CN103525404A - Fluorescent sensor array based on conjugated polymers and application thereof - Google Patents
Fluorescent sensor array based on conjugated polymers and application thereof Download PDFInfo
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Abstract
The invention relates to a fluorescent sensor array based on conjugated polymers and application thereof. Three different synthetic routes are employed for synthesis of four aromatic hydrocarbons with halogens at two ends and two aromatic hydrocarbons with alkynyls at two ends; and different monomers are combined through Sonogashira coupling for synthesis of seven conjugated polymers which constitute the fluorescent sensor array applied to mode identification of nine metal ions. The array has similar response on same-group elements in the element periodic table and has relatively large response difference on different-group elements, so that the ions in different groups can be easily distinguished; and also, the array has slightly different response on the same kinds of ions which are in one same group but in different periods, so that the same-group different-period ions can be subjected to preliminary detection. During practical application, the response mode of a to-be determined standard substance can be stored, and the components of a to-be analyzed substance can be determined by determining the matching degree between the response mode of the to-be analyzed substance and the standard mode.
Description
Technical field
The present invention relates to a kind of fluorescence conjugated polymer sensing material, particularly a kind of fluorescent optical sensor array based on conjugated polymer, for the pattern recognition to metal ion.
Background technology
Conjugated polymer fluorescent sensing material has obvious advantage than other traditional materials, main manifestations be have that signal based on molecular wire effect amplifies and the feature such as adjustable of structure (referring to document: Chem. Rev. 2007,107,1339-1386).The pattern of " lock & key " (a corresponding a kind of assay of sensor) is followed in the design of conventional fluorescent conjugated polymer sensor conventionally.Although there is the successful example much making in this way, this method part that also comes with some shortcomings, energy as expensive in needs designs and synthesizes and has special optionally sensor molecules for certain specific assay.Recently, the layout strategy that is combined into sensor array by a series of Sensing elements is more and more paid close attention to.In such array, each independent Sensing elements need to have different to the response of different analytes, but strong interaction and special selectivity between sensor molecules and specific analyte is optional.This array provides a feature corresponding set for each assay, and it is commonly called sensory pattern or fingerprint (referring to document: Macromolecules. 2005,38,2844-2849; J. Am. Chem. Soc. 2004,126,14964-14971).
Sensor molecules is to main some Specific Interactions based between molecule of the detection of assay, as Subjective and Objective effect, electrostatic adhesion, π-electron effect, dipole-dipole effect and hydrophobic interaction etc.Document (Chem. Sov. Rev. 2006,35,14-28; J. Am. Chem. Soc. 2009,131,11976-11984; Chem. Sci. 2011,2, and 303-307) sensor array of report is based on small molecules system substantially, therefore, substantially can only introduce a kind of Specific Interactions, and form sensor array according to the otherness of this effect.And the constructional feature of conjugated polymer makes them likely realize the different classes of effect to assay on a molecule simultaneously.They can, by the not same-action of side group or main chain and assay, respond thereby provide than the more otherness of small molecules system.This otherness response is the key that realizes effective detection of sensor array.
Summary of the invention
The object of the present invention is to provide a kind of preparation technology simple, easy and simple to handle, metal ion is there is to the fluorescent optical sensor array based on conjugated polymer of otherness response, for the pattern recognition to metal ion.
The technical scheme that realizes the object of the invention is to provide a kind of fluorescent optical sensor array based on conjugated polymer, and fluorescent optical sensor array is comprised of conjugate polymer material P1, P2, P3, P4, P5, P6 and P7, and their structural formula is respectively:
P1：
P2：
P3?：
；
P4：
P5：
P6：
P7：
Wherein, n is the polymerization degree.
In technical solution of the present invention, the preparation method of described conjugate polymer material P1 comprises the steps: by mol, by 1 part of monomer N-(2,5-dibromothiophen-3-ylmethyl)-N, N, N '-trimethylethane-1,2-diamine, 1 part of monomer 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene, 0.05～0.1 part of (PPh
3)
4pd and 0.1～0.2 part of CuI mix, and under argon shield, add 25～50 portions of Diisopropylamines and 125～300 parts of tetrahydrofuran (THF)s, obtain mixture; After mixture is refluxed under argon shield, be cooled to room temperature, add 100～500 parts of chloroforms, after washing, get organic layer, remove solvent, obtain solid crude product, after dissolving, use recrystallizing methanol with chloroform again, vacuum-drying obtains brown solid P1.
