CN106769968A - A kind of method that there is π π hyperconjugations in the fragrant hydrocarbon molecule of judgement conjugation - Google Patents
A kind of method that there is π π hyperconjugations in the fragrant hydrocarbon molecule of judgement conjugation Download PDFInfo
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- CN106769968A CN106769968A CN201710010093.XA CN201710010093A CN106769968A CN 106769968 A CN106769968 A CN 106769968A CN 201710010093 A CN201710010093 A CN 201710010093A CN 106769968 A CN106769968 A CN 106769968A
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- hyperconjugations
- conjugation
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- 230000021615 conjugation Effects 0.000 title claims abstract description 29
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 21
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 21
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 26
- 239000013077 target material Substances 0.000 claims abstract description 16
- 238000012360 testing method Methods 0.000 claims abstract description 6
- 238000002474 experimental method Methods 0.000 claims abstract description 4
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010835 comparative analysis Methods 0.000 claims description 2
- 230000003993 interaction Effects 0.000 abstract description 3
- 230000009878 intermolecular interaction Effects 0.000 abstract description 3
- 230000005693 optoelectronics Effects 0.000 abstract description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 16
- 150000002220 fluorenes Chemical class 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 8
- 238000011160 research Methods 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 5
- 230000001427 coherent effect Effects 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 230000007474 system interaction Effects 0.000 description 2
- KRIISESLIPIHMJ-UHFFFAOYSA-N 9H-fluorene pyrene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 KRIISESLIPIHMJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
Abstract
A kind of method that there is π π hyperconjugations in fragrant hydrocarbon molecule of judgement conjugation, is related to organic optoelectronic areas.Comprise the following steps：Selection control material；The UV spectrograms of test target material and control material；Experiment gained UV spectrograms are analyzed, if the absworption peak peak shape corresponding to main conjugated system there occurs change, and the number of absworption peak is more than the number of conjugated system in its molecule, then illustrate that the target material has π π hyperconjugations, conversely, then without.In the fragrant hydrocarbon molecule of conjugation, a kind of interaction that two π systems will be coupled together and formed by two singly-bounds, referred to as π π hyperconjugations.π π hyperconjugations have a major impact to the carrier transport ability of material and intermolecular interaction, material is even set to produce special photoelectric characteristic, so the present invention has very big promotion and directive function to the design for researching and analysing the photoelectron performance and novel organic luminescent material molecular structure of organic photoelectrical material.
Description
Technical field
The present invention relates to organic photoelectric subdomains, and in particular to there is π-π in the fragrant hydrocarbon molecule of one kind judgement conjugation super common
The method of yoke effect.
Background technology
By the development of decades, organic semiconducting materials are in organic electroluminescent LED (OLED), organic field
The fields such as effect transistor (OFET), organic photovoltaic devices (OPV) are widely used.In the semiconductor devices course of work,
Mainly completed by the transmission in electronics in organic semiconducting materials and hole.Such as at organic electroluminescent LED (OLED)
In, its operation principle is：In the presence of applied voltage electric field, anode exports electricity to luminescent layer output hole, negative electrode to luminescent layer
Son, and exciton is formed in luminescent layer, there is attenuation in the process, its energy is released and forms luminescence phenomenon.Therefore, have
The electron transport ability of machine semiconductor has conclusive effect to the quality of device performance.Organic semiconducting materials are most
It is conjugation aromatic hydrocarbon.
In conjugation aromatic hydrocarbon intramolecular often with the presence of multiple pi-conjugated systems, distinct fragrance hydrocarbon is caused to show various
Photoelectric properties, meet the application of different opto-electronic devices.In the fragrant hydrocarbon molecule of conjugation, different pi-conjugated system is at it to phase
The characteristic peak of different shape and position is embodied in the UV spectrum answered.And between the different pi-conjugated system of intramolecular mutually
Effect also results in photoelectric properties and changes.Therefore, the pi-conjugated system of intramolecular is made clear in the existence form of intramolecular to light
There is directiveness to act on for the research of electrical property.
Found in research process in some specific organic molecules with multiple pi-conjugated architectures, some of which π
Both there is no mutually conjugation in conjugated system, nor being joined directly together by singly-bound, but connected two π systems by two singly-bounds
Pick up and, our this interactions is called π-π hyperconjugations.Its photoelectric properties and intermolecular phase interaction to material
With having a great impact.And be conjugated in the research process of aromatic hydrocarbon, UV spectrum are often used in qualitatively embodying certain functional group is
No presence；π-π hyperconjugations whether there is in therefore, it can judge to be conjugated fragrant hydrocarbon molecule by UV spectrum.
The present invention is particular by the structural analysis with similar molecular architecture conjugation aromatic hydrocarbon, with hands such as UV spectrum
Section, comprehensive analysis whether there is π-π hyperconjugations in studying fragrant hydrocarbon molecule.Research of the present invention to luminous organic material
There is certain impetus.
