CN109187449B - Environment response type intelligent sensing device and preparation method and application thereof - Google Patents
Environment response type intelligent sensing device and preparation method and application thereof Download PDFInfo
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- CN109187449B CN109187449B CN201810834073.9A CN201810834073A CN109187449B CN 109187449 B CN109187449 B CN 109187449B CN 201810834073 A CN201810834073 A CN 201810834073A CN 109187449 B CN109187449 B CN 109187449B
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- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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Abstract
The invention discloses an environment response type intelligent sensing device and a preparation method and application thereof. The environment-responsive smart sensor apparatus includes: the method comprises the following steps of patterning a substrate, wherein at least two recesses which are arranged at intervals are formed in the surface of the substrate, and a flat pattern which is used as a sensing area is formed on the surface of the substrate by filling a first polymer containing an initiator into the at least two recesses; and a plurality of second polymer graft chains, wherein the head ends of the second polymer graft chains are covalently bonded on the flat pattern through reaction with the active functional groups on the surface of the first polymer, and the tail ends of the second polymer graft chains are covalently bonded with dyeing macromolecules, and the dyeing macromolecules are selected from short block polymers, and the short block polymers are provided with fluorescent groups and functional groups capable of being specifically combined with selected small molecules. The polymer grafted chain can respond to different solvents or specific molecules, and realizes the automatic control function under the environment response condition.
Description
Technical Field
The invention relates to a sensing device, in particular to an environment response type intelligent sensing device and a preparation method and application thereof.
Background
"environmental responsive smart material development and performance optimization" attempts to utilize autonomously developed environmental responsive materials for modification and assembly on conventional device substrates to achieve control and regulation of substrate surface properties by means of changing environmental conditions. These changing physical or chemical quantities can be converted into identifiable signals by detection of the morphology of the substrate or detection of the fluorescent signal to achieve the desired properties of the smart material. The intelligent material can be used in the field of environmental monitoring and the field of automatic control. Conventional smart sensor materials can induce conformational changes in the material through changes in environmental conditions, such as through isomerization of functional groups of the material, e.g., cis-trans isomerization reactions, ionization of chromophore groups, etc., which in turn can result in changes in the material properties. Atom Transfer Radical Polymerization (ATRP) is a widely used controllable polymerization method (WANG J S, MATYJAS ZEWSKI K. controlled/"living" radial polymerization. Atom transfer polymerization in the present invention-technical complexes [ J ]. Journal of American Chemical Society, 1995, 117(20): 5614-.
Disclosure of Invention
The invention mainly aims to provide an environment response type intelligent sensing device and a preparation method and application thereof, thereby overcoming the defects in the prior art.
In order to achieve the purpose, the technical scheme adopted by the invention comprises the following steps:
the embodiment of the invention provides an environment response type intelligent sensing device, which comprises:
the method comprises the following steps of patterning a substrate, wherein at least two recesses which are arranged at intervals are formed in the surface of the substrate, and a first polymer containing an initiator is filled in the at least two recesses to form a flat pattern serving as a sensing area on the surface of the substrate; and
and a plurality of second polymer graft chains, wherein the head ends of the second polymer graft chains are covalently bonded on the flat pattern through reaction with the active functional groups on the surface of the first polymer, and the tail ends of the second polymer graft chains are covalently bonded with dyeing macromolecules, and the dyeing macromolecules are selected from short block polymers, and the short block polymers are provided with fluorescent groups and functional groups capable of being specifically combined with selected small molecules.
Further, the second polymer graft chain exhibits a stretched state when placed in a good solvent, and exhibits a collapsed state when placed in a poor solvent, and the length of the second polymer graft chain in the stretched state is at least 6 to 10 times as long as the length thereof in the collapsed state.
The embodiment of the invention also provides a preparation method of the environment response type intelligent sensing device, which comprises the following steps:
(1) providing a patterned substrate, wherein at least two recesses which are arranged at intervals are formed on the surface of the substrate;
(2) backfilling a precursor of a first polymer containing an active functional group into a recess on the surface of the substrate, and then pressing the surface of the substrate in alignment with a plane at a polymerization temperature, wherein the surface energy of the plane is higher than that of the substrate, so that a flat pattern serving as a sensing area is formed on the surface of the substrate;
(3) covalently bonding head ends of a plurality of second polymer graft chains with active functional groups on the surface of the first polymer through atom transfer radical polymerization;
(4) covalently bonding the ends of the second polymer graft chains to the dyed macromolecules by a nucleophilic substitution reaction.
