CN105778142B - The preparation method of the polydiacetylene micron tube of purpurine modification and fiber waveguide device and preparation method thereof - Google Patents
The preparation method of the polydiacetylene micron tube of purpurine modification and fiber waveguide device and preparation method thereof Download PDFInfo
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- CN105778142B CN105778142B CN201610097351.8A CN201610097351A CN105778142B CN 105778142 B CN105778142 B CN 105778142B CN 201610097351 A CN201610097351 A CN 201610097351A CN 105778142 B CN105778142 B CN 105778142B
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Abstract
The present invention provides a kind of preparation methods of the polydiacetylene micron tube of purpurine modification, include the following steps：It is reacted after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidol ether, obtains the polydiacetylene micron tube of allyl glycidyl ether modification；Viologen Compounds are mixed with the end alkene that halogen replaces, the purpurine of end alkenyl substitution is obtained after reaction；The polydiacetylene micron tube that the allyl glycidyl ether is modified and the purpurine that the end alkenyl replaces are carried out under the action of initiator it is light-initiated, obtained after reaction purpurine modification polydiacetylene micron tube.Present invention also provides a kind of fiber waveguide devices comprising the polydiacetylene micron tube of purpurine modification prepared by the application.Fiber waveguide device provided by the present application has the reversible control of optical waveguide.
Description
Technical field
The present invention relates to the preparation sides for the polydiacetylene micron tube that fiber waveguide device technical field more particularly to purpurine are modified
Method and fiber waveguide device and preparation method thereof.
Background technology
Optical waveguide is the medium apparatus for guiding light wave to propagate wherein, is made of light transparent medium (such as quartz glass)
Transmission optical frequency electromagnetic wave leading structure.The transmission principle of optical waveguide is different from metal enclosed waveguide, is in different refractions
On the dielectric interface of rate, the total reflection phenomenon of electromagnetic wave makes light wave be confined to propagate in waveguide and its surrounding finite region.
For optical waveguide itself due to being the integrated of many-sided science, research and application range are also very extensive small
The compact waveguiding structure of type is advantageously implemented the integrated of light path.Light wave transmission in the waveguide, coupling and with outfield phase interaction
It is the basis of integrated optics design and manufacture with caused various physical phenomenons.
Conjugatd polymers have many advantages, such as preferable flexible, machinability, nano laser, biosensor,
There is broader foreground in terms of waveguide sensing.Regulation and control optical waveguide majority is dependent on light regulation and control, chemical regulation, heat regulation and control etc. at present
Aspect, compared with compared to, electricity regulation and control optical waveguide have many advantages, such as remote control and regulation, it is easy to operate, respond it is sensitive, small by external interference,
It is more and more studied in terms of developing electrooptic modulator.It is polymerize as a result, using organic conjugate this application provides a kind of
The fiber waveguide device of object structure.
Invention content
Present invention solves the technical problem that being to provide a kind of fiber waveguide device, fiber waveguide device provided by the present application can be real
Existing reversible electric field regulation and control.
In view of this, this application provides a kind of preparation method of the polydiacetylene micron tube of purpurine modification, including it is following
Step：
It is reacted after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidol ether, obtains allyl contracting
The polydiacetylene micron tube of water glycerin ether modification；
Viologen Compounds are mixed with the end alkene that halogen replaces, the purpurine of end alkenyl substitution is obtained after reaction；
The purpurine that the polydiacetylene micron tube that the allyl glycidyl ether is modified replaces with the end alkenyl is being drawn
Hair agent under the action of carry out it is light-initiated, obtained after reaction purpurine modification polydiacetylene micron tube.
Preferably, the Viologen Compounds are 4,4- bipyridyls, and the end alkene of the halogen substitution is 3- bromopropenes.
Preferably, the surface is the polydiacetylene micron tube of amino and the molar ratio of the acrylic glycidol ether is
1：(1~2)；The molar ratio of the Viologen Compounds and the end alkene of halogen substitution is 1：(2~3).
