CN113527364B - Mn (II) complex multi-photon absorption material and preparation method and application thereof - Google Patents
Mn (II) complex multi-photon absorption material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a Mn (II) complex multi-photon absorption material and a preparation method and application thereof, relating to the technical field of fluorescent probes, and the invention designs and synthesizes a terpyridine Mn (II) complex with a novel structure, wherein the complex has multi-photon absorption property and can be used as a multi-photon absorption material; the complex has obvious multiphoton viscosity response performance and can specifically recognize Bovine Serum Albumin (BSA) by multiple photons, so that the complex can be applied as a multiphoton viscosity response type fluorescent probe and a multiphoton BSA specific recognition fluorescent probe.
Description
The technical field is as follows:
the invention relates to the technical field of fluorescent probes, in particular to a Mn (II) complex multi-photon absorption material and a preparation method and application thereof.
Background art:
viscosity is an important inherent property of a fluid, and the size of the viscosity directly affects the flow of the fluid and the properties of dispersion, heat transfer and the like of the fluid. Viscosity is an important microenvironment parameter, and the sigma bond of the molecule can rotate freely in a solvent to consume the excited state energy of the molecule, so that the emission of the molecule is quenched or weak. And as the viscosity in the environment is increased, the rotation of the molecular rotation is slowed down under the limitation of the surrounding viscosity, the energy consumed by the non-radiative transition of the molecules is reduced, and the emission is enhanced. Thus, changes in viscosity in the environment can be detected by changes in fluorescence intensity (anal. methods.,2019,11, 2626-2629).
Bovine Serum Albumin (BSA) is one of the major proteins in bovine serum. It is involved in many biological functions such as transport of metal ions, nutrients and drugs, maintenance of osmotic pressure and buffering of pH. BSA is widely used in the healthcare and pharmaceutical fields due to its abundant content, low price, easy availability, unique coordination properties, and homology to Human Serum Albumin (HSA) (j.photochem. photobiol. b.,2012,112, 16-22). Therefore, the method has important application value in detecting the serum albumin in the complex mixture.
Based on the consideration, the terpyridine ligand with strong chelating ability and Mn form a complex, and a triphenylamine group is introduced to the terpyridine, so that the terpyridine ligand has strong electron pushing ability, the conjugation degree of molecules is increased, and the fluorescence of the molecules can be effectively adjusted; the sulfonate group improves the water solubility of the complex; the halogen is used as an auxiliary coordination atom to form a D-A structure, which is beneficial to improving the electron pushing and pulling capability and enhancing the multiphoton absorption property of the complex.
The invention content is as follows:
the invention aims to solve the technical problem of providing a Mn (II) complex multi-photon absorption material and a preparation method and application thereof, in particular to a terpyridine Mn (II) complex with multi-photon absorption property obtained by molecular design and chemical synthesis and successfully realizing the application of the complex as a multi-photon viscosity response type fluorescent probe and a multi-photon BSA specific recognition fluorescent probe.
The technical problem to be solved by the invention is realized by adopting the following technical scheme:
mn (II) complex multi-photon absorption material, FS-MnCl for short 2 The structural formula is as follows:
the preparation method of the Mn (II) complex multi-photon absorption material takes triphenylamine as an initial raw material, and firstly triphenylamine, DMF and POCl 3 Reacting to obtain compound F, reacting with chlorosulfonic acid to obtain compound S, reacting with 2-acetylpyridine to obtain compound FS, and reacting with MnCl 2 Reacting to prepare a complex FS-MnCl 2 。
The synthetic route is as follows:
the triphenylamine is mixed with DMF and POCl 3 In a molar ratio of 1:3: 5.
The molar ratio of the compound F to the chlorosulfonic acid is 1:2-5
The molar ratio of the compound S to the 2-acetylpyridine is 1: 2-5.
The compound FS and MnCl 2 The molar ratio of (A) to (B) is 1: 1-3.
The application of the multiphoton absorption Mn (II) complex material as a multiphoton viscosity response type fluorescent probe.
The Mn (II) complex multi-photon absorption material is used as a multi-photon BSA specific recognition fluorescent probe.
The triphenylamine tripyridine sulfonate is a compound containing polypyridine heterocycle, has stronger coordination capacity to transition metal ions Mn (II), introduces sulfonate and triphenylamine groups, on one hand, increases the water solubility of the complex, on the other hand, the stronger electron-pushing capacity of the complex greatly increases the amplitude of a conjugated system, causes the red shift of an absorption peak, and can effectively adjust the fluorescence of molecules; the halogen is used as an auxiliary coordination atom to form a D-A structure, which is beneficial to improving the electron pushing and pulling capability and enhancing the multiphoton absorption property of the complex.
