CN110041251A - Application of the equal benzene trimellitic imide of 4-aminopyridine functionalization in detection formaldehyde and 3- fluorobenzaldehyde - Google Patents

Application of the equal benzene trimellitic imide of 4-aminopyridine functionalization in detection formaldehyde and 3- fluorobenzaldehyde Download PDF

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CN110041251A
CN110041251A CN201910302260.7A CN201910302260A CN110041251A CN 110041251 A CN110041251 A CN 110041251A CN 201910302260 A CN201910302260 A CN 201910302260A CN 110041251 A CN110041251 A CN 110041251A
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fluorobenzaldehyde
formaldehyde
dta
water slurry
nitrobenzaldehyde
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CN110041251B (en
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林奇
樊彦青
姚虹
张有明
魏太保
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Northwest Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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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    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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    • 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"
    • G01N2021/6443—Fluorimetric titration

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Abstract

The invention discloses a kind of new applications of the equal benzene trimellitic imide of 4-aminopyridine functionalization --- and it is used for the detection of formaldehyde and 3- fluorobenzaldehyde as sensor: water slurry is made through ultrasonic disperse in the equal benzene trimellitic imide of 4-aminopyridine functionalization in pure water；Benzaldehyde, glyoxal, glutaraldehyde, 1- octanal, salicylide, 4- nitrobenzaldehyde, formaldehyde, 3- nitrobenzaldehyde, 2- nitrobenzaldehyde, 4- bromobenzaldehyde, 3- bromobenzaldehyde, 2- bromobenzaldehyde, 4- chlorobenzaldehyde, 3- chlorobenzaldehyde, 2- chlorobenzaldehyde, 4- fluorobenzaldehyde, 2- fluorobenzaldehyde, 3- fluorobenzaldehyde, 4- tolyl aldehyde, 3- tolyl aldehyde, 2- tolyl aldehyde solution is added in water slurry respectively, if the state of water slurry becomes clear, illustrate to be added is formaldehyde；If the state of water slurry becomes stable hydrogel, and its fluorescence is remarkably reinforced, and illustrate to be added is 3- fluorobenzaldehyde.

