CN107192695B - Using aggregation-induced emission to crystal growth and conversion fluorescent visual research method - Google Patents
Using aggregation-induced emission to crystal growth and conversion fluorescent visual research method Download PDFInfo
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
The invention belongs to fluorescence analysis detection technique fields, disclose a kind of method realized using aggregation-induced emission property to crystal growth and the research of conversion process fluorescent visual.The present invention distinguishes different crystal forms crystal by different using fluorescence emission wavelengths under compound different crystal forms state, using the method for fluorescence imaging, and/or carries out dynamic imaging tracking to the conversion process of different crystal forms；Compound has structure shown in formula 1:R1It is each independently selected from sulphur atom or NH group；R2It is each independently selected from one of hydrogen atom, methyl, ethyl and methoxyl group.The method of the present invention monitors different crystal forms structure growth and conversion process real-time tracking, can preparing to mechanical scribing method, there is the growth course of the crystal threadiness aggregated structure aligned to carry out fluorescent visual research, have the characteristics that easy to operate, rapid, result is accurate, real-time detection in situ, there is application value in fields such as crystalline state analysis, the researchs of phase transformation mechanism.
Description
Technical field
It is the invention belongs to fluorescence analysis detection technique field, in particular to a kind of to utilize the realization pair of aggregation-induced emission property
The method of crystal growth and the research of conversion process fluorescent visual.
Background technique
The formation and transformation of crystal process for observing crystallization to the theoretic knowledge for deepening crystallization mechanism and pass through crystallization condition
Control obtain target crystal form have vital meaning.The different crystal forms of same molecules are with different physics and chemically
Matter, for example, solubility, fusing point, chemical reactivity, photophysical property, biological medicament utilization rate etc..In pharmaceuticals industry often
It was found that a certain specific crystal formation in polymorphism just has sufficient drug effect, therefore, reasonable control crystallization condition obtains specific
Crystal form to improve drug pharmacological property be with a wide range of applications.
But the shortage of direct observation and follow-up study means to Crystallization and transformation of crystal is still a kind of huge
Big challenge.Traditional means such as single crystal diffraction, X-ray diffraction (XRD), transmission electron microscope (TEM), electronic diffraction (ED) and
Atomic force microscope (AFM) etc. often only to the characterization of crystallization beginning, final state crystal form, only provides the experiment number of indirect ex situ
According to, and the intuitive, observation and description to entire dynamic process especially intermediate state in real time can not be provided, however intermediate state
Observation for in-depth understand crystal formation and transformation mechanism be of crucial importance.In the phase transition process of fluorescent molecule
In, the variation of fluorescence color and efficiency will provide a kind of intuitive fluorescent visual approach.Fluorescent visual method is due to glimmering
The acuteness of light, it is more friendly, quick, inexpensive compared to traditional characterization method, more importantly can provide real-time, former
The observation to entire Crystallization and transformation of crystal of position.
Summary of the invention
In order to overcome the shortcomings and deficiencies of the prior art described above, assemble the primary purpose of the present invention is that providing a kind of utilize
Induced luminescence property realizes the method to crystal growth and the research of conversion process fluorescent visual.
Another object of the present invention is to be to provide a kind of fluorescent emission property of crystal using different crystal forms structure
Difference, realize and tracking be imaged to the real-time Dynamic Fluorescence of different crystal forms structure growth and conversion process.
The purpose of the present invention is realized by following proposal:
A method of it is realized using aggregation-induced emission property and crystal growth and conversion process fluorescent visual is studied,
By different using fluorescence emission wavelengths under compound different crystal forms state, it is brilliant that different crystal forms are distinguished using the method for fluorescence imaging
Body, and/or dynamic imaging tracking is carried out to the conversion process of different crystal forms.
The compound has structure shown in formula 1 or formula 2:
Wherein, R1It is each independently selected from sulphur atom or NH group；R2Be each independently selected from hydrogen atom, methyl, ethyl and
One of methoxyl group.
The compound is preferably 1- phenyl -2- (3- phenyl -2 (1H)-quinoxaline fork)-(2Z)-ethyl ketone (PPQE, Z-
1-phenyl-2-(3-phenylquinoxalin-2(1H)-ylidene)ethan-1-one)。
Described can be by using the ultraviolet of 300~400nm wavelength using fluorescence imaging method differentiation different crystal forms crystal
Light irradiation, visually observes, and according to the difference of the launch wavelength of different crystal forms, realizes the resolution to different crystal forms structural region.
