KR101195377B1 - Method for selectively detecting cyanide ion via complexation between water-soluble hyperbranched fluorescent conjugated polymer and benzyl viologen - Google Patents

Abstract

PURPOSE: A method for selectively detecting cyanide ions based on a complex of water-soluble hyper-branched fluorescent conjugated polymer and benzyl viologen is provided to quantitatively qualitatively analyze the cyanide ions using a chemical sensor and a bio sensor. CONSTITUTION: A complex of water-soluble hyper-branched fluorescent conjugated polymer and benzyl viologen is composed of a water-soluble hyper-branched fluorescent conjugated polymer compound represented by chemical formula 1 and benzyl viologen represented by chemical formula 2. The benzyl viologen is electrostatically bonded to an anionic group at the side chain of the polymer compound. In chemical formula 1, Ar is a C6-20 arylene group or a C3-12 heteroarylene group containing one or more hetero atoms selected from N, O, and S; R1 and R2 are respectively linear or branched C1-6 alkyl groups of which the end groups are substituted with sulfonate groups, carboxylic acid groups, nitro groups, or phosphoryl groups; and m is the integer of 5 to 199.

Description

Method for selectively detecting cyanide ion via complexation between water-soluble hyperbranched fluorescent conjugated polymer and benzyl viologen}

 The present invention relates to a water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex using an electrostatic interaction between a water-soluble fluorescent superbranched conjugated polymer compound and a benzyl biogen, and a method for selectively detecting cyanide ions in an aqueous solution using the same. will be.

Recently, much attention has been focused on the development of sensors using conjugated polymers. Sensors generally use electrical properties such as electricity, resistance, and potential difference or engineering properties such as color and fluorescence as signals by sensing. In particular, color change and fluorescence change can be easily identified by the naked eye, so it is one of the methods that can be easily measured without special equipment. Using a conjugated polymer material to produce a sensor that can change the color and fluorescence, and the measurement material can detect not only ions but also various chemical species such as molecules.

 Conjugated polymers are capable of converting chemical signals into measurable electrical or optical signals, and especially have the advantage of amplification phenomena that increase sensitivity when expressing fluorescent signals in response to interactions with objects under test. And sensor materials such as negative ion detection and explosive detection (DT McQuade, AE Pullen, TM Swager, Chem. Rev. 100, 2537, 2000). In addition, the water-soluble conjugated polymer is widely used as a chemical or biosensor material for biomaterials, proteins, DNA, etc. by utilizing the advantages of sensitivity enhancement using the signal amplification phenomenon of the conjugated polymer and its ability to dissolve in water (C. Li). , M. Numata, M. Yu, S. Wang, S. Shinkai, Angew. Chem. Int. Ed. 42, 4803, 2003; I.-B. Kim, JN Wilson, UHF Bunz, Chem. Commun. 1273, 2005).

The detection of chemical or biomaterials using water-soluble conjugated polymers has been extensively studied. In particular, fluorescence quenching, fluorescence resonance energy transfer (FRET), and fluorescence aggregation by association The detection of ions by the change of color or fluorescence color of polymer sensor materials such as -induced fluorescence change is widely used to improve the sensitivity of detection signals (A. Sartijo, TM Swager. J. Am. Chem. Soc. 129, 16020). , 2007; F. Wang, GC Bazan, J. Am. Chem. Soc. 128, 15786, 2006).

Hyperbranched polymers are spotlighted as ideal materials for a wide range of applications due to their unique physical and chemical properties. The most characteristic property is that it has a lower viscosity than similar linear polymers in solution or in the molten state. This phenomenon can be explained by the characteristics of the branching properties of the hyperbranched polymer. The hyperbranched polymer does not take the form of a random coil of the linear polymer in a solution state but takes a globular shape. In the case of the linear polymer, the viscosity increases linearly in a certain molecular weight range, but if the limit is exceeded, the viscosity rapidly increases. This is explained by the entanglement of polymer chains, which does not occur in hyperbranched polymers. Thus, hyperbranched polymers have a lower viscosity than linear polymers. The branching properties of these hyperbranched polymers also affect the relative solubility in various solvents. Hyperbranched polymers have higher chemical reactivity and higher solubility than similar linear polymers. Linear polymers have a limited number of side chains, whereas hyperbranched polymers have branching properties, resulting in an increase in the number of terminal groups depending on the degree of branching. You will have greater responsiveness. Superbranched polymers having these characteristics can be utilized as sensor materials through conjugation (J. Feng, Y. Li, M. Yang, J. Polym. Sci., Part A: Polym. Chem. 46, 222, 2008; W.-Y. Lai, R. Xia, Q.-Y. He, PA Levemore, W. Huang, DDC Bradley, Adv. Mater. 20, 1, 2008; R. Kikkeri, I. Garcia-Rubio, PH Seeberger, Chem. Commun. 235, 2009).