The content of the invention
The technical problem of solution：For conjugation aromatic hydrocarbon molecular structure investigative technique problem, the present invention provides a kind of judgement
The method that there is π-π hyperconjugations in the fragrant hydrocarbon molecule of conjugation, can simply, directly reflect the pi-conjugated system of intramolecular
Existing forms, to research organic molecule internal structure and its photoelectron performance have critically important directive function.
Technical scheme：A kind of method that there is π-π hyperconjugations in fragrant hydrocarbon molecule of judgement conjugation, including following step
Suddenly：
Step one, selection control material, contain and target material identical in selected control material its molecular structure
Main conjugated system, the main conjugated system refers to the pi-conjugated structure of maximum in molecule, and the target material and control material are equal
It is fragrant hydrocarbon molecule；
The UV spectrograms of step 2, test target material and control material；
Step 3, the UV spectrograms obtained by experiment are analyzed, the UV spectrum using control material determine main conjugated body
It is position and the peak shape of absworption peak, the UV spectrum of comparative analysis target material, if the absorption peak-to-peak corresponding to main conjugated system
Shape there occurs the number of conjugated system in change, and unnecessary its molecule of number of absworption peak, then illustrate that the target material has
π-π hyperconjugations, conversely, then without.
Preferably, the target material has at least two pi-conjugated systems.
Preferably, the control material has at least one pi-conjugated system.
Preferably, the target material and control material use UV light under the solution or filminess that good solvent is configured to
Spectrum is characterized.
Preferably, the good solvent is dichloromethane.
Beneficial effect：1st, the present invention proposes a kind of side for judging and there is π-π hyperconjugations in the fragrant hydrocarbon molecule of conjugation
Method, can directly reflect the existence form of the conjugation pi-conjugated system of aromatic hydrocarbon intramolecular, for research intramolecule structure is provided newly
Method.
2nd, the existence form of the pi-conjugated system of intramolecular directly affects material photoelectron performance, therefore the present invention is to material
The research of photoelectric properties also has impetus.
3rd, the presence of intramolecular π-π hyperconjugations has inevitable contact, therefore the present invention to intermolecular interaction
For the physical properties such as research material aggregation pattern provide a kind of new way.
4th, experiment test condition of the present invention is less demanding, easily operation.
Whether the present invention may determine that in organic molecule containing π-π hyperconjugations, further perfect molecular structure
To intermolecular interaction, the influence of the characteristics of luminescence.
Brief description of the drawings
Fig. 1 is UV spectrograms of the BP1 and PFP1 under solution state；
Fig. 2 is UV spectrograms of the BP1 and PFP1 under filminess；
Fig. 3 schemes for the SEM of PFP1 coherent conditions；
Fig. 4 schemes for the SEM of BP1 coherent conditions；
Fig. 5 is UV spectrograms of the BP2 and PFP2 under solution state；
Fig. 6 is UV spectrograms of the BP2 and PFP2 under filminess；
Fig. 7 schemes for the SEM of PFP2 coherent conditions；
Fig. 8 schemes for the SEM of BP2 coherent conditions.
Specific embodiment
The present invention is described in detail with specific embodiment below in conjunction with the accompanying drawings.
Embodiment 1
Judge the presence of π-π hyperconjugations in organic material PFP1 molecular structures.
Specific steps：
1. select has the BP1 of identical main conjugated system as control material with PFP1, and the main conjugated system refers to point
Maximum pi-conjugated structure in son, PFP1 and BP1 is fragrant hydrocarbon molecule.PFP1, BP1 structure are as follows：
2. UV spectrograms of the PFP1 and BP1 under solution, filminess is tested respectively.
3. reference picture 1, the UV spectrograms of two kinds of compounds can be seen that BP1 and occur only at 355nm under solution state
One peak value wider, this be due in BP1 molecules the pyrene of fluorenes C2 and fluorenes there occurs mutually conjugation form one it is larger
Pyrene-fluorenes pi-conjugated system formed.And occur two sharp peak values in PFP1 molecules, it is evident that the peak value at 335nm
Be the pyrene on fluorenes C9 positions, herein spike also indicate that simultaneously the pyrene of fluorenes C9 do not have with fluorenes mutually conjugation and separately as a π
Conjugated system is deposited in the molecule；Occur a spike at 352nm and form big pi-conjugated System forming with fluorenes-pyrene conjugation
Peak value (should be in 355nm or so) there occurs and partly overlap；It is completely different be for a new peak value occurs at 352nm, this
Place's peak value is that pi-conjugated system and the fluorenes-pyrene conjugation of a pyrene of fluorenes C9 form big pi-conjugated system interaction and formed, i.e.,
π-π hyperconjugations.UV spectrum tests result (such as Fig. 2) under filminess is echoed with Fig. 1 phases.Therefore, further demonstrate
There is π-π hyperconjugations in PFP1 intramoleculars.
