CN111735781A - Triphenylamine grafted ruthenium complex ratio luminescence pH sensor - Google Patents
Triphenylamine grafted ruthenium complex ratio luminescence pH sensor Download PDFInfo
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- 239000012327 Ruthenium complex Substances 0.000 title claims abstract description 10
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000004020 luminiscence type Methods 0.000 title abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000002378 acidificating effect Effects 0.000 claims abstract description 10
- 229910001914 chlorine tetroxide Inorganic materials 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 238000000504 luminescence detection Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 9
- 238000000295 emission spectrum Methods 0.000 description 8
- 238000001139 pH measurement Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 230000005595 deprotonation Effects 0.000 description 5
- 238000010537 deprotonation reaction Methods 0.000 description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012088 reference solution Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- 238000013494 PH determination Methods 0.000 description 1
- 239000005092 [Ru (Bpy)3]2+ Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- CXADQLLYLMBGTG-UHFFFAOYSA-N acetonitrile;1,4-dioxane Chemical compound CC#N.C1COCCO1 CXADQLLYLMBGTG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- -1 hexafluorophosphate ions Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- 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
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses application of a triphenylamine grafted ruthenium complex as a ratio luminescence pH sensor. By measuring the luminous intensity ratio of the complex at 629nm and 611nm under different acidic pH values, the pH value of an unknown water sample can be measured by a working curve. The method is simple and easy to implement, and can eliminate the influence of factors such as luminous intensity change and the like caused by instrument condition change such as light source intensity and the like and complex concentration change.
Description
Technical Field
The invention relates to the field of pH sensing, in particular to application of triphenylamine grafted ruthenium complex in ratio luminescence detection of pH of an acidic water sample.
Background
The ground state and excited state properties of the ruthenium metal complex containing the imidazole ring ligand are changed along with the protonation or deprotonation of imidazole groups, so that the ruthenium metal complex can show obvious spectral response to the change of external pH, and the biological activity of the compound is greatly dependent on the acid-base property of the compound. On the other hand, few reports exist on near-infrared luminescent ruthenium complex pH sensors, so that designing and synthesizing the ruthenium complex with the near-infrared luminescent pH sensor effect has important significance.
Substituted inert ruthenium (II) polypyridine complexes with protonatable/deprotonatable groups are the simplest class of pH sensing molecular devices [ Scandola, f.; bignozzi, c.a.; chiorboli, c.; indelli, m.t.; rampi, m.a.coord.chem.rev. 1990,97,299. The intramolecular electron transfer reaction can be switched through protonation/deprotonation, so that the fluorescence switching of the ruthenium (II) polypyridine complex induced by pH is realized. Ruthenium (II) polypyridine complexes with nitrogen-containing heterocycles are the most studied fluorescent pH sensing complexes. The nitrogen heterocycle has pyridine, pyrazine, pyrimidine, carbazole and imidazole groups. Pyridine, pyrazine and pyrimidine have relatively low anti-bonding pi orbitals and are good pi acceptors, while imidazole is a poor pi acceptor and a good pi donor. Another advantage of imidazole-containing rings is that orbital energy can be controlled by proton transfer. Ruthenium (II) complexes containing imidazole rings have been reported in large numbers as luminescent pH sensors, but they all employ single wavelength pH luminescence sensing [ king, b.w.; wu, t.; tai, c.h.; zhang, m.h.; shen, t.bull.chem.soc.jpn.2000, 73,1749; cao, h.; ye, b.h.; li, H.; li, r.h.; zhou, j.y.; ji, l.n.polyhedron 2000,19, 1975; cao, h.; ye, b.h.; zhang, q.l.; ji, l.n.inorg.chem.commun.1999,2, 338; wang, k.z.; gao, l.h.; bai, g.y.; jin, l.p.inorg.chem.commu.2002, 5,841 ], whereas ratiometric pH sensing is rarely reported. Compared with the traditional single-wavelength pH luminescence sensor, the ratio type pH sensor has incomparable advantages in the aspect of resisting the interference of environmental factors (such as light intensity fluctuation of a light source). The invention discloses a triphenylamine grafted ruthenium complex which has an acidic region ratio luminescence pH sensing performance.
Disclosure of Invention
The invention aims to disclose the acidic region ratio luminescence pH sensing performance of the compound.
It is a further object of this invention to disclose such compounds as disclosing the pH sensing properties of such compounds.
The technical scheme of the invention is as follows:
the binuclear ruthenium complex in this experiment consisted of a cation and an anion, the cation being [ Ru (bpy) ]2(HL)]2+The structural formula is shown in figure 1.