The invention has the beneficial effects that:
1. the novel terpyridine Mn (II) complex is designed and synthesized, and sulfonate and triphenylamine groups are introduced into the structure, so that on one hand, the water solubility of the complex is increased, and on the other hand, the conjugated system is greatly increased due to the strong electron pushing capacity of the complex, the intramolecular charge transfer is facilitated, and the luminescence of the complex is adjusted; halogen atoms are introduced as auxiliary coordination atoms, the electron push-pull capability of the molecules is improved, and the nonlinear optical property is enhanced; compared with other materials, the complex has a larger three-photon absorption cross section.
2. Study of the Complex FS-MnCl Using open-cell Z-Scan and fluorescence contrast 2 Multi-photon absorption properties of (a). Using perforated Z-sweepsDescription of FS-MnCl at an excitation wavelength of 900nm 2 The maximum two-photon absorption cross section of the optical film reaches 7150.75 GM; using fluorescence contrast method, FS-MnCl at 1450nm excitation wavelength 2 Has a maximum three-photon absorption cross section of 24.51X 10 - 80 cm 6 s 2 photon -2 。
3. The Mn (II) complex FS-MnCl of the invention 2 Has obvious viscosity response performance, the content of glycerol in the solution is increased from 0 percent to 90 percent, and the complex FS-MnCl is gradually increased along with the gradual increase of the viscosity 2 Single photon fluorescence is enhanced by 20 times; when 900nm is used as excitation wavelength, the two-photon absorption cross section is increased by nearly 2 times to reach 10396 GM; when 1450nm is used as excitation wavelength, the three-photon absorption cross section is increased by about 4 times to reach 80.81 multiplied by 10 -80 cm 6 s 2 photon -2 。
4. The Mn (II) complex FS-MnCl of the invention 2 The antibody can specifically recognize Bovine Serum Albumin (BSA), and after the BSA is recognized, the fluorescence intensity of the antibody is increased by 12 times relative to a blank sample; when 1450nm is used as excitation wavelength, the three-photon absorption cross section of the complex after BSA recognition is 78.63 × 10 -80 cm 6 s 2 photon -2 This is 3 times that before recognition.
5. The manganese terpyridine complex has the advantages of easily available raw materials, low price, short synthetic route and mild synthetic conditions.
Description of the drawings:
FIG. 1 shows a complex FS-MnCl 2 Crystal structure of (2).
FIG. 2 (a-d) is a graph of the study of complex FS-MnCl by open-cell Z-scan method and fluorescence contrast method 2 Two/three photon absorption spectra in DMSO solvent. (a) The method comprises the following steps FS-MnCl at an excitation wavelength of 700-1000nm using an open-cell Z-scan method 2 The two-photon absorption diagram of (a); (b) the method comprises the following steps FS-MnCl at an excitation wavelength of 700-1000nm using an open-cell Z-scan method 2 A two-photon absorption cross-sectional view; (c) the method comprises the following steps Using fluorescence contrast method, using 1150-1550nm as excitation wavelength, FS-MnCl 2 The three-photon fluorescence spectrum of (a); (d) the method comprises the following steps Using fluorescence contrast method, using 1150-1550nm as excitation wavelength, FS-MnCl 2 Of three photonsAbsorption cross-sectional view.
In FIG. 3, (a-d) is a complex FS-MnCl 2 Viscosity response plots in glycerol mixed solvents of different ratios. (a) The method comprises the following steps Complex FS-MnCl 2 Single photon fluorescence spectrum (c 10) in glycerol mixed solvent with different proportions -5 mol/L); (b) the method comprises the following steps Complex FS-MnCl 2 In the range of 0% to 90% glycerol/H 2 Single photon fluorescence intensity in O; (c) the method comprises the following steps Using fluorescence contrast method, the complex FS-MnCl 2 At 0%, 50%, 90% glycerol/H 2 Two-photon absorption cross section in O (c 10) -3 mol/L); (d) the method comprises the following steps Using fluorescence contrast method, the complex FS-MnCl 2 At 0%, 50%, 90% glycerol/H 2 Three-photon absorption cross section in O (c ═ 10) -3 mol/L)。
In FIG. 4, (a-d) is a complex FS-MnCl 2 Specific recognition pattern for BSA. (a) The method comprises the following steps Complex FS-MnCl irradiated by ultraviolet lamp 2 Adding fluorescence pictures of various proteins (BSA (bovine serum albumin), Cys (cysteine), GSH (glutathione), DNA (deoxyribonucleic acid), RNA (ribonucleic acid), HSA (human serum albumin), Gly (glycine), Pro (proline)) and corresponding fluorescence intensity; (b) the method comprises the following steps In the complex FS-MnCl 2 Single photon fluorescence spectrum after adding BSA (c 10) -5 mol/L); (c) the method comprises the following steps At the excitation wavelength of 1450nm, in the complex FS-MnCl 2 Three-photon fluorescence spectrum after adding BSA (c 10) -3 mol/L); (d) the method comprises the following steps Using a fluorescence contrast method and using 1150-1550nm as an excitation wavelength to obtain a complex FS-MnCl 2 Three-photon absorption cross section before and after adding BSA (c is 10) -3 mol/L)。
The specific implementation mode is as follows:
in order to make the technical means, the original characteristics, the achieved purposes and the effects of the invention easy to understand, the invention is further explained by combining the specific embodiments and the drawings.
