CN105778142A - Preparation method for purpurine modified polydiacetylene microtube and optical waveguide device and preparation method thereof - Google Patents
Preparation method for purpurine modified polydiacetylene microtube and optical waveguide device and preparation method thereof Download PDFInfo
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- CN105778142A CN105778142A CN201610097351.8A CN201610097351A CN105778142A CN 105778142 A CN105778142 A CN 105778142A CN 201610097351 A CN201610097351 A CN 201610097351A CN 105778142 A CN105778142 A CN 105778142A
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Abstract
The invention provides a preparation method for a purpurine modified polydiacetylene microtube.The preparation method comprises the following steps that a polydiacetylene microtube with an amino surface and allyl glycidyl ether are mixed for a reaction, and an allyl glycidyl ether modified polydiacetylene microtube is obtained; a purpurine compound and halogen substituted terminal olefin are mixed, and terminal olefin substituted purpurine is obtained after a reaction; the allyl glycidyl ether modified polydiacetylene microtube and the terminal olefin substituted purpurine are subjected to photo-initiation under the action of an initiator, and the purpurine modified polydiacetylene microtube is obtained after a reaction.The invention further provides an optical waveguide device which comprises the prepared purpurine modified polydiacetylene microtube.The optical waveguide device has optical waveguide reversible control performance.
Description
Technical field
The present invention relates to fiber waveguide device technical field, particularly relate to preparation method and fiber waveguide device and preparation method thereof of the polydiacetylene micron tube that purpurine is modified.
Background technology
Fiber waveguide is the medium apparatus guiding light wave to propagate wherein, and it is the electromagnetic leading structure of the transmission optical frequency being made up of light transparent medium (such as quartz glass).The transmission principle of fiber waveguide is different from metal enclosed waveguide, and it is on the dielectric interface of different refractivity, and electromagnetic total reflection phenomenon makes light wave be confined to waveguide and the interior propagation of finite region about.
Fiber waveguide itself is owing to being the integrated of many-sided science, and therefore its research and range of application are also the waveguiding structures of small compact very widely, are advantageously implemented the integrated of light path.Light wave transmission in the waveguide, coupling and with the various physical phenomenons that outer field interactions causes, be the basis of integrated optics design and manufacture.
Conjugatd polymers has the advantages such as good flexibility, machinability, has broader prospect in nano laser, biosensor, waveguide sensing.Regulation and control fiber waveguide majority depends on the aspects such as light regulation and control, chemical regulation, hot regulation and control at present, than comparing, electricity regulation and control fiber waveguide have remote control and regulation, simple to operate, respond sensitive, by advantages such as external interference are little, more and more studied developing in electrooptic modulator.Thus, this application provides a kind of fiber waveguide device utilizing conjugatd polymers to build.
Summary of the invention
Present invention solves the technical problem that and be in that to provide a kind of fiber waveguide device, the fiber waveguide device that the application provides can realize the regulation and control of reversible electric field.
In view of this, the preparation method that this application provides the polydiacetylene micron tube that a kind of purpurine is modified, comprise the following steps:
React after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidyl ether, obtain the polydiacetylene micron tube that allyl glycidyl ether is modified；
Viologen Compounds is mixed with the end alkene of halogen substiuted, after reaction, obtains the purpurine of end alkenyl substituted；
The purpurine of the polydiacetylene micron tube modified by described allyl glycidyl ether and described end alkenyl substituted carries out light-initiated under the effect of initiator, obtains the polydiacetylene micron tube that purpurine is modified after reaction.
Preferably, described Viologen Compounds is 4,4-bipyridyls, and the end alkene of described halogen substiuted is 3-bromopropene.
Preferably, described surface is the polydiacetylene micron tube of amino is 1:(1～2 with the mol ratio of described acrylic glycidyl ether)；The mol ratio of the end alkene of described Viologen Compounds and described halogen substiuted is 1:(2～3).
Preferably, described light-initiated light is ultraviolet light or infrared light.