Among the chemical detections of various objects, detection of cyanide ions has become an important environmental and physiological factor. In general, cyanide ions are known to be toxic, and inhalation of cyanide ions into the body causes abnormalities in the respiratory system, causing vomiting, dizziness, dyspnea, and even severe death. Therefore, the detection of cyanide ions is essential for the maintenance of the biological environment and the regulation of the respiratory system in the human body.

Various specific bindings are available as a method for detecting cyanide ions. Cyanide ions have specific bonds with boron atoms. When cyanide ions are added to a compound containing boron atoms, 3 equivalents of boron atoms and cyanide ions in the compound react to give neutral boron atoms electrostatic anion properties (R. Badugu, JR Lakowicz, CD Geddes, Dye and Pigments. , 49, 2005; N. DiCesare, MR Pinto, KS Schanze, JR Lakowicz, Langmuir, 7785, 2002).

Efforts to detect cyanide ions through the coupling between cyanide ions and boronic acid have been attempted by low molecular weight and high molecular materials. However, most of the cyanide ion detection methods using polymers are linear polymers. In this case, the detection of very small concentration difference can not be easily distinguished, so it not only has a problem of sensitivity, but also has low solubility in water, which makes it difficult to use as a highly sensitive biosensor.

The present invention is to solve the problems of the prior art as described above, in particular to provide a method for selectively detecting cyanide ions by forming a complex of an anionic water-soluble fluorescent hyperbranched conjugated polymer compound and a cationic benzyl biogen. It is done.

Another object of the present invention is to provide a water-soluble fluorescent superbranched conjugated polymer-benzyl biogenene complex and a method for preparing the same, which are composed of an anionic water-soluble fluorescent hyperbranched conjugated polymer compound and a cationic benzyl biogen.

The present invention relates to a water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex using an electrostatic interaction between a water-soluble fluorescent superbranched conjugated polymer compound and a benzyl biogen, and a method for selectively detecting cyanide ions in an aqueous solution using the same. More specifically, the water-soluble fluorescence using the electrostatic interaction of the water-soluble fluorescent superbranched conjugated polymer compound having the property of dissolving in water by the introduction of a large number of anionic groups in the side chain and the benzyl viologen exhibiting cationicity in aqueous solution It relates to a fluorescent sensor in which the fluorescent color of the water-soluble hyperbranched conjugated polymer compound increases or decreases according to the concentration of cyanide ions using the hyperbranched conjugated polymer-benzyl biogen complex.

The water-soluble fluorescent hyperbranched conjugated polymer compound used in the present invention is represented by the following Chemical Formula 1.

[Formula 1]

,

또는

이고; m은 5 내지 199의 정수이다.]
[In Formula 1, Ar is (C6-C20) arylene or (C3-C12) heteroarylene including at least one hetero atom selected from N, O and S; R ₁ and R ₂ are each independently a linear or branched C 1 to C 6 alkyl group substituted with sulfonate, carboxylic acid, nitro or phosphoryl at the end; R ₃ is

,

or

ego; m is an integer from 5 to 199.]

The alkyl groups of R ₁ and R ₂ are independently of each other methyl, ethyl, i-propyl, n-propyl, i-butyl, n-butyl, t-butyl, n-pentyl, i-pentyl or n-hexyl, and The terminal of the alkyl group of R ₁ and R ₂ may be substituted with sodium sulfonate salt or carboxylic acid, respectively, wherein Ar is divalent phenylene. The molecular weight of the water-soluble fluorescent hyperbranched conjugated polymer compound is not limited in principle, but is preferably 3,000 to 100,000 as the number average molecular weight, and may be suitably adjusted and used depending on the characteristics required for the use thereof.

Benzyl bilogen used in the present invention is represented by the following formula (2).

