CN109265398B - Supermolecule organogel and application thereof in fluorescent recognition of mercury ions - Google Patents

Supermolecule organogel and application thereof in fluorescent recognition of mercury ions Download PDF

Info

Publication number
CN109265398B
CN109265398B CN201811062601.XA CN201811062601A CN109265398B CN 109265398 B CN109265398 B CN 109265398B CN 201811062601 A CN201811062601 A CN 201811062601A CN 109265398 B CN109265398 B CN 109265398B
Authority
CN
China
Prior art keywords
organogel
gel
supramolecular
supermolecule
guest
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.)
Active
Application number
CN201811062601.XA
Other languages
Chinese (zh)
Other versions
CN109265398A (en
Inventor
林奇
杨海龙
孙小文
李丹清
李雪蕾
吴晶晶
当子加
张有明
魏太保
姚虹
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Northwest Normal University
Original Assignee
Northwest Normal University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Northwest Normal University filed Critical Northwest Normal University
Priority to CN201811062601.XA priority Critical patent/CN109265398B/en
Publication of CN109265398A publication Critical patent/CN109265398A/en
Application granted granted Critical
Publication of CN109265398B publication Critical patent/CN109265398B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/0052—Preparation of gels
    • B01J13/0065—Preparation of gels containing an organic phase
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • 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"
    • 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
    • G01N21/6447—Fluorescence; Phosphorescence by visual observation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Optics & Photonics (AREA)
  • Dispersion Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

The invention discloses a supermolecule organogel, which takes functionalized naphthalimide as a gel host and trimesoyl chloride functionalized pyridine as a gel guest and fully dissolves in DMSO-H under heating2Obtaining a transparent solution in O; cooling to room temperature to form a stable supramolecular organogel RQ. Adding a series of cations, only Hg, to the supramolecular organogel RQ2+Can form cation-pi action with RQ and the fluorescence is opened, thereby forming stable metal supermolecule organogel RQ-Hg2+Therefore, the supermolecule organogel can detect Hg with high selectivity and ultrasensitiveness2+。