In addition, the aggregation pattern to PFP1, BP1 is observed (see Fig. 3, Fig. 4), show that intramolecular has π-π
The molecule of hyperconjugation easily forms more homogeneous pattern, and this explanation π-π hyperconjugation affects indirectly intermolecular work
Firmly.
Embodiment 2
Judge the presence of π-π hyperconjugations in organic material PFP2 molecular structures.
Specific steps：
1. select has the BP2 of identical main conjugated system as control material with PFP2, and the main conjugated system refers to point
Maximum pi-conjugated structure in son, PFP2 and BP2 is fragrant hydrocarbon molecule.PFP2, BP2 structure are as follows：
2. UV spectrum of the PFP2 and BP2 under solution, filminess is tested respectively.
3. reference picture 5, the UV spectrograms of two kinds of compounds can be seen that BP2 and occur only at 365nm under solution state
One peak value wider, this be due in BP2 molecules the pyrene of fluorenes C2 and fluorenes there occurs mutually conjugation form one it is larger
The pi-conjugated system of fluorenes-pyrene and formed.And occurring two sharp peak values in PFP2 molecules, the peak value at 335nm is fluorenes C9
Pyrene on position, herein spike also indicate that simultaneously the pyrene of fluorenes C9 do not have with fluorenes mutually conjugation and separately as a pi-conjugated body
System deposits in the molecule；The peak value that one spike of appearance forms big pi-conjugated System forming with fluorenes-pyrene conjugation at 352nm should
Should in 365nm or so) there occurs and partly overlap, it is a new peak value appearance 352nm at equally, peak value is a fluorenes herein
The pi-conjugated system of the pyrene of C9 forms big pi-conjugated system interaction and is formed with fluorenes-pyrene conjugation, i.e. π-π hyperconjugation effect
Should.Analysis draws：There is π-π hyperconjugations in PFP2 intramoleculars.UV spectrum tests result (such as Fig. 6) under filminess with
Fig. 5 phases are echoed.Therefore, further demonstrate in PFP1 intramoleculars there is π-π hyperconjugations.
Similar, the aggregation pattern to PFP2, BP2 is observed (see Fig. 7, Fig. 8), show that intramolecular has π-π super common
The molecule of yoke effect easily forms more homogeneous pattern, furtherly understands that π-π hyperconjugations affect indirectly molecule
Intermolecular forces.
PFP1, BP1, PFP2 and BP2 are synthetic material in above-described embodiment, have there is delivering for correlative theses.Specifically
Name is as follows：PFP1：2- pyrenyls -9- (4 '-(2 "-ethyl alcoxyl hexyl) benzene) -9- pyrenyl fluorenes；BP1：2- pyrenyls -9- (4 ' -
(2 "-ethyl alcoxyl hexyl) benzene) -9- p-methylphenyl fluorenes；PFP2：Pyrenyl-the 9- of 2,7- bis- (4 '-(2 "-ethyl alcoxyl hexyl) benzene)-
9- pyrenyl fluorenes；BP2：Pyrenyl-the 9- of 2,7- bis- (4 '-(2 "-ethyl alcoxyl hexyl) benzene) -9- p-methylphenyl fluorenes.
Claims (5)
1. a kind of method that there is π-π hyperconjugations in fragrant hydrocarbon molecule of judgement conjugation, it is characterised in that including following step
Suddenly：
Step one, selection control material, contain common with target material identical master in selected control material its molecular structure
Yoke system, the main conjugated system refers to the pi-conjugated structure of maximum in molecule, and the target material and control material are virtue
Fragrant hydrocarbon molecule；
The UV spectrograms of step 2, test target material and control material；
Step 3, the UV spectrograms obtained by experiment are analyzed, determine that main conjugated system is inhaled using the UV spectrum of control material
Receive position and the peak shape at peak, the UV spectrum of comparative analysis target material, if the absworption peak peak shape hair corresponding to main conjugated system
Given birth to change, and absworption peak number of the number more than conjugated system in its molecule, then illustrate that there is the target material π-π to surpass
Conjugation, conversely, then without.
2. the method that there is π-π hyperconjugations in a kind of fragrant hydrocarbon molecule of judgement conjugation according to claim 1, it is special
Levy and be, the target material has at least two pi-conjugated systems.
3. the method that there is π-π hyperconjugations in a kind of fragrant hydrocarbon molecule of judgement conjugation according to claim 1, it is special
Levy and be, the control material has at least one pi-conjugated system.
4. the method that there is π-π hyperconjugations in a kind of fragrant hydrocarbon molecule of judgement conjugation according to claim 1, it is special
Levy and be, the target material and control material carry out table under the solution or filminess that good solvent is configured to UV spectrum
Levy.
5. the method that there is π-π hyperconjugations in a kind of fragrant hydrocarbon molecule of judgement conjugation according to claim 4, it is special
Levy and be, the good solvent is dichloromethane.
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