Preferably, the light-initiated light is ultraviolet light or infrared light.
Preferably, the light-initiated wavelength is 365nm.
Present invention also provides a kind of fiber waveguide devices, including the purpurine prepared by the preparation method described in said program is repaiied
The polydiacetylene micron tube of decorations.
Present invention also provides the preparation methods of the fiber waveguide device, include the following steps：
The conductive layer of two panels glass electrode is oppositely arranged, insulating layer coating is applied at the both ends of the conductive layer；
The polydiacetylene of the purpurine modification prepared by the preparation method described in said program is added between the insulating layer
The electrolyte solution of micron tube, obtains fiber waveguide device.
Preferably, the insulating materials of the insulating layer is polymethyl methacrylate.
This application provides a kind of preparation methods of the polydiacetylene micron tube of purpurine modification, are first amino by surface
Polydiacetylene micron tube reacted with acrylic glycidol ether (AGE), obtain AGE modification polydiacetylene micron tube, will be purple
The end alkene reaction of smart class compound and halogen substitution, obtains the purpurine of end alkenyl substitution, and the polydiacetylene for then modifying AGE is micro-
Mitron carries out click with the purpurine of end alkenyl substitution and reacts, and obtains the polydiacetylene micron tube of purpurine modification.Herein described light
Include the polydiacetylene micron tube of purpurine modification, wherein the purpurine base in the polydiacetylene micron tube of purpurine modification in waveguide device
Group is in divalent under normal circumstances, and the conversion of divalent and monovalence, i.e. oxidation state and reduction occur under the action of external electrical field
Reversible phase co-conversion occurs for state, whether absorption with polydiacetylene micron tube generation fluorescence resonance energy transfer with purpurine, in turn
Regulate and control polydiacetylene micron tube optical waveguide.When fiber waveguide device applies negative voltage, purpurine becomes monovalence, poly- diethyl from divalent
Purpurine in alkynes micron tube partially absorbs the phenomenon that can overlap with micron tube fluorescence, reality by resonance energy transfer
Existing micron tube fluorescent quenching；When being passed through forward voltage, purpurine becomes divalent from monovalence, and this variation of valence is along with extraneous electricity
It presses and changes, and there is invertibity, so that the device has regulation and control micron tube waveguide reversible nature.
Description of the drawings
Fig. 1 is the synthetic route and IR Characterization figure of the polydiacetylene micron tube of 1 purpurine of embodiment of the present invention modification；
Fig. 2 is the polydiacetylene micron tube stereoscan photograph and cross-section diagram of purpurine modification prepared by the embodiment of the present invention 1
Piece characterizes photo；
Fig. 3 be the polydiacetylene micron tube optical waveguide mechanism of the electricity regulation and control purpurine modification of the embodiment of the present invention 2, fluorescence spectrum and
Light guiding optics picture；
Fig. 4 is N element in purpurine unit different valence state in the polydiacetylene micron tube of 2 purpurine of embodiment of the present invention modification
XPS spectrum figure；
Fig. 5 be 3 purpurine of the embodiment of the present invention modification polydiacetylene micron tube under different voltages autofluorescence variation and
Waveguide port Fluorescencecontro spectrogram；
The polydiacetylene micron tube regulating and controlling voltage number of 4 purpurine of Fig. 6 embodiments embodiment of the present invention modification and response time
Curve graph.
Specific implementation mode
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still
It should be appreciated that these descriptions are only the feature and advantage further illustrated the present invention, rather than to the claims in the present invention
Limitation.
The embodiment of the invention discloses a kind of preparation methods of the polydiacetylene micron tube of purpurine modification, including following step
Suddenly：
It is reacted after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidol ether, obtains allyl contracting
The polydiacetylene micron tube of water glycerin ether modification；
Viologen Compounds are mixed with the end alkene that halogen replaces, the purpurine of end alkenyl substitution is obtained after reaction；
The purpurine that the polydiacetylene micron tube that the allyl glycidyl ether is modified replaces with the end alkenyl is being drawn
Hair agent under the action of carry out it is light-initiated, obtained after reaction purpurine modification polydiacetylene micron tube.
