WO2015125055A1 - Molécule, détecteur de cadmium et procédé afférent - Google Patents

Molécule, détecteur de cadmium et procédé afférent Download PDF

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WO2015125055A1
WO2015125055A1 PCT/IB2015/051113 IB2015051113W WO2015125055A1 WO 2015125055 A1 WO2015125055 A1 WO 2015125055A1 IB 2015051113 W IB2015051113 W IB 2015051113W WO 2015125055 A1 WO2015125055 A1 WO 2015125055A1
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n8hq
norbornene
formula
derived
ion
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PCT/IB2015/051113
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English (en)
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Raja Shunmugam
Santu SARKAR
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Raja Shunmugam
Sarkar Santu
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Publication of WO2015125055A1 publication Critical patent/WO2015125055A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

Definitions

  • the present subject matter relates to a sensor and a method thereof. More specifical ly, the present subject matter relates to a sensor to sense presence of cadmium in a sample.
  • Cadmium is one such heavy metal. Humans and other l iving and non-living ent it ies are exposed to cadmium through more than one ways. Cadmium is being used largely in industry, military affairs, agriculture and metal lurgy. Exposure to cadmium causes adverse effect on health and environment and therefore it is desirable to detect presence of cadmium to avoid exposure.
  • chemosensors For sensing presence of heavy metals in a sample, often colorimetric and fluorescence chemosensors are used. Although, these sensors are very popular and sense heavy metals such as mercury, copper and lead etc., these sensors often gets confused between cadmium and other heavy metals. Where only cadmium is desired to be sensed, the chemosensors often provide erroneous results. This is because the chemosensors are smal l molecule based sensors and they perform detect ion of heavy metals based on the chemical propert ies and spectral changes that takes place when the molecules of chemo- sensor react with the heavy metals.
  • chemosensors have other limitations. For example, these sensors require a sample to be an organic solution or require presence of an acid for sensing. Therefore, these sensors limited to organic samples, and fail where a sample is aqueous. In addition these sensors are not effective for in-field testing.
  • some sensors may employ 8-hydroxyquinoline as fluorophore for sensing heavy metals.
  • 8-hydroxyquinoline as fluorophore
  • its effective "turn-on" response in organic solvent, low specificity to Cd 2+ , and very low response for aqueous samples has restricted its application in quantitative detection Cd 2+ .
  • the norbornene derived 8-hydroxyquinoline (N8HQ) of the present subject matter increases specificity of detection of cadmium and its response in detection of cadmium in organic solvent as well as aqueous samples is substantially better as compared to any sensors that employ 8- hydroxyquinoline as fluorophore for sensing cadmium.
  • the norbornene derived 8-hydroxyquinoline (N8HQ) of the present subject matter shows relatively higher selectivity and sensitivity in detecting Cd with almost no interference from the other heavy metals, such as Hg, Zn etc.
  • the norbornene derived 8-hydroxyquinol ine (N8HQ) works as rat iometric turn-on sensor for cadmium.
  • the present subject matter provides a polymer norbornene derived 8-hydroxyquinoline (PN8HQ).
  • the polymer norbornene derived 8-hydroxyquinoline (PN8HQ) shows further higher select ivity and sensit ivity for cadmium as compared with the norbornene derived 8- hydroxyquinol ine (N8HQ) with almost no interference from the other heavy metals such as Hg, Zn, Cu etc.
  • the norbornene derived 8- hydroxyquinol ine (N8HQ) or its polymer PN8HQ also demonstrates effect ive detect ion of cadmium in aqueous environment or in aqueous samples.
  • the polymer of the present subject matter is advantageous over convent ion smal l molecule based chemosensors, because a cadmium sensor made out of the polymer of the present subject matter could select ively sense cadmium even without very little interact ion from zinc.
  • the present subject matter provides solut ions to the above d iscussed and other problems.
  • the present subject matter provides a norbornene derived 8-hydroxyquinoline (N8HQ).