The embodiment of the invention also provides a detection method which is implemented based on the environment response type intelligent sensing device, and the detection method comprises the following steps: and enabling the liquid sample to be detected containing the poor solvent and the selected small molecules and the sensing area of the environment response type intelligent sensing device and detecting the fluorescence intensity change of the sensing area, thereby realizing the detection of the selected small molecules in the liquid sample to be detected.
Compared with the prior art, the invention has the advantages that:
according to the environment response type intelligent sensing device provided by the invention, the sensing device is accurately controlled by changing the property of the solvent, or the possibility of measuring the molecular characteristics of the solution by designing a specific substrate is designed, and the sensing device can respond to various environment conditions such as different reagent concentrations, different humiture, different electric fields and magnetic fields by adjusting the material types at the tail end of the polymer grafted chain, so that the automatic control function under the environment response condition is realized. The method provides a brand-new mode for designing intelligent materials, has wide application prospect in the fields of stable fixation of colloidal particles, adsorption control, liquid crystal display, automatic monitoring of water-gas pollutants and the like, and is also an important basic information collection unit for future data development.
Drawings
FIG. 1 is a schematic illustration of a backfill process for forming a patterned substrate and forming second polymer graft chains, in accordance with an exemplary embodiment of the present invention.
Fig. 2a and 2b are microscope images of the surface of a Si substrate on which polystyrene graft chains are grown according to an exemplary embodiment of the present invention, respectively, in which fig. 2a is a linear patterned Si substrate and fig. 2b is a flat patterned substrate.
Fig. 3 is an infrared spectrum of the filled substrate in an exemplary embodiment of the invention.
Fig. 4a and 4c are liquid phase atomic force microscopy images and structural scanning graphs of a planar patterned substrate grown with polystyrene graft chains in ethanol, in an exemplary embodiment of the invention.
Fig. 4b and 4d are liquid phase atomic force microscopy and structural scanning graphs of a planar patterned substrate grown with polystyrene graft chains in DMF according to an exemplary embodiment of the present invention.
FIG. 5 is a schematic representation of the insertion of terminal fluorophores on a backfill surface planar pattern by a first ATRP reaction and a second nucleophilic substitution reaction in an exemplary embodiment of the present invention.
FIG. 6 is a graph of the emission spectrum of a fluorophore with a fluorophore at 356nm excitation light in an exemplary embodiment of the invention.
FIGS. 7a and 7b are graphs showing fluorescence intensities of the grafted second polymer chain in its original state and in its adsorbed state after covalent bonding of a dyed macromolecule, respectively, according to an exemplary embodiment of the present invention.
Detailed Description
In view of the defects in the prior art, the inventor of the present invention has made extensive research and practice to provide a technical solution of the present invention, and the environment-responsive smart material can autonomously select a polymer graft chain, generate a customizable material substrate, and generate specific responses to different environmental conditions. The technical solution, its implementation and principles, etc. will be further explained as follows.
An aspect of an embodiment of the present invention provides an environment-responsive intelligent sensing apparatus, including:
the method comprises the following steps of patterning a substrate, wherein at least two recesses which are arranged at intervals are formed in the surface of the substrate, and a first polymer containing an initiator is filled in the at least two recesses to form a flat pattern serving as a sensing area on the surface of the substrate; and
and a plurality of second polymer graft chains, wherein the head ends of the second polymer graft chains are covalently bonded on the flat pattern through reaction with the active functional groups on the surface of the first polymer, and the tail ends of the second polymer graft chains are covalently bonded with dyeing macromolecules, and the dyeing macromolecules are selected from short block polymers, and the short block polymers are provided with fluorescent groups and functional groups capable of being specifically combined with selected small molecules.
Further, the second polymer graft chain exhibits a stretched state when placed in a good solvent, and exhibits a collapsed state when placed in a poor solvent, and the length of the second polymer graft chain in the stretched state is at least 6 to 10 times as long as the length thereof in the collapsed state.
