CN109925982B - Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel - Google Patents
Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel Download PDFInfo
- Publication number
- CN109925982B CN109925982B CN201910277137.4A CN201910277137A CN109925982B CN 109925982 B CN109925982 B CN 109925982B CN 201910277137 A CN201910277137 A CN 201910277137A CN 109925982 B CN109925982 B CN 109925982B
- Authority
- CN
- China
- Prior art keywords
- gel
- naphthalimide
- fluorescence
- organic metal
- functionalized long
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Images
Landscapes
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a naphthalimide-functionalized long-chain alkane supermolecule organic metal gel, which is prepared by taking a naphthalimide-functionalized long-chain alkane compound as a gel factor and a metal ion compound as an object in cyclohexanol, heating for dissolving, and cooling to room temperature. In cyclohexanol solution, gelator forms supermolecular organic metal gel OGM with white aggregation state induced fluorescence through pi-pi action and metal coordination. Respectively adding anions and amino acid molecules into supermolecular organic metal gel such as OGM and the like, and finding that the metal gel OGM can realize I pair‑、CN‑、N3 ‑And the identification performance of the ultra-sensitive detection of various object ions and molecules such as L-His, L-Trp and the like has important application value in the field of ion and molecule identification.
Description
Technical Field
The invention relates to a supermolecule metal organic gel, in particular to preparation of a naphthalimide-functionalized long-chain alkane supermolecule organic gel.
Background
Ion and molecule players play an important role in the fields of chemistry, biology, environment, etc., and are critical to the detection and separation of certain specific ions or molecules in the environment, such as: iodine is extremely important to the life of animals and plants. The iodides and iodates in seawater are incorporated into the metabolism of most marine organisms. In higher mammals, iodine is concentrated in the thyroid gland as iodinated amino acids, and a lack of iodine causes goiter. Iodine and compounds of about 2/3 are used to prepare preservatives, disinfectants and medicaments. Sodium iodate is used as food additive to supplement iodine intake. Iodine is also used in the manufacture of dyes and photographic films. Cyanide (CN)-) Hydrocyanic acid and cyanide are extremely toxic and poisoned rapidly, and can enter human bodies through various ways, such as skin absorption, wound invasion, respiratory tract inhalation, mistaken eating and the like, and the passive absorption of people and other organisms is rather defensive due to the pollution of water quality and environment. Amino acids (RCHNH)2COOH), a combination of muscles, bones, cartilage, skin, blood vessels, etc. of the human body, and most of each tissue such as viscera, eyeballs, blood cells, etc. is a protein, but the constituent elements of the protein are a combination of amino acids. Amino acids are a source of energy for the human body, and are essential for the metabolism of the human body, and the composition of substances such as hormones, neurotransmitters, enzymes, and high-density lipoproteins that function to transport lipids and receptors in the body, and for each function of metabolism.
At present, various ion/molecule detection methods have been developed, and fluorescence methods have been developed as the main detection means for ion/molecule identification due to their advantages of simple operation, rapidness, high sensitivity, etc. However, in real life, various ions/molecules which are beneficial or harmful to human bodies are mostly present in the water phase, and most of the reported methods for detecting ions are performed in solution, so that the detection of ions/molecules is limited. Therefore, it is necessary to synthesize a compound capable of efficiently detecting and recognizing various ions/molecules in an aqueous phase.
Disclosure of Invention
The first purpose of the invention is to provide a preparation method of a naphthalimide-based functionalized long-chain alkane supramolecular organic metal gel;
the invention also aims to provide a specific application of the supermolecule organic metal gel in recognizing anions and amino acid molecules in water.
Preparation of supermolecule metal organogel
1. Preparation of supramolecular organogelators
The supermolecular organogel factor naphthalimide functionalized long-chain alkane supermolecular compound is marked as G, and the structural formula of the supermolecular organogel factor naphthalimide functionalized long-chain alkane supermolecular compound is as follows:
synthesis of supramolecular organogelators: the method comprises the following steps:
(1) synthesis of bromohexadecane functionalized methyl gallate: acetone is used as a solvent, potassium carbonate and potassium iodide are used as catalysts, and methyl gallate and bromohexadecane react for 70-72 hours at the temperature of 60-65 ℃ in a molar ratio of 1: 3.3-1: 3.6 to obtain bromohexadecane functionalized methyl gallate; the adding amount of the catalyst potassium iodide and potassium carbonate is 1.2-6 times of the molar amount of the gallic acid methyl ester respectively.
