CN113861068B - Molecular probe for related-on-off-on conversion signals of acid and alkali and application thereof - Google Patents

Molecular probe for related-on-off-on conversion signals of acid and alkali and application thereof Download PDF

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CN113861068B
CN113861068B CN202111148393.7A CN202111148393A CN113861068B CN 113861068 B CN113861068 B CN 113861068B CN 202111148393 A CN202111148393 A CN 202111148393A CN 113861068 B CN113861068 B CN 113861068B
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molecular probe
fluorene
schiff base
acid
diphenol
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CN113861068A (en
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王芳
李春辉
王爱丽
王文强
杨敏
李玉美
刘明成
李凌雪
高敏
王筱冰
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Dezhou University
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • 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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/84—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving inorganic compounds or pH
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The invention provides a molecular probe for relative-on-off-on conversion signals of acid and alkali and application thereof, relating to the technical field of detection performance of organic compounds; the molecular probe provided by the invention is prepared by taking 2, 3-dihydroxybenzaldehyde and 2, 7-diaminofluorene as reaction raw materials through one-step polymerization reaction. Because the molecular probe contains an imine group sensitive to protons and an o-diphenol hydroxyl action site sensitive to alkaline environment, the molecular probe presents obvious 'off-on-off-on' four-conversion fluorescence detection response to acid-alkaline environment change, and has obvious application value; the preparation method has the advantages of high yield, simple preparation process, easy implementation and the like, is suitable for industrial popularization, and creates favorable conditions for popularization and application of the diphenol hydroxyl fluorene Schiff base molecular probe.

