CN109422667A - A kind of naphthonitrile class hydrogen sulfide fluorescence probe - Google Patents

A kind of naphthonitrile class hydrogen sulfide fluorescence probe Download PDF

Info

Publication number
CN109422667A
CN109422667A CN201710717870.4A CN201710717870A CN109422667A CN 109422667 A CN109422667 A CN 109422667A CN 201710717870 A CN201710717870 A CN 201710717870A CN 109422667 A CN109422667 A CN 109422667A
Authority
CN
China
Prior art keywords
hydrogen sulfide
naphthonitrile
fluorescence probe
class
fluorescence
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.)
Granted
Application number
CN201710717870.4A
Other languages
Chinese (zh)
Other versions
CN109422667B (en
Inventor
杨绍祥
田红玉
刘永国
孙宝国
王皓
王嘉琳
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.)
Beijing Technology and Business University
Original Assignee
Beijing Technology and Business 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 Beijing Technology and Business University filed Critical Beijing Technology and Business University
Priority to CN201710717870.4A priority Critical patent/CN109422667B/en
Publication of CN109422667A publication Critical patent/CN109422667A/en
Application granted granted Critical
Publication of CN109422667B publication Critical patent/CN109422667B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • 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"
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

Landscapes

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

Abstract

The invention discloses a kind of naphthonitrile class hydrogen sulfide fluorescence probe, particular chemical formula is shown below:

Description

A kind of naphthonitrile class hydrogen sulfide fluorescence probe
Technical field
The present invention relates to a kind of naphthonitrile class hydrogen sulfide fluorescence probe and its applications in detection hydrogen sulfide.
Background technique
Hydrogen sulfide (H2S) there is rotten egg smell in low concentration, the hydrogen sulfide of low concentration is to eye, respiratory system and maincenter mind All had an impact.Sucking a small amount of high-concentration hydrogen sulfide can be a kind of acute severe toxicity in fatal in the short time.
Due to the strong reducing action of grape wine itself, in the storage of grape wine, some sulfide can be converted into sulphur Change hydrogen.Hydrogen sulfide is one of main sulfide in beer, and taste threshold value is 10 μ g/L, very big on beer flavor influence, high-quality It is (1~5) μ g/L at bottled beer content.When content is more than 10 μ g/L in beer, can feel apparent " yeast stink ", " raw vinosity ", " onion flavor " are in rotten-egg odour, it is strong that one are generated when coexisting with biacetyl, acetaldehyde when content reaches 50 μ g/L Strong herbaceous taste.So can not only be had an impact to the quality of beer, grape wine itself when hydrogen sulfide content is higher, also deposit In certain food-safety problem.So carrying out detection method of content research of the hydrogen sulfide in wine has important practical meaning Justice.
Currently, hydrogen sulfide content method for measuring has headspace gas chromatography, sub-methyl blue spectrum analysis, fluorophotometric Method measurement, gas-phase molecular absorption spectrometry method etc..Small organic molecule fluorescence probe detection method is since it is with letter in various methods The characteristics such as single, convenient, at low cost, quick, sensitive and its potential imaging, have proved to be a kind of very effective detection side Method, many small organic molecule fluorescence probes are developed at present.
