CN109283162A - A method of using pure organic room temperature phosphorimetry material tests latent fingerprint - Google Patents
A method of using pure organic room temperature phosphorimetry material tests latent fingerprint Download PDFInfo
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- CN109283162A CN109283162A CN201811107520.7A CN201811107520A CN109283162A CN 109283162 A CN109283162 A CN 109283162A CN 201811107520 A CN201811107520 A CN 201811107520A CN 109283162 A CN109283162 A CN 109283162A
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- room temperature
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- bromobenzaldehyde
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
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Abstract
The present invention relates to a kind of methods using pure organic room temperature phosphorimetry material tests latent fingerprint, method includes the following steps: pure organic room temperature phosphorimetry material is dissolved in tetrahydrofuran by (1), acquired solution is instilled in ultrapure water again, ultrasound obtains uniform suspension in 5~15 minutes；(2) suspension obtained by the fingerprint region a dropping step (1) to be detected of substrate stands 10~30min, uses ultrapure water later, is observed under ultraviolet light irradiation.Compared with prior art, the present invention has many advantages, such as that highly sensitive, signal intuitively with the naked eye can be observed directly and real-time in-situ detects, and used material is simple and easy to get, harmless to the human body.
Description
Technical field
The invention belongs to phosphorescence probe fields, and in particular to a kind of to detect potential finger using pure organic room temperature phosphorimetry material
The effective ways of line.
Background technique
Fingerprint is generated by nature-nurture collective effect, everyone has fingerprint and different, therefore fingerprint quilt
Referred to as " human body identity card ".When the finger of people touches object, the grease and sweat of raised lines secretion will on fingerprint
It is transferred to body surface and leaves the trace of fingerprint, and this trace is generally difficult to the naked eye identify, therefore is called potential finger
Line.The latent fingerprint at detection scene be the police when solving a case for accurately identifying the important means of suspect, therefore will dive
It is had a very big significance in fingerprint visualization.
Have the method for some detection latent fingerprints, such as electrochemical process, ninhydrin spray-on process, metaliding at present.
Such method has complicated for operation, and some is toxic to human body and sensitivity is lower.
Summary of the invention
It is an object of the present invention to overcome the above-mentioned drawbacks of the prior art and provide a kind of highly sensitive, signals
It intuitively with the naked eye can directly observe and real-time in-situ detects, and used material is simple and easy to get, harmless to the human body
Use the method for pure organic room temperature phosphorimetry material tests latent fingerprint.
The purpose of the present invention can be achieved through the following technical solutions: a kind of to use pure organic room temperature phosphorimetry material tests
The method of latent fingerprint, which is characterized in that method includes the following steps:
(1) pure organic room temperature phosphorimetry material is dissolved in tetrahydrofuran, then acquired solution is instilled in ultrapure water, ultrasound 5
Obtain uniform suspension within~15 minutes；
(2) suspension obtained by the fingerprint region a dropping step (1) to be detected of substrate stands 10~30min, later with ultrapure
Water rinses, and is observed under ultraviolet light irradiation.
Step (1) pure organic room temperature phosphorimetry material is to be modified with dredging for urea groups pyrimidine ketone groups at bromobenzaldehyde both ends
Aqueous pure organic room temperature phosphorimetry material has the structure such as formula (I):
Step (1) pure organic room temperature phosphorimetry material is dissolved in tetrahydrofuran, is made into the solution of 0.1~0.7mM, then will
This solution is added in ultrapure water, and the volume ratio of tetrahydrofuran and ultrapure water is 1:0.5~2.
The substrate includes glass, timber, leather, metal, shows paper surface.