The application is prepared for the polydiacetylene micron tube of purpurine modification first, is repaiied as shown in Figure 1, Fig. 1 a are purpurine of the present invention
The synthetic route chart of the polydiacetylene micron tube of decorations.
During preparing the polydiacetylene micron tube of purpurine modification, surface is first the poly- diethyl of amino by the application
Alkynes micron tube is reacted after being mixed with acrylic glycidol ether (AGE), obtains the polydiacetylene micron tube of AGE modifications.The table
The reaction equation that the polydiacetylene micron tube of face amino is reacted with AGE is as follows：
In above process, the surface is the polydiacetylene micron tube of amino and rubbing for the acrylic glycidol ether
You are than preferably 1: (1~2), in embodiment, more preferably 1:1.2.Herein described surface is that the polydiacetylene of amino is micro-
The preparation method of mitron is carried out according to mode well known to those skilled in the art, is not particularly limited to this application.It is described
One end contains double bond one end and contains epoxy group, reaction mechanism according to the invention, in the poly- diethyl that above-mentioned preparation is modified in AGE
During alkynes micron tube, one of raw material AGE can be without being limited thereto, can also be other compounds, as long as one end contain it is double
One section of small molecule containing epoxy group of key.
The application simultaneously mixes Viologen Compounds with the end alkene that halogen replaces, and the purple of end alkenyl substitution is obtained after reaction
Essence.During this, the Viologen Compounds are preferably 4,4- bipyridyls, and the end alkene of the halogen substitution is preferably 3- bromines third
Alkene.By taking 4,4- bipyridyls and 3- bromopropenes as an example, above-mentioned reaction equation is as follows：
In above-mentioned reaction process, the molar ratio of the Viologen Compounds and the end alkene of halogen substitution is preferably 1
: (2~3), in embodiment, more preferably 1:2.2.The end alkene that the application replaces the Viologen Compounds and halogen comes
Source is not particularly limited, prepared according to mode well known to those skilled in the art or be commercial product.
The purpurine that the application finally replaces the polydiacetylene micron tube of AGE modifications with end alkenyl is under the action of initiator
Carry out it is light-initiated, obtained after reaction purpurine modification polydiacetylene micron tube.Above-mentioned reaction is reacted for click, and the application utilizes
Initiator makes the polydiacetylene micron tube that AGE is modified and the purpurine of end alkenyl substitution that click occur anti-under the action of light-initiated
It answers.The application is not particularly limited the initiator, as long as the initiator of sulfydryl and double bond click can be caused,
Can be initiator I-2959, or ultraviolet light-initiated DMPA.The application preferably uses ultraviolet light or infrared light to carry out
Light-initiated, the light-initiated wavelength is preferably 365nm.
Present invention also provides a kind of fiber waveguide devices comprising the purpurine prepared by preparation method described in said program
The polydiacetylene micron tube of modification.
Present invention also provides a kind of fiber waveguide devices comprising following steps：
The conductive layer of two panels glass electrode is oppositely arranged, insulating layer coating is applied at the both ends of the conductive layer；
The polydiacetylene of the purpurine modification prepared by the preparation method described in said program is added between the insulating layer
The electrolyte solution of micron tube, obtains fiber waveguide device.
During preparing fiber waveguide device, the conductive layer of ITO two panels glass electrodes is oppositely arranged by the application first,
Even if the conductive layer of two panels glass electrode is in contact with conductive layer.Electric current is only flowed through from the sides ITO in order to prevent, forms short circuit,
The application applies insulating layer coating at the both ends of the conductive layer.The application is not particularly limited the substance of the insulating layer, is
Insulating materials well known to those skilled in the art, preferably, the insulating materials of the insulating layer is preferably poly- first
Base methyl acrylate.
