CN110105947A - The synthesis and application of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes - Google Patents
The synthesis and application of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes Download PDFInfo
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Abstract
It is based on quaternary ammoniated column [5] aromatic hydrocarbons, 2 ' 2- bibenzimidaz sigmales are object, in DMSO-H the present invention provides a kind of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes2It is formed in O solution by self assembly.In the DMSO-H of the host-guest complex2A series of cations are added in O solution, addition only can be such that the fluorescence of inclusion complex solution is quenched.In above-mentioned addition Fe3+、Cu2+、Hg2+、Ag+CWP5-G solution in, be separately added into a series of anion, wherein CN‑、HSO4 ‑、CN‑、I‑It can make corresponding CWP5-G-M(M=Fe again3+, Cu2+, Hg2+, Ag+) solution fluorescence restore.Therefore, inclusion complex CWP5-G selectively can continuously identify zwitterion pair, this has a very important significance in ion identification technical field.
Description
Technical field
The present invention relates to a kind of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes, are mainly used for positive anion
Continuous identification, belong to ion detection technical field.
Background technique
Benzimidazoles compound is as a kind of heteroaromatic compound containing N, and wherein the N in benzimidazole in C=N key is former
Son can be used as hydrogen bonding sites, while coordination can also occur with metal ion；N-H-cell also can provide hydrogen bond work
With；And the presence of aromatic ring can provide pi-pi accumulation interaction, these features make it in biomedicine, ionic liquid material, fire-retardant
The fields such as agent, supramolecular chemistry, Coordinative Chemistry have important use value.In recent years, based on the fluorescence sense of benzimidazole
Device molecule is widely used in detecting picric acid, pH and ion etc..
Supermolecule macrocyclic host compound one of of the column aromatic hydrocarbons as a new generation, since it is readily synthesized and modifies, has
The excellent properties of different other macrocyclic compound and receive more and more attention.It is very special that column virtue hydrocarbons and their derivates have
Space structure and physicochemical property, be mainly used in host-guest inclusion and molecular recognition, self-assembly system construct and intelligent material
The fields such as material.
Summary of the invention
The object of the present invention is to provide a kind of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes and its synthesis；
It is a further object of the present invention to provide above-mentioned inclusion complexes in the application for continuously identifying zwitterion.
One, quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes
Quaternary ammoniated column [5] aromatic hydrocarbons of the present invention and 2 ' 2- bibenzimidaz sigmale inclusion complexes, are based on quaternary ammoniated column [5] aromatic hydrocarbons (CWP5)
Body, 2 ' 2- bibenzimidaz sigmales (G) are object, in DMSO-H2It is formed in O solution by self assembly, is labeled as CWP5-G.
Wherein, the structural formula of quaternary ammoniated column [5] aromatic hydrocarbons is as follows:
The synthetic method of CWP5 is referring to B. Shi, D. Xia and Y. Yao. A water-soluble
supramolecular polymer constructed by pillar[5]arene-based molecular
recognition. Chem. Commun, 2014, 50, 13932-13935。
The structural formula of 2 ' 2- bibenzimidaz sigmales is as follows:
The synthetic method of G is referring to P. P. Kattimani, R. Kamble and G. Y. Meti, Expedient
synthesis of benzimidazoles using amides. RSC Adv., 2015, 5, 29447-29455。
The synthesis of inclusion complex CWP5-G: to the DMSO-H of 2 ' 2- bibenzimidaz sigmales (being denoted as G)2O(v/v=1:1 ~ 1:2) solution
It is middle that equimolar quaternary ammoniated column [5] aromatic hydrocarbons (being labeled as CWP5) is added, host-guest complex can be formed.
Two, the interaction of host-guest of CWP5 and G
Pass through fluorescence titration and nuclear-magnetism the titration experiment researches interaction of host-guest of CWP5 and G.Fig. 1 is CWP5 to the glimmering of G
Light titration figure.As seen from Figure 1, to 2.0 × 10-5The G(DMSO-H of M2O, v/v=1:1) CWP5 solution is added dropwise in solution, G exists
Fluorescent emission intensity between 400 ~ 600 nm, which gradually increases, finally to tend towards stability, and illustrates that Subjective and Objective phase interaction has occurred in CWP5 and G
With.It is 9.62 × 10 according to the complexing coefficient of Bensi-Hildebrand equation calculation CWP5 and G3M-1, mol ratio 1:
1(is shown in Fig. 2).