The preparation method of described conjugate polymer material P2 comprises the steps: by mol, by 1 part of monomer 2,5-dibromothiophen-3-ylmethyldiethylamine, 1 part of monomer 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene), 0.05～0.1 part of (PPh
3)
4pd and 0.1～0.2 part of CuI mix, and under argon shield, add 25～50 portions of Diisopropylamines and 125～300 parts of tetrahydrofuran (THF)s, obtain mixture; After mixture is refluxed under argon shield, be cooled to room temperature, add 100～500 parts of chloroforms, after washing, get organic layer, remove solvent, obtain solid crude product, after dissolving, use recrystallizing methanol with chloroform again, vacuum-drying obtains brown solid P2.
The preparation method of described conjugate polymer material P3 comprises the steps: by mol, by 1 part of monomer 2,5-didodecyloxy-1,4-diiodobenzene, 1 part of monomer 2,5-bis (dodecyloxycarbonylmethoxy)-Isosorbide-5-Nitrae-diethynylbenzene, 0.05～0.1 part of (PPh
3)
4pd and 0.1～0.2 part of CuI mix, and under argon shield, add 25～50 portions of Diisopropylamines and 125～300 parts of tetrahydrofuran (THF)s, obtain mixture; After refluxing, be cooled to room temperature under argon shield, the suspension liquid obtaining is joined in 5000～15000 parts of methyl alcohol, suction filtration obtains brown solid P3 by vacuum-drying.
Technical solution of the present invention also comprises described fluorescent optical sensor arrayed applications in metal ion is detected.
Compared with prior art, beneficial effect of the present invention is:
1, the present invention utilizes combinatorial chemistry to successfully synthesize a series of conjugated polymers by parallel reaction conditions, and the method, by simplifying the building-up process of conjugated polymer, has been expanded the application of conjugated polymer in sensing detection field.
2, the factor such as the size dimension of ion, electric charge and electronic configuration has caused the otherness of response modes, accordingly, the present invention is applied to conjugated polymer the pattern recognition of metal ion by the method for ion titration, can no longer rely on traditional " lock & key " this man-to-man sensing pattern, by means of computer, realize easy ion detection, there is good application prospect.
Accompanying drawing explanation
Fig. 1 is that structural formula and the synthetic route chart that synthetic method is prepared the required monomer of conjugated polymer combined in the employing that the embodiment of the present invention provides;
Fig. 2 is the structural formula of seven kinds of conjugated polymers preparing of employing combination synthetic method that the embodiment of the present invention provides;
Fig. 3 is that the nuclear-magnetism of seven kinds of conjugated polymers preparing of employing combination synthetic method that the embodiment of the present invention provides characterizes spectrogram;
Fig. 4 is the Infrared Characterization spectrogram of seven kinds of conjugated polymers preparing of employing combination synthetic method that the embodiment of the present invention provides;
Fig. 5 is at the uv absorption spectra of tetrahydrofuran solution under the conjugated polymer room temperature that provides of the embodiment of the present invention;
Fig. 6 is at the fluorescence emission spectrogram of tetrahydrofuran solution under the conjugated polymer room temperature that provides of the embodiment of the present invention;
Fig. 7 is that the conjugated polymer fluorescent optical sensor array that the embodiment of the present invention provides is the detecting pattern figure obtaining under 2 μ M conditions at concentration of metal ions.
Embodiment
Below in conjunction with drawings and Examples, technical solution of the present invention is further elaborated.
The present embodiment adopts the method for combinatorial chemistry to prepare conjugate polymer material by parallel reaction conditions.Referring to attached Fig. 1 and 2, Fig. 1 is that structural formula and the synthetic route chart that synthetic method is prepared the required monomer of conjugated polymer combined in the employing that the embodiment of the present invention provides; Fig. 2 is the structural formula of seven kinds of conjugated polymers preparing of employing combination synthetic method that the embodiment of the present invention provides.