1. Preparation of Compound F
Refined anhydrous DMF (11.70g, 0.16mol) was added to a 250mL round-bottomed flask in the presence of a ice salt bath, and POCl was slowly added dropwise through an isopiestic dropping funnel 3 (9.20g, 0.06mol), a frozen salt was formed. Triphenylamine (4.90g, 0.02mol) is dissolved in a proper amount of refined anhydrousCHCl 3 And dropwise adding the mixture into frozen salt, and refluxing for 6 hours at 65 ℃ after the frozen salt is melted. After the reaction is completed, pouring the reactant into a large amount of ice water, adjusting the pH value to be neutral by using NaOH aqueous solution, extracting by using dichloromethane, distilling the solvent at normal pressure to obtain yellow oily liquid, and purifying by using column chromatography (V) Petroleum ether /V Ethyl acetate 20/1) was dried in vacuo for 24h to give F5.03 g as a yellow solid in 83.5% yield.
2. Preparation of Compound S
A250 mL round bottom flask was surrounded by crushed ice, F (4.09g, 0.015mol) was dissolved in 20mL purified dichloromethane and added to the flask, the mixture was stirred for 20min, chlorosulfonic acid (14.0g, 0.112mol) was slowly added dropwise from a constant pressure dropping funnel, and after completion of the addition, the reaction was continued for two hours under these conditions. Finally, slowly dropwise adding a proper amount of water to quench the reaction, heating to 40 ℃ for reacting for two hours, cooling to room temperature, adjusting the pH to 7-8 by using a 4mol/L NaOH aqueous solution, adding ethanol, then spin-drying the water, performing suction filtration, and performing vacuum drying for 24 hours to obtain a yellow solid S5.86 g with the yield of 81.9%.
3. Preparation of Complex FS
A250 mL three-necked flask was charged with an aqueous NaOH (2.40g, 0.068mol) solution and 2-acetylpyridine (3.03g, 0.025mol), heated to 80 ℃ and stirred for 30 min. Compound S (4.33g, 0.01mol) was dissolved in an appropriate amount of ethanol, added to the above reaction system, and stirred for 30 min. A constant pressure dropping funnel is used for dropping a proper amount of NH 3 ·H 2 And O, continuing to react for 6 hours, stopping the reaction, and standing for one night. And (3) carrying out suction filtration, leaching with ethanol for three times, recrystallizing the solid with methanol, and drying in vacuum to obtain yellow solid FS 4.12g with the yield of 60.1%. 1 H NMR(400MHz,D 2 O)δppm:8.22–8.08(m,2H),7.72–7.60(m,2H),7.52–7.34(m,8H),7.10–6.98(m,2H),6.83–6.74(m,2H),6.73–6.60(m,4H),6.41–6.29(m,2H). 13 C NMR(100MHz,d 6 -DMSO)δppm:155.58,155.04,149.29,148.79,148.61,146.67,137.41,129.72,127.91,124.82,124.44,123.86,122.26,120.87,117.11.ESI-MS m/z:calcd for:(M-2Na + )/2:317.05,found:317.04.
4. Complex FS-MnCl 2 Preparation of
Pouring manganese chloride (0.16g, 1.0mmol) into a 100mL round-bottom flask, adding a proper amount of anhydrous acetonitrile to completely dissolve the manganese chloride, dropwise adding a solution of ligand FS (0.68g, 1.0mmol) in acetonitrile (10mL) at normal temperature, stirring for two hours, stopping the reaction, and filtering to obtain orange yellow solid FS-MnCl20.56g, wherein the yield is as follows: 76 percent. 1 H NMR(400MHz,d 6 -DMSO)δ(ppm):8.66(d,J＝1.6Hz,6H),7.99(tdd,J＝11.8,6.8,5.0Hz,2H),7.82(dt,J＝14.9,7.4Hz,2H),7.52(dd,J＝8.8,1.6Hz,6H),7.13(dd,J＝9.0,1.6Hz,2H),7.00(dd,J＝8.8,1.6Hz,4H). 13 C NMR(100MHz,d 6 -DMSO)δ(ppm):161.14,152.17,149.58,149.20,147.86,144.03,138.96,138.24,135.23,129.56,129.22,128.74,124.14,123.90,122.89,118.57.FT-IR(KBr,cm -1 ):3908(m),3844(s),3749(m),3419(s),2358(m),1652(m),1589(s),1494(s),1398(m),1323(m),1170(s),1113(s),1037(s),834(m),789(m),713(s),618(m),567(m),522(m).MALDI-TOF-MS m/z:calcd for:804.95,found:366.41([M-2Na + ]/z).