[Formula 2]

Hereinafter, a method of preparing a water-soluble fluorescent hyperbranched conjugated polymer compound (Formula 1) and a benzyl viologen (Formula 2) to prepare a water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex.

(A) water soluble Second branch Conjugate  Preparation of Polymer Compound (Formula 1)

As described in Scheme 1, the water-soluble fluorescent super branched aromatic polymer represented by Chemical Formula 1 may be a tetrakis (triphenylphosphine) monomer (b) forming a branch with a water-soluble monomer (a), an aromatic monomer (c), and the like. It is prepared by Suzuki coupling reaction in the presence of a palladium catalyst.

[Reaction Scheme 1]

[Wherein R ₁ , R ₂ and Ar are the same as defined in formula (1);

,

또는

이고;Y is X when Cl, Br or I

,

or

ego;

,

또는

인 경우 Y가 Cl, Br 또는 I이다.]X

,

or

Where Y is Cl, Br or I.]

In addition, the m value of the water-soluble fluorescent hyperbranched conjugated polymer compound represented by Chemical Formula 1 may be controlled by the equivalent ratio of the water-soluble monomer (a) and the aromatic monomer (c) to be introduced, and preferably the aromatic monomer (c) 1.2 to 1.4 equivalents of water-soluble monomer (a) are used.

As the aromatic monomer (c), in the preparation of the present invention, benzene-1,4-diboronic acid was used, and as the monomer (b) forming the branch, tris-4-bromophenylamine was used. Although a liquefied polymer compound has been prepared, it is not limited thereto, and any monomer may be used as long as it is capable of producing the above water-soluble hyperbranched conjugated polymer compound by Suzuki coupling.

The water-soluble monomer (a) forms a polymer by a Suzuki coupling reaction in the presence of a 1.2-fold molar number of the aromatic monomer (c) and a tetrakis (triphenylphosphine) palladium catalyst (N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457, 1995). The water-soluble fluorescent hyperbranched conjugated polymer compound can polymerize an aqueous monomer and an aromatic monomer having functional groups such as borane, boronic acid, or boron ester at both ends by a Suzuki coupling reaction.

(B) benzyl Of biologen (Formula 2)  Produce

Benzyl biogen represented by the formula (2) is dimethyl as 4,4'-dipyridyl (d) and 2.53 times the number of moles of 4- (bromomethyl) phenylboronic acid (e) as described in Scheme 2 below Prepared by reaction in formamide solvent.

Scheme 2

The water-soluble fluorescent hyperbranched conjugated polymer compound of Chemical Formula 1 is sulfonate, carboxylic acid, nitro or phosphoryl is introduced into the side chain and exhibits electrostatic anion, whereas benzyl biogen of Chemical Formula 2 is electrostatic cationic Since the water-soluble fluorescent hyperbranched conjugated polymer compound of Formula 1 and the benzyl biogen of Formula 2 form a complex by electrostatic interaction. In addition, the water-soluble fluorescent hyperbranched conjugated polymer compound of Chemical Formula 1 has inherent fluorescence, and the benzyl biogen of Chemical Formula 2 is an excellent fluorescent attenuator, so that the complex formed by electrostatic interaction is in a state of fluorescence attenuation. exist.

The conjugated polymer constituting the water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex and the boron atoms present in the benzyl biogen are electrostatically anionic by specific interaction with cyanide ions. At this time, since the interaction with the boron atoms in the benzyl biogen is more prevalent than the boron atoms at the terminal of the conjugated polymer, the boron atoms of the benzyl biogen have anionic properties, and the anionic nature of the boron atoms and the water-soluble fluorescent superbranched co-conjugate in the complex The anionic nature of the liquefied polymer pushes each other out. Through this process, the complex collapses. The collapse of the complex reduces the distance between the water-soluble fluorescent superbranched conjugated polymer compound and the benzyl biogen, a fluorescent attenuator, so that the benzyl biogen, a fluorescent attenuator, is dissolved in water and loses the function of the fluorescent attenuator. The conjugated polymer compound recovers the existing fluorescence. Cyanide ions can be selectively and quantitatively detected by fluorescence change in the formation and decay of the complex, and the fluorescence change is measured using a fluorophotometer. That is, the chemical sensor or biocene sensor including the water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex according to the present invention through such fluorescence changes is useful for the detection of cyanide ions having specific interaction with boron ions in the complex. .