  • the present subject matter provides a method comprising: react ing norbornene anhydride with glycine in the presence of a base and a f irst solvent to obtain norbornene funct ionalized acid; and coupling the norbornene funct ional ized acid with 8-hydroxyquinol ine in the presence of second solvent to obtain norbornene derived 8-hydroxyquinoline (N8HQ).
  • the norbornene anhydride is represented by Formula-3
  • the norbornene funct ional ized acid is represented by Formula-
  • the norbornene derived 8-hydroxyquinol ine (N8HQ) is represented by Formula-i
  • the method is represented by equat ion (M) ...Equation(M)
  • the method includes polymerizing norbornene derived 8-hydroxyquinoline (N8HQ) and the polymerized norbornene derived 8-hydroxyquinoline (PN8HQ) is represented by Formula -i
  • the method comprises purifying norbornene derived 8-hydroxyquinoline (N8HQ) with sil ica and hexane-ethyl acetate.
  • the f irst solvent is an organic solvent and is any one or combinat ion of toluene and xylene; the base is selected from triethylamine or d imethylaminopyrid ine; and the second solvent is selected from d icyclohexyl carbod iimide and d ichloromethane.
  • the method comprises polymerizat ion of compound of formula 1 in the presence of Grubbs catalyst and a third solvent, wherein the third solvent is an organic solvent and is selected from d ichloromethane or d ichloromethane -methanol mixture.
  • the present subject matter provides a cadmium detector comprising a strip coated with norbornene derived 8- hydroxyquinol ine (N8HQ) compound of formula 1 or polymer thereof.
  • the strip is a paper, wooden, plast ic, metal, glass, china strip or any strip made of material that supports coat ing of norbornene derived 8- hydroxyquinol ine(N8HQ) or polymer thereof.
  • the present subject matter provides, a norbornene derived 8-hydroxyquinol ine (N8HQ) compound of Formula-i and polymer thereof
  • the present subject matter provides a polymer norbornene derived 8-hydroxyquinol ine (PN8HQ) compound of Formula-i and polymer thereof
  • FIG. 1, FIG. 2 and FIG. 3 show respect ively 1 H NMR, 13 C NMR and 1 H NMR spectroscopy
  • FIG. 1a shows a scheme of synthesis of control molecule of the present subject matter
  • FIG. ⁇ and FIG. 5 show absorbance and fluorescence spectrum respect ively
  • FIG. 6 shows absorbance spectra of N8HQ upon t itrat ion with Cd 2+ in MeOH-H 2 0 and
  • FIG. 7 shows emission spectra of N8HQ upon t itrat ion with Cd 2+ ( x io " M) in MeOH-H 2 0;
  • FIG. 8 shows a plot of emission intensity of N8HQ (4 x io "4 M) at 540 nm with gradual add it ion of Cd 2+ (4x1 ⁇ 4 M) in MeOH-H 2 0 (1:1) ⁇ ⁇ : 310 nm;
  • FIG. 8a shows fluorescence spectra obtained by t itrat ing N8HQ (o.4mM) with Cd 2+ ( ⁇ ) for detect ing the lowest limit of sensing Cd 2+ in MeOH:H 2 0 (1:1).
  • ⁇ ⁇ 310 nm;
  • FIG. 8b shows schemat ic representat ion of the photoinduced Electron transfer
  • FIG. 9 shows a Job's plot showing 1:1 bind ing stoichiometry between N8HQ and Cd 2+ in MeOH-H20 (1:1);
  • FIG. io, FIG. 11 and FIG. 12 show N8HQ molecule and two possible energy minimized structure of N8HQ and possible bind ing sites for CdCI 2 respect ively;
  • FIG. 13a, FIG. 13b and FIG. 13c show response of the device of the present subject matter as observed in a lab; and [0027] FIG. lit, FIG. 15 and FIG. 16 show graphs demonstrat ing select ivity behaviour of N8HQ and PN8HQ, especial ly between Zn 2+ and Cd 2+ .