Description

Molecular probe for related-on-off-on conversion signals of acid and alkali and application thereof
Technical Field
The invention relates to the technical field of organic compound function detection, in particular to a diphenol hydroxyl fluorene Schiff base molecular probe which presents sensitive 'off-on-off-on' fluorescence four-conversion detection signals along with the change of acid-base environment and application thereof.
Background
Specific acid and alkaline environments are often required in industrial processes. However, when the industrial wastewater with too high acidity or alkalinity is discharged to the nature, serious pollution is caused to the whole water system and soil, and huge harm is brought to the ecological system and the human living environment. After the polluted water with over high acidity or alkalinity is used in the industrial and agricultural production process, industrial equipment is destroyed, and the product quality is seriously affected; and the chemical composition of the soil is changed, the fertility is reduced, and the crop yield is reduced and even dead. When people drink water with too high acidity or alkalinity, a series of diseases such as low immunity, dysfunction, cancer and the like can be caused, and even life is endangered. If people drink water polluted by acid or alkali, the incidence rate of cancers such as liver cancer, stomach cancer and the like is much higher than that of clean water. Therefore, the method for monitoring the environmental acidity and alkalinity by developing sensitively and conveniently has very important significance in the fields of industrial and agricultural production, chemistry and chemical industry, environmental science and the like.
The fluorescent molecular probe converts the identification effect in the microscopic world into an optical signal which is easy to observe through ingenious design, realizes an in-situ and real-time detection process on the molecular level, has the characteristics of high sensitivity, good selectivity, quick response, easy real-time on-site detection and the like, and has received more and more attention. Based on different detection principles, numerous pH fluorescent molecular probes with different functions have been developed. However, most of the currently reported detection signals of the pH fluorescent molecular probes change in a single direction, namely, along with the enhancement/weakening of acid and alkaline environments, fluorescence changes in a single signal of 'on-off' or 'on-off'; molecular probes with sensitive on-off-on four-conversion of fluorescence signal intensity along with the change of the acid-base environment of the solution are rarely reported. Along with the development of society, people have an increasing demand for sensitive detection of the change of the acid and alkaline environment around the work and the life of people. Therefore, development of a pH fluorescent molecular probe which is rapid and sensitive, simple to operate, easy to prepare and the like is urgently required in various monitoring fields at present.
In the construction process of the fluorescent molecular probe, a receptor generally selects a group containing N, O atoms with stronger coordination ability as a binding site, and the fluorescent molecular probe with specific detection performance is obtained through an optical signal induced after the complexing with a target to be detected. The imine-C=N-group has stronger proton complexing capability, and after the nitrogen atom is complexed with the proton, sensitive fluorescence signal change can be induced. Based on imine Schiff base groups, oneA series of pH fluorescent molecular probes with different recognition performance [ T.Dhawa, A.Hazra, A.Barma, K.pal, P.Karmakar, P.Roy ] were prepared,RSC Adv.,2020,10,15501; K. K. Sadhu, S. Mizukami, A. Yoshimura, K. Kikuchi, Org. Biomol. Chem., 2013, 11, 563]. However, molecular probes constructed by imine groups and having sensitive "off-on-off-on" fluorescence four-conversion detection signals for acidic and alkaline environmental changes have not been reported yet.
Disclosure of Invention
The invention aims to provide a diphenol hydroxyl fluorene Schiff base molecular probe which has sensitive 'on-off-on-off' four-conversion fluorescence detection signals to acid-base environment change.
The invention also aims to provide a method for sensitively detecting the pH value of the water used for people's work and life, which has the advantages of sensitivity, easy operation, low cost, easy popularization and the like.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a diphenol hydroxyl fluorene Schiff base molecular probe with sensitive 'off-on-off-on' four-conversion fluorescence detection signals for acid-base environment changes has the molecular structure as follows:
a diphenol hydroxyl fluorene Schiff base molecular probe with sensitive 'off-on-off-on' four-conversion fluorescence detection signals for acid-base environment changes is prepared by the following steps:
at N 2 Under the protection condition, sequentially putting alpha mmol of 2, 3-dihydroxybenzaldehyde and gamma mmol of 2, 7-diaminofluorene into a round-bottomed flask, dissolving with beta mL of absolute methanol, heating to 75 ℃ and reacting for 3 hours; filtering the mixture obtained by the reaction, washing with anhydrous methanol, and drying to obtain a dark red diphenol hydroxyl fluorene Schiff base fluorescent molecular probe; alpha, beta and gamma are 2:1:30.
The preparation reaction formula of the diphenol hydroxyl fluorene Schiff base molecular probe with sensitive 'off-on-off-on' four-conversion fluorescence detection signals for acid-base environment changes is as follows:
the invention has the following technical effects: the diphenol hydroxyl fluorene Schiff base fluorescent molecular probe acceptor unit simultaneously contains imine which is sensitive to protons and diphenol hydroxyl groups which are sensitive to alkaline environment; with the continuous enhancement of the acidic environment of the solution, the maximum fluorescence emission intensity of the molecular probe at the position of 410 nm is obviously increased and then reduced, and a sensitive 'off-on-off' dual fluorescence detection signal is displayed for the acidic environment; the maximum fluorescence emission intensity of the molecular probe at the position of 410 nm is obviously increased along with the continuous enhancement of the alkaline environment of the solution, so that the molecular probe presents a sensitive 'on-off-on' four-conversion fluorescence detection signal along with the change of the alkaline environment, and has higher application value; the preparation process of the diphenol hydroxyl fluorene Schiff base fluorescent molecular probe provided by the invention has the advantages of simple process, mild reaction condition, high yield and the like, is suitable for industrial implementation, and creates favorable conditions for popularization and application of the fluorescent molecular probe.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the compound obtained in example 1.