The ruthenium complexes described in the present invention are not restricted to the type of anion, and anions customary in the art can achieve the object according to the invention, especially anions of inorganic salts, such as (ClO)4)-Chloride ions, hexafluorophosphate ions and the like, and as a most preferred scheme, the anion of the binuclear ruthenium complex in the experiment is (ClO)4)-。
The method for detecting the pH of the unknown water sample comprises the following steps:
preparing Britton-Robinson (BR) buffer solution, titrating acid and base in the buffer solution, preparing 1.0 × 10-5Adjusting pH of the solution to be detected with concentrated sulfuric acid to 0.1, adjusting pH with concentrated sodium hydroxide solution, and measuring ultraviolet visible absorption and emission spectrum (lambda) of the complex between acidic and alkaline pH rangesex460 nm). One data was obtained at 0.2 pH intervals, and the ratio of 629nm to 611nm luminescence intensities of the complex solutions was determined according to the pH in the different acidic regions (I)629nm/I611nm) And drawing a standard working curve. Further, by determining I of unknown water samples629nm/I611nmAnd (4) obtaining the pH value of the unknown water sample through the difference of the working curve.
Compared with the prior art, the invention has the advantages that: the pH value of the water sample can be conveniently and accurately detected without being influenced by factors such as luminous intensity change caused by instrument condition change such as light source intensity change and complex concentration change, and the effective range of pH detection is 1.90-3.80.
Drawings
FIG. 1 shows a complex [ Ru (bpy) ]2(HL)](ClO4)2And the structural formula of the ligands bpy and HL contained in the compound.
FIG. 2 shows a complex [ Ru (bpy) ]2(HL)](ClO4)2The synthetic route of (1).
FIG. 3 shows that the complex is a complex [ Ru (bpy) ]2(HL)](ClO4)2The protonation/deprotonation process of (a).
FIG. 4(a) is a graph of the effect of pH increase in the acidic region on the UV-Vis absorption spectrum of a BR solution of a complex, with the inset showing the variation of absorption with pH; FIG. 4(b) is the effect of pH increase in the basic region on the UV-Vis absorption spectrum of a BR solution of the complex, the inset shows the variation of the absorption value with pH.
FIG. 5(a) is the effect of pH increase in the acidic region on the photoluminescence spectrum of a BR solution of the complex, the inset shows the variation of photoluminescence intensity with pH; FIG. 5(b) is the effect of pH increase in the basic region on the photoluminescence spectrum of the complex, the inset shows the variation of photoluminescence intensity with pH.
FIG. 6 is a standard working curve of a water sample for ratiometric luminescence sensing.
Detailed Description
The invention is further illustrated by the following examples.
Example 1: complex [ Ru (bpy)2(HL)](ClO4)2The preparation method comprises the following steps:
complex [ Ru (bpy)2(HL)](ClO4)2Synthesized according to the route shown in figure 2, the specific preparation method consists of the following three steps:
(1) 4-diphenylaminobenzaldehyde according to Lai, G.; bu, x.r.; santos, j.; mintz, e.a. synlett,1997,1275.] synthesis.
(2) Ligand HL as per reference [ Zheng, h.q.; guo, y.p.; yin, m.c.; fan, y.t., chem.phys.lett.,2016,653,17 ].
(3) Complex [ Ru (bpy)2(HL)](ClO4)2According to the modified literature [ Zheng, h.q.; guo, y.p.; yin, m.c.; fan, y.t., chem.phys.lett.,2016,653,17.]The synthesis method comprises the following steps of synthesizing cis- [ Ru (bpy)2Cl2]·2H2A suspension of O (0.0998g,0.19 mmol), ethanol l (8mL), water (8mL) and ligand HL (0.106g,0.23mmol) in N2Reflux for 3 hours under protection. After cooling to room temperature, insoluble impurities were removed by filtration. Recrystallizing the product in acetonitrile-dioxane to obtain a red target product with the yield of 30 percent, and performing elemental analysis C51H37N9Cl2Ru·5H2O (molecular weight: 1038) calculated value: c59.02, H4.56, N12.14; the analytical values are C58.76, H4.13 and N11.82.1H NMR([D6]DMSO), ppm d 9.12-9.21 (2H),9.05(1H), 7.75(1H), 7.54-7.79 (7H), 7.38-7.49 (4H), 7.21-7.34 (10H), 7.06-7.13 (8H), 6.92-7.06 (4H) Mass Spectrometry: m/z 876[ M-2 Cl-5H2O–H+]+,721[M–2Cl–5H2O–H+–bpy]+,257[M–2Cl–5H2O– H+–bpy–HL]+.