  • the present subject matter also provides a device configured to sense cadmium, the device comprises norbornene derived 8-hydroxyquinoline (N8HQ).
  • the representat ive compounds that may be ut ilized for pract icing the subject matter are 8-hydroxyquinoline, glycine, c/s-5-norbornene-enafo-2, 3-d icarboxyl ic anhydride, triethylamine (TEA), d icyclohexyl carbod iimde (DCC), d ichloromethane (DCM), methanol (MeOH), Deionized water, toluene, CDCI 3 .
  • Some representat ive metal salts that may be used for pract ising the subject matter are CdCI 2 , HgCI 2 , Pb(No 3 ) 2 , FeCI 2 . 4H 2 0, CuS0 .5H 2 0, NaCI, MgCI 2 , Ba(N0 3 ) 2 , MnS0 , NiCI 2 .6H 2 0, CdCI 2 , ZnCI 2 etc.
  • the present subject matter provides a method of preparat ion of norbornene derived 8-hydroxyquinoline (N8HQ) comprising: react ing norbornene anhydride of formula-3 with glycine and tri-ethylamine to obtain norbornene funct ionalized acid of Formula-4.
  • the glycine may be used as the glycine possesses both amine and carboxylic acid funct ional ity and therefore provides a moiety that can be incorporated in norbornene anhydride to generate correspond ing acid.
  • the norbornene acid can be employed for coupling with 8-hydroxyquinol ine by simple coupl ing reagents.
  • the triethylamine may be used to generate basic med ium.
  • Other subst itute l ike d imethylaminopyrid ine can also be used.
  • the react ion may be performed in presence of a first organic solvent to prepare norbornene funct ional ized acid of Formula-4 of formula-4.
  • a first organic solvent to prepare norbornene funct ional ized acid of Formula-4 of formula-4.
  • toluene may be the first organic solvent.
  • the toluene may be used in the react ion as it has a boil ing point (iii°C) that is favorable for the react ion as the react ion requires a reflux cond it ion, which is achieved by having boiling point as high as that of toluene.
  • xylene may also be used as the f irst organic solvent.
  • the method comprises react ing compound of formula-4 with 8-hydroxyquinol ine in the presence of a second organic solvent to obtain norbornene derived 8-hydroxyquinol ine (N8HQ) of formula-i.
  • DCM may be used as the second organic solvent, as DCM enables coupl ing react ion. Further for the present subject matter, const ituents of the react ion are soluble in the DCM.
  • the method further provides that the first organic solvent is toluene.
  • the first organic solvent is selected from but not l imited to, toluene and may also be xylene.
  • the second organic solvent is selected from but not l imited to d icyclohexyl carbod iimide also known as DCC, DCM (d ichloromethane).
  • the method comprises polymerizing the compounds of formula-i to obtain polymer norbornene derived 8-hydroxyquinol ine (PN8HQ) of formula- 2.
  • the method comprising polymerizing norbornene derived 8-hydroxyquinol ine (N8HQ) of formula-i in the presence of Grubbs catalyst (G2) in the presence of a third organic solvent.
  • the method provides the third organic solvent is selected from but not l imited to DCM. I n one embod iment, the third organic solvent may be DCM-Methanol mixture.
  • the norbornene funct ional ized acid is synthesized fol lowing a reported procedure (Conrad, R.M.; Grubbs, R.H. Angew. Chem., Int. Ed. 2009, 48, 8238-8330).
  • the norbornene funct ional ized acid (about 548 mg, about 2.48 mmol) is taken and d issolved in about 12 ml of dry DCM and st irred for about 5 min to d issolve in a clean, dry round bottomed flask.
  • Dichloromethane (DCM) may be d ist il led over calcium hydride and used for react ions.
  • DCC (about 767 mg, about 3.72 mmol) is added to the flask and st irred for about 20 min to form white precipitates.
  • 8-hydroxyquinol ine (about 300 mg, about 2.o6mmol) is added to it and st irred for about 24h.