(2) Synthesis of bromohexadecane functionalized gallic acid formylhydrazine: reacting bromohexadecane functionalized methyl gallate with hydrazine hydrate in ethanol at a molar ratio of 1: 1.2-1: 4 at 80-100 ℃ for 10-12 hours, cooling to room temperature, and performing suction filtration to obtain white powdery bromohexadecane functionalized gallic acid formylhydrazine;
(3) synthesis of supramolecular organogelators: reacting bromohexadecane functionalized gallic acid formyl hydrazine with 1, 8-naphthalic anhydride in a molar ratio of 1: 1.2-1: 1.4 in DMF (N, N-dimethylformamide) at 120-140 ℃ for 24-36 hours, cooling to room temperature, and performing suction filtration to obtain a white powdery naphthalimide functionalized long-chain alkane supramolecular compound.
The hydrogen spectrum and the mass spectrum of the compound G are respectively shown in figure 1 and figure 2. The melting point of the compound G is 60-80 ℃.
And heating the compound G in cyclohexanol to completely dissolve the compound G (the content of G in cyclohexanol is 40-50 mg/ml), and cooling to room temperature to obtain the supermolecule organogel, which is named as OG.
FIG. 3 is a partial concentration nuclear magnetic diagram of G. From FIG. 3, it can be found that Ha，Hb，Hc，HdAll move to high field, which shows that there is pi-pi function between molecules of gelator G. Thus proving that the gelator OG mainly forms supermolecular organogel through the pi-pi stacking effect.
FIG. 4 is a graph of fluorescence spectra of OG in molten state and gel state. As can be seen from fig. 4, when the excitation wavelength is 400nm, the supramolecular organogel OG has good fluorescence performance in the gel state and emits white fluorescence. However, under the same excitation wavelength, the fluorescence of the supramolecular organogel OG in the molten state is poor.
FIG. 5 is an infrared spectrum of G, OG. It can also be seen from fig. 5: when gelator G is put in cyclohexanol and heated to prepare supermolecular gel OG, the-NH peak and-C = O peak of gelator G are from 3446cm-1And 1718cm-1Move to 3428cm-1And 1739cm-1It is demonstrated that the supramolecular gel OG coordinates to form a complex through supramolecular interaction.
2. Preparation of supramolecular metal organogel
In cyclohexanol, using naphthalimide-functionalized long-chain alkane supramolecular compound G as an organogelator, adding a metal ion compound, heating to completely dissolve the metal ion compound, and cooling to room temperature to obtain stable supramolecular organometallic gel marked as OGM.
The content of the supramolecular organogel factor G in cyclohexanol is 40-50 mg/ml, and the molar ratio of the supramolecular organogel OG to the metal ion compound is 1: 1-1: 5.
Metal ionThe compound of the seed is Ca (ClO)4)2·6H2O，Cu(ClO4)2·6H2O，Co(ClO4)2·6H2O，Ni(ClO4)2·6H2O，Fe(ClO4)3·6H2And O. The obtained supermolecule organic metal gel is OGCa, OGCu, OGCo, OGNi and OGFe, and the melting point is 70-85 ℃.
The structural formula of the supermolecular metal organogel OGM is as follows:
fluorescent response performance of bi-and supermolecule organic metal gel OGM
1. Fluorescent recognition performance of OGCa on anions
The OGCa has blue-white fluorescence, and when the excitation wavelength is 400nm, the supermolecular metal organogel OGCa has good fluorescence performance in a gel state and emits the blue-white fluorescence.
Adding Cl into the supermolecular organic metal gel OGCa respectively-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -(0.1M) solution, only I-Quenching of the fluorescence of the OGCa (see fig. 6 a). Therefore, the supermolecule organic metal gel OGCa can realize the effect on I-The ultrasensitive detection of (2). Fluorescence titration experiments show that OGCa is used for I-Has a detection limit of 3.38 Í 10-9。
OGCa pair I-The fluorescent recognition principle of (1): it was shown by infrared experiment (see FIG. 7) that I was added to OGCa-Then, the = C-H peak of OGCa becomes weak, and the-C = O peaks are respectively from 1720cm-1Move to 1723cm-1Description of I-And forming a complex by the coordination of the OGCa.
