CN104447768A - Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof - Google Patents

Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof Download PDF

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CN104447768A
CN104447768A CN201310435721.0A CN201310435721A CN104447768A CN 104447768 A CN104447768 A CN 104447768A CN 201310435721 A CN201310435721 A CN 201310435721A CN 104447768 A CN104447768 A CN 104447768A
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yuan
pyridyl
rotaxane
rotaxanes
methionin
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宋森
倪新龙
张建新
陶朱
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Guizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • 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
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    • 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"
    • 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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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms

Abstract

The invention discloses a cucurbit [7] uril [3] rotaxane as well as a preparation method and application thereof, and belongs to the technical fields of organic synthesis and analytical chemistry. A fluorescence probe cucurbit [7] uril [3] rotaxane prepared by the method can be applied to high-selectivity and high-sensitivity detection of lysine or arginine or a mixture of the lysine and the arginine. Under the medium condition of an aqueous solution, a trace amount of lysine or arginine or the mixture of the lysine and the arginine can be detected by taking cucurbit urils supramolecular self-assembly as a probe system by adopting a fluorescence emission spectrophotometry at high sensitivity and high selectivity. The invention also discloses a preparation method and a technological condition of the cucurbit [7] uril [3] rotaxane. The reacting fluorescence excitation wavelength of the cucurbit [7] uril [3] rotaxane and the lysine or the arginine or the mixture of the lysine and the arginine is 317nm; and the maximal emission wavelength is 375nm.