  • the white precipitate of d icyclohexylurea (DCU) is removed by filtrat ion and the filtrate is washed with saturated bicarbonate solut ion.
  • Organic layer (DCM) is separated and dried over sod ium sulphate. DCM is evaporated to get yel lowish white sol id.
  • FIG. 1a shows a scheme of synthesis of control molecule of the present subject matter. It may be observed from the FIG. 1a that the control molecule does not have anhydride funct ional ity and therefore, it does not show any photo induced emission (PET) as against what may be observed in case of the molecule or the polymer of the present subject matter which has anhydride funct ional ity.
  • PET photo induced emission
  • FIG. 1 and FIG. 2 show respect ively 'H NMR and 13 C NMR spectroscopy conf irming format ion of norbornene derived 8-hydroxyquinol ine (N8HQ).
  • the 1 H NMR spectroscopy signals at 6.02-6.06 ppm corresponds to norbornene olef inic bonds and signals at aromat ic region corresponds to 8- hydroxyquinol ine.
  • 13 C NMR spectroscopy, CHN analysis and mass spectroscopy further conf irms the format ion of N8HQ.
  • the polymerizat ion of the N8HQ may be performed as fol lows.
  • About 20 mg of N8HQ is taken in about 10 ml round bottom flask and purged with N 2 .
  • Dry DCM about 0.2 ml is added to d issolve the monomer.
  • About 0.8 mg of second generat ion Grubbs catalyst (G2) is taken separately in a vial under N 2 atmosphere and d issolved in about 0.1 ml of dry DCM.
  • Solut ion of G2 is added to monomer solut ion and st irred at room temperature for about 24 hours.
  • Ethyl-vinyl ether is added to quench the polymerizat ion. Polymer precipitates in d iethyl ether.
  • the format ion of polymer N8HQ (PN8HQ) is confirmed using 1 H NMR techniques.
  • FIG. 3 shows the 1 H NMR spectroscopy confirming format ion of PN8HQ.
  • FIG. ⁇ and FIG. 5 respect ively show absorbance and fluorescence spectrum of N8HQ in methanol-water (1:1) system.
  • the absorbance spectrum of N8HQ exhibits three bands at 288 nm, 300 nm and 313 nm.
  • Free N8HQ showed weak emissions at 346 nm and 372 nm.
  • the observed weak emission of N8HQ may be attributed due to the N lone electron pairs in the molecule that are involved in a rad iat ion less process via the ⁇ * state.
  • FIG. 6 shows absorbance spectra of N8HQ upon t itrat ion with Cd 2+ in MeOH-H20.
  • the metal chelat ing abil ity of N8HQ is stud ied by add ing it in methanol-water solvent system to the metal salts in water.
  • N8HQ shows rat iometric behaviour with Cd 2+ . While t itrat ing N8HQ with Cd 2+ , the absorbance at 288 nm, 300 nm and 313 nm decreases linearly with increasing amount of Cd 2+ (o to 2 equivalent), whereas two new peaks appear gradually at 335 nm and 373 nm with an isobestic point at 326 nm.
  • FIG.7 shows emission spectra of N8HQ (4 x io "4 M) in MeOH-H 2 0.
  • the emission properties of N8HQ are studied with gradual addition of Cd 2+ (o to 2 equivalent) by exciting the solution at 310 nm.
  • the inset of FIG.7 shows titration curve based on emission at 540 nm.
  • Aex 310 nm (where Aex is excitation wavelength) .
  • the intensity at 346 nm and 372 nm decreases gradually with the appearance of a new peak at 536 nm.
  • a red shift of 164 nm is observed from 372 nm to 536 nm accompanied with an isoemissive point at 450 nm.
  • the quantum yield of N8HQ-Cd 2+ complex is found to be 0.31 as measured by taking quinine sulfate as standard.
  • FIG.8 shows a plot of emission intensity of N8HQ with respect to concentration of Cd.
