CN109283162B - Method for detecting potential fingerprints by using pure organic room temperature phosphorescent material - Google Patents
Method for detecting potential fingerprints by using pure organic room temperature phosphorescent material Download PDFInfo
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- CN109283162B CN109283162B CN201811107520.7A CN201811107520A CN109283162B CN 109283162 B CN109283162 B CN 109283162B CN 201811107520 A CN201811107520 A CN 201811107520A CN 109283162 B CN109283162 B CN 109283162B
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Abstract
The invention relates to a method for detecting potential fingerprints by using a pure organic room temperature phosphorescent material, which comprises the following steps: (1) dissolving a pure organic room-temperature phosphorescent material in tetrahydrofuran, dripping the obtained solution into ultrapure water, and performing ultrasonic treatment for 5-15 minutes to obtain a uniform suspension; (2) and (3) dropwise adding the suspension obtained in the step (1) into a to-be-detected fingerprint area of the substrate, standing for 10-30 min, then washing with ultrapure water, and observing under the irradiation of an ultraviolet lamp. Compared with the prior art, the invention has the advantages of high sensitivity, direct signal observation and real-time in-situ detection, simple and easily obtained used materials, no toxicity to human bodies and the like.
Description
Technical Field
The invention belongs to the field of phosphorescent probes, and particularly relates to an effective method for detecting potential fingerprints by using a pure organic room-temperature phosphorescent material.
Background
Fingerprints are generated by the combined action of heredity and environment, and each person has a fingerprint which is different from one another, so that the fingerprints are called 'human identity cards'. When a human finger touches an object, grease and sweat secreted by raised veins on the fingerprint are transferred to the surface of the object to leave a trace of the fingerprint, which is usually difficult to identify with the naked eye and is therefore called a latent fingerprint. The potential fingerprint of the detection site is an important means for accurately identifying the criminal suspect when the police breaks a case, so that the potential fingerprint visualization has great significance.
At present, some methods for detecting potential fingerprints exist, such as an electrochemical method, a ninhydrin spray method, a metal deposition method and the like. Some methods are complex to operate, some are toxic to human bodies and have low sensitivity.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for detecting potential fingerprints by using a pure organic room temperature phosphorescent material, which has the advantages of high sensitivity, intuitive signal, direct observation by naked eyes and real-time in-situ detection, simple and easily obtained used material and no harm to human bodies.
The purpose of the invention can be realized by the following technical scheme: a method for detecting latent fingerprints by using a pure organic room temperature phosphorescent material, which is characterized by comprising the following steps:
(1) dissolving a pure organic room-temperature phosphorescent material in tetrahydrofuran, dripping the obtained solution into ultrapure water, and performing ultrasonic treatment for 5-15 minutes to obtain a uniform suspension;
(2) and (3) dropwise adding the suspension obtained in the step (1) into a to-be-detected fingerprint area of the substrate, standing for 10-30 min, then washing with ultrapure water, and observing under the irradiation of an ultraviolet lamp.
The pure organic room temperature phosphorescent material obtained in the step (1) is a hydrophobic pure organic room temperature phosphorescent material modified with ureidopyrimidone groups at two ends of bromobenzaldehyde, and has a structure shown in a formula (I):
dissolving the pure organic room-temperature phosphorescent material in the step (1) in tetrahydrofuran to prepare a solution of 0.1-0.7 mM, and adding the solution into ultrapure water, wherein the volume ratio of the tetrahydrofuran to the ultrapure water is 1: 0.5-2.
The substrate comprises glass, wood, leather, metal and a surface of revealing paper.
The pure organic room temperature phosphorescent material is prepared by the following method:
1) dissolving bromobenzaldehyde, bromopropyne and potassium carbonate in N, N-dimethylformamide, reacting at 50-100 ℃ for 5-8 hours, and separating by column chromatography after the reaction is finished to obtain the bromobenzaldehyde with the end modified with alkynyl;
2) the method comprises the steps of dissolving bromobenzaldehyde with alkynyl-modified tail ends, ureidopyrimidone modified by sulfydryl and benzil dimethyl ether in chloroform, reacting for 4-6 hours under the irradiation of a high-pressure mercury lamp, and obtaining the bromobenzaldehyde with ureidopyrimidone group-modified two ends through column chromatography separation after the reaction is finished.
The molar ratio of the bromobenzaldehyde to the bromopropyne to the potassium carbonate is 1: (1.2-2.5): (4-6);
the molar ratio of the bromobenzaldehyde with the end modified with alkynyl, the ureidopyrimidone modified with sulfhydryl and the benzil dimethyl ether is 1: (5-10): (0.4-1.0).
Compared with the prior art, the invention has the following beneficial effects:
1. the pure organic room temperature phosphorescent material adopted by the invention belongs to a phosphorescent detection probe, fingerprint images can be observed by naked eyes under the irradiation of an ultraviolet lamp, signals are visual, and the signals can be directly observed by the naked eyes and detected in situ in real time.