Further, when the sensing region of the environment-responsive smart sensor device is contacted with a good solvent, the plurality of second polymer graft chains are stretched to form a vertical bristle-like structure, and when the sensing region of the environment-responsive smart sensor device is contacted with a poor solvent, the plurality of second polymer graft chains are collapsed on the surface of the substrate and have clear boundaries between the patterns arranged at intervals in the flat pattern.
Further, the head end of the second polymer graft chain is covalently bonded to the active functional group on the surface of the first polymer through atom transfer radical polymerization, and the end of the second polymer graft chain is covalently bonded to the dyed macromolecule through nucleophilic substitution reaction.
Further, the first polymer includes any one or a combination of two or more of polystyrene, polymethyl methacrylate, polyethylene terephthalate, and the like, but is not limited thereto.
Further, the second polymer graft chain is covalently bonded to a dyed macromolecular protein, enzyme, nucleic acid, etc. containing an amino group, but is not limited thereto.
Further, the number average molecular weight of the short block polymer is 300-450.
Further, the short block polymer has a segment having 15 to 30 carbon atoms.
Further, the second polymer graft chain is derived from polystyrene, but is not limited thereto.
Further, the dyed macromolecule has a fluorophore derived from a compound of the formula:
further, the flat pattern comprises more than two bar-shaped graphs which are distributed in parallel.
Furthermore, the distance between two adjacent bar patterns is 10-2000 nm.
Another aspect of the embodiments of the present invention also provides a method for manufacturing the aforementioned environment-responsive intelligent sensing device, which includes the following steps:
(1) providing a patterned substrate, wherein at least two recesses which are arranged at intervals are formed on the surface of the substrate;
(2) backfilling a precursor of a first polymer containing an active functional group into a recess on the surface of the substrate, and then pressing the surface of the substrate in alignment with a plane at a polymerization temperature, wherein the surface energy of the plane is higher than that of the substrate, so that a flat pattern serving as a sensing area is formed on the surface of the substrate;
(3) covalently bonding head ends of a plurality of second polymer graft chains with active functional groups on the surface of the first polymer through atom transfer radical polymerization;
(4) covalently bonding the ends of the second polymer graft chains to the dyed macromolecules by a nucleophilic substitution reaction.
Further, the step (4) comprises: contacting a liquid-phase reaction system comprising a dyed macromolecule and a good solvent with the sensing region, allowing the second polymer graft chain to assume a stretched state, and allowing the end of the second polymer graft chain to covalently bond with the dyed macromolecule through a nucleophilic substitution reaction.
Another aspect of the embodiments of the present invention further provides a detection method, which is implemented based on the foregoing environment-responsive intelligent sensing apparatus, and the detection method includes: and enabling the liquid sample to be detected containing the poor solvent and the selected small molecules and the sensing area of the environment response type intelligent sensing device and detecting the fluorescence intensity change of the sensing area, thereby realizing the detection of the selected small molecules in the liquid sample to be detected.
Further, the detection method specifically comprises the following steps:
enabling a series of standard liquid samples containing poor solvents and selected small molecules with different concentrations to be in contact with a sensing area of the environment response type intelligent sensing device, detecting the fluorescence intensity of the sensing area, and establishing a sensor capable of reflecting the selected small moleculesThe relation between the small molecule concentration and the fluorescence intensity is F ═ kλc/S, wherein F is the fluorescence intensity in units of a.u., kλIs the coefficient of an excitation light source, c is the concentration of selected small molecules in a standard liquid sample, the unit is mol/L, and S is the specific surface area of a functional group and a detection area of a dyed macromolecule;
and enabling the liquid sample to be detected containing the poor solvent and the selected micromolecules with unknown concentration to be in the sensing area of the environment response type intelligent sensing device, detecting the fluorescence intensity of the sensing area, and calculating the concentration of the selected micromolecules in the liquid sample to be detected according to the relational expression.
Further, the liquid sample to be tested may further include a benign solvent. Further, the environment response type intelligent sensing device can make accurate response to a benign solvent system and a poor solvent system, and the detected object can be a solution system of oil liquid layering, or a solid system which adsorbs different solvents and presents uneven distribution, or a complex biological structure and the like. In the invention, the environment response type intelligent sensing device utilizes atom transfer radical polymerization to combine the second polymer grafted chain with the first polymer chemical bond filled in the patterned substrate. The second polymer grafted chain has different swelling effects under different environmental conditions, generates feedback to environmental stimuli and generates morphological change, thereby leading the surface structure of the substrate to be changed and realizing the automatic control function under the environmental response condition.