 As described above, the water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogenogen complex according to the present invention can be used as a cognitive substance for anion, and particularly, benzyl biogen in which boronic acid is introduced into the complex has high selectivity to cyanide ions. As sensors and biosensors, it is possible to quantitatively and qualitatively analyze cyanide ions so that diagnostics, medical research, clinical experiments, and chemical analysis can be widely used.

In addition, the water-soluble fluorescent hyperbranched conjugated polymer compound used in the present invention can be applied to various technical fields such as chemical sensor materials and biosensor materials, and in particular, sensor functions such as responsiveness and selectivity by control of guest molecules, etc. It can be applied to molecular sensor materials due to its physical properties.

The present invention will be described in detail through the following examples. However, these examples are for illustrative purposes only and the present invention is not limited thereto.

[ Manufacturing example  1] 1,4- Dibromo -2,5-bis (4- Sulfonatobutoxy ) Benzene Sodium Salt Preparation of (a)

8 g (29.9 mmol) of 2,5-dibromohydroquinone and 2.61 g (65.36 mmol) of sodium hydroxide were added to 60 ml ethanol and heated to 80 ° C. To the solution was added 8.9 g (65.36 mmol) of 1,4-butane sultone. After stirring for 20 hours, the mixture was cooled to room temperature and the reaction was filtered. The obtained solid was washed with ethanol and dried to obtain 16.31 g (93.4%) of 1,4-dibromo-2,5-bis (4-sulfonatobutoxy) benzene sodium salt.

¹ H NMR (300 MHz, D ₂ O): delta = 7.40 (2H, aromatic), 4.13 (4H, alkyl group), 3.08 (4H, alkyl group), 2.00 (4H, alkyl group), 1.96 (4H, alkyl group) ppm.

[ Manufacturing example  2] water soluble fluorescence Second branch Conjugate  Polymer compound A (Formula 1, R _One = R ₂ =- CH ₂ CH ₂ CH ₂ CH ₂ SO ₃ ^- Na ⁺ , Ar = 1,4- Phenylene , R ₃ = -B ( OH ) ₂ Manufacturing

1 g (1.85 mmol) of 1,4-dibromo-2,5-bis (4-sulfonatobutoxy) benzenesodium salt, 0.38 g (2.31 mmol) of 1,4-benzenediboronic acid and tris (4-bro 0.148 g (0.308 mmol) of mophenyl) amine, and 0.13 g (0.12 mmol) of tetrakis (triphenylphosphine) palladium catalyst were dehumidified with 30 ml of DMF and 18 ml of 2M K ₂ CO ₃ It was dissolved in the mixed solution and refluxed at 90 ° C. for 40 hours. After the reaction, the mixture was cooled to room temperature, poured into acetone to precipitate crystals, and the precipitate was filtered. The solid obtained by filtration was melt | dissolved in tertiary distilled water, and the filtration using an osmosis membrane obtained the water-soluble fluorescent hyperbranched conjugated polymer compound A which has a number average molecular weight of 12,400 or more.

¹ H NMR (300 MHz, D ₂ O) δ = 7.7 to 6.8 (8H, aromatic), 4.2 to 3.7 (6H, alkyl group), 3.2 to 2.8 (6H, alkyl group), 2.1 to 1.6 (12H, alkyl group) ppm.

[ Manufacturing example  3] water soluble fluorescence Second branch Conjugate  Polymer compound B (Formula 1, R _One = R ₂ =- CH ₂ COOH , Ar = 1,4- Phenylene , R ₃ = -B ( OH ) ₂ Manufacture of))

1.42 g (3.7 mmol) of 2,2 '-(2,5-dibromo-1,4-phenylene) bis (oxy) diacetic acid and 0.76 g (4.62 mmol) of 1,4-benzenediboronic acid and tris 0.296 g (0.616 mmol) of (4-bromophenyl) amine, and 0.26 g (0.24 mmol) of tetrakis (triphenylphosphine) palladium catalyst were dehumidified 60 ml of DMF and 36 ml of 2M K ₂ CO ₃ It was dissolved in the mixed solution and refluxed at 90 ° C. for 40 hours. After the reaction, the mixture was cooled to room temperature, poured into acetone to precipitate crystals, and the precipitate was filtered. After dissolving the solid obtained by filtration in tertiary distilled water, the water-soluble fluorescent hyperbranched conjugated polymer compound B which has a number average molecular weight of 12,400 or more was obtained by the filtration using an osmosis membrane.