Description

Seven yuan of melon ring [3] rotaxanes and its preparation method and application
Technical field
The invention belongs to organic synthesis and analytical chemistry field.Specifically seven yuan of melon ring [3] rotaxanes and its preparation method and application.
Background technology
Be based upon the fluorescent probe technique on molecular recognition basis, by the selective binding to specific target molecules, ion, realize identifying information and be converted to by corresponding fluorescent signal conduction the spectral signal being easy to detect, thus realize original position on a molecular scale, detect in real time, and abundant spectral information can be provided, play an important role in various ion detection, DNA and protein molecular marker, cell imaging, immunoassay etc.
Amino acid is the base substance forming life entity, is the basic substance of cellular metabolism.Amino acid whose quick identification is analyzed significant to cellular metabolism, and therefore amino acid whose Selective recognition and detection cause the great interest of people.At present, the common method identified amino acid is high performance liquid chromatography (HPLC), gas-chromatography (GC) and the various chromatography such as kapillary, electrophoresis (CE).These methods have the advantage that tolerance range is high and detection limit is low, but time for sample pretreatment is long, cost is high, are difficult to adapt to rapid detection, limit their application.In recent years, due to the highly sensitive of fluorometric analysis and highly selective, real-time in-situ detects, equipment is simple, the multiple fluorescent optical sensor for amino acid discriminating is in the news in succession, but most fluorescent optical sensor can only optionally identify that some contain the amino acid molecular of the specific function groups such as sulfydryl, then relatively less to the highly selective recognition detection of other amino acid molecular.
Melon ring has another name called Cucurbituril (Cucurbit [n] uril is called for short Q [n] or CB [n]) as a class Novel macrocyclic compound, because of its structure seemingly pumpkin gain the name for ring again, that the class Novel macrocyclic compound that formed by methylene-bridged by glycosides urea unit is when (during n=7, claiming seven yuan of melon rings to be abbreviated as Q [7]).Due to its have interior hydrophobic outer hydrophilic cavity and by around the port that forms of carbonylic oxygen atom, make Supramolecular self assembly structure that melon ring can be formed by the multiple cation guests of non covalent bond effect bonding such as hydrophobic interaction, hydrogen bond, ion dipole and neutral molecule in molecular switch, molecule shuttle, information storage etc., and there is potential using value the aspect such as medicament slow release, molecular recognition.At present, had about the report of seven yuan of melon ring-fluor supramolecular systems as molecular probe, but there is not been reported to detect amino acid molecular based on melon ring rotaxane system as fluorescent molecular probe.
Summary of the invention
The object of the invention is to the water-soluble fluorescent probe synthesizing a kind of highly sensitive and highly selective identification specific amino acid molecule.Object of the present invention is achieved through the following technical solutions;
A kind of seven yuan of melon ring [3] rotaxanes of the present invention be with 1,2-di(4-pyridyl)ethylene, bromocaproic acid and seven yuan of melon cyclisation things Q [7] for raw material synthesizes seven yuan of melon ring [3] rotaxanes through two steps, be called for short [3] rotaxane.
[3] rotaxane molecular formula: C 66h 74n 30o18
Structural formula:
Molecular weight: 2896.5
Fusing point: >300 DEG C
Solvability: water-soluble
Spectral quality: fluorescence exciting wavelength is in aqueous 317nm, emission wavelength is 375nm.
The preparation method of a kind of seven yuan of melon ring [3] rotaxanes of the present invention is with 1,2-bis-(4-pyridyl) ethene, bromocaproic acid and seven yuan of melon cyclisation things Q [7] are synthesized through two steps for raw material, its synthetic route is step (1), with 1,2-bis-(4-pyridyl) ethene and bromocaproic acid are obtained by reacting N, N '-two caproic acids-1,2-di(4-pyridyl)ethylene bromide writes a Chinese character in simplified form G
