescence quantum efficiency fluorescence dye based on dipyrrol borane BODIPY. The compound and alkali substances used in the invention generate a reversible reaction for forming a compound. The detection of formaldehyde is based on alkali reaction in the compound, and the reaction result causes the BODIPY to regenerate and develop colors, and simultaneously recover fluorescence. The detection method is a novel detection reagent which can be recycled. On the other hand, based on the high fluorescence quantum efficiency characteristics of the BODIPY compounds, the detection reagent has high sensitivity and lower detection limit.

Description

technical field [0001] The invention relates to a class of dipyrrole borane compounds and a preparation method thereof, and a preparation and use method of a formaldehyde detection reagent based on the dipyrrole borane compound and a polymer film reagent thereof. The reagent can be used for the detection of formaldehyde, especially for the in-situ detection of indoor formaldehyde. Background technique [0002] Boron Dipyrromethene (BODIPY) has received extensive attention since it was first reported in 1968. Compared with traditional fluorescent compounds, BODIPY has the advantages of strong absorption, high quantum efficiency, narrow spectrum, easy modification, and adjustable spectral range. Because of the above advantages, BODIPY compounds can be widely used in environmental and biological detection. Probes based on such dyes have the advantages of high sensitivity, low detection limit, and strong anti-interference. [0003] Formaldehyde is a colorless, pungent gas wit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64G01N21/75C08J5/18C08L33/12C08K5/55
Inventor 杨国强胡德辉冯娇马金石王双青
Owner INST OF CHEM CHINESE ACAD OF SCI
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