Description

Supermolecule organogel and application thereof in fluorescent recognition of mercury ions
Technical Field
The invention relates to a supermolecule organogel, and simultaneously relates to the supermolecule organogel for identifying Hg in single selective fluorescence2+Belonging to the field of supramolecular organogel and the technical field of particle recognition.
Background
The supramolecular organogel is of low molecular weightAn organic compound (gelator) which is bound to the surface of the substrate by hydrogen bond, van der Waals force,π-πStacking action, hydrophilic-hydrophobic action and other weak interaction between molecules, and self-assembling to form supermolecular (soft) material. This material has the specific advantages of both solid and liquid materials: the supramolecular organogel material keeps the chemical property of the supramolecular organogel material, can perform some reactions in a solution, and has the advantages of stability similar to a solid, such as easy storage and the like, so the supramolecular organogel material has wide application in the field of supramolecular soft materials.
Mercury, a heavy metal with severe physiological toxicity, is very likely to enter the food chain through various routes and accumulate in the organism step by step, and is difficult to be discharged out of the body through the metabolic function of the organism. The biological agent has lasting toxicity, high biological enrichment and extremely strong destructiveness to the environment, and causes serious harm to the biological health. In recent years, with the frequent application of mercury in industrial production, the environmental pollution and the biological hazard caused by the mercury are becoming more serious, and research on the evaluation of mercury biohazard is also attracting much attention. Therefore, the development of a mercury ion detection method with high sensitivity and high selectivity can realize real-time, in-situ, dynamic and specific detection of the content of mercury ions in the environment, and has important theoretical significance and practical value.
Disclosure of Invention
The invention aims to provide a supramolecular organogel;
the invention also aims to provide application of the supramolecular organogel in single selective fluorescent recognition of mercury ions.
Mono-and supermolecule organic gel
The supermolecule organogel takes functionalized naphthalimide (marked R) as a gel host and trimesoyl chloride functionalized pyridine (marked Q) as a gel guest, and is fully dissolved in DMSO-H under heating2Obtaining a transparent solution in O; cooling to room temperature to form a stable supramolecular organogel RQ.
The structural formula of the gel main body R is as follows:
Figure DEST_PATH_IMAGE001
the structural formula of gelled guest Q is as follows:
Figure 146572DEST_PATH_IMAGE002
the molar ratio of the gel host R to the gel guest Q is 1: 3-1: 3.5; host-guest gel and DMSO-H2The mass-to-volume ratio of O is 40-50 mg/mL; DMSO-H2In O, DMSO and H2The volume ratio of O is 1.5: 1-2: 1.
Fluorescence property of bi-and supramolecular organogel RQ
Experiments show that the trans-dissolving temperature of the supramolecular organogel RQ is 70-75 ℃. The organogel RQ has good stability, and the shape of the gel remains unchanged after being placed for several days.
FIG. 4 shows the change of fluorescence intensity with temperature (lambda) during gel formation of RQex=345 nm). The results in FIG. 4 show that RQ fluoresces very weakly in the Sol state (RQ-Sol), and as the temperature is lowered, the Sol transforms into a Gel, resulting in a weaker dark black-yellow aggregate state fluorescence (RQ-Gel).
Identification experiment of supramolecular organogel RQ on cations
1. RQ to Hg2+Fluorescence response of
A small amount (about 0.02 g) of 13 parts of each organogel RQ was applied to a white spot plate, and 20. mu.L of different cations (C =0.1moL/L, Mg) were added to each organogel RQ2+，Ca2+，Cr3+，Fe3+，Co2+，Ni2+，Cu2+，Zn2+，Ag+，Cd2+，Hg2+，Pb2+) An aqueous solution of (a). The gel was then observed for fluorescent color change under an ultraviolet lamp. Fig. 5 is a full scan of RQ versus cation. The results in fig. 5 show that supramolecular organogels encounter Hg2+The fluorescence turns on and is blue-green when in solution, but encounters the dissolution of other cationsWhen liquid, the fluorescence of the supramolecular organogel is not turned on and the color does not change. Therefore, the organogel RQ can specifically and selectively carry out fluorescence recognition on Hg2+. Meanwhile, when the Hg-containing component is added into the supermolecule organogel RQ2+When the sample to be detected is solid, the sample to be detected can be directly dissolved to realize the detection of mercury ions, so that the detection process of the sample is simplified. Therefore, the use of the material greatly simplifies the detection method of mercury ions and reduces the detection cost.
2. Organogel RQ vs Hg2+Fluorescence titration experiment of