Step (2), is obtained by reacting seven yuan of melon ring [3] rotaxanes with compound G and seven yuan of melon ring Q [7].
Above-mentioned steps (1) object N, the synthetic technological condition of N '-two caproic acids-1,2-di(4-pyridyl)ethylene bromide G is with 1,2-bis-(4-pyridyl) ethene, bromocaproic acid is raw material, N, N-dimethyl methyl imide is solvent, and Reactive Synthesis obtains:
In flask, add 1,2-di(4-pyridyl)ethylene and bromocaproic acid, at N 2the lower heating reflux reaction of protection, cool after reacting completely, suction filtration, will precipitate crystallization soluble in water, distillation washing, and acetone is washed, obtained object N, N '-two caproic acid-1,2-di(4-pyridyl)ethylene bromide G after dry:
Temperature of reaction: 90 DEG C
Reaction times: 24h
Reaction solvent: N, N-dimethyl methyl imide
Recrystallisation solvent: distilled water
Mol ratio: 1,2-bis-(4-pyridyl) Yi Xi ︰ bromocaproic acid=1 ︰ 3.
The synthetic technological condition of above-mentioned steps (2) seven yuan of melon ring [3] rotaxanes is to obtain product with compound G and seven yuan of melon ring Q [7] Reactive Synthesis.
In there-necked flask, add the object N that (1) step is obtained, N '-two caproic acid-1,2-bis-(4-pyridyl) vinyl bromide G, seven yuan of melon rings, distilled water, reacting by heating, lower the temperature after reacting completely, rotary evaporation of solvent, washing with acetone, suction filtration, vacuum-drying, obtained [3] rotaxane probe:
Temperature of reaction: 50 DEG C
Reaction times: 12h
Reaction solvent: distilled water
Mol ratio: G ︰ Q [7]=1 ︰ 20.
The application of a kind of seven yuan of melon ring [3] rotaxanes of the present invention is the fluorescent probes for Methionin or arginine or Methionin and ar-ginine mixtures, for the fluorophotometric qualitative and quantitative analysis of Methionin or arginine or Methionin and ar-ginine mixtures.
The excitation wavelength 317nm of the fluorescence spectrum of above-mentioned fluorophotometric qualitative and quantitative analysis, maximum emission wavelength 375 nm. detectability is low to moderate 10 most -6molL -1, correct linearity range 1 × 10 -5~ 1.2 × 10 -4mol/L.
The present invention is under aqueous medium condition, fluorescence emission spectrum is utilized to detect micro-Methionin or arginine molecule or Methionin and ar-ginine mixtures, fluorescence spectral characteristic is for after [3] rotaxane adds Methionin or arginine molecule or Methionin and ar-ginine mixtures, and the fluorescence intensity at maximum emission wavelength 375nm place obviously reduces.The features such as it is easy that this invention has working method, highly sensitive, selectivity is superior, and concentration linearity range is wider, and detectability is low.
Accompanying drawing explanation
The chemical structural formula of Fig. 1 a) host molecule seven yuan of melon rings; B) chemical structural formula of guest molecule G; C) the packaging assembly formula of [3] rotaxane.D) [3] rotaxane detects as fluorescent probe and identifies Methionin or arginic molecule mechanism.
Fig. 2 concentration is 1.00 × 10 -5molL -1the aqueous solution of object G, does not add seven yuan of melon rings respectively or adds 1.00 × 10 -5molL -1([2] rotaxane, object G fluorescence intensity reduces) and 2.00 × 10 -5molL -1fluorescence spectrum figure after ([3] rotaxane, object G fluorescence intensity strengthens) melon ring.Excitation wavelength is 317nm, and maximum emission wavelength is 375nm.
Fig. 3 concentration is 1.00 × 10 -5molL -1[3] aqueous solution of rotaxane, does not add amino acid molecular respectively or adds 5.00 × 10 -5molL -1fluorescence emission spectrogram after various amino acid molecular.The system fluorescence intensity of making that adds of Methionin and arginine molecule significantly reduces, and other experiment amino acid molecular adds probe solution all without obvious fluorescence intensity change.Excitation wavelength is 317nm, and maximum emission wavelength is 375nm.