2. Fluorescent recognition performance of OGNi on anions
The OGNi has blue-white fluorescence, and when the excitation wavelength is 400nm, the supermolecular metal organogel OGNi has good fluorescence performance in a gel state and emits blue-white fluorescence.
In the supermolecular organic metal gel OGNi, respectively adding aqueous solution of L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp (0.1M), and only L-Trp can quench the fluorescence of OGNi (see figure 6 b). Therefore, the supermolecule organic metal gel OGNi can realize the super-sensitive detection of L-Trp. Fluorescence titration experiments show that the limit of detection of L-Trp by OGNi is 1.92 multiplied by 10-8。
Fluorescent recognition of L-Trp by OGNi: infrared experiments show that when L-Trp is added into OGNi, the = C-H peak and the-C = O peak of the OGNi are respectively 2919cm-1And 1770cm-1Moved to 2920cm-1And 1726cm-1It shows that L-Trp coordinates with OGNi to form a complex.
3. Fluorescent recognition performance of OGCo on amino acid
The OGCo has white fluorescence, and when the excitation wavelength is 400nm, the supermolecular metal organogel OGCo has good fluorescence performance in a gel state and emits white fluorescence.
Respectively adding aqueous solutions of L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp (0.1M) into the supermolecule organic metal gel OGCo, wherein only the L-His can quench the fluorescence of OGCo. (see FIG. 6 (c)). Therefore, the supermolecule organic metal gel OGCo can realize the super-sensitive detection of L-His. Fluorescence titration experiments show that the detection limit of OGCo to L-His is 2.44 multiplied by 10-9。
Fluorescent recognition of L-His by OGCo: infrared experiments show that when L-His is added into OGCo, the = C-H peak and the-C = O peak of the OGCo are respectively 2919cm-1And 1724cm-1Moved to 2920cm-1And 1732cm-1It is shown that L-His coordinates to OGCo to form a complex.
4. Fluorescent recognition performance of OGCu on amino acid
The OGCu has blue-white fluorescence, and when the excitation wavelength is 400nm, the supermolecular metal organogel OGCu has good fluorescence performance in a gel state and emits blue-white fluorescence.
Respectively adding Cl into the supermolecular organic metal gel OGCu-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -(0.1M) solution, only I-And N3 -Quenching of fluorescence of OGCu (see fig. 6d, 6 e). Therefore, the supermolecular organic metal gel OGCu can realize the pair I-、N3 -The ultrasensitive detection of (2). Fluorescence titration experiments show that the detection limit of OGCu on the OGCu is 5.22 multiplied by 10 respectively-9、4.66×10-8。
OGCu pair I-、N3 -The fluorescent recognition principle of (1): the addition of I to OGCu was shown by infrared experiments (see FIG. 9)-And N3 -The = C-H peak and the-C = O peak of OGCu were from 2918cm, respectively-1And 1639cm-1Move to 2919cm respectively-1、2920cm-1And 1724cm-1、1728cm-1Description of I-And N3 -Respectively coordinated with OGCu to form a complex.
5. Fluorescent recognition performance of OGFe on anions and amino acids
The OGFe has off-white fluorescence, and when the excitation wavelength is 400nm, the supermolecular metal organogel OGFe has good fluorescence performance in a gel state and emits off-white fluorescence.
Adding Cl into the supermolecular organic metal gel OGFe-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -(0.1M) solution, CN only-Quenching of the fluorescence of OGFe (see fig. 6 f). Therefore, the temperature of the molten metal is controlled,the supermolecule organic metal gel OGFe can realize the aim of CN-The ultrasensitive detection of (2). Fluorescence titration experiments show that OGFe is applied to CN-Has a detection limit of 1.06X 10-8。
By adding aqueous solutions of L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys, and L-Trp (0.1M), respectively, to the supramolecular organometallic gel OGFe, it was found that only L-Trp quenches the fluorescence of OGFe (see FIG. 6 g). Therefore, the supermolecule organic metal gel OGFe can realize the super-sensitive detection of the L-Trp. Fluorescence titration experiments show that the detection limit of OGFe on L-Trp is 2.40 multiplied by 10-9。
OGFe to CN-And the fluorescent recognition base of L-Trp: infrared experiments show that CN is added into OGFe (see figure 10)-And the = C-H peak and the-C = O peak of OGFe in the case of L-Trp are respectively from 2919cm-1And 1722cm-1Move to 2918cm respectively-1、2920cm-1And 1721cm-1、1723cm-1Description of CN-And L-Trp coordinates with OGFe to form a complex respectively.