  • a graph of emission intensity of N8HQ (4 x 10-4 M) at 540 nm with gradual addition of Cd 2+ (4x1 ⁇ 4 M) in MeOH-H 2 0 (1:1) ⁇ ⁇ : 310 nm is plotted. From the graph dissociation constant (K d ) may be calculated by the following equation:
  • F F 0 + (F max - F 0 ) ([Cd 2+ ] f ) / (K d + [Cd 2+ ] f )
  • F is the fluorescence intensity
  • F max is the maximum fluorescence intensity
  • F 0 is the fluorescence intensity with no addition of Cd 2+
  • [Cd 2+ ]f is the free Cd 2+ Concentration.
  • the apparent dissociation constant of N8HQ-Cd 2+ is calculated to be 50 ⁇ .
  • FIG.8a shows fluorescence spectra obtained by titrating N8HQ (o.4mM) with Cd 2+ ( ⁇ ) for detect ing the lowest limit of sensing Cd 2+ in MeOH:H 2 0 (1:1).
  • the lowest detect ion limit of the Cd 2+ is at least upto 1.6 nM may be achievable through fluorescence t itrat ion experiment.
  • it shal l become clear to a person that the polymer N8HQ may provide better results.
  • d ifferent test cond it ions may provide varying results.
  • the Cd detect ion results may be improved by varying solvent systems and by using solvent mixtures.
  • the present subject matter also provides, the reversibility behaviour of the molecule N8HQ.
  • N8HQ ethylene d iamine tetraacet ic acid
  • EDTA ethylene d iamine tetraacet ic acid
  • fluorescence emission completely turns off and the emissions are similar to the free N8HQ.
  • This feature of present subject matter provides N8HQ as a reversible sensor molecule.
  • the reversible sensor includes regenerat ion of N8HQ by using EDTA to the N8HQ- Cd 2+ complex.
  • the red shift may be attributed to fluorescence signal transduct ion.
  • fluorescence signal transduct ion mechanism There are three major fluorescence signal transduct ion mechanism f irst being intermolecular charge transfer (ICT), fluorescence resonance energy transfer (FRET) and photo-induced electron transfer (PET).
  • ICT intermolecular charge transfer
  • FRET fluorescence resonance energy transfer
  • PET photo-induced electron transfer
  • the FRET requires, separate donor and acceptor, therefore likel i hood of FRET mechanism may be responsible to for red shift is less, as in the present system there are no separate donor and acceptors.
  • the ICT mechanism may as wel l be less l ikely to cause the red shift as, the lowest unoccupied molecular orbital (LUMO) on amide port ion of norbornene is much higher in energy than quinol ine LUMO, which may prohibit the intermolecular charge transfer.
  • LUMO lowest unoccupied molecular orbital
  • the sensor should have a receptor (at the bind ing site) and a flourophore, when a metal binds with the sensor, a fluorescence is observed due to PET.
  • the present system does not have a separate biding site or a fluorophore and despite of that if fluorescence or red shift is observed, then such fluorescence/red shift may be attributed to the fact that the entire sensor molecule itself is involved in photo-induced electron transfer and thereby causing fluorescence/red shift during binding of metal i.e. cadmium.
  • the red shift may be attributed to the PET because of: a) the prevention of non-radiative relaxation pathways of N- lone electron pairs in the molecule by Cd 2+ binding and ii) photoinduced electron transfer (PET) between 8-hydroxyquinoline and norbornene motif.
  • FIG. 8b shows schematic representation of the PET as may be contemplated for explaining the present subject matter.
  • FIG.9 is a Job's plot showing 1:1 binding stoichiometry between N8HQ and Cd 2+ in MeOH-H20 (1:1).
  • Job's plot is a method of continuous variation of mole fractions of two binding partners and is generally used to determine stoichiometry binding events. While titrating with Cd 2+ it is observed that fluorescence intensity at 536 nm increases linearly and remains constant after addition of 1 equivalent of Cd 2+ This is a support for a 1:1 binding stoichiometry between N8HQ & Cd 2+ .To determine the stoichiometry between N8HQ and Cd 2+ , method of continuous variation i.e. Job's method may followed. Results of FIG.9 confirm 1:1 binding of Cd 2+ to N8HQ.