Fig. 3 is CWP5 to G's1H-NMR titration figure.Fig. 3 shows: to the DMSO- of Gd 6After CWP5 is added in solution, it is located at G
On H1Proton, which is split, is divided into two peaks, and one of peak is obviously displaced to High-Field, and H2Proton peak is slightly to low field displacement；CWP5
In HfAnd HgSlight High-Field displacement also occurs for proton peak.This is because G penetrates change in displacement caused by the cavity of CWP5,
Further prove that host-guest inclusion interaction has occurred in CWP5 and G.
Three, recognition performance of the CWP5-G to ion
1, recognition performance of the CWP5-G to metal cation
The DMSO-H of the CWP5-G prepared to 2mL2O(v/v=1:1) solution (2.0 × 10-5Mol/L Ca is separately added into)2+, Mg2 +, Pb2+, Ni2+, Co2+, Hg2+, Zn2+, Cd2+, Ag+, Cu2+, Cr3+, Al3+, Ba2+, La3+, Eu3+, Fe3+Aqueous solution (0.1M),
It was found that Fe3+, Cu2+, Hg2+And Ag+It can make its fluorescent quenching (Fig. 4).Cation M(M=Fe is gradually added dropwise using accumulation sample-adding method3 +, Cu2+, Hg2+, Ag+), it is found that fluorescence intensity of the CWP5-G at 490 nm is gradually decrease until fluorescent quenching (Fig. 5 ~ 8).Pass through
Processing to fluorescence titration data and apply 3σ/ s formula, calculating CWP5-G is 10 to the minimum detection limit range of ion-9~
10-10Mol/L realizes the highly sensitive detection to cation.
2, continuous identification of the CWP5-G to anion
Pipette the DMSO-H of 2.0mL CWP5-G-M2O(v/v=1:1) solution (2.0 × 10-5Mol/L), CN is added thereto-,
I-, F-, Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-, OH-, S2-Aqueous solution, wherein CN-、HSO4 -、CN-、I-It can make again
Corresponding CWP5-G-M(M=Fe3+, Cu2+, Hg2+, Ag+) solution fluorescence restore.By the processing to titration data and answer
With 3σ/ s method calculates CWP5-G-M and reaches 10 to the minimum detection limit of anion-7M。
2 ' single 2- bibenzimidaz sigmales (G) are had detected under the same conditions, and Fe is being added3+, Cu2+, Hg2+, Ag+It is right afterwards
The continuous recognition property of anion finds the effect of no this one-to-one continuity identification zwitterion pair.
Above-mentioned experimental result illustrates that the addition of CWP5 can regulate and control the ion identification property of G, to reach to one-to-one correspondence
Zwitterion pair specificity, continuity identification (as shown in figs9-12,1-13 is respectively indicated: CWP5-G-M, F-, Cl-, S2-,
Ac-, H2PO4 -, Br-, N3 -, SCN-, HSO4 -, ClO4 -, I-And CN-).
Detailed description of the invention
Fig. 1 is fluorescence titration figure of the CWP5 to G.
Fig. 2 is the linear graph according to Bensi-Hildebrand equation model.
Fig. 3 is CWP5 to G's1H-NMR titration figure.
Fig. 4 is fluorescence response figure of the CWP5-G to cation.
Fig. 5 is CWP5-G to Fe3+Fluorescence titration figure.
Fig. 6 is CWP5-G to Cu2+Fluorescence titration figure.
Fig. 7 is CWP5-G to Hg2+Fluorescence titration figure.
Fig. 8 is CWP5-G to Ag+Fluorescence titration figure.
Fig. 9 is CWP5-G-Fe3+And G-Fe3+To the fluorescence response figure of anion.
Figure 10 is CWP5-G-Cu2+And G-Cu2+To the fluorescence response figure of anion.