Drawings
FIG. 1 is a hydrogen spectrum of G.
FIG. 2 is a mass spectrum of G.
FIG. 3 is a nuclear magnetic hydrogen spectrum of partial concentration of OG.
FIG. 4 is a fluorescence spectrum of the molten state and gel state of OG.
FIG. 5 is an infrared spectrum of G, OG.
FIG. 6 shows fluorescence titration charts of (a) OGCa, (b) OGNi, (c) OGCo, (d, e) OGCu, and (f, g) OGFe, respectively.
FIG. 7 shows OGCa and OGCa + I-An infrared spectrum of (1).
FIG. 8 is an IR spectrum of OGNi, OGCo, OGNi + L-Trp and OGCo + L-His.
FIG. 9 shows OGCu and OGCu + I-、OGCu+N3 -An infrared spectrum of (1).
FIG. 10 shows OGFe and OGFe + CN-And an infrared spectrum of OGFe + L-Trp.
Detailed Description
The preparation and use of the supramolecular organometallic gels of the invention are further illustrated by the specific examples below.
Synthesis of gelator G
Example 1 Synthesis and application of supramolecular organometallic gel OGCa
(1) Synthesis of gelator G
Taking 3.68g (20 mmol) of methyl gallate and 20.13g (66 mmol) of bromohexadecane, adding into 200mL of acetone, adding 16.56g of potassium carbonate and 4g of potassium iodide, and reacting at 60-65 ℃ for 70-72 hours to obtain bromohexadecane functionalized methyl gallate;
weighing 3g (13.9 mmol) of bromohexadecane functionalized gallic acid methyl ester, adding into 160ml ethanol, adding 3.125g (70 mmol) of hydrazine hydrate, reacting at 90 ℃ for 10-12 hours, cooling to room temperature, and performing suction filtration to obtain 2.58g of white powdery bromohexadecane functionalized gallic acid formyl hydrazine.
1.0272g (1.2 mmol) of bromohexadecane functionalized gallic acid formyl hydrazine is weighed and added into 60ml DMF, 0.297g (1.5 mmol) of 1, 8-naphthalic anhydride is added and reacted for 24 hours at 130 ℃, cooled to room temperature and filtered by suction to obtain 0.9952g of white powdery naphthalimide functionalized long-chain alkane supramolecular compound.
(2) Synthesis of OGCa
To 0.3ml of cyclohexanol was added G (0.0150G, 1.4X 10)-5mol) and Ca (ClO)4)2·6H2O (0.0054 g, 0.0146 mmol) was dissolved completely by heating, and then cooled to room temperature to obtain stable supramolecular organometallic gel OGCa.
(3) OGCa assay I-
Adding Cl into the supermolecular organic metal gel OGCa respectively-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -(0.1M) solutionIf fluorescence of OGCa is quenched, it indicates that I is added-If fluorescence of OGCa is not quenched, it indicates that other anions are added.
Example 2 Synthesis and application of supramolecular organometallic gel OGCu
(1) Synthesis of gelator G: the same as example 1;
(2) synthesis of OGCu: to 0.3ml of cyclohexanol was added G (0.0150G, 1.4X 10)-5mol) and Cu (ClO)4)2·6H2O (0.0057 g, 0.0145 mmol) was dissolved completely by heating, and then cooled to room temperature to obtain stable supramolecular organometallic gel OGCu.
(3) OGCu detection I-、N3 -: adding Cl into the supermolecular organic metal gel OGCa respectively-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -(0.1M) solution, if fluorescence of OGCu is quenched, it is indicated that I is added-And N3 -If the fluorescence of OGCu is not quenched, it indicates that other anions are added.
Example 3 Synthesis and application of supramolecular organometallic gel OGCo
(1) Synthesis of gelator G: the same as example 1;
(2) synthesis of OGCo: to 0.3ml of cyclohexanol was added G (0.0150G, 1.4X 10)-5mol) and Co (ClO)4)2·6H2O (0.0053 g, 0.0145 mmol) was dissolved completely by heating, and then cooled to room temperature to obtain stable supramolecular organometallic gel OGCo.