Naphthonitrile class compound have stronger fluorescence intensity, become fluorescence probe using very extensive fluorophor it One.
Summary of the invention
It is an object of the present invention to provide a kind of naphthonitrile class hydrogen sulfide fluorescence probes, it is suitable in food, drug, cosmetics etc. Hydrogen sulfide is detected in product.
More particularly, the present invention relates to a kind of naphthonitrile class hydrogen sulfide fluorescence probes, it is indicated by following formula:
Detailed description of the invention
Fig. 1 be in phosphate buffered saline solution, with the addition of various concentration hydrogen sulfide, fluorescence probe of the invention (10 μ M fluorescence intensity change).Insertion figure: the concentration of cysteine.
Fig. 2 is in phosphate buffered saline solution, and fluorescence probe of the invention (10 μM) fluorescence intensity is with concentration of hydrogen sulfide The standard curve of variation.
Specific embodiment
The preparation of 1. naphthonitrile class hydrogen sulfide fluorescence probe of embodiment
Synthetic route is shown below:
1.01g (6mmol) 6- hydroxyl -2- naphthonitrile (1) and 1.12g (6mmol) 2,4-dinitrofluorobenzene (2) are added to In 50mL three-necked flask, then triethylamine being dripped by one and is added thereto, 10mL chloroform is added, is heated to reflux 5h.Afterwards by temperature It is down to room temperature, recrystallizing methanol obtains yellow crystals 1.67g, yield 83.5%.
Product is levied by nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon stave.
1H NMR (600MHz, DMSO), δ (ppm): 8.94 (d, J=2.79Hz, 1H), 8.65 (s, 1H), 8.47 (dd, J =9.21Hz, J=2.79Hz, 1H), 8.23 (d, J=9.03Hz, 1H), 8.08 (d, J=8.61Hz, 1H), 7.85 (m, 2H), 7.62 (dd, J=9.03Hz, J=2.46Hz, 1H), 7.39 (d, J=9.21Hz, 1H)13C NMR (125MHz, DMSO), δ (ppm): 154.80,154.34,142.71,140.52,135.95,134.80,132.27,130.21,130.18,129.44, 127.95,122.44,121.85,121.46,119.45,116.60,108.78.
The fluorescence intensity of fluorescence probe of the invention is as the variation of hydrogen sulfide according to the variation as shown in Figure 1, can make The standard curve that fluorescence probe (10 μM) fluorescence intensity changes with concentration of hydrogen sulfide, standard curve was as shown in Fig. 2, by should The foundation of standard curve, fluorescence probe of the invention can be used for the quantitative detection of hydrogen sulfide.
Hydrogen sulfide content in 2. naphthonitrile class hydrogen sulfide fluorescence probe quantitative detection beer of embodiment
By 20 μ L naphthonitrile class hydrogen sulfide fluorescence probes, the buffer solution of 480 μ L DMSO, 1.5mL pH=7.0 is added to Cuvette.20 μ L beer samples are added again, are reacted 15 minutes under the conditions of 25 DEG C, fluorescence detection is carried out with 287nm excitation wavelength, then 5 μM, 10 μM of hydrogen sulfide standard solution are added respectively, and carrying out fluorescence detection will be upper according to the standard curve of fluorescence intensity and concentration It states detected value and is converted into concentration of hydrogen sulfide, calculate TIANZHU XINGNAO Capsul.Surveyed beer sample concentration of hydrogen sulfide is 1.82 μM, adds standard Sample concentration is respectively 6.26 μM, 11.16 μM after solution, and TIANZHU XINGNAO Capsul is respectively 92%, 95%.
It can be used for hydrogen sulfide content in beer according to the provable naphthonitrile class hydrogen sulfide fluorescence probe of the invention of embodiment 2 Measurement.