¹ H NMR (300 MHz, D ₂ O) δ = 7.6 to 7.3 (10H, aromatic), 6.9 to 6.4 (4H, aromatic), 4.8 (4H, alkyl group) ppm.

[ Manufacturing example  4] benzyl Biologen  Preparation of (Formula 2)

0.574 g (3.68 mmol) of 4,4'-dipyridyl and 2 g (9.32 mmol) of 4- (bromomethyl) phenylboronic acid were dissolved in 17.2 ml of dimethylformamide, which had been dehumidified, for 48 hours at 55 ° C. At reflux. Yellow precipitate occurred during the reaction. After cooling to room temperature, the crystals were poured into 86 ml of acetone, and the precipitate was centrifuged. The solid obtained was washed with 100 ml of acetone five times, filtered, and dried to obtain 2.012 g (93.3%) of benzyl biogen.

¹ H NMR (300 MHz, D ₂ O) δ = 9.30 (4H, aromatic), 8.68 (4H, aromatic), 7.98 (4H, aromatic), 7.67 (4H, aromatic), 6.09 (4H, alkyl group) ppm.

[ Example  1] water soluble fluorescence Second branch Conjugate  Polymer-Benzyl Biologen  Formation of complexes and Fluorescence Attenuation Effect  evaluation

In order to form a composite by the electrostatic interaction of the water-soluble fluorescent hyperbranched conjugated polymer compound prepared in Preparation Example 2 and the benzyl biogenene prepared in Preparation Example 4, the water-soluble fluorescent superbranched conjugated polymer compound was prepared in tertiary distilled water. Melted and adjusted to 1.0 × 10 ^-5 molarity. Benzyl biogen was added from 1.0 × 10 ⁻⁸ molar concentration to 1.0 × 10 ⁻⁵ molar concentration, and the change in fluorescence of the solution was observed using a fluorophotometer to evaluate fluorescence attenuation.

As a result, the fluorescence was gradually changed depending on the concentration of benzyl biogen added. That is, when the benzyl biogen, which is a fluorescent attenuator, is added to the water-soluble fluorescent hyperbranched conjugated polymer compound, the fluorescence of the polymer is reduced compared to the case where only the water-soluble fluorescent hyperbranched conjugated polymer compound is present, and the concentration of the benzyl biogen added. The higher the value, the more the proportion of fluorescence decrease of the polymer. When the benzyl biogen was added at a molar concentration of 1.0 × 10 ⁻⁵ , the blue fluorescence at 416 nm was reduced by 95% compared to the case where only the water-soluble fluorescent hyperbranched conjugated polymer compound was present. As a result, the water-soluble fluorescent hyperbranched conjugated polymer compound was able to confirm excellent fluorescence attenuation during complex formation by electrostatic interaction with benzyl biogen.

[ Example  2] water soluble fluorescence Second branch Conjugate  Performance Evaluation of Polymer Compound-benzyl Biogenogen Composite as Cyanide Ion Sensor

A water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex is produced by the electrostatic interaction of the water-soluble fluorescent superbranched conjugated polymer compound prepared in Preparation Example 2 and the benzyl biogen prepared in Preparation Example 4. In order to confirm the chemical detection capability of the cyanide ions of the resulting water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogenene complex, the water-soluble fluorescent hyperbranched conjugated polymer compound prepared in Preparation Example 2 was dissolved in tertiary distilled water to 1.0 × 10. ^{Adjusted to -5} molarity. Benzyl biogen was added to this to adjust the molarity of 1.0 × 10 ⁻⁵ . Observed by the addition of cyanide ions in different concentrations to ² mole concentration using the fluorescence change in the fluorescence photometer of the solution ^- this in order to determine the fluorescence change in the concentration of the cyanide ion from 1.0 × 10 ^-5 molar concentration of 1.0 × 10 in It was.