Preferably, described light-initiated wavelength is 365nm.
Present invention also provides a kind of fiber waveguide device, including the polydiacetylene micron tube that the purpurine prepared by the preparation method described in such scheme is modified.
The preparation method that present invention also provides described fiber waveguide device, comprises the following steps:
The conductive layer of two panels glass electrode is oppositely arranged, is coated with insulating layer coating at the two ends of described conductive layer；
Between described insulating barrier, add the electrolyte solution of the polydiacetylene micron tube that the purpurine prepared by preparation method described in such scheme is modified, obtain fiber waveguide device.
Preferably, the insulant of described insulating barrier is polymethyl methacrylate.
The preparation method that this application provides the polydiacetylene micron tube that a kind of purpurine is modified, first the polydiacetylene micron tube that surface is amino is reacted by it with acrylic glycidyl ether (AGE), obtain the AGE polydiacetylene micron tube modified, end alkene reaction by Viologen Compounds Yu halogen substiuted, obtain the purpurine of end alkenyl substituted, then the purpurine of the AGE polydiacetylene micron tube modified with end alkenyl substituted is carried out click reaction, obtain the polydiacetylene micron tube that purpurine is modified.Herein described fiber waveguide device comprises the polydiacetylene micron tube that purpurine is modified, purpurine group in the polydiacetylene micron tube that wherein purpurine is modified is in bivalence under normal circumstances, the conversion of bivalence and monovalence is there is under the effect of external electrical field, namely there is reversible phase co-conversion with reduction-state in oxidation state, absorb with purpurine and whether shift with polydiacetylene micron tube generation Fluorescence Resonance Energy, and then regulation and control polydiacetylene micron tube fiber waveguide.When fiber waveguide device applies negative voltage, purpurine is become monovalence from bivalence, and the purpurine in polydiacetylene micron tube partially absorbs and can overlap phenomenon with micron tube fluorescence, by resonance energy transfer and then realize micron tube fluorescent quenching；When passing into forward voltage, purpurine is become bivalence from monovalence, and this variation of valence is accompanied by external voltage and changes, and has reversibility, hence in so that this device has possessed the regulation and control reversible character of micron tube waveguide.
Accompanying drawing explanation
Fig. 1 is synthetic route and the Infrared Characterization figure of the polydiacetylene micron tube that the embodiment of the present invention 1 purpurine is modified；
Fig. 2 is polydiacetylene micron tube stereoscan photograph and the section picture sign photo of the purpurine modification of the embodiment of the present invention 1 preparation；
Fig. 3 is polydiacetylene micron tube fiber waveguide mechanism, fluorescence spectrum and the light guiding optics picture that the embodiment of the present invention 2 electricity regulation and control purpurine is modified；
Fig. 4 is the XPS spectrum figure of N element in purpurine unit different valence state in the polydiacetylene micron tube that the embodiment of the present invention 2 purpurine is modified；
Fig. 5 is polydiacetylene micron tube autofluorescence change and the waveguide port Fluorescencecontro spectrogram under different voltages that the embodiment of the present invention 3 purpurine is modified；
The polydiacetylene micron tube regulating and controlling voltage number of times of Fig. 6 embodiment embodiment of the present invention 4 purpurine modification and the curve chart of response time.
Detailed description of the invention
In order to be further appreciated by the present invention, below in conjunction with embodiment, the preferred embodiment of the invention is described, but it is to be understood that these describe simply as further illustrating the features and advantages of the present invention, rather than limiting to the claimed invention.
The preparation method that the embodiment of the invention discloses the polydiacetylene micron tube that a kind of purpurine is modified, comprises the following steps:
React after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidyl ether, obtain the polydiacetylene micron tube that allyl glycidyl ether is modified；
Viologen Compounds is mixed with the end alkene of halogen substiuted, after reaction, obtains the purpurine of end alkenyl substituted；
The purpurine of the polydiacetylene micron tube modified by described allyl glycidyl ether and described end alkenyl substituted carries out light-initiated under the effect of initiator, obtains the polydiacetylene micron tube that purpurine is modified after reaction.