Pure organic room temperature phosphorimetry material is made by the following method:
1) bromobenzaldehyde, propargyl bromide and potassium carbonate are dissolved in n,N-Dimethylformamide, react 5 at 50 DEG C~100 DEG C
~8 hours, the end modified bromobenzaldehyde for having alkynyl can be obtained by column chromatography for separation after reaction；
2) the double methyl ethers of the end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone and benzil are dissolved in
In chloroform, is reacted under high voltage mercury lamp radiation 4~6 hours, it is terminal modified to can be obtained two by column chromatography for separation after reaction
There is the bromobenzaldehyde of urea groups pyrimidine ketone groups.
The molar ratio of the bromobenzaldehyde, propargyl bromide and potassium carbonate is 1:(1.2~2.5): (4~6)；
The end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone rub with the double methyl ethers of benzil
You are than being 1:(5~10): (0.4~1.0).
Compared with prior art, the invention has the following advantages:
1. pure organic room temperature phosphorimetry material that the present invention uses belongs to phosphorescence detection probe, can lead under ultraviolet light irradiation
It crosses and is observed visually fingerprint image, signal intuitively with the naked eye can directly observe and real-time in-situ detection.
2. the material of main part that the present invention uses is that the hydrophobicity that is modified with urea groups pyrimidine ketone groups at bromobenzaldehyde both ends is pure
Organic room temperature phosphorimetry material, -4 [1H]-pyrimidone (UPy) of Quadrupolar hydrogen bond functional group 2- urea with self-complementary have stronger
Complexing and directionality, the material can readily enter in the fine structure of fingerprint, realize the clear of fingerprint fine structure
Imaging；The material has good luminosity, the property of good dispersibility and modified surface.By surface modification,
It can be by functional group by being implemented in combination with the imaging of fingerprint, detection spirit with the albumen or polypeptid specificity being widely present in fingerprint
Sensitivity is high.
3. the probe of material preparation be due to that with longer luminescent lifetime, can inhibit substrate background fluorescence to interfere, because
This can be used for the fingerprint detection in complicated substrate.
4. material used in is simple and easy to get, harmless to the human body.
Detailed description of the invention
Fig. 1 is the normalization phosphorescence emission spectra figure of 1 chemical compounds I of embodiment；
Fig. 2 is the phosphorescent lifetime test chart of 1 chemical compounds I of embodiment；
Fig. 3 is the schematic diagram that 1 chemical compounds I of embodiment is used to detect stealthy fingerprint.
Specific embodiment
The present invention is described in detail with specific embodiment below in conjunction with the accompanying drawings.
Embodiment 1
(1) both ends with formula (I) structure are modified with the pure organic room temperature phosphorimetry of bromobenzaldehyde point of urea groups pyrimidine ketone groups
The synthesis of son:
1) bromobenzaldehyde (2.5mmol, 1eq), propargyl bromide (5mmol, 2eq) and potassium carbonate are dissolved in N, N- dimethyl formyl
Amine reacts 6 hours at 80 DEG C, the end modified bromobenzene first for having alkynyl can be obtained by column chromatography for separation after reaction
Aldehyde；
2) by the end modified bromobenzaldehyde (0.054mmol, 1eq) for having alkynyl, mercapto-modified urea groups pyrimidone
The double methyl ethers (0.038mmol, 0.7eq) of (0.32mmol, 6eq) and benzil are dissolved in chloroform, anti-under high voltage mercury lamp radiation
It answers 4 hours, the bromobenzaldehyde that both ends are modified with urea groups pyrimidine ketone groups can be obtained by column chromatography for separation after reaction.
Through verification test: the phosphorescent emissions peak of the chemical compounds I of preparation is 269 μ s, hair in 490nm, green light of turning blue, service life
Quantum yield is 0.41%, sees Fig. 1 and Fig. 2, it can be seen that has most strong transmitting, and the phosphorus in 0.25 millisecond at 490nm
Light emitting intensity is high, and detection sensitivity is high.