Preparing a part of organic gel RQ with the volume of 250 mu L (the gel concentration is 50 mg/mL) in a micro-fluorescence colorimetric pool, and adding different equivalent Hg into the RQ2+The change in fluorescence intensity of the gel was measured in an aqueous solution (C =1.0 moL/L). FIG. 6 is RQ vs Hg2+Fluorescence titration of (lambda)ex=345 nm). FIG. 6 shows the Hg dependence2+The fluorescence at 470nm is gradually enhanced and finally tends to be stable; and RQ to Hg2+The detection limit of the fluorescence spectrum of (1) is 4.52X 10-8M (FIG. 7). The detection limit is very low, and the level of ultra-sensitive detection is achieved. Shows that RQ can detect Hg with ultra sensitivity in environment2+。
3. Organogel RQ vs Hg2+Fluorescence response of
A small amount (about 0.02 g) of 13 parts of each organogel RQ was applied to a white spot plate, and 20. mu.L of different cations (C =0.1moL/L, Mg) were added to each organogel RQ2+，Ca2+，Cr3+，Fe3+，Co2+，Ni2+，Cu2+，Zn2+，Ag+，Cd2+，Hg2+，Pb2+) An aqueous solution of (a). The gel was then observed for fluorescent color change under an ultraviolet lamp. Only Hg is encountered in the organogel RQ2+The fluorescence is turned on in solution and is blue-green, organogel RQ and Hg2+Formation of supramolecular organometallic gels RQ + Hg by cation-pi action2+。
Four, RQ to Hg2+Mechanism of recognition of
RQ to Hg2+By the recognition mechanism of (1), weIt was investigated by IR, XRD, SEM and the like. IR indicates (FIG. 8) that-NH after R forms RQ2The stretching vibration peak of-NH, -C = O is shifted to the low wave number direction, which indicates that the hydrogen bonding action exists. XRD showed (FIG. 9), 2𝜽=25.08，d=3.54 a, indicating the presence of pi-pi interactions. SEM showed (fig. 10) that the RQ morphology appears massive. IR showed (FIG. 11) when Hg was added to RQ2+Will result in-NH2-NH, -C = O stretching vibration peak shifts to high wavenumber; XRD showed (FIG. 12), when Hg was added to RQ2+So that the pi-pi effect is weakened. SEM shows (FIG. 13), when Hg was added to RQ2+，RQ+Hg2+The morphology appears helical, further indicating that Hg2+Where interactions occur, forming cation-pi interactions.
In conclusion, the ultrasensitive recognition process of the supramolecular organogel RQ is realized by a novel cation-pi action. When Hg is added to RQ2+Due to Hg2+Can generate cation-pi action with RQ, destroy pi-pi action between gels, cause rotation, present spiral shape, cause fluorescence opening of RQ, and realize RQ to Hg2+And (4) ultra-sensitive detection.
Drawings
FIG. 1 is R1A HNMR map;
FIG. 2 is a MS diagram of R;
FIG. 3 is Q1A HNMR map;
FIG. 4 shows the change of fluorescence intensity with temperature (lambda) during gel formation of RQex=345 nm)；
FIG. 5 is a full scan of RQ vs. cation;
FIG. 6 is RQ vs Hg2+Fluorescence titration of (lambda)ex=345nm)；
FIG. 7 is RQ vs Hg2+The fitting curve of (1);
FIG. 8 is a graph of the infrared spectrum of R, Q, RQ;
FIG. 9 is an XRD pattern of R, Q, RQ;
FIG. 10 shows SEM pictures of R (a), Q (b), RQ (c);
FIG. 11 shows RQ, RQ + Hg2+An infrared spectrum of (1);
FIG. 12 shows RQ, RQ + Hg2+XRD pattern of (a);
FIG. 13 shows RQ (d), RQ + Hg2+(e) SEM image of (d).
Detailed Description
The synthesis of the supramolecular organogel RQ of the invention, and the identity selection for Hg identification by the specific examples below2+The method of (1) is further illustrated.
Example 1 Synthesis of supramolecular organogel RQ
(1) Gel host-synthesis of functionalized naphthalimide R: a100 mL round-bottom flask was charged with p-phenylenediamine (1.08 g, 10 to 10.5 mmol), 1, 8-naphthalic anhydride (1.98 g, 10 to 10.5 mmol) and 100mL of ethanol, and the mixture was heated under reflux at 80 ℃ for 24 hours. And after the reaction is finished, performing suction filtration, leaching with hot ethanol, and drying by suction filtration to obtain yellow powder R, wherein the yield is as follows: 85 percent. In FIGS. 1 and 2, R is respectively1HNMR map, MS map.
(2) Gel guest-Synthesis of 4-aminopyridine functionalized trimesoyl chloride Q: to a 100mL round bottom flask was added 4-aminopyridine (0.75 g, 8.0-8.05 mmol) and CHCl3(40 mL), trimesoyl chloride (0.52 g, 5.0-5.05 mmol) and CHCl were added to a constant pressure funnel3(40 mL), slowly dropping it into a round-bottom flask overnight; suction filtration gave a white solid Q in yield: 80 percent. Of Q1H NMR is shown in FIG. 3.
(3) Preparation of supramolecular organogel RQ: 0.0034g (3.84X 10) of the gel main body R was weighed out separately-6mol), gel guest Q0.0016g (1.15X 10)-6mol) was added to 100. mu.L of DMSO-H2O（40μLDMSO，60μLH2O), fully dissolving the mixture under heating to obtain a transparent solution; upon cooling to room temperature, the solution formed a stable supramolecular organogel RQ. The temperature of RQ is 70-75 ℃. RQ has a weaker dark black-yellow aggregate fluorescence.
Example 2 identification of experimental Hg by supramolecular organogel RQ2+
13 parts of a small amount (about 0.02 g) of supramolecular organogel RQ are each applied to a white spot plate,adding different cations (C =0.1moL/L, Mg) to the organogels respectively2+，Ca2+，Cr3+，Fe3+，Co2+，Ni2+，Cu2+，Zn2+，Ag+，Cd2+，Hg2+，Pb2+) An aqueous solution of (a). The gel was then observed for fluorescent color change under an ultraviolet lamp. The fluorescence color of the organogel RQ changed from dark yellow to blue-green indicating that Hg was added2+The fluorescence colour of the solution, supramolecular organogel RQ, does not change, indicating the addition of an aqueous solution of other cations.