  • FIG. 10, FIG. 11 and FIG. 12 show N8HQ molecule and two possible energy minimized structure of N8HQ and possible binding sites for CdCl2, respectively.
  • the metal ion binding sites of N8HQ may be optimized using density functional theory (DFT) calculation.
  • the optimization N8HQ shown is FIG.10 may be carried out without Cd 2+ at the B3LYP/6-3iG(d) level using the Gaussian package.
  • the structure with Cd 2+ may be performed with the biding sites shown in FIG.11 and FIG.12.
  • FIG. 11 it is found that for the coordination of Cd through carboxylate oxygen while the optimization of the structure of FIG.
  • FIG. 12 results in the coord inat ion through norbornene anhydride oxygen. It is also observed that the opt imized structure that a Cd 2+ ion suitably fit between the nitrogen of 8-hydroxyquinol ine. Also, the bond length in the case of structure of FIG. 12 is found to be shorter than the structure of FIG. 11. Further, the structure of FIG. 12 shows a lower in energy (11.4 Kcal/mol) structure as compared to the structure of FIG. 11. Furthermore mass spectroscopy also supports possibility of structure of FIG. 12 over the structure of FIG. 12.
  • N8HQ alone shows a mass peak at about 3 gnm whereas after add it ion of cadmium, N8HQ-Cd 2+ peak is observed at 46mm whereas peak for N8HQ-CdCl2 is observed at 53mm. It may be therefore believed that the structure of FIG. 12 having bind ing site the cadmium coord inat ion to norbornene anhydride oxygen is more l ikely.
  • FIG. lit, FIG. 15 and FIG. 16 show graphs correspond ing to detect ion of cadmium accord ing to an aspect of the present subject matter.
  • FIG. lit shows graph of rat iometric detect ion of cadmium using
  • FIG. 1 is an emission ratio spectra of N8HQ at 536nm and 372 nm (I536/I372) in the presence of indicated metal ions in MeOH: H2O (1:1). Aex: 310 nm.
  • FIG. 15 shows graph of detect ion of cadmium using PN8HQ where equal amount of metal impurit ies Hg 2+ , Pb 2+ , Co 2+ , Fe 2+ , Cu 2+ , Na + , Mg 2+ , Ba 2+ , Mn 2+ , Ni 2+ , Cd 2+ and Zn 2+ are present in a sample.
  • FIG. 15 is fluorescence intensity of PN8HQ f ilm on quartz slide in presence of Cd 2+ and d ifferent metal ions. Aex: 310 nm.
  • FIG. 16 shows graph of detect ion of cadmium using N8HQ where equal amount of anion impurit ies such as CI “ , Br “ , I “ , S0 “ , P0 “ , AcO “ , N0 3 “ , H 2 P0 “ , HS0 3 " are present in samples.
  • FIG. 16 shows graph correspond ing to change in fluorescence intensity of N8HQ in presence of Cd 2+ and different anions in MeOH-H 20 (1:1) at ⁇ ⁇ : 310 nm. It is observable from FIG. 14, FIG. 15 and FIG. 16 that only cadmium induces a significant red shift. [0053] It is apparent from the FIG. 1 and FIG.
  • FIG. 13a is grey scale image equivalent of response of solut ions to N8HQ-metal complexes of various metal ions in MeOH- H2O (1:1) taken under UV lamp.
  • FIG.i3b demonstrates paper strip coated with PN8HQ post and prior to exposure to Cd 2+ in water.
  • FIG 13c shows PN8HQ film on quartz slide after d ipping into cadmium solut ion exposed under UV lamp.
  • FIG. lit, FIG. 15 and FIG. 16 demonstrate select ivity behaviour of N8HQ and PN8HQ, especial ly between Zn 2+ and Cd 2+ .