(2) pure organic room temperature phosphorimetry material tests latent fingerprint is used:
By chemical compounds I stealthy fingerprint for identification, applying step are as follows:
A) chemical compounds I is dissolved in 1ml THF, is made into the solution of 0.3mM, the solution is instilled into 1mL ultrapure water
In, ultrasound obtains uniform suspension in 10 minutes.
B) finger is pressed lightly on clean glass plate, obtains the sightless stealthy fingerprint of naked eyes.
C) suspension of step 1) is dripped on stealthy fingerprint, stands 20 minutes, use ultrapure water later, at this point, with
Clearly fingerprint trace can be observed in ultraviolet light irradiation (referring to Fig. 3).
Embodiment 2
A kind of fingerprint detection probe based on pure organic room temperature phosphorimetry material, the fingerprint detection probe are in bromobenzaldehyde two
The terminal modified pure organic room temperature phosphorimetry material of hydrophobicity for having urea groups pyrimidine ketone groups has the structure such as formula (I):
The preparation method of the above-mentioned fingerprint detection probe based on pure organic room temperature phosphorimetry material, this method includes following step
It is rapid:
1) bromobenzaldehyde, propargyl bromide and potassium carbonate are dissolved in n,N-Dimethylformamide, react 8 hours at 50 DEG C, instead
The end modified bromobenzaldehyde for having alkynyl can be obtained by column chromatography for separation after answering；The bromobenzaldehyde, propargyl bromide
Molar ratio with potassium carbonate is 1:1.2:4；
2) the double methyl ethers of the end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone and benzil are dissolved in
In chloroform, is reacted under high voltage mercury lamp radiation 4 hours, both ends can be obtained by column chromatography for separation after reaction and be modified with urea
The bromobenzaldehyde of yl pyrimidines ketone groups.The end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone with
The molar ratio of the double methyl ethers of benzil is 1:5:0.4.
It is used for above-mentioned fingerprint detection probe to detect fingerprint, comprising the following steps:
(a) fingerprint detection probe is dissolved in tetrahydrofuran, is made into the solution of 0.1mM, then acquired solution instilled ultrapure
In water, the volume ratio of the solution and ultrapure water is 1:0.5, and ultrasound obtains uniform suspension in 15 minutes.
(b) suspension of the probe containing fingerprint obtained by the fingerprint region a dropping step (a) to be detected of leather stands 10min, it
Ultrapure water is used afterwards, is observed under ultraviolet light irradiation.
Embodiment 3
Fingerprint detection probe is made by the following method:
1) bromobenzaldehyde, propargyl bromide and potassium carbonate are dissolved in n,N-Dimethylformamide, react 5 hours at 100 DEG C, instead
The end modified bromobenzaldehyde for having alkynyl can be obtained by column chromatography for separation after answering；The bromobenzaldehyde, propargyl bromide
Molar ratio with potassium carbonate is 1:2.5:6；
2) the double methyl ethers of the end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone and benzil are dissolved in
In chloroform, is reacted under high voltage mercury lamp radiation 6 hours, both ends can be obtained by column chromatography for separation after reaction and be modified with urea
The bromobenzaldehyde of yl pyrimidines ketone groups.The end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone with
The molar ratio of the double methyl ethers of benzil is 1:10:1.
Fingerprint detection probe is for detecting fingerprint, comprising the following steps:
(a) will there is the fingerprint detection probe of formula (I) structure to be dissolved in tetrahydrofuran, is made into the solution of 0.7mM, then by institute
It obtains solution to instill in ultrapure water, the volume ratio of the solution and ultrapure water is 1:2, and ultrasound obtains uniform suspension in 5 minutes.
(b) suspension of the probe containing fingerprint obtained by the fingerprint region a dropping step (1) to be detected of leather stands 30min, it
Ultrapure water is used afterwards, is observed under ultraviolet light irradiation.Remaining is the same as embodiment 1.
