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Fluorescent chemical sensor as well as preparation and detection method thereof

A chemical sensor and fluorescence technology, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of multiple reaction steps, complex post-reaction processing, expensive design and synthesis of fluorescent chemical sensors, etc., to achieve fast sensing, The effect of easy operation

Inactive Publication Date: 2011-07-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the reported methods, the design and synthesis of fluorescent chemical sensors involves problems such as expensive reagents, many reaction steps, and complex post-reaction treatments.

Method used

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  • Fluorescent chemical sensor as well as preparation and detection method thereof
  • Fluorescent chemical sensor as well as preparation and detection method thereof
  • Fluorescent chemical sensor as well as preparation and detection method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Mix 1mmol of 1,8-diiodonaphthalene, 10mmol of 2-methyl-3-butyn-2-ol, 10% molar equivalent of cuprous iodide, and 5% molar equivalent of tetrakistriphenylphosphine palladium as catalyst in 35~ 50ml of diisopropylamine organic solvent was reacted at 23°C for 16h, and 1,8-bis(3-methyl-3-hydroxy-1-butynol)naphthalene was isolated after simple post-treatment with a yield of 99%. The reaction formula is as follows:

[0022]

[0023] Compound structural characteristics: mp(toluene)120-121℃; 1 H NMRδCDCl 3 (Bruker AVANCED MX500): 1.69 (s, 6H), 3.28 (br, 1H), 7.38 (t, 1H, J=5.2Hz), 7.69 (dd, 1H, J 1 =7.25Hz,J 2 =1.05Hz), 7.76(d, 1H, J=8.25Hz)ppm.

Embodiment 2

[0025] 1mmol 1,8-diiodonaphthalene, 1mmol 2-methyl-3-butyn-2-ol, 10% molar equivalent of triphenylphosphine, 10% molar equivalent of cuprous iodide, 5% molar equivalent of catalyst Tetrakistriphenylphosphine palladium was mixed in 35-50ml triethylamine organic solvent, reacted at 23°C for 10-13 hours, and was isolated by simple post-treatment to obtain 1-iodo-8-(3-methyl-3-hydroxy-1 -butynol)naphthalene, 86% yield. The reaction formula is as follows:

[0026]

[0027] Compound Structural Features: 1 H NMRδCDCl 3 (Bruker AVANCE DMX500): 8.26 (dd, J 1 =7.0Hz,J 2 =0.75Hz), 7.80(m, 3H), 7.39(t, 1H, J=7.25Hz), 7.08(t, 1H, J=7.75Hz), 2.10(br, 1H), 1.69(s, 6H)ppm .

Embodiment 3

[0029] With 1mmol 1,8-diiodonaphthalene, 10mmol 2-methyl-3-butyn-2-alcohol, 10% molar equivalent of triphenylphosphine, catalytic amount (0.05~0.10 molar equivalent) of cuprous iodide and Ditriphenylphosphine palladium dichloride is mixed in 75-100ml of triethylamine organic solvent, vacuumed and ventilated with nitrogen, then added with 3-5mmol of water, heated and refluxed for about 8-14 hours and separated to obtain the product.

[0030] The organic solvent of the present invention is trialkylamine; 3-5 molar equivalents of water must be added; the chromatographic column and eluent are silica gel chromatographic column and mixed eluent of dichloromethane and n-hexane. The reaction formula is as follows:

[0031]

[0032] Compound Structural Features: 1 H NMRδCDCl 3 (Bruker AVANCE DMX400): 1.80(s, 6H), 7.17(d, 1H, J=6.4Hz), 7.64(t, 1H, J=7.8Hz), 7.94(d, 1H, J=9.2Hz), 8.12 (dd, 1H, J 1 =7.6Hz,J 2 = 1.2Hz), 8.68(dd, 1H, J 1 =7.6Hz, J2=1.2Hz), 13.22(s, 1H)ppm; 13 C NM...

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Abstract

The present invention discloses a fluorescent chemical sensor and the preparation and the texting method thereof. The compound can be prepared from 1, 8-naphthalene diiodide, 1mmol of 1, 8-naphthalene diiodide, 10mmol of 2-methyl-3-butine-2-alcohol, 10 percent mol equivalence of triphenylphosphine, catalysis amount (0.05-0.10 mol equivalence) of cuprous iodide, and dimethyl-triphenylphosphine palladiurn bichloride are mixed into 75-100ml triethylamine organic solvent, 3-5mmol of water is added in solvent after vacuumizing the solvent and charging nitrogen into the solvent, and the product is obtained after heating and refluxing reactions for about 8-14 hours. The compound which is disclosed by the invention and can sense the ambient anion is a new compound; the adopted compounding method is a new method; and the sensing brought by the new compound is rapid and sensitive.

Description

technical field [0001] The invention relates to a fluorescent chemical sensor and its preparation and detection method. Background technique [0002] With the development of supramolecular chemistry, molecular recognition plays an increasingly important role in synthetic chemistry, life science, information science and material science. Molecular recognition refers to the process in which molecules (subject and object or receptor and substrate) are selectively combined by non-covalent bond force to produce a specific function. In order to transmit the information contained in molecular recognition to the outside world simply and effectively, this information can be expressed through optical signals emitted by ingeniously designed molecular devices. Because the fluorescence detection technology has the advantages of convenience, high sensitivity, and good selectivity, a lot of work has focused on designing and synthesizing complex fluorescent molecules that can effectively e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/00C09K11/06G01N21/64
Inventor 王红波吕萍
Owner ZHEJIANG UNIV
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