Fig. 4 impact (for Methionin) of amino acid molecular on [3] rotaxane system Fluorometric assay Methionin and arginine molecule that coexist is 1.00 × 10 in concentration -5molL -1in the aqueous solution of [3] taking turns, 1 expression adds 5.00 × 10 -5molL -1methionin after the fluorescence intensity change of system.2-15 represents the fluorescence intensity change after other interference amino acid molecular adding isodose in [3] rotaxane/Methionin system again.Data sheet phaneroplasm system is not subject to the impact of other common amino acid molecular that coexists on the change in fluorescence of Methionin.
Embodiment
Embodiment one: the synthesis of object N, N '-two caproic acids-1,2-di(4-pyridyl)ethylene bromide (G)
In 25 mL flasks, in 15 mLDMF solution, add 1,2-di(4-pyridyl)ethylene 182 mg (1.0 mmol) and bromocaproic acid 546 mg (3.0 mmol), N 2lower heating reflux reaction 24 h of protection, cool after reacting completely, suction filtration, will precipitate crystallization soluble in water, distillation washing, and acetone is washed, obtained object N, N '-two caproic acid-1,2-di(4-pyridyl)ethylene bromide G 400 mg after dry, productive rate 70%. 1H NMR (D 2O, 400MHz) δ: 8.67(d, 4H, ArH), 8.07(d, 4H, ArH), 7.71(s, 2H, CH=CH ), 4.43 (t, 4H,CH 2), 2.21(t, 4H, CH 2), 1.88 (t, 4H, CH 2), 1.48 (t, 4H, CH 2), 1.21 (t, 4H, CH 2).
Embodiment two: the assemble method of [3] rotaxane system:
Take seven yuan of melon ring Q [7] 48 mg(0.4 mmol respectively), object G 12 mg(0.02 mmol), join in 25ml distilled water, at 80 ~ 95 DEG C of stirring reaction 2h.After being cooled to room temperature, rotary evaporation removes water solvent.Acetone precipitation, suction filtration, drying.Prepare faint yellow solid 55 mg, productive rate 91%.m.p. >300 C.； 1H NMR (400 MHz, D 2O):δ/ ppm 8.35 (d, 4H, J= 6.4 Hz, ArH), 8.24 (d, 4H, J = 6.4 Hz, ArH), 7.94 (s,2H, CH=CH), 5.61 (t, 14H, J = 3.1 Hz, CH2), 5.38 (s, 14H, CH), 4.90 (d, 14H, J = 15.2 Hz, CH2), 4.10 (d, 4H, J = 15.2 Hz, CH2), 1.68 (s, 4H, CH2),1.06 (s, 4H, CH2), 0.85 (s, 4H, CH2), 0.45 (s, 4H, CH2).
Embodiment three: [3] rotaxane is as the recognition detection of fluorescent probe to amino acid molecular
(1) compound method of rotaxane solution: [3] rotaxane taking 30 mg, dissolve with distilled water, be mixed with 10mL solution, concentration is 1.00 × 10 -3molL -1;
(2) amino acid whose standardized solution: take the pure Methionin of top grade or arginine or Methionin and arginic mixture and be mixed with the 100mL aqueous solution, amino acid solution concentration is 1.00 × 10 -3molL -1, use distilled water stepwise dilution to suitable concentration as required;
[3] rotaxane water storing solution (1.00 × 10 is added in 10.0 mL volumetric flasks -4molL -1, 1mL), amino acid solution concentration (5.00 × 10 -4molL -1, 1 mL).Be diluted to scale with distilled water solution, shake up, place 2 h in room temperature, the quartz colorimetric utensil moving into 3cm carries out fluorescence spectrometry.System fluorescence spectrometry to excite with emission wavelength be 310/375 nm.
Agents useful for same is analytical reagent, and test water is redistilled water.
Spectrophotofluorometer model used is Cary Eclipse spectrophotofluorometer, and VARIAN company of the U.S. manufactures.
In aqueous, [3] rotaxane has stronger fluorescent emission, and excitation wavelength is 310 nm, and emission wavelength is 375 nm, observes transmitting blue-fluorescence under 365nm ultraviolet lamp.After adding Methionin or arginine or Methionin and arginic mixture solution, observe its fluorescent emission intensity and significantly reduce, and other experiment amino acid moleculars to detection system all without obvious response signal (as Fig. 3).Show that [3] rotaxane has recognition detection performance to Methionin or arginine or Methionin and arginic mixture.
[3] rotaxane system on the fluorescence (Fig. 4) of Methionin or arginine or Methionin and arginic mixture not by the impact of other amino acid molecular that coexists.Other is common coexists amino acid molecular when concentration is suitable with test amino acid molecular, on the relative deviation of the fluorescence intensity impact detected all within 5%, and all not interference measurements.
In aqueous, take 310/375nm as fluorescence excitation and emission wavelength, measure the working curve of the fluorescent emission of amino acid concentration change and molecule rotaxane probe.By the slope of calibration curve and the standard deviation measuring 10 blank values, measure and calculate linearity range and detection limit lists in table 1.