(3) OGCo assay L-His: respectively adding L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp (0.1M) aqueous solutions into the supermolecule organic metal gel OGCo, wherein if OGCo fluorescence is quenched, the addition of L-His is indicated, and if OGCo fluorescence is not quenched, the addition of other amino acid molecules is indicated.
Example 4 Synthesis and application of supramolecular organometallic gel OGNi
(1) Synthesis of gelator G: the same as example 1;
(2) synthesis of OGNi: to 0.3ml of cyclohexanol was added G (0.0150G, 1.4X 10)-5mol) and Ni (ClO)4)2·6H2O (0.0053 g, 0.0145 mmol) was dissolved completely by heating, and then cooled to room temperature to obtain stable supramolecular organometallic gels OGNi, respectively.
(3) OGNi detection of L-Trp: respectively adding aqueous solutions of L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp (0.1M) into the supermolecular organometallic gel OGNi, wherein if the fluorescence of OGNi is quenched, the addition of L-Trp is indicated, and if the fluorescence of OGNi is not quenched, the addition of other amino acid molecules is indicated.
Example 5 Synthesis and application of supramolecular organometallic gel OGFe
(1) Synthesis of gelator G: the same as example 1;
(2) synthesis of OGFe: to 0.3ml of cyclohexanol was added G (0.0150G, 1.4X 10)-5mol) and Fe (ClO)4)3·6H2O (0.0067 g, 0.0145 mmol) was dissolved completely by heating, and then cooled to room temperature to obtain stable supramolecular organometallic gel OGFe, respectively.
(3) OGFe detection CN-: adding Cl into the supermolecular organic metal gel OGFe-，Br-，I-，F-，AcO-，H2PO4 -，HSO4 -，N3 -，CN-，ClO4 -Plasma (0.1M) of aqueous anion, if fluorescence quenching of OGFe, indicates that CN was added-If the fluorescence of OGFe is not quenched, it indicates that other anions are added.
(4) OGFe detection of L-Trp: adding aqueous solutions of amino acids (0.1M) such as L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys, L-Trp, etc. to the supramolecular organometallic gel OGFe, respectively, and if the fluorescence of the supramolecular organometallic gel OGFe is quenched, indicating that L-Trp is added; if there is no change in fluorescence of the supramolecular organometallic gel OGFe, it indicates that other amino acid molecules are added.
Claims (8)
1. A preparation method of supermolecule organic metal gel based on naphthalimide functionalized long-chain alkane comprises the steps of taking the naphthalimide functionalized long-chain alkane compound as a gel factor in cyclohexanol, adding a metal ion compound, heating to completely dissolve the naphthalimide functionalized long-chain alkane compound, and cooling to room temperature to obtain stable supermolecule organic metal gel;
the structural formula of the naphthalimide functionalized long-chain alkane compound is as follows:
the compound of the metal ion is Ca (ClO)4)2·6H2O，Cu(ClO4)2·6H2O，Co(ClO4)2·6H2O，Ni(ClO4)2·6H2O or Fe (ClO)4)3·6H2And the molar ratio of the naphthalimide-functionalized long-chain alkane compound to the metal ion compound is 1: 0.5-1: 1.
2. Process for the preparation of supramolecular organometallic gels based on naphthalimide functionalized long-chain alkanes according to claim 1, characterized in that: the amount of the gel factor in the cyclohexanol is 10-15 mg/mL.
3. Use of supramolecular organometallic gels based on naphthalimide-functionalized long-chain alkanes, prepared according to the process of claim 1, for the recognition of anions: adding Cl into the supermolecular organic metal gel OGCa respectively-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -Solution of only I-Can quench the fluorescence of OGCa.
4. Use of supramolecular organometallic gels based on naphthalimide functionalized long-chain alkanes, prepared according to the process of claim 1, for the recognition of anions, characterized in that: respectively adding Cl into the supermolecular organic metal gel OGCu-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -Solution of only I-And N3 -Can quench the fluorescence of OGCu.
5. Use of supramolecular organometallic gels based on naphthalimide functionalized long-chain alkanes, prepared according to the process of claim 1, for the recognition of anions, characterized in that: adding Cl into the supermolecular organic metal gel OGFe-、Br-、I-、F-、AcO-、H2PO4 -、HSO4 -、CN-、ClO4 -、N3 -Solution of only CN-Can quench the fluorescence of OGFe.
