CN109422667B - 一种萘甲腈类硫化氢荧光探针 - Google Patents

一种萘甲腈类硫化氢荧光探针 Download PDF

Info

Publication number
CN109422667B
CN109422667B CN201710717870.4A CN201710717870A CN109422667B CN 109422667 B CN109422667 B CN 109422667B CN 201710717870 A CN201710717870 A CN 201710717870A CN 109422667 B CN109422667 B CN 109422667B
Authority
CN
China
Prior art keywords
hydrogen sulfide
fluorescent probe
naphthalocyanine
beer
sulfide fluorescent
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
CN201710717870.4A
Other languages
English (en)
Other versions
CN109422667A (zh
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/zh
Publication of CN109422667A publication Critical patent/CN109422667A/zh
Application granted granted Critical
Publication of CN109422667B publication Critical patent/CN109422667B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

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

本发明公开了一种萘甲腈类硫化氢荧光探针，具体化学结构式如下式所示：

Description

一种萘甲腈类硫化氢荧光探针
技术领域
本发明涉及一种萘甲腈类硫化氢荧光探针以及其在检测硫化氢中的应用。
背景技术
硫化氢(H2S)在低浓度时有臭鸡蛋气味，低浓度的硫化氢对眼、呼吸***及中枢神经都有影响。吸入少量高浓度硫化氢可于短时间内致命，是一种急性剧毒。
由于葡萄酒自身的强还原作用，在葡萄酒的贮藏过程中，一些硫化物会转化为硫化氢。硫化氢是啤酒中主要的硫化物之一，其味阈值为10μg/L，对啤酒风味影响很大，优质成熟啤酒含量为(1～5)μg/L。当啤酒中含量超过10μg/L时，就能感到明显的“酵母臭味”、“生酒味”、“洋葱味”，当含量达到50μg/L时，呈臭鸡蛋味，与双乙酰、乙醛共存时产生一股强烈的青草味。所以，当硫化氢含量较高时不仅会对啤酒、葡萄酒本身的品质产生影响，也存在一定的食品安全问题。所以开展硫化氢在酒中的含量检测方法研究具有重要的实际意义。
目前，硫化氢含量测定的方法有顶空气相色谱法、亚甲基蓝分光光度法、荧光光度法测定、气相分子吸收光谱法等。在各种方法中有机小分子荧光探针检测法由于其具有简单、便捷、成本低、快速、灵敏及其潜在的成像等特性，已被证明是一种非常有效的检测方法，目前许多的有机小分子荧光探针被开发出来。
萘甲腈类化合物具有较强的荧光强度，成为荧光探针使用非常广泛的荧光基团之一。
发明内容
本发明目的是提供一种萘甲腈类硫化氢荧光探针，它适于在食品、药品、化妆品等产品中检测硫化氢。
更具体的是，本发明涉及一种萘甲腈类硫化氢荧光探针，它通过下式表示：
Figure BSA0000149538960000011
附图说明
图1是在磷酸缓冲盐溶液中，随着不同浓度硫化氢的加入，本发明的荧光探针(10μM)的荧光强度变化。嵌入图：半胱氨酸的浓度。
图2是在磷酸缓冲盐溶液中，本发明的荧光探针(10μM)荧光强度随着硫化氢浓度变化的标准曲线。
具体实施方式
实施例1.萘甲腈类硫化氢荧光探针的制备
合成路线如下式所示：
Figure BSA0000149538960000021
将1.01g(6mmol)6-羟基-2-萘甲腈(1)与1.12g(6mmol)2，4-二硝基氟苯(2)加入到50mL三口烧瓶中，再将一滴三乙胺加入到其中，加入10mL三氯甲烷，加热回流5h。后将温度降至室温，甲醇重结晶得黄色晶体1.67g，产率83.5％。
产物经过核磁氢谱及核磁碳谱表征。
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.
本发明的荧光探针的荧光强度随着硫化氢的变化如图1所示，依据该变化可作出该荧光探针(10μM)荧光强度随着硫化氢浓度变化的标准曲线，标准曲线如图2所示，通过该标准曲线的建立，本发明的荧光探针可用于硫化氢的定量检测。
实施例2.萘甲腈类硫化氢荧光探针定量检测啤酒中硫化氢含量
将20μL萘甲腈类硫化氢荧光探针，480μL DMSO，1.5mL pH＝7.0的缓冲溶液加入到比色皿。再将20μL啤酒样加入，25℃条件下反应15分钟，以287nm激发波长进行荧光检测，再分别添加5μM、10μM硫化氢标准溶液，进行荧光检测，根据荧光强度与浓度的标准曲线，将上述检测值换算成硫化氢浓度，计算添加回收率。所测啤酒样硫化氢浓度为1.82μM，添加标准溶液后样品浓度分别为6.26μM、11.16μM，添加回收率分别为92％，95％。
依据实施例2可证明本发明的萘甲腈类硫化氢荧光探针可用于啤酒中硫化氢含量测定。