Claims (6)
1. a kind of method using pure organic room temperature phosphorimetry material tests latent fingerprint, which is characterized in that this method includes following
Step:
(1) pure organic room temperature phosphorimetry material is dissolved in tetrahydrofuran, then acquired solution is instilled in ultrapure water, ultrasound 5~15
Minute obtains uniform suspension；
(2) suspension obtained by the fingerprint region a dropping step (1) to be detected of substrate stands 10~30min, is rushed later with ultrapure water
It washes, is observed under ultraviolet light irradiation.
2. the method according to claim 1 using pure organic room temperature phosphorimetry material tests latent fingerprint, which is characterized in that
Step (1) pure organic room temperature phosphorimetry material, which is that the hydrophobicity that is modified with urea groups pyrimidine ketone groups at bromobenzaldehyde both ends is pure, to be had
Machine room temperature phosphorimetry material has the structure such as formula (I):
3. the method according to claim 1 using pure organic room temperature phosphorimetry material tests latent fingerprint, which is characterized in that
Step (1) pure organic room temperature phosphorimetry material is dissolved in tetrahydrofuran, is made into the solution of 0.1~0.7mM, then this solution is added
Enter in ultrapure water, the volume ratio of tetrahydrofuran and ultrapure water is 1:0.5~2.
4. the method according to claim 1 using pure organic room temperature phosphorimetry material tests latent fingerprint, which is characterized in that
The substrate includes glass, timber, leather, metal, shows paper surface.
5. the method according to claim 1 using pure organic room temperature phosphorimetry material tests latent fingerprint, which is characterized in that
Pure organic room temperature phosphorimetry material is made by the following method:
A) bromobenzaldehyde, propargyl bromide and potassium carbonate are dissolved in n,N-Dimethylformamide, it is small that 5~8 is reacted at 50 DEG C~100 DEG C
When, the end modified bromobenzaldehyde for having alkynyl can be obtained by column chromatography for separation after reaction；
B) the double methyl ethers of the end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone and benzil are dissolved in chloroform
In, it is reacted under high voltage mercury lamp radiation 4~6 hours, both ends can be obtained by column chromatography for separation after reaction and be modified with urea
The bromobenzaldehyde of yl pyrimidines ketone groups.
6. the method according to claim 5 using pure organic room temperature phosphorimetry material tests latent fingerprint, which is characterized in that
The molar ratio of bromobenzaldehyde described in step (a), propargyl bromide and potassium carbonate is 1:(1.2~2.5): (4~6)；
The end modified bromobenzaldehyde for having alkynyl, mercapto-modified urea groups pyrimidone described in step (b) and the double methyl ethers of benzil
Molar ratio be 1:(5~10): (0.4~1.0).
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Citations (7)
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| US6949205B2 (en) * | 2001-07-20 | 2005-09-27 | Pendergrass Paula B | Fluorescent composition for marking non-porous objects |
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| US20170032202A1 (en) * | 2015-07-20 | 2017-02-02 | Uriel Halavee | Sweat Pores Imaging Method and Device |
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| US6949205B2 (en) * | 2001-07-20 | 2005-09-27 | Pendergrass Paula B | Fluorescent composition for marking non-porous objects |
| US20170032202A1 (en) * | 2015-07-20 | 2017-02-02 | Uriel Halavee | Sweat Pores Imaging Method and Device |
| CN106188391A (en) * | 2016-07-18 | 2016-12-07 | 华东理工大学 | A kind of pure organic room temperature phosphorimetry fluorescence double polymeric material launched of humidity response |
| CN106565725A (en) * | 2016-11-10 | 2017-04-19 | 中国科学技术大学 | Pure organic room-temperature phosphorescent material, preparation method thereof and application thereof |
| CN106749418A (en) * | 2016-11-16 | 2017-05-31 | 南京工业大学 | A kind of complex of iridium and its preparation method and application |
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| KWON MS ET AL.: "Tailoring intermolecular for efficient room-temperature phosphorescence from purely organic materials in amorphous polymer matrices", 《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》 * |
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