Claims (5)

1. A supermolecule organogel is prepared from functional naphthalimide as gel host and trimesoyl chloride-functionalized pyridine as gel guest through heating and dissolving them in DMSO-H2Obtaining a transparent solution in O; cooling to room temperature to form a stable supramolecular organogel;
the structural formula of the gel body is as follows:
Figure DEST_PATH_IMAGE002
the structural formula of the gel guest is as follows:
Figure DEST_PATH_IMAGE004
。
2. the supramolecular organogel as claimed in claim 1, wherein: the molar ratio of the gel host to the gel guest is 1: 3-1: 3.5.
3. The supramolecular organogel as claimed in claim 1, wherein: host-guest gel and DMSO-H2The mass-to-volume ratio of O is 40-50 mg/mL.
4. The supramolecular organogel as claimed in claim 1, wherein:DMSO-H2in O, DMSO and H2The volume ratio of O is 1.5: 1-2: 1.
5. The supramolecular organogel as claimed in claim 1, characterized by single selective fluorescence recognition of Hg2+The method is characterized by comprising the following steps: respectively adding Fe into the supermolecule organogel3+，Hg2+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2+，Zn2+，Cr3+，Mg2+In the case of an aqueous solution of (2), only Hg is contained2+The fluorescent color of the supramolecular organogel can be changed from dark yellow to blue-green by adding the cationic dye, and the fluorescent color of the supramolecular organogel cannot be changed by adding other cations; the use is for non-disease diagnosis or treatment purposes.
CN201811062601.XA 2018-09-12 2018-09-12 Supermolecule organogel and application thereof in fluorescent recognition of mercury ions Active CN109265398B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811062601.XA CN109265398B (en) 2018-09-12 2018-09-12 Supermolecule organogel and application thereof in fluorescent recognition of mercury ions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811062601.XA CN109265398B (en) 2018-09-12 2018-09-12 Supermolecule organogel and application thereof in fluorescent recognition of mercury ions

Publications (2)

Publication Number Publication Date
CN109265398A CN109265398A (en) 2019-01-25
CN109265398B true CN109265398B (en) 2021-05-18

Family

ID=65187963

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811062601.XA Active CN109265398B (en) 2018-09-12 2018-09-12 Supermolecule organogel and application thereof in fluorescent recognition of mercury ions

Country Status (1)

Country Link
CN (1) CN109265398B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109925982B (en) * 2019-04-08 2021-03-02 西北师范大学 Preparation and application of naphthalimide-functionalized long-chain alkane supramolecular organic metal gel
CN110015989B (en) * 2019-04-16 2021-07-16 西北师范大学 Application of 4-aminopyridine functionalized trimesoimide in detecting nitrate ions
CN110054586B (en) * 2019-04-16 2021-09-28 西北师范大学 Preparation of rare earth metal complex gel and application of rare earth metal complex gel in histidine detection
CN110041251B (en) * 2019-04-16 2021-07-20 西北师范大学 Application of 4-aminopyridine functionalized trimesoimide in detecting formaldehyde and 3-fluorobenzaldehyde

