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8-oxy-8h acenaphthene (1,2-6) pyrrol-9 nitrile fluorescence chromophore and its derivative

A chromophore and derivative technology, which is applied to 8-oxy-8H acenaphthene (1), can solve the problems of reducing the sensitivity of the probe and achieve the effect of high fluorescence quantum efficiency

Inactive Publication Date: 2004-09-22
DALIAN UNIV OF TECH
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Problems solved by technology

However, the absorption and emission of naphthalene-based fluorescent compounds are located in a shorter wavelength region (350-500nm), and most of the autofluorescence of organisms is also in this region, thus reducing the sensitivity of the probe

Method used

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  • 8-oxy-8h acenaphthene (1,2-6) pyrrol-9 nitrile fluorescence chromophore and its derivative
  • 8-oxy-8h acenaphthene (1,2-6) pyrrol-9 nitrile fluorescence chromophore and its derivative
  • 8-oxy-8h acenaphthene (1,2-6) pyrrol-9 nitrile fluorescence chromophore and its derivative

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Experimental program
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Effect test

Embodiment 1

[0032]

[0033] 1 g of 2-(2-oxo-2H-acenaphthyl)malononitrile, 0.2 g of potassium carbonate, and 10 ml of dimethyl sulfoxide were heated to 100°C, stirred for 15 minutes, and cooled to precipitate crystals. After filtering, washing and drying with water, the product 8-oxo-8Hacenaphtho(1,2-b)pyrrole-9-carbonitrile was obtained as a yellow-brown crystal with a yield of 99%.

[0034] 1 H NMR (400M, DMSO): δ8.71-8.69 (d, J=8.0Hz, 1H), 8.67-8.65 (d, J=7.6Hz, 1H), 8.64-8.62 (d, J=8.0Hz, 1H ), 8.42-8.40(d, J=7.6Hz, 1H), 8.04-8.08(t, J=8.0Hz, 1H), 7.99-7.95(t, J=7.8Hz, 1H); 13C NMR (100M, DMSO): δ177.48, 138.26, 137.73, 134.40, 132.72, 131.82, 131.37, 128.91, 127.94, 127.37, 126.13, 122.22, 119.72, 113.82, 113.38; IR (KBr) cm -1 : 2231, 1643, 1577; ESI-MS: M+Na + (253, m / z).

Embodiment 2

[0036]

[0037] Add 0.32 g of butylamine to 50 ml of acetonitrile solution of 1 g of 8-oxo-8H acenaphtho(1,2-b)pyrrole-9-carbonitrile, stir at room temperature for 30 minutes, evaporate part of the solvent, and precipitate the product 3-butylamino 8- Oxy-8Hacenaphtho(1,2-b)pyrrole-9-carbonitrile Al. Yield 70%.

[0038] 1 H NMR (400M, DMSO): δ9.604 (br s, -NH-, 1H), 8.95-8.93 (d, J=7.6Hz, 1H), 8.60-8.58 (d, J=7.2Hz, 1H), 7.98-7.96(d, J=8.8Hz, 1H), 7.88-7.92(t, J=7.8Hz, 1H), 7.04-7.02(d, J=9.2Hz, 1H), 3.60-3.59(br s,- NHCH 2 CH 2 -, 2H0, 1.75-1.71 (m, -NHCH 2 CH 2 CH 2 -, 2H), 1.43-1.47 (m, -CH 2 CH 2 CH 2 CH 3 ), 0.94-0.98 (t, J=7.2Hz, -CH 2 CH 3 );IR(KBr)cm -1 : 3284, 2217, 1619, 1562, 1529; ESI-MS: [M-H] - (300m / z).

Embodiment 3

[0040]

[0041] Add 0.43 g of cyclohexylamine to 50 ml of acetonitrile solution of 1 gram of 8-oxo-8H acenaphtho(1,2-b)pyrrole-9-carbonitrile, stir at room temperature for 30 minutes, evaporate part of the solvent, and precipitate the product 3-cyclohexylamino -8-Oxo-8Hacenaphtho(1,2-b)pyrrole-9-carbonitrile A2. Yield 68%.

[0042] 1 H NMR (400M, DMSO): δ9.13-9.11 (d, J = 7.6Hz, -NH-, 1H) 9.03-9.01 (d, J = 7.6Hz, 1H), 8.54-8.52 (d, J = 7.2 Hz, 1H), 7.90-7.87(d, J=9.2Hz, 1H), 7.87-7.83(t, J=8.0Hz, 1H), 7.09-7.07(d, J=9.2Hz, 1H), 3.90(br s, -NHCH-, 1H), 2.05-2.02 (br d, -NHCH (CH 2 * CH 2 ) 2 , CH 2 , 2H), 1.85-1.82 (br d, -NHCH (CH 2 * CH 2 ) 2 CH 2 , 2H), 1.72-1.69 (brd, -NHCH (CH 2 CH 2 ) 2 CH 2 * , 1H), 1.43-1.58 (m, -NHCH (CH 2 CH 2 ) 2 CH 2 , 4H), 1.19-1.23 (brd, -NHCH (CH 2 CH 2 ) 2 CH 2 * , 1H); IR(KBr)cm -1 : 3324, 2215, 1631, 1575, 1492; ESI-MS: [M+H] + (328, m / z).

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Abstract

A fluorescent chromophore, its fluorescent derivative and their preparing process are disclosed. The fluorescent chromophore is 8-oxy-8H acenaphtho-(1,2-b) pyrrole-9-nitrile, and is prepared from 2-(2-oxy-2H-acenaphthenyl) propanedinitrile through cyclizing reaction in solvent under the existance of alkali catalyst. The fluorescent derivative is 3,6-bisubstituent-8-oxy-8H -acenaphtho (1,2-b) pyrrole-9-nitrile and is prepared by substitution reaction of the said fluorescent chromophore on neucleophile in solvent. It can be used as ideal fluorescent probe compound with very high fluorescent quantum efficiency (near to 1).

Description

technical field [0001] The invention relates to a novel fluorescent chromophore 8-oxo-8H acenaphtho(1,2-b)pyrrole-9-carbonitrile, fluorescent derivatives thereof and a preparation method thereof. Background technique [0002] In recent years, organic fluorescent materials have been widely used as functional pigments in various fields of science and technology. In particular, due to the high sensitivity of fluorescence detection, easy operation, and safer detection methods than traditional isotope labeling, and organic fluorescent molecules have the advantages of stable performance and easy structure modification, organic fluorescent materials are used as fluorescent molecular detectors in the field of life sciences. Needles and chemical sensors have become powerful analytical tools, and many traditional fluorescent dye precursors for textile printing and dyeing have undergone appropriate structural modification to become fluorescent probes with good performance. However, th...

Claims

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Application Information

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IPC IPC(8): C09K11/06
Inventor 钱旭红肖义
Owner DALIAN UNIV OF TECH
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