First the application is prepared for the polydiacetylene micron tube that purpurine is modified, as it is shown in figure 1, the synthetic route chart that Fig. 1 a is the polydiacetylene micron tube that purpurine of the present invention is modified.
In the process of the polydiacetylene micron tube of preparation purpurine modification, the application reacts after first the polydiacetylene micron tube that surface is amino being mixed with acrylic glycidyl ether (AGE), obtains the AGE polydiacetylene micron tube modified.The reaction equation that polydiacetylene micron tube and the AGE of described surface amino groups react is as follows:
In above process, described surface is that the polydiacetylene micron tube of amino is preferably 1 with the mol ratio of described acrylic glycidyl ether: (1～2), in an embodiment, more preferably 1:1.2.The preparation method that herein described surface is the polydiacetylene micron tube of amino carries out according to mode well known to those skilled in the art, and this application is had no particular limits.In described AGE, one end is contained double bond one end and is contained epoxide group, reaction mechanism according to the present invention, in the process of the modified polydiacetylene micron tube of above-mentioned preparation, one of raw material AGE can be not limited to this, can also is that other compound, as long as the double bond one section little molecule containing epoxide group is contained in one end.
Viologen Compounds is mixed with the end alkene of halogen substiuted by the application simultaneously, obtains the purpurine of end alkenyl substituted after reaction.In this process, described Viologen Compounds is preferably 4,4-bipyridyls, and the end alkene of described halogen substiuted is preferably 3-bromopropene.With 4,4-bipyridyls with 3-bromopropene for example, above-mentioned reaction equation is as follows:
In above-mentioned course of reaction, the mol ratio of the end alkene of described Viologen Compounds and described halogen substiuted is preferably 1: (2～3), in an embodiment, more preferably 1:2.2.The source of the end alkene of described Viologen Compounds and halogen substiuted is had no particular limits by the application, prepares according to mode well known to those skilled in the art or for commercially available prod.
The purpurine of the AGE polydiacetylene micron tube modified with end alkenyl substituted is finally carried out light-initiated by the application under the effect of initiator, obtains the polydiacetylene micron tube that purpurine is modified after reaction.Above-mentioned reaction is click reaction, and the application utilizes initiator under light-initiated effect, makes the AGE polydiacetylene micron tube modified and the purpurine holding alkenyl substituted occurs click to react.Described initiator is had no particular limits by the application, as long as the initiator of sulfydryl and double bond click can be caused, it is possible to for initiator I-2959, it is also possible to for the DMPA that ultraviolet light causes.The application preferably employs ultraviolet light or infrared light carries out light-initiated, and described light-initiated wavelength is preferably 365nm.
Present invention also provides a kind of fiber waveguide device, it includes the polydiacetylene micron tube that the purpurine prepared by the preparation method described in such scheme is modified.
Present invention also provides a kind of fiber waveguide device, it comprises the following steps:
The conductive layer of two panels glass electrode is oppositely arranged, is coated with insulating layer coating at the two ends of described conductive layer；
Between described insulating barrier, add the electrolyte solution of the polydiacetylene micron tube that the purpurine prepared by preparation method described in such scheme is modified, obtain fiber waveguide device.
In the process preparing fiber waveguide device, first the conductive layer of ITO two panels glass electrode is oppositely arranged by the application, even if the conductive layer of two panels glass electrode contacts with conductive layer.In order to prevent electric current from only flowing through from ITO side, forming short circuit, the application is coated with insulating layer coating at the two ends of described conductive layer.The material of described insulating barrier is had no particular limits by the application, and for insulant well known to those skilled in the art, preferably, the insulant of described insulating barrier is preferably polymethyl methacrylate.
According to the present invention, then by adding the electrolyte solution of the polydiacetylene micron tube that purpurine is modified in the middle of part-two insulating barrier of uncoated for ito glass electrode insulating barrier, obtain fiber waveguide device.