Described can be by using the ultraviolet of 300~400nm wavelength using fluorescence imaging method differentiation different crystal forms crystal
Light irradiation is realized according to the difference of the launch wavelength of different crystal forms to different crystal forms structural area using Induced Fluorescence Microscopy
The resolution in domain.
The conversion process to different crystal forms carries out dynamic imaging tracking can be by using the purple of 300~400nm wavelength
Outer light irradiation carries out Time-resolved imaging using Induced Fluorescence Microscopy, and different crystal forms structure conversion process is moved in realization
State tracking.
Wherein, when preparing the different crystal forms crystal, can by the way that the compound is prepared as hot saturated solution, quickly or
Slow cooling solution, obtains crystal.
Or can be by the way that the compound is prepared as room temperature saturated solution, slow solvent flashing, obtains crystal at room temperature.
Or it then can be immediately placed in liquid nitrogen and be quickly cooled down, obtain without fixed by melting the compound at high temperature
The sample of shape state.
The high-temperature fusion can be 200 DEG C.
Above-mentioned is that solution preferably uses single solvent or mixed solvent.
The solvent may include dimethyl sulfoxide, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, acetonitrile, methanol,
Ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, the tert-butyl alcohol, ethyl acetate, 1,4- dioxane, tetrahydrofuran, chloroform, dichloromethane
Alkane, acetone, ether, petroleum ether, n-hexane and hexamethylene etc..
Gained crystal or the sample of amorphous state use the ultraviolet light of 300~400nm wavelength, visually observe, root
According to the difference of the launch wavelength of different crystal forms, the resolution to different crystal forms structural region is realized.
Gained crystal or the sample of amorphous state use the ultraviolet light of 300~400nm wavelength, using fluorescence microscopy
Imaging technique realizes the resolution to different crystal forms structural region according to the difference of the launch wavelength of different crystal forms.
It is above-mentioned that preferably the tiny area of sample is imaged using Induced Fluorescence Microscopy.
Gained crystal or the sample of amorphous state use the ultraviolet light of 300~400nm wavelength, using fluorescence microscopy
Imaging technique carries out Time-resolved imaging, realizes the dynamically track to different crystal forms structure conversion process.
It is above-mentioned that preferably the tiny area of sample is imaged using Induced Fluorescence Microscopy.
Above compound is the molecule with heterocycle structure, is hardly shone in solution and unformed shape, but crystallizing
It can get the aggregation-induced emission property of hyperfluorescence transmitting under state.It can get the compound not by different crystallization conditions
Isomorphous crystal, different crystal forms can change under given conditions, by the difference of the fluorescence emission wavelengths of different crystal forms,
It is convenient to growth and transformation of crystal process to crystal and carries out visualization tracking and monitoring.
In addition, also assembling to prepared by mechanical scribing method with the crystal threadiness aligned using the method for the present invention
The growth course of structure carries out fluorescent visual research.The method of the present invention is stablized with compound used therefor property, and preparation is simple, respectively
The crystal of crystal form prepares convenient and efficient, and different crystal forms crystallo-luminescence nature difference obtained is big, and transformation of crystal process observation is simple
It is convenient, sensitive quick feature is monitored to crystal form conversion process, can be widely applied to crystal habit conversion process research, phase turns
Become the fields such as mechanism study.
The present invention compared with the existing technology, have the following advantages and the utility model has the advantages that
Fluorescent molecule of the present invention with aggregation-induced emission property has preparation method easy to operate, and raw material is easy
, the mild feature of reaction condition.
The method provided by the invention monitored to different crystal forms structure growth and conversion process real-time tracking, has operation letter
Just, rapidly, the characteristics of result is accurate, be not required to be further processed sample, real-time detection in situ.This method is in crystalline state point
The fields such as analysis, the research of phase transformation mechanism have practical application value.
Detailed description of the invention
Fig. 1 is the chemistry and mono-crystalline structures of compound PPQE in embodiment 1, wherein three kinds of different crystals A, B, C's is glimmering
The intermolecular Mathematical Model of heaped-up top view (2) and side view of light microscope photo (1) and three kinds of different crystal A, B, C structure cells
(3)。
Fig. 2 is crystal A, B, C of compound PPQE and the photoluminescence spectra of amorphous state sample in embodiment 1.