As a result of observing with a fluorescence photometer, the water-soluble fluorescent hyperbranched conjugated polymer compound (Production Example 2) -benzyl biogen (Production Example 4) showed different fluorescence changes depending on the concentration of cyanide ions used in the experiment. When cyanide ions are added to the water-soluble fluorescent hyperbranched conjugated polymer compound (Preparation Example 2) -benzyl biogen (Preparation Example 4) composite, in which fluorescence is attenuated, the fluorescence increases before the addition of cyanide ions (if only the complex is present). I could see the phenomenon. As a result of measuring the fluorescence by the fluorescence photometer, it was confirmed that the fluorescence increased 125% by the addition of cyanide ions in the case of the water-soluble fluorescent hyperbranched conjugated polymer compound (Preparation Example 2) -benzyl biogen (Preparation Example 4). .

As a result, it can be seen that the prepared water-soluble fluorescent hyperbranched conjugated polymer compound (Preparation Example 2) -benzyl biogen (Preparation Example 4) complex can be used as a selective biosensor according to the type of anion added. there was. In addition, the boron and cyanide ions present in the constituents of the complex benzyl biogen decompose the complex through specific interactions, and this decay reduces the distance between the high molecular compound and the benzyl biogen, which is a fluorescent attenuator, to dissolve in water. As a result, it was confirmed that the fluorescence increased by the existing fluorescence of the polymer compound by losing the function of the fluorescence attenuator.

[ Comparative example Evaluation of detection performance for other anions

In order to confirm the selectivity of detecting cyanide ions of the present invention, bromine ions, iodine ions, fluorine ions, chlorine ions and acetate ions having the same molarity were used instead of cyanide ions. Each ion was added under the same conditions as in Example 2, and fluorescence was measured by a fluorescence photometer. As a result, unlike the case of cyanide ions identified in Example 2, blue fluorescence at 416 nm was 57% bromine and 52% at 416 nm, respectively, by the addition of bromine, iodine, fluorine, chloride and acetate ions. %, Fluorine ions 63%, chloride ions 2%, acetate ions 64%.

From the above results, it was confirmed that the water-soluble fluorescent hyperbranched conjugated polymer compound-benzyl biogen complex according to the present invention can be used as a selective chemical sensor for cyanide ions in which fluorescent color changes depending on the presence and concentration of cyanide ions. Could.

Claims (10)

A water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogenene complex in which the benzyl biogen of formula 2 is electrostatically bonded to an anionic group of the side chain of the water-soluble fluorescent superbranched conjugated polymer compound represented by Formula 1 below.
[Formula 1]

[In Formula 1, Ar is (C6-C20) arylene or (C3-C12) heteroarylene including at least one hetero atom selected from N, O and S; R ₁ and R ₂ are each independently a linear or branched C 1 to C 6 alkyl group substituted with sulfonate, carboxylic acid, nitro or phosphoryl at the end; R ₃ is

,

or

ego; m is an integer from 5 to 199.]

(2)

The method of claim 1,
The alkyl groups of R ₁ and R ₂ are independently of each other methyl, ethyl, i-propyl, n-propyl, i-butyl, n-butyl, t-butyl, n-pentyl, i-pentyl or n-hexyl, and The terminal of the alkyl group of R ₁ and R ₂ is a water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogenene complex, characterized in that substituted with sodium sulfonate salt or carboxylic acid, respectively.
The method of claim 1,
Ar is phenylene, water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex.
The method of claim 1,
The water-soluble hyperbranched conjugated polymer compound of Chemical Formula 1 has a number average molecular weight of 3,000 to 100,000, wherein the water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex.
Sensor comprising a water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex according to any one of claims 1 to 4.
6. The method of claim 5,
The sensor is characterized in that the chemical sensor or biosensor.
The method according to claim 6,
The sensor is characterized in that for the selective detection of cyanide ions using a fluorescence photometer.
A method for selectively detecting cyanide ions using a sensor according to claim 5.
A method of selectively detecting cyanide ions using the water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex according to claim 1.
Electrostatic coupling of cationic benzylbiogen to the anionic groups of the side chains of the water-soluble fluorescent hyperbranched conjugated polymer compound by adding benzyl biogen of Formula 2 to an aqueous solution of the water-soluble fluorescent hyperbranched conjugated polymer compound represented by Formula 1 To prepare a water-soluble fluorescent hyperbranched conjugated polymer-benzyl biogen complex according to claim 1.
[Formula 1]

[In Formula 1, Ar, R ₁ , R ₂ , R ₃ and m are the same as defined in claim 1.]

(2)