2. The main material used in the invention is a hydrophobic pure organic room temperature phosphorescent material modified with ureido pyrimidinone groups at two ends of bromobenzaldehyde, and the material has self-complementary quadruple hydrogen bond functional groups 2-carbamide-4 [1H ] -pyrimidinone (UPy) with strong complexation and directionality, and can easily enter a fine structure of a fingerprint to realize clear imaging of the fine structure of the fingerprint; the material has good luminescence property, good dispersibility and surface modification property. Through surface modification, functional groups can be specifically combined with proteins or polypeptides widely existing in fingerprints to realize fingerprint imaging, and the detection sensitivity is high.
3. The probe prepared by the material has longer luminescence life, can inhibit background fluorescence interference of a substrate, and can be used for fingerprint detection on a complex substrate.
4. The used materials are simple and easy to obtain and are non-toxic to human bodies.
Drawings
FIG. 1 is a normalized phosphorescence emission spectrum of compound I of example 1;
FIG. 2 is a graph showing phosphorescence lifetime test of Compound I of example 1;
FIG. 3 is a schematic representation of compound I of example 1 for detecting invisible fingerprints.
Detailed Description
The invention is described in detail below with reference to the figures and specific embodiments.
Example 1
(1) Synthesizing a pure organic room temperature phosphorescent molecule of bromobenzaldehyde with a structure of formula (I) and modified ureidopyrimidone groups at two ends:
1) dissolving bromobenzaldehyde (2.5mmol,1eq), bromopropyne (5mmol,2eq) and potassium carbonate in N, N-dimethylformamide, reacting at 80 ℃ for 6 hours, and separating by column chromatography after the reaction is finished to obtain the bromobenzaldehyde the tail end of which is modified with alkynyl;
2) the method comprises the steps of dissolving bromobenzaldehyde (0.054mmol,1eq) with the end modified with alkynyl, ureidopyrimidinone (0.32mmol,6eq) with the end modified with sulfhydryl and benzil dimethyl ether (0.038mmol,0.7eq) in chloroform, reacting for 4 hours under the irradiation of a high-pressure mercury lamp, and separating by column chromatography after the reaction is finished to obtain the bromobenzaldehyde with the ends modified with ureidopyrimidinone groups.
Through the inspection and test: the prepared compound I has a phosphorescence emission peak at 490nm, emits bluish green light, has a lifetime of 269 mus, and has a luminescence quantum yield of 0.41%, as shown in FIGS. 1 and 2, and it can be seen that it has the strongest emission at 490nm, and has a high phosphorescence emission intensity within 0.25 msec, and a high detection sensitivity.
(2) Detection of latent fingerprints using purely organic room temperature phosphorescent materials:
the compound I is used for identifying invisible fingerprints, and the application steps are as follows:
a) the compound I was dissolved in 1mL of THF to prepare a 0.3mM solution, and the solution was dropped into 1mL of ultrapure water and subjected to ultrasonic treatment for 10 minutes to obtain a uniform suspension.
b) The finger is lightly pressed on a clean glass plate to obtain invisible fingerprints which can not be seen by naked eyes.
c) Dripping the suspension liquid obtained in the step 1) on the invisible fingerprint, standing for 20 minutes, then washing with ultrapure water, and irradiating by using an ultraviolet lamp at the moment to observe a clear fingerprint blot (see figure 3).
Example 2
A fingerprint detection probe based on a pure organic room temperature phosphorescent material is a hydrophobic pure organic room temperature phosphorescent material modified with ureido pyrimidone groups at two ends of bromobenzaldehyde, and has a structure as shown in formula (I):
the preparation method of the fingerprint detection probe based on the pure organic room temperature phosphorescent material comprises the following steps:
1) dissolving bromobenzaldehyde, bromopropyne and potassium carbonate in N, N-dimethylformamide, reacting for 8 hours at 50 ℃, and separating by column chromatography after the reaction is finished to obtain the bromobenzaldehyde the tail end of which is modified with alkynyl; the molar ratio of the bromobenzaldehyde to the bromopropyne to the potassium carbonate is 1: 1.2: 4;
2) the bromobenzaldehyde of which the tail end is modified with alkynyl, ureidopyrimidone modified with sulfydryl and benzil dimethyl ether are dissolved in chloroform to react for 4 hours under the irradiation of a high-pressure mercury lamp, and after the reaction is finished, the bromobenzaldehyde of which both ends are modified with ureidopyrimidone groups can be obtained through column chromatography separation. The molar ratio of the bromobenzaldehyde with the end modified with alkynyl, the ureidopyrimidone modified with sulfhydryl and the benzil dimethyl ether is 1: 5: 0.4.
the fingerprint detection probe is used for detecting fingerprints and comprises the following steps:
(a) dissolving a fingerprint detection probe in tetrahydrofuran to prepare a 0.1mM solution, then dripping the obtained solution into ultrapure water, wherein the volume ratio of the solution to the ultrapure water is 1:0.5, and carrying out ultrasonic treatment for 15 minutes to obtain a uniform suspension.