Fig. 3 is in embodiment 2, and the conversion process fluorescent visual of monocrystalline of the compound PPQE from crystal C to B to monocrystalline is supervised
Control imaging, A~D are 10 minutes, and E~H is 5 hours, and I~L is 1 day and M~P is 2 days；A~C, E~G, I~K and M~O are days
Photo under light lamp；D, H, L and P are the photos shot under fluorescence microscope.
Fig. 4 is to pass through acetone/tert-butyl alcohol mixed solution of the PPQE in syringe needle scribing solvent volatilization process in embodiment 3
The fluorescent microscopy images of the crystal accumulation line of induced synthesis.
Fig. 5 is in embodiment 4, and the amorphous state sample of the PPQE observed under different multiples fluorescence microscope is with the time
Elapse the process changed to crystalline state.Initial amorphous state sample: emission wavelength lambdaem=595nm, fluorescence quantum yield Φ=
0.8%；Amorphous state sample after being placed at room temperature for 48 hours: emission wavelength lambdaem=566nm, fluorescence quantum yield Φ=
8.5%.
Fig. 6 is principle of the invention effect picture.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto.
Reagent used in the following example can be obtained from commercial channel.
Embodiment 1
1- phenyl -2- (3- phenyl -2 (1H)-quinoxaline fork)-(2Z)-ethyl ketone, PPQE, Z-1-phenyl-2- (3-
Phenylquinoxalin-2 (1H)-ylidene) ethan-1-one, structural formula:
The preparation of molecule monocrystalline A: 1mL dimethyl sulfoxide solvent is added in 200mg PPQE for method one, heats at 150 DEG C
To being completely dissolved, heating stirring is closed, the Slow cooling in oil bath pan is recrystallized to give orange block-like monocrystalline A；Method two,
It is slowly added to suitable tert-butyl alcohol under slight boiling condition, in PPQE to just dissolving, prepares the hot saturated solution of the tert-butyl alcohol of PPQE,
Then the slow Temperature fall of solution in oil bath pan obtains orange block-like monocrystalline A.
The preparation of PPQE molecule monocrystalline B: the slightly boiled solution of acetonitrile that concentration is 12.5mg/mL PPQE is slow in oil bath pan
Temperature fall is recrystallized to give orange diamond shape monocrystalline B.
The synthesis of PPQE molecule monocrystalline C: the slightly boiled solution of acetonitrile that concentration is 6mg/mL PPQE rapid and natural in air drops
Temperature is recrystallized to give orange whiskers C.
The preparation of PPQE molecule amorphous state sample: PPQE is complete in 200 DEG C of meltings, it is then immediately placed in liquid nitrogen fast
Quickly cooling but obtains the amorphous state sample of red glass shape.See Fig. 1~2.
Embodiment 2
The conversion of PPQE molecule monocrystalline C to monocrystalline B is observed: typical experimental implementation is to heat 100mgPPQE at 80 DEG C
Under the conditions of be dissolved completely in 8mL acetonitrile, the then culture dish of fast transfer to diameter 6cm is quickly cooled down in room temperature.In crystal
Growth and monocrystalline conversion process in, save culture dish strictly seal the volatilization to prevent solvent.So quickly cooling down
Cheng Zhong, acicular monocrystalline C are quickly generated, and then as the propulsion of time, monocrystalline C in situ is to monocrystalline B's in acetonitrile solution
Conversion can be observed directly in room temperature, and carry out the photograph taking under fluorescent lamp and UV lamp irradiation simultaneously in different periods.See
Fig. 3.
Embodiment 3
For PPQE molecule in the crystal growing process in tert-butyl alcohol supersaturated solution, the crystal of metal needle scribing induction is raw
Long and arrangement: by the way that in the PPQE tert-butyl alcohol supersaturated solution in substrate of glass, two tools are can be obtained in metal needle scribing drop
Have a PPQE crystal accumulation line that different shapes are parallel with luminescent color, Green and yellow fluorescence crystal accumulation line respectively by
The crystal form C and A of dynamic stabilization are formed.The observation of this crystal form coherent condition by way of UV light micro-imaging with photo
Shooting approach is recorded.See Fig. 4.