Preferably, the polydiacetylene micron tube that then purpurine is modified by the application, through irradiation under ultraviolet ray, is polymerized to blue micron tube, then through heat treated, forms the reddish tint micron tube with fiber waveguide character.
Described electrolyte solution is electrolyte solution well known to those skilled in the art, and this application is had no particular limits, and preferably, described electrolyte solution is preferably Klorvess Liquid.
In order to detect purpurine modify polydiacetylene micron tube for after fiber waveguide device, the performance of fiber waveguide device, the polydiacetylene micron tube that purpurine is modified by the application is placed between two panels ito glass electrode, add-1.5 ,-1.0 ,-0.5,0,0.5,1.0,1.5V voltage time, same position 532nm light excites micro-tube wall, surveys the change of port fluorogram；After applying negative voltage, there is Fluorescence Resonance Energy transfer (FRET) with micro-pipe itself in the purpurine part in polydiacetylene micron tube, at 640nm place, fluorescence is gradually reduced, and is finally reached cancellation efficiency more than 60%；When passing into forward voltage in system, fluorescence peak rises, and eventually returns to original fluorescence intensity；Thus illustrating, the polydiacetylene micron tube fiber waveguide that purpurine is modified has good voltage-dependent, reversibility and device stability, and belongs to low voltage drive system, and this system may continue as electric field regulation and control polydiacetylene micron tube fiber waveguide device.
It is owing to purpurine group is in bivalence under normal circumstances that the polydiacetylene micron tube that purpurine prepared by the application is modified can carry out fiber waveguide as fiber waveguide device, under extraneous electric field action, there is bivalence and reversible phase co-conversion occurs between monovalence and oxidized and reduced, absorb with purpurine and whether shift with polydiacetylene micron tube generation Fluorescence Resonance Energy, and then regulate and control polydiacetylene micron tube fiber waveguide, shown in following reaction equation.Test result indicate that: the polydiacetylene micron tube tube wall 532nm light modified in purpurine excites, and fluorescence along tube wall waveguide, and then can be launched in port.Under the effect of electric field, purpurine absorbs meeting from ultraviolet region red shift to visible region, overlapping with polydiacetylene micron tube fluorescence generating portion, it is achieved that the cancellation of micron tube port fluorescence, this change is reversible, and then realizes electric field to the polydiacetylene reversible regulation and control of micron tube waveguide.This regulation and control method operating process is easy, electric field response is sensitive, quick, and environment resistant interference performance is strong, have the advantages such as remote control and regulation.
In order to be further appreciated by the present invention, the preparation method of polydiacetylene micron tube purpurine provided by the invention modified below in conjunction with embodiment and fiber waveguide device are described in detail, and protection scope of the present invention is not limited by the following examples.
Embodiment 1
Amino replaces the tripolycyanamide of diacetylene and 18-amine. replacement and is dissolved in a small amount of ethanol with mol ratio 4:1, is then poured into by solution in the 300mL ultra-pure water of 75 DEG C, and ultrasonic 60min is placed on dark place and naturally cools to room temperature, places into the refrigerator overnight of 4 DEG C；After the polymerization of 254nm ultraviolet light irradiation, take the above-mentioned vesicle solution of 10ml and be gradually added into 5*10-5MPb2+, incubation at room temperature grows 1 week, obtains polydiacetylene micron tube；After the polymerization of 254nm ultraviolet light irradiation, by this micron tube suspension drips the allyl glycidyl ether (AGE) of 1.2 times of equivalents, under room temperature, stir this suspension 24h, water washing 2-3 time, obtain the AGE polydiacetylene micron tube modified；4,4-bipyridyls are dissolved in DMF solution, the 3-bromopropene solution of 2.2 times of equivalents of dropping, stir 72h under 50 DEG C of conditions, filter, product absolute ether washs 3 times, and vacuum drying obtains the purpurine that pi-allyl replaces；Putting in a certain amount of deionized water solution by the AGE polydiacetylene micron tube modified with the purpurine that pi-allyl replaces, under initiator I-2959 effect, 365nm is light-initiated, is reacted by click, finally gives the polydiacetylene micron tube that purpurine is modified.The synthetic route of polydiacetylene micron tube, infrared spectrum and XPS spectrum that the present embodiment purpurine is modified are as shown in Figure 1.