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN108061728A (en) * 2017-12-22 2018-05-22 西北师范大学 A kind of supermolecule sensor and its synthesis and fluorescence identifying fluorine ion and arginic application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN108061728A (en) * 2017-12-22 2018-05-22 西北师范大学 A kind of supermolecule sensor and its synthesis and fluorescence identifying fluorine ion and arginic application

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
双组分超分子凝胶的研究进展;苏婷，等;《现代化工》;20170228;57-61 *
超分子凝胶可视化选择性识别有机小分子的研究进展;贺有周，等;《化学研究与应用》;20170731;913-920 *

Also Published As

Publication number Publication date
CN109265398A (en) 2019-01-25

Similar Documents

Publication Publication Date Title
CN109265398B (en) Supermolecule organogel and application thereof in fluorescent recognition of mercury ions
Yu et al. Ultrathin two-dimensional metal-organic framework nanosheets decorated with tetra-pyridyl calix [4] arene: Design, synthesis and application in pesticide detection
She et al. Design strategy and recent progress of fluorescent probe for noble metal ions (Ag, Au, Pd, and Pt)
CN109320454B (en) Bi-component supermolecule organogel and preparation and application of metal gel thereof
Sutar et al. Coordination polymer gels with modular nanomorphologies, tunable emissions, and stimuli-responsive behavior based on an amphiphilic tripodal gelator
CN109536160B (en) Tripodal pseudorotaxane supramolecular gel based on trimesoyl chloride and preparation and application of metal gel of tripodal pseudorotaxane supramolecular gel
He et al. A fluorescent chemical sensor for Hg (II) based on a corrole derivative in a PVC matrix
Peng et al. Highly selective detection of Cu2+ in aqueous media based on Tb3+-functionalized metal-organic framework
Farhi et al. A quinoline-based fluorescent probe for selective detection and real-time monitoring of copper ions–a differential colorimetric approach
Liu et al. Specific recognition of formaldehyde by a cucurbit [10] uril-based porous supramolecular assembly incorporating adsorbed 1, 8-diaminonaphthalene
Ju et al. A Salen-based covalent organic polymer as highly selective and sensitive fluorescent sensor for detection of Al3+, Fe3+ and Cu2+ ions
Zhang et al. Rapid capture and visual detection of copper ions in aqueous solutions and biofluids using a novel cellulose-Schiff base
Dalapati et al. Post-synthetic modification of a metal–organic framework with a chemodosimeter for the rapid detection of lethal cyanide via dual emission
Chatterjee et al. Safranin O-functionalized cuboid mesoporous silica material for fluorescent sensing and adsorption of permanganate
Tan et al. Functionalized lanthanide coordination polymer nanoparticles for selective sensing of hydrogen peroxide in biological fluids
Lu et al. Modulating the optical properties of the AIE fluophor confined within UiO-66's nanochannels for chemical sensing
Nagarajan et al. Recent advancements in the role of N-Heterocyclic receptors on heavy metal ion sensing
Du et al. Design of a calix [4] arene-functionalized metal-organic framework probe for highly sensitive and selective monitor of hippuric acid for indexing toluene exposure
Luo et al. Dual-modes of ratiometric fluorescent and smartphone-integrated colorimetric detection of glyphosate by carbon dots encapsulated porphyrin metal–organic frameworks
Liu et al. Development of Eu-based metal-organic frameworks (MOFs) for luminescence sensing and entrapping of arsenate ion
CN108088828B (en) Double-column aromatic mercury ion fluorescent sensor and preparation and application thereof
CN105384769A (en) Preparation and application of terpyridine group modified nano silica particles
Yan et al. A novel hydrolytically stable fluorescent Cd (II) coordination polymer showing solvent-dependent multi-responsive fluorescence sensing to pH and some metal ions
Lakshmi et al. Vinyl-functionalized polyphenolic-carbon dot-based fluorometric turn-off–on biosensor for the dual detection of mercury and cysteine and their in vivo sensing in zebrafish larvae
CN108658862B (en) Sensor molecule based on naphthalimide derivative and synthesis and application thereof

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