Figure 11 is CWP5-G-Hg2+And G-Hg2+To the fluorescence response figure of anion.
Figure 12 is CWP5-G-Ag+And G-Ag+To the fluorescence response figure of anion.
Specific embodiment
Yin-yang is continuously identified in ion to the synthesis of host-guest complex CWP5-G of the present invention below by specific embodiment
Application in ion is described further.
Embodiment 1
The CWP5 and G of equimolar amounts are weighed, DMSO-H is added2O(v/v=1:1) in solution, fully shake, it is uniformly mixed, is made
Concentration is 2.0 × 10-5The CWP5-G solution of mol/L.
The DMSO-H of 2.0mL CWP5-G is pipetted respectively2O solution (2.0 × 10-5Mol/L) in a series of test tubes, respectively
Ca is added2+, Mg2+, Pb2+, Ni2+, Co2+, Hg2+, Zn2+, Cd2+, Ag+, Cu2+, Cr3+, Al3+, Ba2+, La3+, Eu3+, Fe3+Water
Solution (0.1M)；If the fluorescence of CWP5-G solution quenches, that illustrate to be added is Fe3+、Cu2+、Hg2+Or Ag+。
Embodiment 2
The DMSO-H of 2.0mL CWP5-G is pipetted respectively2O(v/v=1:1) solution (2.0 × 10-5Mol/L) in a series of test tubes,
It is separately added into Fe3+Aqueous solution (0.1M), the fluorescence of CWP5-G solution quenches；CN is added thereto respectively again-, I-, F-,
Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-, OH-, S2-Aqueous solution；If CWP5-G-Fe3+The fluorescent emission of solution is extensive
Multiple, then that illustrate to be added is CN-.It is thereby achieved that CWP5-G is to Fe3+- CN-Specificity, continuity identification.
Embodiment 3
The DMSO-H of 2.0mL CWP5-G is pipetted respectively2O(v/v=1:1) solution (2.0 × 10-5Mol/L) in a series of test tubes,
It is separately added into Cu2+Aqueous solution (0.1M), the fluorescence of CWP5-G solution quenches；CN is added thereto respectively again-, I-, F-,
Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-, OH-, S2-Aqueous solution；If CWP5-G- Cu2+The fluorescent emission of solution is extensive
Multiple, then that illustrate to be added is HSO4 -。
Embodiment 4
The DMSO-H of 2.0mL CWP5-G is pipetted respectively2O(v/v=1:1) solution (2.0 × 10-5Mol/L) in a series of test tubes,
It is separately added into Hg2+Aqueous solution (0.1M), the fluorescence of CWP5-G solution quenches；CN is added thereto respectively again-, I-, F-,
Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-, OH-, S2-Aqueous solution；If CWP5-G- Hg2+The fluorescent emission of solution is extensive
Multiple, then that illustrate to be added is CN-.It is thereby achieved that CWP5-G is to Hg2+- CN-Specificity, continuity identification.
Embodiment 5
The DMSO-H of 2.0mL CWP5-G is pipetted respectively2O(v/v=1:1) solution (2.0 × 10-5Mol/L) in a series of test tubes,
It is separately added into Ag+Aqueous solution (0.1M), the fluorescence of CWP5-G solution quenches；CN is added thereto respectively again-, I-, F-,
Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-, OH-, S2-Aqueous solution；If CWP5-G- Ag+The fluorescent emission of solution is extensive
Multiple, then that illustrate to be added is I-.It is thereby achieved that CWP5-G is to Ag+- I-Specificity, continuity identification.
Claims (8)
1. a kind of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes are based on quaternary ammoniated column [5] aromatic hydrocarbons 2 '
2- bibenzimidaz sigmale is object, in DMSO-H2It is formed in O solution by self assembly；
Wherein, the structural formula of quaternary ammoniated column [5] aromatic hydrocarbons is as follows:
The structural formula of 2 ' 2- bibenzimidaz sigmales is as follows:
。
2. the synthetic method of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes as described in claim 1, is to 2 ' 2-
The DMSO-H of bibenzimidaz sigmale2Equimolar quaternary ammoniated column [5] aromatic hydrocarbons is added in O solution, host-guest complex can be formed.