6. Use of supramolecular organometallic gels based on naphthalimide functionalized long-chain alkanes, prepared according to the process of claim 1, for the recognition of amino acids, characterized in that: respectively adding aqueous solutions of L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp into the supermolecular organometallic gel OGNi, wherein only the L-Trp can quench the fluorescence of the OGNi.
7. Use of supramolecular organometallic gels based on naphthalimide functionalized long-chain alkanes, prepared according to the process of claim 1, for the recognition of amino acids, characterized in that: respectively adding aqueous solutions of L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp into the supermolecule organic metal gel OGCo, wherein only L-His can quench the fluorescence of OGCo.
8. Use of supramolecular organometallic gels based on naphthalimide functionalized long-chain alkanes, prepared according to the process of claim 1, for the recognition of amino acids, characterized in that: respectively adding L-Phe, L-Gln, L-Ile, L-Thr, L-Glu, L-Ala, L-Ser, L-Met, L-Val, L-Tyr, L-Ary, DL-Asp, L-Pro, L-His, L-Leu, L-Gly, L-Cys and L-Trp aqueous solution into the supermolecular organometallic gel OGFe, and only L-Trp can quench the fluorescence of OGFe.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910277137.4A CN109925982B (en) | 2019-04-08 | 2019-04-08 | Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910277137.4A CN109925982B (en) | 2019-04-08 | 2019-04-08 | Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109925982A CN109925982A (en) | 2019-06-25 |
| CN109925982B true CN109925982B (en) | 2021-03-02 |
Family
ID=66989405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910277137.4A Expired - Fee Related CN109925982B (en) | 2019-04-08 | 2019-04-08 | Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109925982B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110954515B (en) * | 2019-12-03 | 2020-11-10 | 山西大学 | 1, 8-naphthalimide derivative and application thereof |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101016325A (en) * | 2007-03-08 | 2007-08-15 | 复旦大学 | Cholesteric organogel compounds and preparing method theroef |
| WO2008085691A2 (en) * | 2007-01-03 | 2008-07-17 | The Hong Kong University Of Science And Technology | Multifunctional supramolecular hydrogels as biomaterials |
| CN101857569A (en) * | 2010-06-10 | 2010-10-13 | 复旦大学 | Organic fluorescent gel compound based on anhydride naphthalene |
| CN104826562A (en) * | 2015-04-21 | 2015-08-12 | 西北师范大学 | Preparation method of supramolecular copolymerization column five-aromatic hydrocarbon gel |
| CN105601489A (en) * | 2015-12-17 | 2016-05-25 | 西北师范大学 | Long chain ketene supramolecular gel factor and synthesis and application thereof |
| CN107827818A (en) * | 2017-11-20 | 2018-03-23 | 西北师范大学 | The application of gelator and organogel of the one kind based on post [5] aromatic hydrocarbons |
| CN107935926A (en) * | 2017-11-06 | 2018-04-20 | 西北师范大学 | It can identify the preparation and application of the gelator and its supermolecule polymer gel of fragrant acid isomer |
| CN108070092A (en) * | 2017-11-20 | 2018-05-25 | 西北师范大学 | The application of supermolecular gel and its identification iron ion and L-Cys of the one kind based on functionalization column [5] aromatic hydrocarbons |
| CN108772027A (en) * | 2018-06-20 | 2018-11-09 | 西北师范大学 | The preparation and application of a kind of supramolecular organogel and its metal gel |
| 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 |
-
2019
- 2019-04-08 CN CN201910277137.4A patent/CN109925982B/en not_active Expired - Fee Related
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008085691A2 (en) * | 2007-01-03 | 2008-07-17 | The Hong Kong University Of Science And Technology | Multifunctional supramolecular hydrogels as biomaterials |
| CN101016325A (en) * | 2007-03-08 | 2007-08-15 | 复旦大学 | Cholesteric organogel compounds and preparing method theroef |
| CN101857569A (en) * | 2010-06-10 | 2010-10-13 | 复旦大学 | Organic fluorescent gel compound based on anhydride naphthalene |
| CN104826562A (en) * | 2015-04-21 | 2015-08-12 | 西北师范大学 | Preparation method of supramolecular copolymerization column five-aromatic hydrocarbon gel |
| CN105601489A (en) * | 2015-12-17 | 2016-05-25 | 西北师范大学 | Long chain ketene supramolecular gel factor and synthesis and application thereof |