The preparation of P1: add monomer (M1) N-(2 in two dry neck flasks, 5-dibromothiophen-3-ylmethyl)-N, N, N '-trimethylethane-1,2-diamine (0.356 g), monomer (M6) 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene (0.611 g), (PPh
3)
4pd (58 mg) and CuI (20 mg).To applying argon gas in bottle, vacuumize, repeatedly several times. under argon shield, add fast the dried Diisopropylamine 4ml of distillation and tetrahydrofuran (THF) 20ml.Said mixture is cooled to room temperature after refluxing under argon shield 24 hours. and then in system, add 20ml chloroform, respectively wash twice with sodium bicarbonate aqueous solution and deionized water. get organic layer, revolve and evaporate solvent.Hot water and hot methanol washing for the solid obtaining. crude product is used twice of recrystallizing methanol after dissolving with a small amount of chloroform.Final product obtains orange solids for 24 hours at vacuum drying oven inner drying and is P1 (0.664g), and the structural formula of P1 is:
The preparation of P2: add monomer (M2) 2 in two dry neck flasks, 5-dibromothiophen-3-ylmethyldiethylamine (0.327 g), monomer (M6) 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene) (0.611 g), (PPh
3)
4pd (58 mg) and CuI (20 mg). to applying argon gas in bottle, vacuumize, repeatedly several times. under argon shield, add fast the dried Diisopropylamine 4ml of distillation and tetrahydrofuran (THF) 20ml.Said mixture is cooled to room temperature after refluxing under argon shield 24 hours, then in system, adds 20ml chloroform, respectively washs twice with sodium bicarbonate aqueous solution and deionized water. and get organic layer, revolve and evaporate solvent.Hot water and hot methanol washing for the solid obtaining, crude product is used twice of recrystallizing methanol after dissolving with a small amount of chloroform.Final product obtains brown solid for 24 hours at vacuum drying oven inner drying and is P2 (0.654 g).The structural formula of P2 is:
The preparation of P3: add monomer (M3) 2 in two dry neck flasks, 5-didodecyloxy-1,4-diiodobenzene (0.494 g), monomer (M6) 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene) (0.611 g), (PPh
3)
4pd (58 mg) and CuI (20 mg).To applying argon gas in bottle, vacuumize, repeatedly several times.Under argon shield, add fast the dried Diisopropylamine 4ml of distillation and tetrahydrofuran (THF) 20ml.Said mixture is cooled to room temperature after refluxing under argon shield 24 hours.Then this suspension liquid is poured in the methyl alcohol that 400ml is cold.Suction filtration gained solid is placed in vacuum drying oven inner drying and within 24 hours, obtains brown solid and be P3 (0.813g).The structural formula of P3 is:
P4 according to document (J. Am. Chem. Soc. 2004,126,14964-14971) synthetic, its structural formula is:
(Macromolecules 2005,38,2844-2849) synthetic according to document for P5 and P6.
The structural formula of P5 is:
The structural formula of P6 is:
(Macromolecules 1994,27,562-571) synthetic according to document for P7; Its structural formula is:
From Fig. 2, can obviously find out that these seven kinds of polymers have different side-chain structures.
Referring to accompanying drawing 3 and 4, they are respectively that the nuclear-magnetism of seven kinds of conjugated polymers preparing of employing combination synthetic method that the present embodiment provides characterizes spectrogram and Infrared Characterization spectrogram.
The molecular weight of the conjugated polymer that the embodiment of the present invention provides and optical physics data are referring to table 1.
Table 1:
The present invention is based on seven kinds of different conjugated polymers and form fluorescent optical sensor array, because these conjugated polymers are no matter on molecular structure, or all shown certain difference on photophysical property, therefore, the array forming is more similar to response ratio of the same clan in the periodic table of elements, and difference in response not of the same clan is apart from larger.By these different response energies, change places and distinguish ion not of the same clan; Due to also slightly different to the response of the similar ion of different cycles of the same clan, therefore also can to ion different cycles of the same clan, carry out Preliminary detection according to this simultaneously.