Claims (6)

1. one kind seven yuan melon ring [3] rotaxanes, it is characterized in that with 1,2-bis-(4-pyridyl) ethene, bromocaproic acid and seven yuan of melon cyclic cpds cucurbit [7] uril are called for short Q [7] and synthesize seven yuan of melon ring [3] rotaxanes for raw material through two steps, are called for short [3] rotaxane
[3] rotaxane molecular formula: C 66h 74n 30o 18
Structural formula:
Molecular weight: 2896.5
Fusing point: >300 DEG C
Solvability: water-soluble
Spectral quality: fluorescence exciting wavelength is in aqueous 317nm, emission wavelength is 375nm.
2. the preparation method of a kind of seven yuan of melon ring [3] rotaxanes in accordance with claim is characterized in that with 1,2-bis-(4-pyridyl) ethene, bromocaproic acid and seven yuan of melon cyclic cpdss are that raw material synthesizes through two steps, its synthetic route is step (1), with 1,2-bis-(4-pyridyl) ethene and bromocaproic acid are obtained by reacting N, N '-two caproic acids-1,2-di(4-pyridyl)ethylene bromide, writes a Chinese character in simplified form G
Step (2), is obtained by reacting seven yuan of melon ring [3] rotaxanes with compound G and seven yuan of melon ring Q [7]
。
3. according to the preparation method of seven yuan of melon ring [3] rotaxanes of the one described in claim 2, it is characterized in that step (1) object N, N '-two caproic acid-1, the synthetic technological condition of 2-bis-(4-pyridyl) vinyl bromide G is with 1,2-bis-(4-pyridyl) ethene, bromocaproic acid is raw material, N, N-dimethyl methyl imide is solvent, and Reactive Synthesis obtains:
In flask, add 1,2-di(4-pyridyl)ethylene and bromocaproic acid, at N 2the lower heating reflux reaction of protection, cool after reacting completely, suction filtration, will precipitate crystallization soluble in water, distillation washing, and acetone is washed, obtained object N, N '-two caproic acid-1,2-di(4-pyridyl)ethylene bromide G after dry:
Temperature of reaction: 90 DEG C
Reaction times: 24h
Reaction solvent: N, N-dimethyl methyl imide
Recrystallisation solvent: distilled water
Mol ratio: 1,2-bis-(4-pyridyl) Yi Xi ︰ bromocaproic acid=1 ︰ 3.
4., according to a kind of described in claim 2 preparation method of seven yuan of melon ring [3] rotaxanes, it is characterized in that the synthetic technological condition of step (2) seven yuan of melon ring [3] rotaxanes is obtained by reacting product with compound G and seven yuan of melon ring Q [7]
In there-necked flask, add the object N that (1) step is obtained, N '-two caproic acid-1,2-bis-(4-pyridyl) vinyl bromide G, seven yuan of melon rings, distilled water, reacting by heating, lower the temperature after reacting completely, rotary evaporation of solvent, washing with acetone, suction filtration, vacuum-drying, obtained [3] rotaxane probe:
Temperature of reaction: 50 DEG C
Reaction times: 12h
Reaction solvent: distilled water
Mol ratio: G ︰ Q [7]=1 ︰ 20.
5. it is characterized in that the fluorescent probe as Methionin or arginine or Methionin and ar-ginine mixtures according to a kind of described in claim 1 application of seven yuan of melon ring [3] rotaxanes, for the fluorophotometric qualitative and quantitative analysis of Methionin or arginine or Methionin and ar-ginine mixtures.
6. according to a kind of described in claim 5 application of seven yuan of melon ring [3] rotaxanes, it is characterized in that with [3] rotaxane for fluorescent probe, for the excitation wavelength 317nm of the fluorescence spectrum of Methionin or arginine or Methionin and ar-ginine mixtures, maximum emission wavelength 375nm. detectability is low to moderate 10 most -6molL -1, correct linearity range 1 × 10 -5~ 1.2 × 10 -4molL -1.
CN201310435721.0A 2013-09-23 2013-09-23 Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof Pending CN104447768A (en)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104877674A (en) * 2015-05-26 2015-09-02 贵州大学 Aqueous solution capable of generating white fluorescence through excitation and preparation method thereof
CN105038761A (en) * 2015-05-26 2015-11-11 贵州大学 Fluorescence wavelength adjustable material and applications thereof
CN105061775A (en) * 2015-08-09 2015-11-18 大连理工大学 Method for assembling and preparing novel organic solid fluorescent material by cucurbituril anions
CN106117253A (en) * 2016-07-13 2016-11-16 贵州大学 The super molecular complex of a kind of melon ring and Amino acid synthesis and preparation method and application
CN106565721A (en) * 2016-10-25 2017-04-19 贵州大学 Fluorescent reagent for selectively recognizing lysine and methionine and recognition application thereof
CN106674235A (en) * 2016-11-12 2017-05-17 贵州大学 TMeQ [6] and D, L-serine supramolecular complex as well as preparation method and application thereof
CN106674236A (en) * 2016-11-12 2017-05-17 贵州大学 TMeQ[6] and D,L-glutamine supramolecular complex as well as preparation method and application thereof
CN106674234A (en) * 2016-11-12 2017-05-17 贵州大学 TMeQ[6] and amino acid super-molecular complex and preparation method and application thereof
CN106905958A (en) * 2017-03-21 2017-06-30 贵州大学 A kind of fluorescence probe based on trans cucurbit(7)uril, preparation method and application
CN109232589A (en) * 2018-10-19 2019-01-18 贵州大学 A kind of fluorescence probe and its preparation and application
CN110759926A (en) * 2019-11-06 2020-02-07 南开大学 Water-soluble phenylpyridine derivative-cucurbituril supramolecular pseudorotaxane assembly and application thereof in cell phosphorescence imaging
CN112014364A (en) * 2019-05-28 2020-12-01 南京工业大学 Method for screening microorganisms by using supramolecular fluorescence microfluidic technology
CN116217573A (en) * 2023-02-24 2023-06-06 南开大学 Vertical monomolecular film field effect control switch and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009097439A1 (en) * 2008-01-29 2009-08-06 The Regents Of The University Of California Nano-devices having valves for controlled release of molecules
CN102268251A (en) * 2011-06-09 2011-12-07 西北农林科技大学 Application of dye and cucurbit [8] uril self-assembled compound as fluorescent probe