Description

The equal benzene trimellitic imide of 4-aminopyridine functionalization is in detection formaldehyde and 3- fluorobenzaldehyde Application
Technical field
The present invention relates to a kind of new applications of the equal benzene trimellitic imide of 4-aminopyridine functionalization --- detection formaldehyde and Application in fluorobenzene formaldehyde belongs to the field of Molecular Detection.
Background technique
The equal benzene trimellitic imide of 4-aminopyridine functionalization is by 1,3,5- pyromellitic trimethylsilyl chloride and 4-aminopyridine It reacts and obtains in DMF.Its structural formula is as follows:
Currently, the equal benzene trimellitic imide of 4-aminopyridine functionalization is applied to supramolecular organogel mainly as gelator Preparation and application.
Summary of the invention
The object of the present invention is to provide a kind of new applications of the equal benzene trimellitic imide of 4-aminopyridine functionalization --- as Chemical sensor is used for the highly sensitive detection of selectivity of formaldehyde and fluorobenzene formaldehyde isomers.
One, PARA FORMALDEHYDE PRILLS(91,95) detects
1, the building of chemical sensor
The pyromellitic trimethylsilyl chloride (being labeled as DTA) of 4-aminopyridine functionalization is added in pure water, is obtained by ultrasonic disperse Uniform concentration is 2.20 × 10-3~2.28×10-3The DTA water slurry of M, as based on the chemical sensor of DTA.
2, open hole detection formaldehyde
In DTA water slurry, be separately added into benzaldehyde, glyoxal, glutaraldehyde, 1- octanal, salicylide, 4- nitrobenzaldehyde, Formaldehyde, 3- nitrobenzaldehyde, 2- nitrobenzaldehyde, 4- bromobenzaldehyde, 3- bromobenzaldehyde, 2- bromobenzaldehyde, 4- chlorobenzaldehyde, 3- Chlorobenzaldehyde, 2- chlorobenzaldehyde, 4- fluorobenzaldehyde, 2- fluorobenzaldehyde, 3- fluorobenzaldehyde, 4- tolyl aldehyde, 3- methylbenzene first Aldehyde, 2- tolyl aldehyde solution observe the variation of DTA water slurry.
As a result, it has been found that DTA water slurry becomes clear by muddiness only when formalin is added；Only when adding When entering 3- fluorobenzaldehyde, DTA water slurry becomes stable hydrogel from muddiness, and when other aldehyde of equivalent are added, shape State does not change.
3, fluorescence detection
In DTA water slurry, be separately added into benzaldehyde, glyoxal, glutaraldehyde, 1- octanal, salicylide, 4- nitrobenzaldehyde, Formaldehyde, 3- nitrobenzaldehyde, 2- nitrobenzaldehyde, 4- bromobenzaldehyde, 3- bromobenzaldehyde, 2- bromobenzaldehyde, 4- chlorobenzaldehyde, 3- Chlorobenzaldehyde, 2- chlorobenzaldehyde, 4- fluorobenzaldehyde, 2- fluorobenzaldehyde, 3- fluorobenzaldehyde, 4- tolyl aldehyde, 3- methylbenzene first Aldehyde, 2- tolyl aldehyde solution observe the change in fluorescence of DTA water slurry.
Fig. 1 is response fluorescence spectrum of the DTA to different aldehyde.Wherein, when formaldehyde (FA) is added, fluorescence enhancement；Add When entering 3- fluorobenzaldehyde (3-FB), fluorescence is remarkably reinforced and issues bright blue fluorescence.And the addition of other aldehyde, it can not generate Corresponding phenomenon, being indicated above DTA can be with highly selective formaldehyde and 3- fluorobenzaldehyde.
4, interference--free experiments
Containing different aldehyde (benzaldehyde, glyoxal, glutaraldehyde, 1- octanal, salicylide, 4- nitrobenzaldehyde, formaldehyde, 3- respectively Nitrobenzaldehyde, 2- nitrobenzaldehyde, 4- bromobenzaldehyde, 3- bromobenzaldehyde, 2- bromobenzaldehyde, 4- chlorobenzaldehyde, 3- chlorobenzene first Aldehyde, 2- chlorobenzaldehyde, 4- fluorobenzaldehyde, 2- fluorobenzaldehyde, 3- fluorobenzaldehyde, 4- tolyl aldehyde, 3- tolyl aldehyde, 2- first Benzaldehyde solution) DTA in when being sequentially added into formaldehyde, the above-mentioned DTA containing different aldehyde is changed into clear Solution (such as Fig. 2)；And when 3- fluorobenzaldehyde is added wherein respectively, the DTA water slurry containing different aldehyde, which is all changed into, to be had The hydrogel (such as Fig. 3) of strong fluorescence transmitting.The anti-interference reality detected by DTA water slurry PARA FORMALDEHYDE PRILLS(91,95) and 3- fluorobenzaldehyde Test, it was demonstrated that other can compatible aldehyde formaldehyde and 3- fluorobenzaldehyde are detected to DTA there is no interfere.Therefore, DTA can Gao Xuan The formaldehyde and 3- fluorobenzaldehyde of selecting property detection.
5, the measurement of detection limit
The fluorescence titration figure of Fig. 4,5 respectively DTA PARA FORMALDEHYDE PRILLS(91,95), 3- fluorobenzaldehyde.It can be obtained by fluorescence titration experiment, with formaldehyde Concentration is continuously increased in the sensor with the detection of 3- fluorobenzaldehyde, it can be found that its fluorescence intensity constantly enhances.Pass through 3 σ methods Calculate sensor (DTA) PARA FORMALDEHYDE PRILLS(91,95) detection be limited to 1.68 × 10-8M.9.62 × 10 are limited to the detection of 3- fluorobenzaldehyde-9 M has obtained hypersensitive level.