Seven kinds of conjugate polymer material P1, P2, P3, P4, P5, P6 and P7 prepared by the present embodiment, reference literature (J. Phys. Chem.
b2004,
108, the method providing in 1537-1543), is mixed with 5 * 10 by every kind of polymer
-6the tetrahydrofuran solution of mol/L concentration; Be ready to the aqueous chloride solution of metal ion, concentration of metal ions is 2.5 * 10
-4mol/L.
Get a certain amount of macromolecular solution (50 mL, 5 * 10
-6mol/L), add gradually wherein metal ion solution, after adding a certain amount of metal ion solution and mixing, make concentration of metal ions in mixing solutions reach successively 0.125 μ M, 0.25 μ M, 0.5 μ M, 1 μ M, 2 μ M, 3 μ M, 4 μ M, 5 μ M, 6 μ M, 7 μ M, 8 μ M, 9 μ M, 10 μ M.To the above-mentioned mixing solutions obtaining, in each concentration, immediately carry out the fluoroscopic examination of mixing solutions.Ion titration experiments all requires solution now with the current.Every group of Data duplication three times, the fluorescence intensity change at fluorogram emission maximum place, is response.Referring to accompanying drawing 5 and 6, they are respectively at uv absorption spectra and the fluorescence emission spectrogram of tetrahydrofuran solution under the conjugated polymer room temperature that provides of the embodiment of the present invention; By Fig. 5, Fig. 6, can be found out, polymer provided by the invention has typical fluorescence conjugated polymer feature.
These responses and ion and ionic concn are carried out associated, the set of composition is the response modes of conjugated polymer fluorescent optical sensor array to metal ion in the present invention.Referring to accompanying drawing 7, it is that the conjugated polymer fluorescent optical sensor array that the embodiment of the present invention provides is the detecting pattern figure obtaining under 2 μ M conditions at concentration of metal ions; As seen from Figure 7, every kind of polymkeric substance is different for the response of different ions, this is to have nothing in common with each other due to polymkeric substance and interionic interaction, and these differences are due to different cycles, main group, not equal with the different quantities of electric charge and size under different ions.Just because of these different responses, the present invention is based on seven kinds of different conjugated polymers and form fluorescent optical sensor array, because these conjugated polymers are no matter on molecular structure, or all shown certain difference on photophysical property, therefore, the array forming is more similar to response ratio of the same clan in the periodic table of elements, and difference in response not of the same clan is apart from larger.By these different response energies, change places and distinguish ion not of the same clan; Due to also slightly different to the response of the similar ion of different cycles of the same clan, therefore also can to ion different cycles of the same clan, carry out Preliminary detection according to this simultaneously.
Claims (5)
1. the fluorescent optical sensor array based on conjugated polymer, is characterized in that: fluorescent optical sensor array is comprised of conjugate polymer material P1, P2, P3, P4, P5, P6 and P7, and their structural formula is respectively:
P1：
；
P2：
P3?：
P4：
P5：
P6：
P7：
Wherein, n is the polymerization degree.
2. a kind of fluorescent optical sensor array based on conjugated polymer according to claim 1, it is characterized in that: the preparation method of described conjugate polymer material P1 comprises the steps: by mol, by 1 part of monomer N-(2,5-dibromothiophen-3-ylmethyl)-N, N, N '-trimethylethane-1,2-diamine, 1 part of monomer 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene, 0.05～0.1 part of (PPh
3)
4pd and 0.1～0.2 part of CuI mix, and under argon shield, add 25～50 portions of Diisopropylamines and 125～300 parts of tetrahydrofuran (THF)s, obtain mixture; After mixture is refluxed under argon shield, be cooled to room temperature, add 100～500 parts of chloroforms, after washing, get organic layer, remove solvent, obtain solid crude product, after dissolving, use recrystallizing methanol with chloroform again, vacuum-drying obtains brown solid P1.
3. a kind of fluorescent optical sensor array based on conjugated polymer according to claim 1, it is characterized in that: the preparation method of described conjugate polymer material P2 comprises the steps: by mol, by 1 part of monomer 2,5-dibromothiophen-3-ylmethyldiethylamine, 1 part of monomer 2,5-bis (dodecyloxycarbonylmethoxy)-Isosorbide-5-Nitrae-diethynylbenzene), 0.05～0.1 part of (PPh
3)
4pd and 0.1～0.2 part of CuI mix, and under argon shield, add 25～50 portions of Diisopropylamines and 125～300 parts of tetrahydrofuran (THF)s, obtain mixture; After mixture is refluxed under argon shield, be cooled to room temperature, add 100～500 parts of chloroforms, after washing, get organic layer, remove solvent, obtain solid crude product, after dissolving, use recrystallizing methanol with chloroform again, vacuum-drying obtains brown solid P2.