  • the bind ing sites of N8HQ/PN8HQ appear to suitably f it for only cadmium in presence of other metal ions and emit bright green emission as shown in FIG. 13.
  • the subject matter further provides a device, comprising norbornene derived 8-hydroxyquinoline (N8HQ).
  • the device comprises a strip having coat ing of norbornene derived 8-hydroxyquinoline (N8HQ).
  • the device comprises polymer norbornene derived 8-hydroxyquinoline (PN8HQ).
  • the strip comprises coat ing for polymer of norbornene derived 8-hydroxyquinoline (PN8HQ).
  • the strip is a paper, wooden, plast ic, metal, glass, china clay strip or any strip made of material that supports coat ing of norbornene derived 8-hydroxyquinol ine(N8HQ) or its polymer and to enable detect ing of cadmium.
  • the device being a polymer based device.
  • a paper strip may be prepared coat ing the N8HQ or the polymer PN8HQ solut ion on a filter paper. The paper strip so prepared may be easily transported to field. Therefore the device of the present subject matter demonstrates easy in-f ield device applicat ion.
  • the paper strips made of PN8HQ showed a turn on response similar to its monomer N8HQ under the UV lamp.
  • the device accord ing to the present subject matter whether prepared on paper strip or on quartz strip or any other strip shows select ivity for cadmium and despite of being from the same group in the period ic table, other metals such as Zn, Hg etc do not respond to the device.
  • the fluorescence spectroscopy confirms that the PN8HQ coated quartz slide gets excited at 310 nm and responds to cadmium only even in the presence of zinc.
  • the device of present subject matter also provides a sensor that senses cadmium in presence of anions.
  • the methods may be performed in manner or order d ifferent than what is explained without depart ing from the spirit of the present subject matter. It should be understood that the subject matter is not intended to be limited to the part icular forms d isclosed. Rather, the subject matter is to cover all mod ificat ions, equivalents, and alternat ives fall ing within the spirit and scope of the subject matter as described above.

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Abstract

L'objet de cette invention porte sur un dispositif, une molécule et un procédé afférent. Le dispositif contient une 8-hydroxyquinoléine dérivée du norbornène (N8HQ). Dans un mode de réalisation, le dispositif comprend une bandelette portant un revêtement à base de 8-hydroxyquinoléine dérivée du norbornène (N8HQ). Dans un mode de réalisation, le dispositif contient une 8-hydroxyquinoléine dérivée d'un polymère de norbornène (PN8HQ). Dans un autre mode de réalisation, la bandelette porte un revêtement à base de 8-hydroxyquinoléine dérivée d'un polymère de norbornène (PN8HQ). Selon un autre aspect, la bandelette est une bandelette en papier, bois, plastique, métal, verre, porcelaine ou toute bandelette à base d'une matière qui supporte un revêtement à base de 8-hydroxyquinoléine dérivée du norbornène (N8HQ) ou de son polymère et capable de détecter le cadmium. Selon un aspect, l'objet de l'invention porte sur un dispositif qui est un dispositif à base de polymère.
PCT/IB2015/051113 2014-02-20 2015-02-15 Molécule, détecteur de cadmium et procédé afférent WO2015125055A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082819A2 (fr) * 2004-02-26 2005-09-09 Universiteit Gent Complexes metalliques s'utilisant dans la metathese d'olefine et les reactions de transfert d'atomes ou de groupes
US8470532B2 (en) * 2005-08-11 2013-06-25 The Board Of Trustees Of The University Of Illinois Aptamer-based colorimetric sensor systems

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082819A2 (fr) * 2004-02-26 2005-09-09 Universiteit Gent Complexes metalliques s'utilisant dans la metathese d'olefine et les reactions de transfert d'atomes ou de groupes
US8470532B2 (en) * 2005-08-11 2013-06-25 The Board Of Trustees Of The University Of Illinois Aptamer-based colorimetric sensor systems

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