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Application of diarylethene compound in fingerprint fluorescence color development

A diarylethene compound technology, applied in the application field of diarylene compounds in fingerprint fluorescent color development, to achieve the effect of increased polarity, high contrast, and not easy to aggregate

Active Publication Date: 2020-06-19
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This solves the technical problems that need to be improved, such as the integrity, uniformity, three-l

Method used

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  • Application of diarylethene compound in fingerprint fluorescence color development
  • Application of diarylethene compound in fingerprint fluorescence color development
  • Application of diarylethene compound in fingerprint fluorescence color development

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] A compound is compound T1, and the representative method of synthesizing compound T1 is as follows:

[0168]

[0169] Compound 1 (200 mg, 0.733 mmol, 1 eq.), compound 2 (159 mg, 0.733 mmol, 1 eq.) and piperidine (2 drops) in EtOH (3 mL) were reacted at 80 °C for 16 h. It was concentrated under reduced pressure, and the crude product was purified by flash preparative liquid chromatography (mobile phase gradient: DCM / MeOH=0-15%) to obtain red solid compound T1 (220 mg, yield 64%). Mass spectrum (ESI, m / z): 393.3 (M-Br) + .

[0170] Compound T1 is hydrophilic, soluble in water, and has a certain oil solubility, for example, it can be well dissolved in methanol, ethanol, DMF, DMSO, acetonitrile, tetrahydrofuran, dichloromethane and other oil-soluble solvents; insoluble in n-hexane , ether and ethyl acetate and other less polar solvents. Compound T1 has almost no fluorescence in aqueous solution, and emits strong orange-red fluorescence in 99% ethyl acetate / water syste...

Embodiment 2

[0180] A diarylethene compound T2, which has the structural formula shown below:

[0181]

[0182] Methods of synthesizing this compound:

[0183] Compound 3 (363 mg, 1.00 mmol, 1 eq.), compound 4 (262 mg, 1.00 mmol, 1 eq.) and piperidine (3 drops) in EtOH (5 mL) were reacted at 80 °C for 16 h. Concentrated under reduced pressure, the crude product was purified by flash preparative liquid chromatography (mobile phase gradient: DCM / MeOH=0-18%) to give a red solid (271 mg, yield 48%). Mass spectrum (ESI, m / z): 483.3 (M-Br) + .

[0184] The compound is amphiphilic, with weak fluorescence in aqueous solution and strong orange-red fluorescence in 99% ethyl acetate / water system, and has a remarkable aggregation-induced luminescence effect.

[0185] The compound fluoresces strongly for the word lipids, indicating that this probe can indeed identify lipids in sweat latent fingerprints.

Embodiment 3

[0187] A diarylethene compound T3, it has the structural formula shown below:

[0188]

[0189] Methods of synthesizing this compound:

[0190] Compound 5 (546 mg, 2.00 mmol, 1 eq.), compound 6 (432 mg, 2.4 mmol, 1 eq.) and piperidine (6 drops) in MeCN (30 mL) were reacted at 80 °C for 16 h. Concentrated under reduced pressure, the crude product was purified by a flash preparative liquid chromatography (mobile phase gradient: DCM / MeOH=0-20%), and the isolated intermediate product T3-1 was dissolved in 50 mL of a mixed solution of ethanol / water (volume ratio: 9:1), add LiOHH 2 O (419 mg, 10 mmol), after stirring at room temperature overnight, 1M hydrochloric acid was added dropwise to adjust the Ph value to 2-3. The organic solvent was removed by rotary evaporation, extracted three times with dichloromethane, and the combined extracts were concentrated and separated by fast liquid preparative chromatography (mobile phase gradient: DCM / MeOH=0~25%) to obtain a red solid (254...

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Abstract

The invention relates to the field of new materials, and particularly discloses an application of a diarylethene compound in fingerprint fluorescence color development, the compound is used as a fluorescence developer, and the fluorescence developer has the following structural general formula: in the general formula, Ar1 is a hydrophobic aromatic ring, and Ar2 is a hydrophilic aromatic heterocyclic cation. By using the fluorescent developer solution disclosed by the invention, fingerprints on different substrates can be rapidly, safely and efficiently developed, the developed fingerprint hashigh resolution and high contrast, can clearly distinguish 1-3 levels of details of the fingerprint, can provide effective and reliable evidences for individual identification, and provides a rapid, efficient and safe fingerprint fluorescence developing technology for the fields of criminal investigation, judicial expertise, science popularization public welfare and the like.

Description

technical field [0001] The invention relates to the field of new materials, and more particularly, to the application of a diarylethene compound in the fluorescence color development of fingerprints. Background technique [0002] The complex pattern of raised ridges and recessed grooves is characteristic of the corrugated skin of the terminal parts of the human body. This complex pattern of raised ridges and concave grooves remains the same after an individual is born, and not only do different people have different patterns, but different fingers also have different patterns. When a finger comes into contact with the surface of an object, aqueous exudates such as sweat and oily substances such as sebum can transfer and deposit on the surface of the object, thereby forming fingerprints. Thus, fingerprints represent contact indentations of raised ridges of the skin. Because of the complexity, uniqueness and stability of the raised ridge pattern, fingerprints formed by raise...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D215/20C07D217/10C07D409/06C07D401/06C07D215/233C07D213/38G01N21/64
CPCC07D213/38C07D215/20C07D215/233C07D217/10C07D401/06C07D409/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1092G01N21/6428G01N21/6456G01N2021/6439
Inventor 李冲朱明强
Owner HUAZHONG UNIV OF SCI & TECH
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