4. a kind of fluorescent optical sensor array based on conjugated polymer according to claim 1, it is characterized in that: the preparation method of described conjugate polymer material P3 comprises the steps: by mol, by 1 part of monomer 2,5-didodecyloxy-1,4-diiodobenzene, 1 part of monomer 2,5-bis (dodecyloxycarbonylmethoxy)-1,4-diethynylbenzene, 0.05～0.1 part of (PPh
3)
4pd and 0.1～0.2 part of CuI mix, and under argon shield, add 25～50 portions of Diisopropylamines and 125～300 parts of tetrahydrofuran (THF)s, obtain mixture; After refluxing, be cooled to room temperature under argon shield, the suspension liquid obtaining is joined in 5000～15000 parts of methyl alcohol, suction filtration obtains brown solid P3 by vacuum-drying.
5. a kind of fluorescent optical sensor array based on conjugated polymer as claimed in claim 1, is characterized in that: be applied to metal ion to detect.
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| CN104198451A (en) * | 2014-09-02 | 2014-12-10 | 深圳市坤健创新药物研究院 | Sensor array and application of sensor array to aided identification of metal ions |
| CN107936946A (en) * | 2017-10-17 | 2018-04-20 | 中国科学院化学研究所 | Fluorescence method distinguishes the preparation and application of the organic fluorescence sensor array of a few class explosives |
| CN112143178A (en) * | 2020-09-24 | 2020-12-29 | 中国药科大学 | Electrostatic compound fluorescent array sensor and application |
| CN113087878A (en) * | 2021-04-19 | 2021-07-09 | 苏州大学 | Fluorescent conjugated polymer, preparation method and application in oil fingerprint and blood fingerprint display |
| CN113121798A (en) * | 2021-04-19 | 2021-07-16 | 苏州大学 | Water-soluble cationic fluorescent conjugated polymer, preparation method and application in fingerprint display |
| CN113801299A (en) * | 2021-09-16 | 2021-12-17 | 苏州大学 | Fluorescent conjugated polymer containing spiropyran side group, preparation method and application |
| CN114088496A (en) * | 2021-11-25 | 2022-02-25 | 内蒙古工业大学 | Device for preparing transmission electron microscope powder sample |
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Cited By (10)
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| CN104198451A (en) * | 2014-09-02 | 2014-12-10 | 深圳市坤健创新药物研究院 | Sensor array and application of sensor array to aided identification of metal ions |
| CN107936946A (en) * | 2017-10-17 | 2018-04-20 | 中国科学院化学研究所 | Fluorescence method distinguishes the preparation and application of the organic fluorescence sensor array of a few class explosives |
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| CN112143178A (en) * | 2020-09-24 | 2020-12-29 | 中国药科大学 | Electrostatic compound fluorescent array sensor and application |
| CN112143178B (en) * | 2020-09-24 | 2022-06-28 | 中国药科大学 | Electrostatic composite fluorescent array sensor and application |
| CN113087878A (en) * | 2021-04-19 | 2021-07-09 | 苏州大学 | Fluorescent conjugated polymer, preparation method and application in oil fingerprint and blood fingerprint display |
| CN113121798A (en) * | 2021-04-19 | 2021-07-16 | 苏州大学 | Water-soluble cationic fluorescent conjugated polymer, preparation method and application in fingerprint display |
| CN113801299A (en) * | 2021-09-16 | 2021-12-17 | 苏州大学 | Fluorescent conjugated polymer containing spiropyran side group, preparation method and application |
| CN113801299B (en) * | 2021-09-16 | 2022-06-28 | 苏州大学 | Fluorescent conjugated polymer containing spiropyran side group, preparation method and application |
| CN114088496A (en) * | 2021-11-25 | 2022-02-25 | 内蒙古工业大学 | Device for preparing transmission electron microscope powder sample |
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