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009097439A1 (en) * 2008-01-29 2009-08-06 The Regents Of The University Of California Nano-devices having valves for controlled release of molecules
CN102268251A (en) * 2011-06-09 2011-12-07 西北农林科技大学 Application of dye and cucurbit [8] uril self-assembled compound as fluorescent probe

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ARTEM I. VEDERNIKOV ET AL.: "Pseudorotaxane complexes between viologen vinylogues and cucurbit[7]uril:New prototype of photocontrolled molecular machine", 《JOURNAL OF MOLECULAR STRUCTURE》, vol. 989, 22 January 2011 (2011-01-22), pages 114 - 121, XP 028183328, DOI: doi:10.1016/j.molstruc.2011.01.013 *
DAVID M. BAILEY ET AL.: "Supramolecular Tandem Enzyme Assays for Multiparameter Sensor Arrays and Enantiomeric Excess Determination of Amino Acids", 《CHEMISTRY-A EUROPEAN JOURNAL》, vol. 14, 28 May 2008 (2008-05-28), pages 6069 - 6077, XP 055185862, DOI: doi:10.1002/chem.200800463 *
ONUR BUYUKCAKIR ET AL.: "Autonomous Shuttling Driven by an Oscillating Reaction: Proof of Principle in a Cucurbit[7]uril-Bodipy Pseudorotaxane", 《ORGANIC LETTERS》, vol. 15, no. 5, 11 February 2013 (2013-02-11), pages 1012 - 1015 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105038761A (en) * 2015-05-26 2015-11-11 贵州大学 Fluorescence wavelength adjustable material and applications thereof
CN104877674A (en) * 2015-05-26 2015-09-02 贵州大学 Aqueous solution capable of generating white fluorescence through excitation and preparation method thereof
CN105061775B (en) * 2015-08-09 2017-08-01 大连理工大学 It is a kind of that the method for preparing new fluorescent organic solid material is assembled by Cucurbituril anion
CN105061775A (en) * 2015-08-09 2015-11-18 大连理工大学 Method for assembling and preparing novel organic solid fluorescent material by cucurbituril anions
CN106117253A (en) * 2016-07-13 2016-11-16 贵州大学 The super molecular complex of a kind of melon ring and Amino acid synthesis and preparation method and application
CN106117253B (en) * 2016-07-13 2019-02-19 贵州大学 A kind of super molecular complex and preparation method and application of melon ring and Amino acid synthesis
CN106565721A (en) * 2016-10-25 2017-04-19 贵州大学 Fluorescent reagent for selectively recognizing lysine and methionine and recognition application thereof
CN106565721B (en) * 2016-10-25 2018-11-13 贵州大学 A kind of fluorescent reagent and its identification application of selection identification lysine and methionine
CN106674234A (en) * 2016-11-12 2017-05-17 贵州大学 TMeQ[6] and amino acid super-molecular complex and preparation method and application thereof
CN106674236A (en) * 2016-11-12 2017-05-17 贵州大学 TMeQ[6] and D,L-glutamine supramolecular complex as well as preparation method and application thereof
CN106674235A (en) * 2016-11-12 2017-05-17 贵州大学 TMeQ [6] and D, L-serine supramolecular complex as well as preparation method and application thereof
CN106674234B (en) * 2016-11-12 2019-05-03 贵州大学 A kind of TMeQ [6] and amino acid super molecular complex and preparation method and application
CN106905958A (en) * 2017-03-21 2017-06-30 贵州大学 A kind of fluorescence probe based on trans cucurbit(7)uril, preparation method and application
CN109232589A (en) * 2018-10-19 2019-01-18 贵州大学 A kind of fluorescence probe and its preparation and application
CN109232589B (en) * 2018-10-19 2021-04-06 贵州大学 Fluorescent probe and preparation and application thereof
CN112014364A (en) * 2019-05-28 2020-12-01 南京工业大学 Method for screening microorganisms by using supramolecular fluorescence microfluidic technology
CN110759926A (en) * 2019-11-06 2020-02-07 南开大学 Water-soluble phenylpyridine derivative-cucurbituril supramolecular pseudorotaxane assembly and application thereof in cell phosphorescence imaging
CN110759926B (en) * 2019-11-06 2021-11-12 南开大学 Water-soluble phenylpyridine derivative-cucurbituril supramolecular pseudorotaxane assembly and application thereof in cell phosphorescence imaging
CN116217573A (en) * 2023-02-24 2023-06-06 南开大学 Vertical monomolecular film field effect control switch and preparation method thereof

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