The polydiacetylene micron tube above-mentioned purpurine modified deposits on silicon chip, observe SEM pattern, as shown in Figure 2, as shown in Figure 2, prepared by the present invention micron tube is smooth surface, and hollow has the flexible tubular structure of certain wall thickness, length up to centimetre more than, caliber is 2-3 μm, and wall thickness is approximately 1 μ m in size.
Embodiment 2
Take the reddish tint polydiacetylene micron tube that single purpurine is modified, it is deposited between two panels ito glass electrode, add-4V voltage, Fluorescence Resonance Energy transfer (FRET) is there is in the purpurine part in polydiacetylene micron tube with micro-pipe itself, 532nm light excites micro-tube wall, surveying port fluorescence to be gradually reduced at 640nm place generation fluorescence, final cancellation efficiency reaches 60%；When passing into forward 4V in system, same position 532nm light excites micro-tube wall, survey port fluorescence to rise at 640nm fluorescence peak, eventually return to original fluorescence intensity, as it is shown on figure 3, Fig. 3 is polydiacetylene micron tube fiber waveguide mechanism, fluorescence spectrum and the light guiding optics picture that electricity of the present invention regulation and control purpurine is modified.
Purpurine group occurs reversible redox to change under extraneous electric field action, absorb with purpurine and whether occur to regulate and control polydiacetylene micron tube fluorescence waveguide with the transfer of polydiacetylene micron tube generation Fluorescence Resonance Energy, as shown in Figure 4, Fig. 4 is the XPS spectrum figure of N element in purpurine unit different valence state in the polydiacetylene micron tube that the embodiment of the present invention 2 purpurine is modified, the polydiacetylene micron tube that purpurine is modified occurs above-mentioned change to be embodied in the N element receiving and losing electrons on pyridine ring, shows the N element of different valence state.
Embodiment 3
The polydiacetylene micron tube that purpurine is modified is placed between two panels ito glass electrode, add-1.5,-1.0,-0.5, 0, 0.5, 1.0, during 1.5V voltage, same position 532nm light excites micro-tube wall, survey the change of port fluorogram, as shown in Figure 5, Fig. 5 a is that same position excites, the fluorescent quenching efficiency of micron tube tube wall self is with change in voltage figure, Fig. 5 b is that same position excites, the fluorescent quenching efficiency of micron tube port is with change in voltage figure, in figure ● represent that cancellation efficiency applies the changing value from-1.5V to 1V with voltage, ■ represents that cancellation efficiency applies the changing value from-1V to-1.5V with voltage.After applying negative voltage, there is Fluorescence Resonance Energy transfer (FRET) with micro-pipe itself in the purpurine part in polydiacetylene micron tube, produces fluorescence at 640nm place and is gradually reduced, and final port cancellation efficiency reaches more than 60%；When passing into forward voltage in system, fluorescence peak rises, and eventually returns to original fluorescence intensity.By contrast, the fluorescent quenching efficiency of tube wall self is maximum not up to 60%.The experiment proved that, the change of port optical wave guide fluorescence is comparatively sensitive compared with autofluorescence change.
Embodiment 4
The polydiacetylene micron tube that purpurine is modified is placed between two panels ito glass electrode, when addition-1.5 repeatedly, 0V voltage, same position 532nm light excites micro-tube wall, survey the change of port fluorogram, and calculate port fluorescent quenching efficiency, as shown in Figure 6, Fig. 6 a is electricity regulation and control micron tube response time figure, from Fig. 6 a, the about 0.9s of port fluorescent quenching, recovery time, about 0.5s, Fig. 6 b was the cycle-index figure of energising (-1.5V) and power-off (0V) fiber waveguide device.Conclusion: after 180 circulations, when passing into negative voltage, fluorescent quenching efficiency still maintains and is about 60%, when being not added with electric field, fluorescence recovers.Meanwhile, response time is also sensitive, and response time is about about 6s.Therefore, this system can as building electric field regulation and control polydiacetylene micron tube fiber waveguide device.