6, detection mechanism
We pass through1H NMR titration illustrates the possibility recognition mechanism of DTA PARA FORMALDEHYDE PRILLS(91,95) and 3- fluorobenzaldehyde with MS.Figure 6,7 be respectively that the nuclear-magnetism of DTA PARA FORMALDEHYDE PRILLS(91,95) titrates the mass spectrogram of figure, DTA and formaldehyde.In DTA and the mass spectrum of formaldehyde mixture, Ionic molecule peak at 553.46 belongs to the methylolated product of DTA (DTA-OH).In addition, in DTA for the part core of formaldehyde Magnetic titrates in figure, with the increase of content of formaldehyde, Hb(11.32 ppm, NH) disappear, while H1(4.62 ppm, NH) and H2 The appearance of (3.25ppm, NH) illustrates that the hydroxymethylation between the imino group of DTA and formaldehyde is present in the knowledge of DTA PARA FORMALDEHYDE PRILLS(91,95) Other process finally obtained methylolation product (DTA-OH).
Likewise, we pass through1H NMR titration and FT-IR elaborate DTA to the detection mechanism of 3- fluorobenzaldehyde.Such as Fig. 8 It is shown, as concentration is continuously increased 3- fluorobenzaldehyde in DTA, relevant proton signal peak (Ha(8.86 ppm), Hb (11.27 ppm), Hc(7.98 ppm), Hd(8.58 ppm), H3(10.02 ppm), H4(7.79 ppm), H5, H6 (7.67ppm), H7(7.57ppm)) equal low field displacement, show that DTA and 3- fluorobenzaldehyde was mainly assembled by hydrogen bond to realize Journey.Fig. 9 is the infrared figure of DTA and 3- fluorobenzaldehyde.It is shown in FT-IR information, after the assembling of DTA and 3- fluorobenzaldehyde, the NH of DTA (3420 cm-1) and C=O(1675 cm-1) vibration absorption peak distinguish red shift to 3449 cm-1With 1696 cm-1, the above results Demonstrate the presence of hydrogen bond.
Detailed description of the invention
Fig. 1 is fluorescence spectrum of the DTA to different aldehyde responses.
Fig. 2 is the interference--free experiments picture (1, DTA of DTA PARA FORMALDEHYDE PRILLS(91,95) detection；2, benzaldehyde；3, glyoxal；3, glutaraldehyde； 4,1- octanals；5, salicylide；6,4- nitrobenzaldehydes；7,3- fluorobenzaldehydes；8,3- nitrobenzaldehydes；9,2- nitrobenzaldehydes； 10,4- bromobenzaldehydes；11,3- bromobenzaldehydes；12,2- bromobenzaldehydes；13,4- chlorobenzaldehydes；14,3- chlorobenzaldehydes；15,2- chlorine Benzaldehyde；16,4- fluorobenzaldehydes；17,2- fluorobenzaldehydes；18,4- tolyl aldehydes；19,3- tolyl aldehydes；20,2- methyl Benzaldehyde；21, formaldehyde).
Fig. 3 is the interference--free experiments picture (1, DTA that DTA detects 3- fluorobenzaldehyde；2, benzaldehyde；3, glyoxal；3, Glutaraldehyde；4,1- octanals；5, salicylide；6,4- nitrobenzaldehydes；7, formaldehyde；8,3- nitrobenzaldehydes；9,2- nitrobenzaldehydes； 10,4- bromobenzaldehydes；11,3- bromobenzaldehydes；12,2- bromobenzaldehydes；13,4- chlorobenzaldehydes；14,3- chlorobenzaldehydes；15,2- chlorine Benzaldehyde；16,4- fluorobenzaldehydes；17,2- fluorobenzaldehydes；18,4- tolyl aldehydes；19,3- tolyl aldehydes；20,2- methyl Benzaldehyde；21,3- fluorobenzaldehydes).
Fig. 4 is the fluorescence titration figure of DTA PARA FORMALDEHYDE PRILLS(91,95).
Fig. 5 is fluorescence titration figure of the DTA to 3- fluorobenzaldehyde.
Fig. 6 is that the nuclear-magnetism of DTA PARA FORMALDEHYDE PRILLS(91,95) titrates figure.
Fig. 7 is the mass spectrogram of DTA and formaldehyde mixture.
Fig. 8 is that DTA titrates figure to the nuclear-magnetism of 3- fluorobenzaldehyde.
Fig. 9 is the infrared figure of DTA and 3- fluorobenzaldehyde.
Figure 10 is the hydrogen spectrogram of DTA.
Specific embodiment
Below by specific embodiment to the synthesis of DTA of the present invention and unicity selection identification formaldehyde and 3- fluorobenzene first The method of aldehyde is described further.
1, the synthesis of DTA
3.2 mmol 4-aminopyridines (0.300g) are taken, are dissolved in 15mL DMF solution, then take 1mmol pyromellitic trimethylsilyl chloride (0.264g) is added drop-wise in DMF solution, and it is overnight to react 12 ~ 14h(at room temperature), then recrystallized with DMF and water, obtain 0.422g The pyromellitic trimethylsilyl chloride (DTA) of 4-aminopyridine functionalization, yield 97%.Figure 10 is the hydrogen spectrogram of DTA.
2, DTA detects formaldehyde, 3- fluorobenzaldehyde
0.002 g DTA is accurately weighed, is added in 2 mL pure water, the water slurry of DTA is obtained after ultrasonic disperse, Concentration is 2.28 × 10-3 M。
In the water slurry of DTA, it is separately added into benzaldehyde, glyoxal, glutaraldehyde, 1- octanal, salicylide, 4- nitrobenzene Formaldehyde, formaldehyde, 3- nitrobenzaldehyde, 2- nitrobenzaldehyde, 4- bromobenzaldehyde, 3- bromobenzaldehyde, 2- bromobenzaldehyde, 4- chlorobenzene first Aldehyde, 3- chlorobenzaldehyde, 2- chlorobenzaldehyde, 4- fluorobenzaldehyde, 2- fluorobenzaldehyde, 4- tolyl aldehyde, 3- tolyl aldehyde, 2- first Benzaldehyde solution, if the state of the water slurry of DTA gradually changes to clear by muddiness, illustrate to be added is formaldehyde；If The state of the water slurry of DTA gradually becomes stable hydrogel by suspension, and its fluorescence is remarkably reinforced, and illustrates addition It is 3- fluorobenzaldehyde.