3. a kind of synthetic method of quaternary ammoniated column [5] aromatic hydrocarbons and 2 ' 2- bibenzimidaz sigmale inclusion complexes as described in claim 1, special
Sign is: the DMSO-H of 2 ' 2- bibenzimidaz sigmales2In O, DMSO and H2The volume ratio of O is 1:1 ~ 1:2.
4. quaternary ammoniated column [5] aromatic hydrocarbons as described in claim 1 answering in identification cation with 2 ' 2- bibenzimidaz sigmale inclusion complexes
With, it is characterised in that: the DMSO-H of CWP5-G2Ca is separately added into O solution2+, Mg2+, Pb2+, Ni2+, Co2+, Hg2+, Zn2+, Cd2 +, Ag+, Cu2+, Cr3+, Al3+, Ba2+, La3+, Eu3+, Fe3+Aqueous solution, find Fe3+, Cu2+, Hg2+And Ag+Its fluorescence can be made sudden
It goes out.
5. quaternary ammoniated column [5] aromatic hydrocarbons as described in claim 1 answering in identification cation with 2 ' 2- bibenzimidaz sigmale inclusion complexes
With, it is characterised in that: in the DMSO-H of inclusion complex CWP5-G a series of2In O, it is separately added into Fe3+Aqueous solution, CWP5-G solution
Fluorescence quench；CN is added thereto respectively again-, I-, F-, Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-, OH-,
S2-Aqueous solution；If the fluorescent emission of solution is restored, that illustrate to be added is CN-。
6. quaternary ammoniated column [5] aromatic hydrocarbons as described in claim 1 and 2 ' 2- bibenzimidaz sigmale inclusion complexes are in continuously identification anion
Application, it is characterised in that: in the DMSO-H of inclusion complex CWP5-G a series of2In O, it is separately added into Cu2+Aqueous solution, CWP5-G
The fluorescence of solution quenches；CN is added thereto respectively again-, I-, F-, Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-,
OH-, S2-Aqueous solution；If the fluorescent emission of solution is restored, that illustrate to be added is HSO4 -。
7. quaternary ammoniated column [5] aromatic hydrocarbons as described in claim 1 and 2 ' 2- bibenzimidaz sigmale inclusion complexes are in continuously identification anion
Application, it is characterised in that: in the DMSO-H of inclusion complex CWP5-G a series of2In O, it is separately added into Hg2+Aqueous solution, CWP5-G
The fluorescence of solution quenches；CN is added thereto respectively again-, I-, F-, Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-,
OH-, S2-Aqueous solution；If the fluorescent emission of solution is restored, that illustrate to be added is CN-。
8. quaternary ammoniated column [5] aromatic hydrocarbons as described in claim 1 and 2 ' 2- bibenzimidaz sigmale inclusion complexes are in continuously identification anion
Application, it is characterised in that: in the DMSO-H of inclusion complex CWP5-G a series of2In O, it is separately added into Ag+Aqueous solution, CWP5-G
The fluorescence of solution quenches；CN is added thereto respectively again-, I-, F-, Cl-, N3 -, ClO4 -, H2PO4 -, HSO4 -, SCN-, Br-,
OH-, S2-Aqueous solution；If the fluorescent emission of solution is restored, that illustrate to be added is I-。
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| CN110824827A (en) * | 2019-11-08 | 2020-02-21 | 西北师范大学 | Application of 2, 2' -biphenyl imidazole and derivatives thereof in secret graphic information |
| CN111393370A (en) * | 2020-03-30 | 2020-07-10 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN111393370B (en) * | 2020-03-30 | 2022-07-19 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN113173919A (en) * | 2021-05-20 | 2021-07-27 | 西北师范大学 | Preparation and application of amphiphilic bis-benzimidazole derivative and supramolecular sensor thereof |
| CN113248443A (en) * | 2021-05-31 | 2021-08-13 | 天津师范大学 | Tridentate benzimidazole salt compound and preparation method and application thereof |
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