According to the present invention, ito glass electrode is then not coated with addition purpurine among-two insulating layer of part of insulating layer coating and is repaiied
The electrolyte solution of the polydiacetylene micron tube of decorations, obtains fiber waveguide device.
Preferably, then the polydiacetylene micron tube of purpurine modification is passed through ultraviolet light, polymerization by the application
For blue micron tube the red phase micron tube with optical waveguide property is formed using heat treatment.
The electrolyte solution is electrolyte solution well known to those skilled in the art, is not limited particularly this application
System, preferably, the electrolyte solution is preferably Klorvess Liquid.
After polydiacetylene micron tube in order to detect purpurine modification is used for fiber waveguide device, the performance of fiber waveguide device, this
Between the polydiacetylene micron tube that purpurine modify is placed in two panels ito glass electrode by application, addition -1.5, -1.0, -0.5,0,
0.5,1.0, when 1.5V voltages, same position 532nm light excites micro-pipe tube wall, surveys the variation of port fluorogram；Apply negative sense electricity
After pressure, fluorescence resonance energy transfer (FRET) occurs for purpurine part and micro-pipe itself in polydiacetylene micron tube, at 640nm
Fluorescence is gradually reduced, and is finally reached and 60% or more efficiency is quenched；When being passed through forward voltage into system, fluorescence peak rises, most
It can be restored to original fluorescence intensity eventually；Thus illustrate, the polydiacetylene micron tube optical waveguide of purpurine modification has good electricity
Dependence, invertibity and device stability are pressed, and belongs to low voltage drive system, this system may continue as electric field regulation and control
Polydiacetylene micron tube fiber waveguide device.
The application prepare purpurine modification polydiacetylene micron tube can be used as fiber waveguide device carry out optical waveguide be by
Be in divalent under normal circumstances in purpurine group, occur under extraneous electric field action divalent and monovalence, that is, oxidized and reduced it
Between reversible phase co-conversion occurs, with purpurine absorb with polydiacetylene micron tube occur fluorescence resonance energy transfer whether, in turn
Regulate and control polydiacetylene micron tube optical waveguide, shown in following reaction formula.The experimental results showed that：It is micro- in the polydiacetylene of purpurine modification
Mitron tube wall is excited with 532nm light, and fluorescence can be along tube wall waveguide, and then is emitted at port.Under the action of electric field,
Purpurine absorption can partly overlap with polydiacetylene micron tube fluorescence, realize from ultraviolet region red shift to visible light region
Micron pipe port fluorescence is quenched, and this variation is reversible, and then realizes electric field to the reversible tune of polydiacetylene micron tube waveguide
Control.The regulation and control method operating process is easy, electric field response is sensitive, quick, and environment resistant interference performance is strong, has remote control and regulation
The advantages that.
For a further understanding of the present invention, the polydiacetylene modified purpurine provided by the invention with reference to embodiment is micro-
The preparation method of mitron is described in detail with fiber waveguide device, and protection scope of the present invention is not limited by the following examples.
Embodiment 1
Amino replaces diacetylene and the melamine of octadecylamine substitution with molar ratio 4:1 is dissolved in a small amount of ethyl alcohol, then will be molten
Liquid is poured into 75 DEG C of 300mL ultra-pure waters, and ultrasonic 60min is placed on cooled to room temperature at dark, places into 4 DEG C of ice
In case overnight；After the polymerization of 254nm ultraviolet light irradiations, the above-mentioned vesicle solutions of 10ml is taken to be gradually added into 5*10-5M Pb2+, incubation at room temperature
Growth 1 week, obtains polydiacetylene micron tube；After the polymerization of 254nm ultraviolet light irradiations, 1.2 times will be added dropwise in the micron tube suspension
The allyl glycidyl ether (AGE) of equivalent, stirs the suspension for 24 hours at room temperature, water washing 2-3 times, obtains poly- the two of AGE modifications
Acetylene micron tube；4,4- bipyridyls are dissolved in DMF solution, the 3- bromopropene solution of 2.2 times of equivalents is added dropwise, is stirred under the conditions of 50 DEG C
72h is mixed, is filtered, product is washed 3 times with anhydrous ether, is dried in vacuo, and the purpurine of allyl substitution is obtained；By the poly- of AGE modifications
Diacetylene micron tube and the purpurine of allyl substitution are put into a certain amount of deionized water solution, are acted in initiator I-2959
Under, 365nm is light-initiated, is reacted by click, finally obtains the polydiacetylene micron tube of purpurine modification.The present embodiment purpurine is repaiied
The synthetic route of the polydiacetylene micron tube of decorations, infrared spectrum and XPS spectrum are as shown in Figure 1.