Claims (2)

1. a kind of naphthonitrile class hydrogen sulfide fluorescence probe, particular chemical formula are as follows:
2. the application that fluorescence probe described in claim 1 detects hydrogen sulfide in food, drug, cosmetics.
CN201710717870.4A 2017-08-23 2017-08-23 Naphthalocyanine hydrogen sulfide fluorescent probe Active CN109422667B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710717870.4A CN109422667B (en) 2017-08-23 2017-08-23 Naphthalocyanine hydrogen sulfide fluorescent probe

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710717870.4A CN109422667B (en) 2017-08-23 2017-08-23 Naphthalocyanine hydrogen sulfide fluorescent probe

Publications (2)

Publication Number Publication Date
CN109422667A true CN109422667A (en) 2019-03-05
CN109422667B CN109422667B (en) 2021-10-08

Family

ID=65498849

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710717870.4A Active CN109422667B (en) 2017-08-23 2017-08-23 Naphthalocyanine hydrogen sulfide fluorescent probe

Country Status (1)

Country Link
CN (1) CN109422667B (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004023097A2 (en) * 2002-09-03 2004-03-18 Anticancer, Inc. Homocysteine assay adaptable to screening
CN103865522A (en) * 2014-02-28 2014-06-18 浙江大学 Fluorescence molecular probe and application thereof in hydrogen sulfide detection
CN104447421A (en) * 2014-10-28 2015-03-25 苏州罗兰生物科技有限公司 Preparation and application of novel cysteine and homocysteine fluorescence probe
CN104531136A (en) * 2014-12-29 2015-04-22 大连理工常熟研究院有限公司 Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe
US20160274123A1 (en) * 2013-11-18 2016-09-22 Postech Academy-Industry Foundation One-Photon and/or Two-Photon Fluorescent Probe for Sensing Hydrogen Sulfide, Imaging Method of Hydrogen Sulfide Using Same, and Manufacturing Method Thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004023097A2 (en) * 2002-09-03 2004-03-18 Anticancer, Inc. Homocysteine assay adaptable to screening
US20160274123A1 (en) * 2013-11-18 2016-09-22 Postech Academy-Industry Foundation One-Photon and/or Two-Photon Fluorescent Probe for Sensing Hydrogen Sulfide, Imaging Method of Hydrogen Sulfide Using Same, and Manufacturing Method Thereof
CN103865522A (en) * 2014-02-28 2014-06-18 浙江大学 Fluorescence molecular probe and application thereof in hydrogen sulfide detection
CN104447421A (en) * 2014-10-28 2015-03-25 苏州罗兰生物科技有限公司 Preparation and application of novel cysteine and homocysteine fluorescence probe
CN104531136A (en) * 2014-12-29 2015-04-22 大连理工常熟研究院有限公司 Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
AVIJIT KUMAR DAS，等: "Neighbouring group participation of thiol through aldehyde group assisted thiolysis of active ether: ratiometric and vapor phase fast detection of hydrogen sulfide in mixed aqueous media", 《NEW J. CHEM.》 *
高敏，等: "检测硫化氢分子的荧光探针", 《化学进展》 *

Also Published As

Publication number Publication date
CN109422667B (en) 2021-10-08

Similar Documents

Publication Publication Date Title
Beccari et al. Presence of Fusarium species and other toxigenic fungi in malting barley and multi-mycotoxin analysis by liquid chromatography–high-resolution mass spectrometry
Burini et al. Determination of formaldehyde in spirits by high-performance liquid chromatography with diode-array detection after derivatization
da Silva Ferreira et al. Heterocyclic acetals from glycerol and acetaldehyde in port wines: evolution with aging
Ajtony et al. Determination of ethyl carbamate in wine by high performance liquid chromatography
CN104101591A (en) Fast detection method for surface enhanced Raman scattering of trace pesticide residues in oranges
Xia et al. Quantitative strategies for detecting different levels of ethyl carbamate (EC) in various fermented food matrices: An overview
CN106018624B (en) The HPLC detection methods of food nitrite nitramine
Azab et al. Fluorescence and electrochemical sensing of pesticides methomyl, aldicarb and prometryne by the luminescent europium-3-carboxycoumarin probe
CN113278015B (en) Fluorescent probe and preparation method and application thereof
CN110004148B (en) Alternariol aptamer affinity column and preparation method and application thereof
Takase et al. Analysis of rotundone in Japanese Syrah grapes and wines using stir bar sorptive extraction (SBSE) with heart-cutting two-dimensional GC-MS
Li et al. Furfural and organic acid targeted carbon dot sensor array for the accurate identification of Chinese baijiu
CN105968051B (en) A kind of organic molecule fluorescence probe and preparation method for detecting methanol
CN110818646B (en) Aggregation-induced emission-based small-molecule fluorescent probe and preparation method and application thereof
Zeußel et al. Colorimetric Method for Instant Detection of Lysine and Arginine Using Novel Meldrum's Acid‐Furfural Conjugate
CN104132920A (en) Method for measuring Ag<+> or F<-> through fluorescence quenching
CN109422738A (en) A kind of Coumarins hydrogen sulfide fluorescence probe
Ghanem et al. Differentiation and identification of cachaça wood extracts using peptide-based receptors and multivariate data analysis
CN109400563B (en) Hypochlorous acid fluorescent probe and preparation method and application thereof
Harpaz et al. Portable biosensors for rapid on-site determination of cannabinoids in cannabis, a review
CN104650105B (en) Rhodamine B derivative containing 8 quinolin-2-ylamine groups, preparation method, application and to Cr3+And Cu2+The method carrying out fluorescence analysiss
CN109021000A (en) A kind of fluorescence probe, synthetic method and application detecting hydrogen peroxide
CN109422667A (en) A kind of naphthonitrile class hydrogen sulfide fluorescence probe
Chen et al. Assay of picogram level isocarbophos residue on tangerines and oranges with luminol–albumin chemiluminescence system
CN109422669A (en) A kind of aphthols hydrogen sulfide fluorescence probe

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