Analysis of the attached figures:
FIG. 1 shows a complex FS-MnCl 2 Crystal structure diagram, the exact structure of the molecule is proved. Hydrogen atoms and solvent molecules were deleted for clarity of showing the crystal structure. Complex FS-MnCl 2 The single crystal of (A) is obtained by a solvent evaporation method, and a proper amount of FS-MnCl is added 2 Dissolved in 10mL of dichloromethane, filtered into a 25mL conical flask, covered with 5mL of ethanol, and placed in a vibration-free dark environment to obtain orange-yellow prismatic crystals with a size of 0.30X 0.20X 0.10mm after two weeks. The complex belongs to a monoclinic system and a C2/C space group. In FS-MnCl 2 In the crystal structure of (a), triphenylamine sulfonate terpyridine is used as a main ligand to coordinate with central Mn, two Cl ions are used as coordination atoms to coordinate with the central Mn, and the coordinated ligand and metal ions are positioned in the same plane, namely the part of N ^ N ^ N-Mn is positioned in the same plane.
FIGS. 2 a-b use the open-cell Z-scan method with 700nm,800nm,900nm,1000nm as excitation wavelengths, FS-MnCl 2 The two-photon absorption property of (1). Wherein, at an excitation wavelength of 900nm, FS-MnCl 2 The maximum two-photon absorption cross section of the optical film reaches 7150.75 GM; c. C-d graph shows FS-MnCl using fluorescence contrast method at 1150nm-1550nm as the continuous excitation wavelength 2 The three-photon fluorescence property of (1). Wherein, at the excitation wavelength of 1450nm, FS-MnCl 2 The maximum three-photon absorption cross section reaches 24.51 multiplied by 10 -80 cm 6 s 2 photon -2 。
5. Viscosity measurement
Prepared complex FS-MnCl 2 Mixed solvent of glycerol/PBS buffer solution in different proportions (glycerol amount increased from 0% to 90%, c 10% -3 mol/L). Measurement of Complex FS-MnCl 2 Three-photon fluorescence in mixed solvents of glycerol/PBS buffer at different ratios.
FIG. 3 a-b illustrates that as the glycerol content of the solution increases from 0% to 90%, the viscosity of the solution gradually increases and the complex FS-MnCl 2 The fluorescence intensity is enhanced by 20 times; c illustrates the complex FS-MnCl in 90% glycerol/water at 900nm excitation wavelength 2 The two-photon absorption section is increased by 2 times and reaches 10396 GM; d illustrates the complex FS-MnCl at 1450nm excitation wavelength 2 The three-photon absorption cross section is increased by 4 times, and the maximum three-photon absorption cross section reaches 80.81 multiplied by 10 - 80 cm 6 s 2 photon -2 。
6. Screening experiment for specific recognition BSA
Taking FS-MnCl 2 DMSO stock solution (c ═ 10) -3 mol/L), diluting to 10 with PBS buffer solution -5 mol/L to FS-MnCl 2 To the PBS solution was added 200. mu.L (c 10) of each -2 mol/L) BSA (bovine serum albumin), Cys (cysteine), GSH (glutathione), DNA (deoxyribonucleic acid), RNA (ribonucleic acid), HSA (human serum albumin), Gly (glycine), Pro (proline), followed by fluorescence testing.
FIGS. 4A-B illustrate the complex FS-MnCl 2 Has good fluorescence response to BSA (bovine serum albumin), and increases with BSA concentration (c 10 ═ c) -2 mol/L, from 0 to 460 μ L, 20 μ L each time), the fluorescence intensity of which is increased by 6 times relative to the blank sample, and the single photon fluorescence spectrum of other biomacromolecules is unchanged after the biomacromolecules are added; c shows BSA addition at 1450nm excitation wavelengthAfter the reaction, the complex FS-MnCl 2 The three-photon fluorescence is obviously enhanced, and the fluorescence intensity after identification is 4 times that before identification; d illustrates that at 1450nm excitation wavelength, the complex FS-MnCl 2 The three-photon absorption cross section is increased by 3 times, and the maximum three-photon absorption cross section reaches 78.63 multiplied by 10 -80 cm 6 s 2 photon -2 。
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (3)
1. A mn (ii) complex multiphoton absorbent material characterized by: abbreviated as FS-MnCl 2 The structural formula is as follows:
2. use of the mn (ii) complex multiphoton absorbent material according to claim 1 as a multiphoton viscosity-responsive fluorescent probe.
3. Use of the mn (ii) complex multiphoton absorbent material according to claim 1 as a multiphoton BSA-specific recognition fluorescent probe.
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