The polydiacetylene micron tube that above-mentioned purpurine is modified is deposited on silicon chip, SEM patterns are observed, as shown in Fig. 2, by scheming
2 it is found that micron tube prepared by the present invention is that surface is smooth, the hollow flexible tubular structure with certain wall thickness, and length is reachable
Centimetre or more, caliber is 2-3 μm, and wall thickness is about 1 μ m in size.
Embodiment 2
The red phase polydiacetylene micron tube for taking single purpurine modification, is deposited between two panels ito glass electrode, addition -4V
Fluorescence resonance energy transfer (FRET) occurs for voltage, purpurine part and micro-pipe itself in polydiacetylene micron tube, and 532nm light swashs
Micro-pipe tube wall is sent out, survey port fluorescence generates fluorescence at 640nm and is gradually reduced, efficiency is finally quenched and reaches 60%；When to system
In when being passed through positive 4V, same position excites micro-pipe tube wall with 532nm light, surveys port fluorescence and rises in 640nm fluorescence peaks, finally
It can be restored to original fluorescence intensity, as shown in figure 3, Fig. 3 is the polydiacetylene micron tube light that present invention electricity regulates and controls purpurine modification
Waveguide mechanism, fluorescence spectrum and light guiding optics picture.
Reversible redox transformation occurs under extraneous electric field action for purpurine group, is absorbed with purpurine micro- with polydiacetylene
Mitron occurs to regulate and control polydiacetylene micron tube fluorescence waveguide whether fluorescence resonance energy transfer occurs, as shown in figure 4, Fig. 4 is
In the polydiacetylene micron tube of 2 purpurine of embodiment of the present invention modification in purpurine unit different valence state N element XPS spectrum figure, purpurine
The N element receiving and losing electrons that above-mentioned variation is embodied on pyridine ring occur for the polydiacetylene micron tube of modification, show difference
The N element of valence state.
Embodiment 3
By purpurine modify polydiacetylene micron tube be placed in two panels ito glass electrode between, be added -1.5, -1.0, -
0.5,0,0.5,1.0, when 1.5V voltages, same position 532nm light excites micro-pipe tube wall, surveys the variation of port fluorogram, such as Fig. 5
Shown, Fig. 5 a excite for same position, and for the fluorescent quenching efficiency of micron tube wall itself with voltage change figure, Fig. 5 b are identical bits
Set excitation, the fluorescent quenching efficiency of micron pipe port is with voltage change figure, in figure ● expression be quenched efficiency with voltage apply from-
The changing value of 1.5V to 1V, ■ indicate that efficiency, which is quenched, to be applied with voltage from the -1V extremely changing values of -1.5V.After applying negative voltage,
Fluorescence resonance energy transfer (FRET) occurs for purpurine part and micro-pipe itself in polydiacetylene micron tube, is generated at 640nm
Fluorescence is gradually reduced, and final port is quenched efficiency and reaches 60% or more；When being passed through forward voltage into system, on fluorescence peak
It rises, is eventually restored to original fluorescence intensity.In contrast, the fluorescent quenching efficiency maximum of tube wall itself is not up to 60%.
The experiment proved that optical waveguide fluorescence variation in port is more sensitive compared with autofluorescence changes.