The explanation of above example is only intended to help to understand method and the core concept thereof of the present invention.It should be pointed out that, for those skilled in the art, under the premise without departing from the principles of the invention, it is also possible to the present invention carries out some improvement and modification, these improve and modify in the protection domain also falling into the claims in the present invention.
Described above to the disclosed embodiments, makes professional and technical personnel in the field be capable of or uses the present invention.The multiple amendment of these embodiments be will be apparent from for those skilled in the art, and generic principles defined herein can without departing from the spirit or scope of the present invention, realize in other embodiments.Therefore, the present invention is not intended to be limited to the embodiments shown herein, and is to fit to the widest scope consistent with principles disclosed herein and features of novelty.
Claims (8)
1. a preparation method for the polydiacetylene micron tube that purpurine is modified, comprises the following steps:
React after the polydiacetylene micron tube that surface is amino is mixed with acrylic glycidyl ether, obtain the polydiacetylene micron tube that allyl glycidyl ether is modified；
Viologen Compounds is mixed with the end alkene of halogen substiuted, after reaction, obtains the purpurine of end alkenyl substituted；
The purpurine of the polydiacetylene micron tube modified by described allyl glycidyl ether and described end alkenyl substituted carries out light-initiated under the effect of initiator, obtains the polydiacetylene micron tube that purpurine is modified after reaction.
2. preparation method according to claim 1, it is characterised in that described Viologen Compounds is 4,4-bipyridyls, the end alkene of described halogen substiuted is 3-bromopropene.
3. preparation method according to claim 1, it is characterised in that described surface is the polydiacetylene micron tube of amino is 1:(1～2 with the mol ratio of described acrylic glycidyl ether)；The mol ratio of the end alkene of described Viologen Compounds and described halogen substiuted is 1:(2～3).
4. preparation method according to claim 1, it is characterised in that described light-initiated light is ultraviolet light or infrared light.
5. preparation method according to claim 4, it is characterised in that described light-initiated wavelength is 365nm.
6. a fiber waveguide device, including the polydiacetylene micron tube that the purpurine prepared by the preparation method described in any one of Claims 1 to 5 is modified.
7. the preparation method of the fiber waveguide device described in claim 6, comprises the following steps:
The conductive layer of two panels glass electrode is oppositely arranged, is coated with insulating layer coating at the two ends of described conductive layer；
Between described insulating barrier, add the electrolyte solution of the polydiacetylene micron tube that the purpurine prepared by preparation method described in any one of Claims 1 to 5 is modified, obtain fiber waveguide device.
8. preparation method according to claim 7, it is characterised in that the insulant of described insulating barrier is polymethyl methacrylate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111019030A (en) * | 2019-12-10 | 2020-04-17 | 安徽师范大学 | Preparation method of fluorescent polymer nano-microspheres and MnO detection4-Application of |
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| JPH0359014A (en) * | 1989-07-28 | 1991-03-14 | Fujitsu Ltd | Epitaxial growth of diacetylene or polydiacetylene |
| 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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2016
- 2016-02-22 CN CN201610097351.8A patent/CN105778142B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0359014A (en) * | 1989-07-28 | 1991-03-14 | Fujitsu Ltd | Epitaxial growth of diacetylene or polydiacetylene |
| 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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111019030A (en) * | 2019-12-10 | 2020-04-17 | 安徽师范大学 | Preparation method of fluorescent polymer nano-microspheres and MnO detection4-Application of |
| CN111019030B (en) * | 2019-12-10 | 2021-09-28 | 安徽师范大学 | Preparation method of fluorescent polymer nano-microspheres and MnO detection4-Application of |
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