The present invention is described in further detail below with reference to specific examples, which are intended to facilitate the understanding of the present invention without limiting it in any way.
As shown in fig. 1, in one embodiment of the invention, a precursor containing reactive functional groups (styrene, divinylbenzene, 4-chloromethylstyrene in a ratio of 7: 1: 2) was backfilled to a linear patterned Si substrate with a length and width of 2cm by 2cm and a spacing of 500nm by a polymer fill process. The substrate is then aligned and pressed at a suitable pressure (4MPa) against another Si plane with higher surface energy at the polymerization temperature (110 ℃). Since the Si plane has a higher surface energy than the substrate, the polymer having the reactive functional group can be easily filled into the latter, resulting in a flat patterned substrate in which the reactive functional groups are alternately present. By varying the concentration of the functional monomer, the density of the active initiator can be readily adjusted so that ATRP can be used to generate polymer graft chains in specific regions. The polymer graft chain of the embodiment is a polystyrene graft chain containing 40-100 carbon atoms, which can respond to different solvents.
The experimental procedure for the atom transfer radical polymerization in this example was: placing the Si substrate containing the Cl initiation group into a styrene reagent, adding analytically pure cuprous chloride, cupric bromide and 2,2' -bipyridyl (the mass ratio is 7: 1: 28), fully mixing, and heating to 120 ℃ to generate the Si substrate with the Cl group at the tail end of the polymer grafted chain. As shown in fig. 2, the Si substrate surface changed significantly before and after the reaction, and the line-shaped patterned Si substrate (fig. 2a) was converted into a flat patterned substrate (fig. 2 b). As shown in FIG. 3, the filled substrate contains Cl groups.
These response characteristics may provide a basis for the development of "smart" surfaces. The solvent may be roughly classified as a poor solvent or a good solvent for the polymer graft chain based on the nature of the interaction with the polymer graft chain. The polymer graft chain is always in a collapsed state in a poor solvent due to the interaction between the solvent and the polymer graft chain. Instead, they adopt a stretched conformation in a good solvent. The thickness of the stretch is controlled by the balance between osmotic pressure and tensile tension. As the solvent quality changes from good to bad, the polymer graft chains gradually shrink from the stretched state and eventually collapse. Most polymer graft chains may expand 6 to 10 times their contracted state.
The morphological changes of the polymer graft chains in different solvents were observed using liquid phase atomic force microscopy (LiquidAFM) and fluorescence microscopy. Although conventional samples can be characterized by characterization techniques such as scanning electron microscopy and transmission electron microscopy, the real-time state of the polymer graft chain in the solvent needs to be directly studied by in-situ analysis techniques in the solvent. Liquid phase atomic force microscopy (Liquid AFM) and fluorescence microscopy can be performed in Liquid media/environment to give substrate surface topography information.
The present inventors examined the in-situ state of the polymer graft chains of this example in Dimethylformamide (DMF) and ethanol using a liquid phase atomic force microscope, which does not allow the use of toluene. DMF is a good solvent and ethanol is a poor solvent for the polymer chain. The conformational changes of the polymer chains in these two solvents can be very significant (fig. 4 a-4 d). As shown in fig. 4a and 4c, in ethanol, the polymer chains are in a collapsed state. Thus, the polymer graft chains have a height of less than 10 nanometers. As shown in fig. 4b and 4d, the polymer graft chain of this example showed an extended state in DMF to a height of about 40 nm. Meanwhile, the width of the polymer graft chain of this example was also varied. The bristle-like structure of the polymer graft chains has a transverse width of 500nm in the dry state, which is greater than the width in the extended state (about 330 nm).
The response characteristic of the polymer grafted chain to the environment has good application in the field of biological protein. As shown in FIG. 5, in one embodiment of this example, and with reference to the foregoing, polymer graft chains are first produced by ATRP polymerization as well. Then, the dyeing macromolecular protein with biological activity (such as Alexa Fluor 350) reacts with the polymer grafted chain, and the reaction process is as follows: and (3) putting the Si substrate with the Cl group at the tail end of the polymer grafted chain into a DMF reagent, adding Alexa Fluor 350, heating to 60 ℃, and connecting the macromolecular protein at the tail end of the polymer grafted chain. Since the macromolecular protein is dyed by using the fluorescent group, the state of the polymer grafted chain can be conveniently observed by using a fluorescence microscope. The dyed macromolecular protein has a fluorophore structure as shown in the following formula, and its emission spectrum measured at a wavelength of 356nm is shown in FIG. 6.