Claims (2)

  1. Application of the equal benzene trimellitic imide of 1.4- aminopyridine functionalization in detection formaldehyde and 3- fluorobenzaldehyde, the 4- amino The structural formula of the equal benzene trimellitic imide of pyridine functional is as follows:
    。
  2. 2. the equal benzene trimellitic imide of 4-aminopyridine functionalization is in detection formaldehyde and 3- fluorobenzene first as described in claims 1 Application in aldehyde, it is characterised in that: by the equal benzene trimellitic imide ultrasonic disperse of 4-aminopyridine functionalization in pure water, be made Concentration is 2.20 × 10-3~2.28×10-3The water slurry of M；Benzaldehyde, glyoxal, penta 2 is added in water slurry respectively Aldehyde, 1- octanal, salicylide, 4- nitrobenzaldehyde, formaldehyde, 3- nitrobenzaldehyde, 2- nitrobenzaldehyde, 4- bromobenzaldehyde, 3- bromine Benzaldehyde, 2- bromobenzaldehyde, 4- chlorobenzaldehyde, 3- chlorobenzaldehyde, 2- chlorobenzaldehyde, 4- fluorobenzaldehyde, 2- fluorobenzaldehyde, 3- fluorine Benzaldehyde, 4- tolyl aldehyde, 3- tolyl aldehyde, 2- tolyl aldehyde solution, if the state of water slurry by it is muddy gradually Clear is changed to, illustrate to be added is formaldehyde；If the state of water slurry gradually becomes stable hydrogel by suspension, and And its fluorescence is remarkably reinforced, illustrate to be added is 3- fluorobenzaldehyde.
CN201910302260.7A 2019-04-16 2019-04-16 Application of 4-aminopyridine functionalized trimesoimide in detecting formaldehyde and 3-fluorobenzaldehyde Expired - Fee Related CN110041251B (en)

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Citations (2)

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CN109265398A (en) * 2018-09-12 2019-01-25 西北师范大学 A kind of application of supramolecular organogel and its fluorescence identifying mercury ion
CN109320454A (en) * 2018-11-29 2019-02-12 西北师范大学 The preparation and application of a kind of bi-component supramolecular organogel and its metal gel

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109265398A (en) * 2018-09-12 2019-01-25 西北师范大学 A kind of application of supramolecular organogel and its fluorescence identifying mercury ion
CN109320454A (en) * 2018-11-29 2019-02-12 西北师范大学 The preparation and application of a kind of bi-component supramolecular organogel and its metal gel

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