(b) And (3) dropwise adding the suspension containing the fingerprint probe obtained in the step (a) into a fingerprint area to be detected of the leather, standing for 10min, then washing with ultrapure water, and observing under the irradiation of an ultraviolet lamp.
Example 3
The fingerprint detection probe is prepared by the following method:
1) dissolving bromobenzaldehyde, bromopropyne and potassium carbonate in N, N-dimethylformamide, reacting for 5 hours at 100 ℃, and separating by column chromatography after the reaction is finished to obtain the bromobenzaldehyde the tail end of which is modified with alkynyl; the molar ratio of the bromobenzaldehyde to the bromopropyne to the potassium carbonate is 1: 2.5: 6;
2) the bromobenzaldehyde of which the tail end is modified with alkynyl, ureidopyrimidone modified with sulfydryl and benzil dimethyl ether are dissolved in chloroform to react for 6 hours under the irradiation of a high-pressure mercury lamp, and after the reaction is finished, the bromobenzaldehyde of which both ends are modified with ureidopyrimidone groups can be obtained through column chromatography separation. The molar ratio of the bromobenzaldehyde with the end modified with alkynyl, the ureidopyrimidone modified with sulfhydryl and the benzil dimethyl ether is 1: 10: 1.
the fingerprint detection probe is used for detecting fingerprints and comprises the following steps:
(a) dissolving a fingerprint detection probe with a structure shown in a formula (I) in tetrahydrofuran to prepare a 0.7mM solution, then dripping the obtained solution into ultrapure water, wherein the volume ratio of the solution to the ultrapure water is 1:2, and performing ultrasonic treatment for 5 minutes to obtain a uniform suspension.
(b) And (3) dropwise adding the suspension containing the fingerprint probe obtained in the step (1) into a to-be-detected fingerprint area of the leather, standing for 30min, then washing with ultrapure water, and observing under the irradiation of an ultraviolet lamp. The rest is the same as example 1.
Claims (5)
1. A method for detecting latent fingerprints by using a pure organic room temperature phosphorescent material, which is characterized by comprising the following steps:
(1) dissolving a pure organic room-temperature phosphorescent material in tetrahydrofuran, dripping the obtained solution into ultrapure water, and performing ultrasonic treatment for 5-15 minutes to obtain a uniform suspension;
(2) dropwise adding the suspension obtained in the step (1) into a to-be-detected fingerprint area of a substrate, standing for 10-30 min, then washing with ultrapure water, and observing under the irradiation of an ultraviolet lamp;
the pure organic room temperature phosphorescent material obtained in the step (1) is a hydrophobic pure organic room temperature phosphorescent material modified with ureidopyrimidone groups at two ends of bromobenzaldehyde, and has a structure shown in a formula (I):
2. the method for detecting latent fingerprints using pure organic room temperature phosphorescent material as claimed in claim 1, wherein the pure organic room temperature phosphorescent material in step (1) is dissolved in tetrahydrofuran to prepare a solution with a concentration of 0.1-0.7 mM, and the solution is added into ultrapure water, wherein the volume ratio of tetrahydrofuran to ultrapure water is 1: 0.5-2.
3. The method for detecting latent fingerprints using pure organic phosphorescent materials at room temperature as claimed in claim 1, wherein the substrate comprises glass, wood, leather, metal or revealing paper.
4. The method for detecting latent fingerprints according to claim 1, wherein the pure organic room temperature phosphorescent material is prepared by the following steps:
a) dissolving bromobenzaldehyde, bromopropyne and potassium carbonate in N, N-dimethylformamide, reacting at 50-100 ℃ for 5-8 hours, and separating by column chromatography after the reaction is finished to obtain the bromobenzaldehyde with the end modified with alkynyl;
b) the method comprises the steps of dissolving bromobenzaldehyde with alkynyl-modified tail ends, ureidopyrimidone modified by sulfydryl and benzil dimethyl ether in chloroform, reacting for 4-6 hours under the irradiation of a high-pressure mercury lamp, and obtaining the bromobenzaldehyde with ureidopyrimidone group-modified two ends through column chromatography separation after the reaction is finished.
5. The method for detecting latent fingerprints by using pure organic room temperature phosphorescent material as claimed in claim 4, wherein the molar ratio of bromobenzaldehyde, bromopropyne and potassium carbonate in the step (a) is 1: (1.2-2.5): (4-6);
the molar ratio of the bromobenzaldehyde with the end modified with alkynyl, the ureidopyrimidone modified with sulfhydryl and the benzildimethyl ether in the step (b) is 1: (5-10): (0.4-1.0).
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| US20170032202A1 (en) * | 2015-07-20 | 2017-02-02 | Uriel Halavee | Sweat Pores Imaging Method and Device |
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