Under the illumination of a 356nm light source, fluorescence emitted from the polymer grafted chain ends can be observed by a fluorescence microscope.
The sensing device is not interfered by other molecules and only responds to specific molecules in the solution. FIGS. 7a and 7b are graphs showing fluorescence intensities of a polymer graft chain in an original state and in an adsorbed state after covalent bonding of a dyed macromolecular protein, respectively.
Therefore, when the sensing area of the environment-responsive intelligent sensing device constructed in this embodiment is placed in a reagent in which small molecules are dissolved, it can be observed that the fluorescence intensity of the surface with the grafted chains of the macromolecular protein graft polymer changes. By measuring this change, the concentration of the small molecule in the solution can be determined.
More specifically, the surface of the macromolecular protein has a bioactive functional group, so that specific adsorption can be performed on specific small molecules (such as amino acid, silver ions and the like), and the number of adsorbed molecules can be judged by observing the change of fluorescence intensity on the surface of the polymer grafted chain. The concentration of a particular molecule in solution can be determined by the intensity of fluorescence after equilibrium is reached, as shown in the following equation:
F＝kλ·c/S，
wherein F is fluorescence intensity in units of a.u., kλIs the coefficient of an excitation light source, c is the concentration of selected small molecules in a standard liquid sample, the unit is mol/L, and S is the specific surface area of a functional group and a detection area of a dyed macromolecule.
In another application of this embodiment, the polymer graft chain can be made by the same ATRP step, and then the short block polymer (such as polystyrene coated with PdS or CdS) is modified to the end of the polymer graft chain by the ATRP reaction under the same conditions.
In this application scheme, a two-step ATRP treatment of the polymer graft chain is used. Wherein the long polymer chains produced in the first ATRP step can maintain a similar swollen state, while the short block polymers do not significantly change the long chain behavior; also, short block polymers can be formed to approximately uniform thickness. Thus, the fluorescence observed from the microscope will have substantially uniform intensity, and the boundaries of the polymer chains can be clearly observed.
In summary, according to the above technical solution, the polymer grafted chain of the environmental response type intelligent sensing device of the present invention has an extended conformation in a good solvent, and a collapsed conformation in a poor solvent, and simultaneously has a possibility of screening a specific molecule, which is equivalent to an automatic response to different environmental conditions, and provides a possibility of accurately controlling the substrate of the sensing material by changing the solvent property, or designing a specific substrate to measure the molecular characteristics of the solution, and the sensing device can respond to various environmental conditions, such as different reagent concentrations, different temperatures and humidities, different electric fields and magnetic fields, by adjusting the material types at the end of the polymer grafted chain. The method provides a brand-new way for designing intelligent materials, has wide application prospect in the field of automatic monitoring, and is an important basic information collection unit for future data development.
It should be understood that the above description is only an example of the present invention, and not intended to limit the scope of the present invention, and all equivalent structures or equivalent flow transformations that are made by the present specification and drawings, or applied directly or indirectly to other related technical fields, are included in the scope of the present invention.
Claims (12)
1. An environment-responsive intelligent sensing device, comprising:
the method comprises the following steps of patterning a substrate, wherein at least two recesses which are arranged at intervals are formed in the surface of the substrate, first polymers containing an initiator are filled in the at least two recesses, flat patterns serving as sensing regions are formed on the surface of the substrate, and the first polymers are selected from any one or the combination of more than two of polystyrene, polymethyl methacrylate and polyethylene terephthalate; and the number of the first and second groups,
a plurality of second polymer graft chains, the head ends of which are covalently bonded to the flat pattern by atom transfer radical polymerization with the active functional groups on the surface of the first polymer, while the ends of which are covalently bonded by nucleophilic substitution reactions with a dyed macromolecule containing amino groups, the dyed macromolecule being selected from short block polymers having a fluorescent group and a functional group capable of specifically binding to a selected small molecule; the second polymer graft chain is derived from polystyrene;
when placed in a good solvent, the second polymer graft chains assume a stretched state to constitute an upright bristle-like structure, and when placed in a poor solvent, the second polymer graft chains assume a collapsed state, and the length of the second polymer graft chains in the stretched state is at least 6 to 10 times as long as the length thereof in the collapsed state.