Embodiment 4
The micro- monitoring of the dynamic of PPQE molecule amorphous state to crystalline state: typical experimental implementation is, by 500mg
PPQE is melted completely under 200 DEG C of heating conditions, and then fast transfer is cooling into liquid nitrogen, obtains amorphous state solid as red
Translucent glass shape solid, at room temperature basic unstressed configuration emission characteristic.Microscopic imaging fluorescence tracking is carried out to sample, with
Extend in the standing time of room temperature, can obviously observe that sample surfaces become coarse, granulating, while fluorescence by smooth
Transmitting is generated and is remarkably reinforced.This crystal form state transformation observation by way of visible light and UV light micro-imaging with photo
Shooting approach is recorded.See Fig. 5.The principle of the present invention effect picture is shown in Fig. 6.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (6)
1. using aggregation-induced emission to crystal growth and conversion fluorescent visual research method, it is characterised in that by utilizationization
It closes that fluorescence emission wavelengths under object different crystal forms state are different, different crystal forms crystal and/or right is distinguished using the method for fluorescence imaging
The conversion process of different crystal forms carries out dynamic imaging tracking；
The compound has structure shown in formula 1:
Wherein, R1It is each independently selected from sulphur atom or NH group；R2It is each independently selected from hydrogen atom, methyl, ethyl and methoxy
One of base.
2. according to claim 1 to crystal growth and convert fluorescent visual research method using aggregation-induced emission,
It is characterized by: described distinguish different crystal forms crystal by using the ultraviolet of 300~400nm wavelength using fluorescence imaging method
Light irradiation, visually observes, and according to the difference of the launch wavelength of different crystal forms, realizes the resolution to different crystal forms structural region；
Or it is described using fluorescence imaging method distinguish different crystal forms crystal by using 300~400nm wavelength ultraviolet lighting
It penetrates, is realized according to the difference of the launch wavelength of different crystal forms to different crystal forms structural region using Induced Fluorescence Microscopy
It differentiates.
3. according to claim 1 to crystal growth and convert fluorescent visual research method using aggregation-induced emission,
It is characterized by: the conversion process to different crystal forms carries out dynamic imaging tracking by using the purple of 300~400nm wavelength
Outer light irradiation carries out Time-resolved imaging using Induced Fluorescence Microscopy, and different crystal forms structure conversion process is moved in realization
State tracking.
4. according to claim 1 to crystal growth and convert fluorescent visual research method using aggregation-induced emission,
It is characterized by: when preparing the different crystal forms crystal of the compound, by the way that the compound is prepared as hot saturated solution, fastly
Speed or Slow cooling solution, obtain crystal；
Or by the way that the compound is prepared as room temperature saturated solution, slow solvent flashing, obtains crystal at room temperature；
Or it by melting the compound at high temperature, is then immediately placed in liquid nitrogen and is quickly cooled down, obtain amorphous state
Sample.
5. according to claim 4 to crystal growth and convert fluorescent visual research method using aggregation-induced emission,
It is characterized by: the high-temperature fusion is 200 DEG C；The solution uses single solvent or mixed solvent；The solvent packet
Include dimethyl sulfoxide, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, acetonitrile, methanol, ethyl alcohol, normal propyl alcohol, isopropanol,
N-butanol, the tert-butyl alcohol, ethyl acetate, 1,4- dioxane, tetrahydrofuran, chloroform, methylene chloride, acetone, ether, petroleum ether,
At least one of n-hexane and hexamethylene.
6. described in claim 1 to crystal growth and convert fluorescent visual research method to machine using aggregation-induced emission
The growth course with the crystal threadiness aggregated structure aligned of tool scribing method preparation carries out fluorescent visual research
Using.
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| CN105567217A (en) * | 2015-12-15 | 2016-05-11 | 华南理工大学 | Multi-stimulus-response organic small-molecular luminescent material, and preparation and application thereof |
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| CN103645193A (en) * | 2013-12-18 | 2014-03-19 | 中国科学院空间科学与应用研究中心 | Colloidal crystal growth detection control device |
| CN105567217A (en) * | 2015-12-15 | 2016-05-11 | 华南理工大学 | Multi-stimulus-response organic small-molecular luminescent material, and preparation and application thereof |
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