Example 2: measurement of ultraviolet-visible absorption spectrum and emission spectrum at different pH values and drawing of working curve
Acid-base drops of complexThe test was carried out in Britton-Robinson (BR) buffer solution, which was a mixture of 0.04M glacial acetic acid, 0.04M boric acid and 0.1M sodium chloride, which was added to maintain the ionic strength of the system and thus reduce the effect of the external environment on the test, 40 ml of 1.0 × 10 was prepared-5Adjusting pH of the complex solution to be detected to 0.1 with concentrated sulfuric acid, adjusting pH with concentrated sodium hydroxide solution, and measuring ultraviolet visible absorption and emission spectrum (excitation wavelength lambda) under the condition of pH value ranging from 0.10-13.6ex460 nm). Measuring a spectrum at intervals of 0.2 pH, reading absorbance at 411nm at different pH and measuring integrated luminous intensity of emission spectrum, calculating luminous quantum efficiency, and plotting luminous intensity ratio (I) of 629nm and 611nm of complex solution629nm/I611nm) The pH values in the different acidic regions were plotted to generate a standard working curve.
The UV-visible absorption spectrum is measured on a UV-2600 UV-visible spectrophotometer by using BR buffer solution as a reference solution. According to the absorption spectrum, the change of the ultraviolet-visible absorption spectrum can be divided into two successive deprotonation processes as shown in fig. 3 in the change range of pH 0.2-11.4: the first step is shown in FIG. 4(a), where during the pH increase from 0.10 to 5.80, the absorption peak at 34723nm gradually increases, the absorption intensity divided by 411nm gradually decreases, and an isosbestic point occurs at 375nm, which is attributed to the dissociation process of the proton of the protonated imidazole ring on ligand HL. In the second step, as shown in FIG. 4(b), the pH was increased from 6.4 to 13.6, the absorption peaks at 268 and 411nm in the UV-visible absorption spectrum were decreased, and the absorption intensity at 526nm was increased. This process is caused by deprotonation of the imidazole ring on the ligand HL.
Fluorescence emission spectra were measured on a Cary Eclipse fluorescence spectrophotometer with an excitation wavelength of 460 nm. As can be seen from FIGS. 5(a) and 5(b), the emission spectrum of the complex is very sensitive to pH change, the change process is divided into two stages, the maximum emission peak position of the complex is blue-shifted from 629nm to 607nm as the pH is increased from 0.1 to 4.5, and an equal emission point appears at 611nm (see FIG. 5 (a)); the emission intensity or quantum efficiency decreased monotonically as the solution pH increased from 7.50 to 10.0 (see fig. 5 (b)).
The luminescent quantum efficiency was determined by terpyridyl ruthenium [ Ru (bpy ]3]2+As a standard substance (phi)std0.028), concentration was measured to be 1.0 × 10-6mol/L of [ Ru (bpy)3]2+Reading ultraviolet visible absorption spectrum and emission spectrum of the aqueous solution, and reading absorbance A at 450nm of the ultraviolet visible absorption spectrumstdAnd integrated intensity of emission spectrum IstdAccording to formula (1):
Φ＝Φstd(Astd/A)(I/Istd) (1)
phi and phistdLuminescence quantum efficiencies of the analyte and the standard, A and A, respectivelystdIs the absorbance at the excitation wavelengths of the test substance and the standard substance, I and IstdIs the integrated intensity of luminescence of the undetermined material and the standard sample.
The ratio of the luminescence intensity of the complex solution at 629nm to 611nm was read at different pH values as shown in FIG. 5(a) (I)629nm/I611nm). With pH as abscissa, I629nm/I611nmOn the ordinate, a standard working curve is plotted as shown in FIG. 6, which shows a pH of 1.90 to 3.80629nm/I611nmA good linear relationship with pH.
Example 3: determination of pH of unknown Water sample
Taking 23ml of unknown water sample, adding sodium chloride to the unknown water sample until the concentration is 0.1M, keeping the ionic strength consistent with BR buffer, taking 3ml of the water sample added with the sodium chloride as a reference solution, and adding a quantitative complex into the remaining 20ml of the water sample to ensure that the concentration is 1.0 × 10-5mol/L, which is consistent with the concentration of the complex during acid-base titration. The emission spectra of the water samples were measured under the instrument conditions to plot the operating curves shown in figure 6. Reading the 629nm and 611nm luminous intensity ratio (I) of an unknown water sample629nm/I611nm) The pH of the unknown water sample can be determined from the working curve shown in fig. 5.
Claims (1)
1. The application of triphenylamine grafted ruthenium complex in ratio luminescence detection of pH of an acidic water sample is characterized in that: the composition of the ruthenium metal complex is [ Ru (bpy) ]2(HL)](ClO4)2{ bpy ═ 2, 2' -bipyridine;HL-2- (4' -dianilinophenyl) imidazolyl [4,5-f][1,10]Phenanthroline }.
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