2. The environmentally responsive smart sensor apparatus of claim 1 wherein: when the sensing area of the environment response type intelligent sensing device is contacted with a good solvent, the plurality of second polymer grafted chains are stretched to form a vertical bristle-shaped structure, and when the sensing area of the environment response type intelligent sensing device is contacted with a poor solvent, the plurality of second polymer grafted chains are collapsed on the surface of the substrate, and the patterns arranged at intervals in the flat pattern have clear boundaries.
3. The environmentally responsive smart sensor apparatus of claim 1 wherein: the staining macromolecule is selected from any one or the combination of more than two of staining macromolecule protein, enzyme and nucleic acid.
4. The environmentally responsive smart sensor apparatus of claim 1 wherein: the number average molecular weight of the short block polymer is 300-450.
5. The environmentally responsive smart sensor apparatus of claim 1 wherein: the short block polymer has a chain segment containing 15 to 30 carbon atoms.
6. The environmentally-responsive smart sensor apparatus of claim 1 wherein the dyed macromolecule has a fluorophore derived from a compound of the formula:
7. the environmentally responsive smart sensor apparatus of claim 1 wherein: the flat pattern is selected from more than two bar-shaped patterns distributed in parallel.
8. The environmentally responsive smart sensor apparatus of claim 7 wherein: the distance between two adjacent bar-shaped patterns is 10-2000 nm.
9. The method for manufacturing an environmentally responsive smart sensor assembly of any one of claims 1-8, comprising the steps of:
(1) providing a patterned substrate, wherein at least two recesses which are arranged at intervals are formed on the surface of the substrate;
(2) backfilling a precursor of a first polymer containing an active functional group into a recess on the surface of the substrate, and then pressing the surface of the substrate in alignment with a plane at a polymerization temperature, wherein the surface energy of the plane is higher than that of the substrate, so that a flat pattern serving as a sensing area is formed on the surface of the substrate;
(3) covalently bonding head ends of a plurality of second polymer graft chains with active functional groups on the surface of the first polymer through atom transfer radical polymerization;
(4) covalently bonding the ends of the second polymer graft chains to the dyed macromolecules by a nucleophilic substitution reaction;
contacting a liquid-phase reaction system comprising a dyed macromolecule and a good solvent with the sensing region, allowing the second polymer graft chain to assume a stretched state, and allowing the end of the second polymer graft chain to covalently bond with the dyed macromolecule through a nucleophilic substitution reaction.
10. A detection method implemented based on the environment-responsive smart sensor apparatus according to any one of claims 1-8, wherein the detection method comprises: and enabling the liquid sample to be detected containing the poor solvent and the selected small molecules and the sensing area of the environment response type intelligent sensing device and detecting the fluorescence intensity change of the sensing area, thereby realizing the detection of the selected small molecules in the liquid sample to be detected.
11. The detection method according to claim 10, characterized by specifically comprising:
enabling a series of standard liquid samples containing poor solvents and selected small molecules with different concentrations to be in contact with a sensing area of the environment response type intelligent sensing device, detecting fluorescence intensity of the sensing area, and establishing a relation F = k capable of reflecting the concentration of the selected small molecules and the fluorescence intensityλc/S, wherein F is the fluorescence intensity in units of a.u., kλIs the coefficient of an excitation light source, c is the concentration of selected small molecules in a standard liquid sample, the unit is mol/L, and S is the specific surface area of a functional group and a detection area of a dyed macromolecule;
and enabling the liquid sample to be detected containing the poor solvent and the selected micromolecules with unknown concentration to be in the sensing area of the environment response type intelligent sensing device, detecting the fluorescence intensity of the sensing area, and calculating the concentration of the selected micromolecules in the liquid sample to be detected according to the relational expression.
12. The detection method according to claim 11, characterized in that: the liquid sample to be tested also comprises a benign solvent.
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| CN109187449A (en) | 2019-01-11 |
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