Embodiment 4
Between the polydiacetylene micron tube that purpurine is modified is placed in two panels ito glass electrode, -1.5,0V electricity is added repeatedly
When pressure, same position 532nm light excites micro-pipe tube wall, surveys the variation of port fluorogram, and calculate port fluorescent quenching efficiency, such as
Shown in Fig. 6, Fig. 6 a are electricity regulation and control micron tube response time figure, by Fig. 6 a it is found that port fluorescent quenching about 0.9s, recovery time
About 0.5s, Fig. 6 b are the cycle-index figure for being powered (- 1.5V) and powering off (0V) fiber waveguide device.Conclusion：After 180 cycles,
When being passed through negative voltage, fluorescent quenching efficiency still maintains about 60%, when being not added with electric field, and fluorescence restores.At the same time,
Response time is also sensitive, or so response time about 6s.Therefore, this system can be used as structure electric field regulation and control polydiacetylene micron tube
Fiber waveguide device.
The explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvement and modification are also fallen within the protection scope of the claims of the present invention.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention
It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one
The widest range caused.
Claims (8)
1. a kind of preparation method of the polydiacetylene micron tube of purpurine modification, includes the following steps：
It is reacted after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidol ether, it is sweet to obtain allyl glycidyl
The polydiacetylene micron tube of oily ether modification；
Viologen Compounds are mixed with the end alkene that halogen replaces, the purpurine of end alkenyl substitution is obtained after reaction；
The purpurine that the polydiacetylene micron tube that the allyl glycidyl ether is modified is replaced with the end alkenyl is in initiator
Under the action of carry out it is light-initiated, obtained after reaction purpurine modification polydiacetylene micron tube.
2. preparation method according to claim 1, which is characterized in that the Viologen Compounds are 4,4- bipyridyls, institute
The end alkene for stating halogen substitution is 3- bromopropenes.
3. preparation method according to claim 1, which is characterized in that the surface be amino polydiacetylene micron tube with
The molar ratio of the acrylic glycidol ether is 1：(1~2)；The Viologen Compounds and the end alkene of halogen substitution
Molar ratio is 1：(2~3).
4. preparation method according to claim 1, which is characterized in that the light-initiated light is ultraviolet light or infrared light.
5. preparation method according to claim 4, which is characterized in that the light-initiated wavelength is 365nm.
A kind of purpurine modification 6. fiber waveguide device, including prepared by Claims 1 to 5 any one of them preparation method it is poly-
Diacetylene micron tube.
7. the preparation method of the fiber waveguide device described in claim 6, includes the following steps：
The conductive layer of two panels glass electrode is oppositely arranged, insulating layer coating is applied at the both ends of the conductive layer；
The poly- of the purpurine modification prepared by Claims 1 to 5 any one of them preparation method is added between the insulating layer
The electrolyte solution of diacetylene micron tube, obtains fiber waveguide device.
8. preparation method according to claim 7, which is characterized in that the insulating materials of the insulating layer is polymethyl
Sour methyl esters.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5207862A (en) * | 1989-09-08 | 1993-05-04 | Bell Communications Research, Inc. | Technique for epitaxial growth of oriented thin films of polydiacetylenes |
| CN103172872A (en) * | 2013-04-03 | 2013-06-26 | 中国科学技术大学 | Polydiacetylene micro-tube material and preparation method thereof by using hierarchical self-assembly |
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| JP2848403B2 (en) * | 1989-07-28 | 1999-01-20 | 富士通株式会社 | Epitaxial growth of diacetylene or polydiacetylene |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5207862A (en) * | 1989-09-08 | 1993-05-04 | Bell Communications Research, Inc. | Technique for epitaxial growth of oriented thin films of polydiacetylenes |
| CN103172872A (en) * | 2013-04-03 | 2013-06-26 | 中国科学技术大学 | Polydiacetylene micro-tube material and preparation method thereof by using hierarchical self-assembly |
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