FIG. 2 shows fluorescence emission spectra of diphenol hydroxyl fluorene Schiff base molecular probes added with HCl with different concentrations in 95% DMSO aqueous solution.
FIG. 3 shows fluorescence emission spectra of diphenol hydroxyl fluorene Schiff base molecular probes added with NaOH with different concentrations in 95% DMSO aqueous solution.
FIG. 4 shows fluorescence emission spectra of molecular probes of diphenol hydroxyl fluorene Schiff base added with HCl with different concentrations in 95% DMF aqueous solution.
FIG. 5 shows fluorescence emission spectra of molecular probes of diphenol hydroxyl fluorene Schiff base added with NaOH with different concentrations in 95% DMF aqueous solution.
Detailed Description
The invention discloses a diphenol hydroxyl fluorene Schiff base molecular probe with sensitive 'on-off-on' four-conversion fluorescence detection signals for acid-base environmental changes, which has the molecular structure as follows:
；
the preparation method can be prepared by taking 2, 3-dihydroxybenzaldehyde and 2, 7-diaminofluorene as reaction raw materials through one-step polymerization, and the preparation reaction formula is as follows:
。
example 1
At N 2 Under the protection condition, 2 mmol of 2, 3-dihydroxybenzaldehyde and 1 mmol of 2,7 diaminofluorene are sequentially placed into a round bottom flask, then are dissolved by 30 mL absolute methanol, and then are heated to 75 ℃ for reaction for 3 hours; the resultant mixture was filtered, washed with anhydrous methanol and dried to obtain a dark red Schiff base compound A,218, mg in 50% yield.
The compound a obtained in example 1 was analyzed and measured, and nuclear magnetic resonance hydrogen spectrum data are as follows: at the position of 1 H NMR (DMSO-d 6 400 MHz), comprising 4 OH proton signal peaks: 13.79 (s, 2H), 9.75 (s, 2H); proton signal peaks on 2 c=n-carbons: 8.90 (s, 2H); 12 aromatic ring proton signal peaks: 8.51 (s, 2H), 7.97 (d, 2H), 7.64 (s, 4H), 7.44 (d, 2H), 6.99 (d, 2H), 6.46 (d, 2H); CH on 2 fluorene groups 2 Proton signal peak: 4.02 (s, 2H) which is basically consistent with the theoretical value of the molecular probe of the bisphenol hydroxyl fluorene Schiff base. From this, it was confirmed that the molecular structure of compound a was:
namely a diphenol hydroxyl fluorene Schiff base molecular probe.
Example 2
Fluorescence detection function of diphenol hydroxyl fluorene Schiff base molecular probe in 95% DMSO aqueous solution for different acidic environments: at a concentration of 2X 10 -5 mol/L diphenol hydroxyl fluorene Schiff base molecule 95% DMSO waterHCl with different concentrations is respectively added into the solution, and the molar equivalent ratio of the HCl to the solution is respectively 1:0, 1:0.5, 1:1, 1:2, 1:3, 1:4, 1:6, 1:8, 1:10, 1:20, 1:40, 1:60, 1:80, 1:100 and 1:500. Detailed fluorescence spectrum property studies indicate that: as the amount of HCl species in the solution increases from 0 to 3 molar equivalents, the maximum fluorescence emission intensity of the diphenol hydroxyfluorene schiff base molecular probe at 410 nm increases significantly; however, when the amount of HCl substance is increased to 100 times, the strong fluorescence emission is quenched again, which indicates that the diphenol hydroxyl fluorene Schiff base molecular probe has sensitive fluorescence three-conversion signal detection potential of 'off-on-off' in 95% DMSO aqueous solution to an acidic environment.
Example 3
Fluorescence detection function of diphenol hydroxyl fluorene Schiff base molecular probe in 95% DMSO aqueous solution for different alkaline environments: at a concentration of 2X 10 -5 NaOH with different concentrations is respectively added into 95% DMSO aqueous solution of diphenol hydroxyl fluorene Schiff base molecules of mol/L, and the molar equivalent ratio of the diphenol hydroxyl fluorene Schiff base molecules to the DMSO aqueous solution is respectively 1:0, 1:0.5, 1:1, 1:2, 1:3, 1:4, 1:6, 1:8, 1:10, 1:20, 1:40, 1:60, 1:80, 1:100 and 1:500. The series of fluorescence spectrum property researches show that: as the amount of NaOH material in the solution increases from 0 to 100 molar equivalents, the maximum fluorescence emission intensity of the diphenol hydroxyfluorene schiff base molecular probe at 410 nm increases gradually; when the amount of NaOH substance is increased even to 500 times, the strong fluorescence emission change is less, which indicates that the diphenol hydroxyl fluorene Schiff base molecular probe has sensitive 'off-on' fluorescence signal detection potential to alkaline environment in 95% DMSO aqueous solution.
Example 4
Fluorescence detection function of diphenol hydroxyl fluorene Schiff base molecular probe in 95% DMF aqueous solution for different acidic environments: at a concentration of 2X 10 -5 HCl with different concentrations is respectively added into 95% DMF (dimethyl formamide) aqueous solution of mol/L diphenol hydroxyl fluorene Schiff base molecules, and the molar equivalent ratio of the HCl to the DMF aqueous solution is 1:0, 1:0.2, 1:0.4, 1:0.6, 1:0.8, 1:1.0, 1:1.5, 1:2, 1:2.5, 1:3, 1:4, 1:6, 1:8, 1:10, 1:20, 1:40, 1:60, 1:80, 1:100 and 1:500 respectively. As the amount of HCl material in the solution increases from 0 to 4 molar equivalents, the diphenols are presentThe maximum fluorescence emission intensity of the hydroxyfluorene Schiff base molecular probe at 410 nm is obviously increased; however, when the amount of HCl substance is increased to 100 times, the strong fluorescence emission is quenched again, which indicates that the molecular probe of the diphenol hydroxyl fluorene Schiff base has the fluorescence signal detection potential of 'on-off' to the acidic environment in 95% DMF aqueous solution.
Example 5
Fluorescence detection function of diphenol hydroxyl fluorene Schiff base molecular probe in 95% DMF aqueous solution for different alkaline environments: at a concentration of 2X 10 -5 NaOH with different concentrations is respectively added into 95% DMF aqueous solution of diphenol hydroxyl fluorene Schiff base molecules per liter, and the molar equivalent ratio of the NaOH to the 95% DMF aqueous solution is 1:0, 1:0.5, 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:4, 1:6, 1:8, 1:10, 1:20, 1:40, 1:60, 1:80, 1:100 and 1:500 respectively. The series of studies show that: as the amount of NaOH material in the solution increases from 0 to 100 molar equivalents, the maximum fluorescence emission intensity of the diphenol hydroxyfluorene schiff base molecular probe at 410 nm increases gradually; when the amount of NaOH substance is increased even to 500 times, the strong fluorescence emission change is less, which indicates that the diphenol hydroxyl fluorene Schiff base molecular probe has sensitive 'off-on' fluorescence signal detection potential to alkaline environment in 95% DMF aqueous solution.

Claims (1)

1. The non-disease diagnosis application of the molecular probe of the diphenol hydroxyl fluorene Schiff base in the acid-base environment detection is characterized in that the molecular probe of the diphenol hydroxyl fluorene Schiff base has the structure as follows:
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