| CN107935926A (en) * | 2017-11-06 | 2018-04-20 | 西北师范大学 | It can identify the preparation and application of the gelator and its supermolecule polymer gel of fragrant acid isomer |
| CN107827818A (en) * | 2017-11-20 | 2018-03-23 | 西北师范大学 | The application of gelator and organogel of the one kind based on post [5] aromatic hydrocarbons |
| CN108070092A (en) * | 2017-11-20 | 2018-05-25 | 西北师范大学 | The application of supermolecular gel and its identification iron ion and L-Cys of the one kind based on functionalization column [5] aromatic hydrocarbons |
| CN108772027A (en) * | 2018-06-20 | 2018-11-09 | 西北师范大学 | The preparation and application of a kind of supramolecular organogel and its metal gel |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| Novel multi-analyte responsive ionic supramolecular gels based on pyridinium functionalized-naphthalimide;Qi Lin et al.;《Soft Matter》;20170907;第13卷(第40期);第7360-7364页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109925982A (en) | 2019-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | Lipophilic coordination compounds: aluminum, gallium, and indium complexes of 1-aryl-3-hydroxy-2-methyl-4-pyridinones | |
| Asperger et al. | Isomers of the Dichlorobis (l-cyclohexanediamine) cobalt (III) Ion | |
| CN108070092B (en) | Supermolecular gel based on functionalized column [5] arene and application thereof in identifying iron ions and L-Cys | |
| Lin et al. | Synthesis and characterization of three ytterbium coordination polymers featuring various cationic species and a luminescence study of a terbium analogue with open channels | |
| Uddin et al. | Metal complexes of Schiff bases derived from 2-thiophenecarboxaldehyde and mono/diamine as the antibacterial agents | |
| CN108840879A (en) | A kind of double ligand MOF complexs and its synthesis and the application in fluorescence identifying iron ion | |
| CN109925982B (en) | Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel | |
| Chan et al. | Water-compatible fluorescent [2] rotaxanes for Au 3+ detection and bioimaging | |
| CN107573366B (en) | Preparation method of o-carboxyl benzaldehyde 1, 3-propane diamine Schiff base copper complex | |
| CN109053728B (en) | 4-aminopyridine-based functionalized 1,4,5, 8-naphthalimide supramolecular organogel and application thereof | |
| Lazarou et al. | Complexes derived from the copper (II) perchlorate/maleamic acid/2, 2′-bipyridine and copper (II) perchlorate/maleic acid/2, 2′-bipyridine reaction systems: Synthetic, reactivity, structural and spectroscopic studies | |
| MacDonald et al. | Copper Schiff base complexes with polyfunctional amino acids | |
| US20200317607A1 (en) | Composition for Detecting Acidic Compound | |
| Jiang et al. | Composite Eu-mof@ CQDs “off & on” ratiometric luminescent probe for highly sensitive chiral detection of L-lysine and 2-methoxybenzaldehyde | |
| Kaliva et al. | Synthesis, isolation, spectroscopic and structural characterization of a new pH complex structural variant from the aqueous vanadium (V)-peroxo-citrate ternary system | |
| RU2582680C1 (en) | COMPLEXONATES OF ETHYLENEDIAMINE-β-PROPIONIC ACIDS WITH DIVALENT METALS: COPPER, ZINC, NICKEL AND COBALT, AND METHODS FOR PRODUCTION THEREOF | |
| CN113845535A (en) | Binuclear cadmium complex and preparation method and application thereof | |
| Pushpaveni et al. | Structural and multi-functional properties of novel thorium complex bearing higher analogue of guanidine base | |
| CN116059164B (en) | Doxycycline hydrochloride solution and preparation method thereof | |
| Nigović et al. | Complex formation between transition metals and 2-pyrrolidone-5-hydroxamic acid | |
| Wang et al. | Self-assembly and cytotoxicity study of waterwheel-like dinuclear metal complexes: The first metal complexes appended with multiple free hydroxamic acid groups | |
| Tounsi et al. | Copper (II) complexes with lactamides: solution and solid state studies | |
| Bhatt et al. | Synthesis and Characterization of Homo and Heterodinuclear Complexes of Co (II) and Ni (II) | |
| CN112410021B (en) | Supermolecule gel capable of identifying arsenite ions through single selective fluorescence and preparation and application thereof | |
| KR101521756B1 (en) | Novel compound and salicylic acid based compound detecting chemical sensor including the compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20210302 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |