CN106996840A - A kind of force-responsive type fluorescent optical sensor based on dissaving polymer and preparation method thereof - Google Patents
A kind of force-responsive type fluorescent optical sensor based on dissaving polymer and preparation method thereof Download PDFInfo
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- CN106996840A CN106996840A CN201710251499.7A CN201710251499A CN106996840A CN 106996840 A CN106996840 A CN 106996840A CN 201710251499 A CN201710251499 A CN 201710251499A CN 106996840 A CN106996840 A CN 106996840A
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- 230000003287 optical effect Effects 0.000 title claims abstract description 42
- 229920000642 polymer Polymers 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 229920001971 elastomer Polymers 0.000 claims abstract description 34
- 239000005060 rubber Substances 0.000 claims abstract description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229920006254 polymer film Polymers 0.000 claims description 9
- 244000043261 Hevea brasiliensis Species 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229920003052 natural elastomer Polymers 0.000 claims description 8
- 229920001194 natural rubber Polymers 0.000 claims description 8
- -1 poly amino ester Chemical class 0.000 claims description 7
- 229920002614 Polyether block amide Polymers 0.000 claims description 6
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 5
- 229920002379 silicone rubber Polymers 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- 238000010559 graft polymerization reaction Methods 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 16
- 230000002441 reversible effect Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000000053 physical method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- RMXVNDUWESWVKI-UHFFFAOYSA-N 3-(1-adamantyl)dioxetane Chemical group C1OOC1C1(C2)CC(C3)CC2CC3C1 RMXVNDUWESWVKI-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01L—MEASURING FORCE, STRESS, TORQUE, WORK, MECHANICAL POWER, MECHANICAL EFFICIENCY, OR FLUID PRESSURE
- G01L1/00—Measuring force or stress, in general
- G01L1/24—Measuring force or stress, in general by measuring variations of optical properties of material when it is stressed, e.g. by photoelastic stress analysis using infrared, visible light, ultraviolet
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Force Measurement Appropriate To Specific Purposes (AREA)
- Laminated Bodies (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a kind of force-responsive type fluorescent optical sensor based on dissaving polymer and preparation method thereof, wherein force-responsive type fluorescent optical sensor is the laminated film assembled by dissaving polymer and transparent rubber, and transparent rubber layer, dissaving polymer layer and transparent rubber layer are followed successively by from top to bottom.The mass ratio of dissaving polymer layer and transparent rubber layer is 10~1 in force-responsive type fluorescent optical sensor:1.Force-responsive type fluorescent optical sensor of the present invention stimulates very sensitive to external force：As external force acts on the increase of caused material strain, the fluorescence intensity of sensor can gradually strengthen；Moreover, this fluorescence intensity change has invertibity, with the reduction of strain, its fluorescence intensity can be reduced gradually.Moreover, this force-responsive type fluorescent optical sensor also has the advantages that fast response time.
Description
Technical field
The present invention relates to a kind of force-responsive type fluorescent optical sensor based on dissaving polymer and preparation method thereof, belonging to should
Power or strain-responsive fluorescent optical sensor technical field.
Background technology
Force-responsive fluorescent material refer to mechanical force stimulate under, the photoluminescent property (for example, fluorescence intensity and color) of material
Can reversibly it be regulated and controled.Due to external strength our daily life be readily available with it is easy-to-handle, therefore
This material with force-responsive fluorescence capability has potential application in fields such as sensor, display and safety anti-fake materials
Prospect.Force-responsive type fluorescent optical sensor is built based on force-responsive fluorescent material and has been subjected to the extensive of researcher in recent years
Concern.
According to the classification of material type, force-responsive fluorescent material can be divided into polymer type and organic molecule class
Type.It is relatively fewer about the force-responsive fluorescent material of polymer type in current report, and most polymers type
Force-responsive fluorescent material belong to conjugated system.For example, in Rowan et al. report, the 4- dodecane oxygen that they utilize
(N- methylbenzenes imidazoles-the 2)-pyridine of base -2,6- bis- and platinum (II) formation complex, are mixed into polymethyl methacrylate and make
Into force-responsive fluorescent optical sensor.During by scraping, the wavelength of fluorescence of this sensor there occurs Red Shift Phenomena (Journal of
Materials Chemistry,2012,22,14196).Xin et al. utilizes the double benzoxazolyl hexichol second of aromatic dyestuff
Alkene (BBS) is mixed with force-responsive fluorescence elastomer sensor with thermoplastic polyurethane (TPU).Under different strained conditions,
Its wavelength of fluorescence there occurs change (ACS applied materials＆interfaces, 2013,5,4625).A small number of non-co-
Although conjugated polymer system can show force-responsive photoluminescent property, this property is often irreversible.For example, Sijbesma etc.
People utilizes the acrylate polymer with two (adamantyl) -1,2- dioxetanes groups in molecular skeleton that power has been made
Response type fluorescent optical sensor.Can be sent when being acted on by external force bright blue-fluorescence (Nature Chemistry, 2012,
4,559).Trace it to its cause is because chemical constitution there occurs irreversible change.The force-responsive fluorescent material of organic molecule type
Refer to the fluorescent crystal that those organic molecules are formed after orderly accumulation.These fluorescent crystals not only have force-responsive characteristic, and
And photoluminescent property is reversible.For example, in Jia et al. by tetraphenylethylene (TPE) cell formation the force-responsive fluorescence of single crystal form
Sensor.Primary crystalline can launch navy blue fluorescence.After grinding, TPE units are converted into amorphous phase by crystalline phase, and material is thus
Become blue-green.Although the fluorescence response of this material can be reversible, outside stimulus is needed, such as using solvent vapo(u)r
Or could be realized after heating.In Jia et al. report, TPE crystal is needed after Overheating Treatment, the luminous spy of its crystal
Property can return to original state (Angewandte Chemie International Edition, 2016,55,519).With
Upper report is the force-responsive type fluorescent optical sensor that physical method is made.Only in report few in number, chemistry has been used
Method builds force-responsive type fluorescent optical sensor.For example, Jia et al. has synthesized a kind of new functional molecular based on rhodamine.
It, which is covalently embedded into elastic polyurethane, can form force-responsive sensor.Under the stimulation of mechanical force, rhodamine there occurs different
Structure, from the spirolactams closed loop states formation open loop situations of a distortion, its fluorescence color there occurs change (Advanced
Materials,2015,27,6469).But the fluorescent optical sensor of this force-responsive type is still based on conjugated system.By mesh
Before, do not find based on aliphatic non-conjugated polymeric thing, and the force-responsive fluorescent optical sensor with reversible fluorescence response
Report.
The content of the invention
It is an object of the invention to provide a kind of force-responsive type fluorescent optical sensor based on dissaving polymer and its preparation
Method.The sensor can stimulate stress or strain the significant fluorescence response of generation and fluorescence response is reversible.
The fluorescence response of force-responsive type fluorescent optical sensor of the present invention has invertibity, and the fluorescence intensity of component can be with deformation quantity
Reduce and reduce.
Force-responsive type fluorescent optical sensor of the invention based on dissaving polymer, is by dissaving polymer and transparent rubber
The laminated film assembled, is followed successively by transparent rubber layer, dissaving polymer layer and transparent rubber layer from top to bottom.
The mass ratio of dissaving polymer layer and transparent rubber layer is 10~1 in force-responsive type fluorescent optical sensor of the present invention:
1, the quality of wherein transparent rubber layer refer to above and below two layers of transparent rubber layer gross mass.
The thickness of transparent rubber layer is 10~100 μm, and the thickness of dissaving polymer layer is 100~1000 μm.
The dissaving polymer is over-branched polyamidoamine, hyperbranched poly amino ester, hyperbranched poly ether amide or over-expense
Change one or more of blends or copolymer in polyethyleneimine.
Wherein, over-branched polyamidoamine is self-control, and preparation method is referring to document Zhang Y, Huang W, Zhou Y, et
al.A physical gel made from hyperbranched polymer gelator[J].Chemical
Communications,2007(25):2587-2589；Hyperbranched poly amino ester is self-control, and preparation method is referring to document Wu D
C,Liu Y,He C B,et al.Blue photoluminescence from hyperbranched poly(amino
ester)s[J].Macromolecules,2005,38(24):9906-9909；Hyperbranched poly ether amide is self-control, preparation method
Referring to document Lin Y, Gao J W, Liu H W, et al.Synthesis and characterization of
hyperbranched poly(ether amide)s with thermoresponsive property and
unexpected strong blue photoluminescence[J].Macromolecules,2009,42(9):3237-
3246；Hyperbranched polyethyleneimine obtains to be purchased in market.
The transparent rubber is in silicon rubber, natural rubber, polyurethane rubber, butadiene rubber, butadiene-styrene rubber, EP rubbers
One or more.
Force-responsive type fluorescent optical sensor of the invention based on dissaving polymer can be by physical method or chemical method system
It is standby to obtain：
Physical method comprises the following steps：
It is 10~100 μ that the dissaving polymer film that thickness is 100~1000 μm is directly fitted in into thickness at normal temperatures
The surface of m transparent rubber, the transparent rubber for one layer of 10~100 μ m-thick of then being fitted again on the surface of dissaving polymer film
Glue, you can obtain force-responsive type fluorescent optical sensor.
Chemical method comprises the following steps：
Dissaving polymer is dissolved in methanol, N is then utilized2Plasma gas handles the surface of transparent rubber to draw
Enter amino group, transparent rubber film be completely immersed in the solution of dissaving polymer using the liquid phase method that deaerates and is graft-polymerized,
Reaction temperature is 50 DEG C, and the reaction time is 3 days；Then fitted again on the surface of dissaving polymer film one layer 10~100 μm
Thick transparent rubber, you can obtain force-responsive type fluorescent optical sensor.
Force-responsive type sensor laminated film of the present invention is symmetrical structure, and positive and negative need not be considered during use.
Beneficial effects of the present invention are embodied in：
1st, the force-responsive type sensor of the invention based on fluorescence dissaving polymer, its fluorescence intensity is with external force size into just
Proportionate relationship, and can with external force size variation produce can reverse response.
2nd, the dissaving polymer in the force-responsive type sensor of the invention based on fluorescence dissaving polymer is aliphatic
Non-conjugated polymeric thing, with good biocompatibility and environment friendly.
Brief description of the drawings
Fig. 1 is fluorescence spectrum of the fluorescent optical sensor based on dissaving polymer under different stress, and excitation wavelength is
365nm；As can be seen from Figure 1 the fluorescence intensity of the sensor based on fluorescence dissaving polymer with the rise of stress by
Gradually rise.
Fig. 2 is the relation of fluorescence intensity and stress of the fluorescent optical sensor based on dissaving polymer under different stress.
As can be seen from Figure 2 the fluorescence intensity of the sensor based on fluorescence dissaving polymer and stress are substantially linear.
Fig. 3 is the reversible force response of the fluorescent optical sensor based on dissaving polymer.Fig. 3 a are based on hyperbranched polymerization
Fluorescence spectrum of the fluorescent optical sensor of thing in stress (2MPa) and the multiple cyclic process of release stress (0MPa), excitation wavelength
For 365nm；Fig. 3 b are that the fluorescent optical sensor based on dissaving polymer is multiple in stress (2MPa) and release stress (0MPa)
In cyclic process, the relation of fluorescence intensity and cycle-index.It can be seen that based on glimmering after repeatedly circulation from Fig. 3 a and Fig. 3 b
Light dissaving polymer force-responsive sensor still has good invertibity.
Embodiment
The present invention is described in detail in following examples, it is to be understood that this is simply enumerated to the exemplary of the present invention, rather than
For limiting the present invention, more not intended to limit present invention protection domain as claimed in claim.
Embodiment 1：
1st, 1.0g over-branched polyamidoamine is weighed, in the sample bottle for adding 5mL, 2mL methanol is then added and is dissolved,
It can obtain dissaving polymer solution.
2nd, the dissaving polymer solution that step 1 is obtained is cast on polyfluortetraethylene plate, dries, obtain at room temperature
To the dissaving polymer film that thickness is 200 μm.
3rd, the dissaving polymer obtained step 2 is film adhered on the surface for the silicon rubber that thickness is 20 μm, then
Fitted again on the surface of dissaving polymer film the silicon rubber of one layer of 20 μ m-thick, you can obtain force-responsive fluorescent optical sensor.
The force-responsive type sensor of resulting fluorescence dissaving polymer is carried out under different stress corresponding glimmering
Optical tests, are as a result shown in Fig. 1 and Fig. 2.
Embodiment 2：
1st, 1.0g natural rubber is weighed, is dissolved in normal heptane, then pours into a mould on the glass substrate and dries 50 μ of acquisition
Natural rubber films thick m, then utilize N2Plasma gas handles the surface of natural rubber, introduces amino group, operation
Process is is passed through nitrogen using plasma gas processing instrument, and flow is 50mL/min, and operating pressure is 30Pa, and power is 60W, day
The amino group increase of right rubber surface.
2nd, hyperbranched poly ether amide of the 5.5g end with double bond is weighed, is dissolved in methanol, will under conditions of 50 DEG C
The natural rubber films that step 1 is obtained, which are completely immersed in hyperbranched polyether amide solution, to be reacted 3 days, and reaction is taken out after terminating,
Dry 2~3 days at room temperature.
3rd, fitted again on the surface of dissaving polymer film the natural rubber of one layer of 50 μ m-thick, you can obtain force-responsive type
Sensor.
The force-responsive type sensor of resulting fluorescence dissaving polymer is carried out under different stress corresponding glimmering
Optical tests.
Embodiment 3：
The preparation process be the same as Example 1 of the present embodiment, the difference is that over-branched polyamidoamine is replaced with into hyperbranched poly second
Alkene imines, in addition replaces with the silicon rubber of 20 μ m-thicks the natural rubber of 10 μ m-thicks, and other preparation conditions are constant.It will finally prepare
Obtained force-responsive type fluorescent optical sensor is tested, and test condition is identical with embodiment 1.
Embodiment 4：
The preparation process be the same as Example 2 of the present embodiment, the difference is that hyperbranched poly ether amide is replaced with into hyperbranched poly ammonia
Base ester, other preparation conditions are constant.Finally the force-responsive type sensor prepared is tested, test condition and embodiment
2 is identical.
Claims (8)
1. a kind of force-responsive type fluorescent optical sensor based on dissaving polymer, it is characterised in that：The force-responsive type fluorescence is passed
Sensor is the laminated film assembled by dissaving polymer and transparent rubber, and transparent rubber layer is followed successively by from top to bottom, is surpassed
Branched polymeric nitride layer and transparent rubber layer.
2. force-responsive type fluorescent optical sensor according to claim 1, it is characterised in that：
The mass ratio of dissaving polymer layer and transparent rubber layer is 10~1 in the force-responsive type fluorescent optical sensor:1.
3. force-responsive type fluorescent optical sensor according to claim 1, it is characterised in that：
The thickness of every layer of transparent rubber layer is 10~100 μm, and the thickness of dissaving polymer layer is 100~1000 μm.
4. force-responsive type fluorescent optical sensor according to claim 1, it is characterised in that：
The dissaving polymer is over-branched polyamidoamine, hyperbranched poly amino ester, hyperbranched poly ether amide or hyperbranched poly
One or more of blends or copolymer in aziridine.
5. force-responsive type fluorescent optical sensor according to claim 1, it is characterised in that：
The transparent rubber is one in silicon rubber, natural rubber, polyurethane rubber, butadiene rubber, butadiene-styrene rubber, EP rubbers
Plant or several.
6. a kind of preparation method of the force-responsive type fluorescent optical sensor described in claim 1,2,3,4 or 5, comprises the following steps：
It is 10~100 μm that the dissaving polymer film that thickness is 100~1000 μm is directly fitted in into thickness at normal temperatures
The surface of transparent rubber, the transparent rubber for one layer of 10~100 μ m-thick of then being fitted again on the surface of dissaving polymer film, i.e.,
Force-responsive type fluorescent optical sensor can be obtained.
7. a kind of preparation method of the force-responsive type fluorescent optical sensor described in claim 1,2,3,4 or 5, comprises the following steps：
Dissaving polymer is dissolved in methanol, N is then utilized2Plasma gas handles the surface of transparent rubber to introduce ammonia
Transparent rubber film, is completely immersed in the solution of dissaving polymer and is graft-polymerized by base group using the liquid phase method that deaerates, reaction
Temperature is 50 DEG C, and the reaction time is 3 days；Then fitted again on the surface of dissaving polymer film one layer of 10~100 μ m-thick
Transparent rubber, you can obtain force-responsive type fluorescent optical sensor.
8. preparation method according to claim 7, it is characterised in that：
The reaction temperature of graft polymerization is 50 DEG C, and the reaction time is 3 days.
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| CN201710251499.7A CN106996840B (en) | 2017-04-18 | 2017-04-18 | A kind of force-responsive type fluorescent optical sensor and preparation method thereof based on dissaving polymer |
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Cited By (2)
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| CN108998006A (en) * | 2018-07-20 | 2018-12-14 | 合肥工业大学 | A kind of environmental-friendly strain-responsive type fluorescence supramolecular materials and preparation method thereof |
| CN110631746A (en) * | 2019-09-23 | 2019-12-31 | 维沃移动通信有限公司 | Pressure detection assembly, detection method and terminal |
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| CN108998006A (en) * | 2018-07-20 | 2018-12-14 | 合肥工业大学 | A kind of environmental-friendly strain-responsive type fluorescence supramolecular materials and preparation method thereof |
| CN108998006B (en) * | 2018-07-20 | 2021-06-08 | 合肥工业大学 | Environment-friendly strain response type fluorescent supramolecular material and preparation method thereof |
| CN110631746A (en) * | 2019-09-23 | 2019-12-31 | 维沃移动通信有限公司 | Pressure detection assembly, detection method and terminal |
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| CN106996840B (en) | 2019-04-05 |
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