Claims (2)

1.一种萘甲腈类硫化氢荧光探针，具体化学结构式如下所示：
Figure FSA0000149538950000011
2.权利要求1所述荧光探针在食品、药品、化妆品中检测硫化氢的应用。
CN201710717870.4A 2017-08-23 2017-08-23 一种萘甲腈类硫化氢荧光探针 Active CN109422667B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710717870.4A CN109422667B (zh) 2017-08-23 2017-08-23 一种萘甲腈类硫化氢荧光探针

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710717870.4A CN109422667B (zh) 2017-08-23 2017-08-23 一种萘甲腈类硫化氢荧光探针

Publications (2)

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

Family

ID=65498849

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710717870.4A Active CN109422667B (zh) 2017-08-23 2017-08-23 一种萘甲腈类硫化氢荧光探针

Country Status (1)

Country Link
CN (1) CN109422667B (zh)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103865522A (zh) * 2014-02-28 2014-06-18 浙江大学 一种荧光分子探针及其在硫化氢检测中的应用

Family Cites Families (4)

* 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
KR101481921B1 (ko) * 2013-11-18 2015-01-15 포항공과대학교 산학협력단 황화수소 감지용 일광자 및/또는 이광자 형광 프로브, 이를 이용한 세포 내 황화수소의 영상화 방법 및 이의 제조방법
CN104447421B (zh) * 2014-10-28 2016-06-08 苏州罗兰生物科技有限公司 一种新型半胱氨酸和同型半胱氨酸荧光探针的制备与应用
CN104531136B (zh) * 2014-12-29 2016-10-05 大连理工常熟研究院有限公司 一种用于识别苯硫酚的特异性荧光探针及其应用

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103865522A (zh) * 2014-02-28 2014-06-18 浙江大学 一种荧光分子探针及其在硫化氢检测中的应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
检测硫化氢分子的荧光探针;高敏，等;《化学进展》;20140525;第1065-1078页 *

Also Published As

Publication number Publication date
CN109422667A (zh) 2019-03-05

Similar Documents

Publication Publication Date Title
Dimitriadis et al. The development and use of a rapid analytical technique for estimation of free and potentially volatile monoterpene flavorants of grapes
Glushko et al. Pyrene fluorescence fine structure as a polarity probe of hydrophobic regions: behavior in model solvents
Ajtony et al. Determination of ethyl carbamate in wine by high performance liquid chromatography
CN107216270A (zh) 一种检测硫化氢高选择性反应型荧光探针的应用
CN107383037B (zh) 一种长波长型h2s荧光探针及其合成方法和应用
Nalewajko-Sieliwoniuk et al. Flow injection chemiluminescence determination of the total phenolics levels in plant-derived beverages using soluble manganese (IV)
CN109280033B (zh) 基于四苯基吡嗪的腈基乙烯基功能化的aie分子的制备和应用
CN102838095B (zh) 一种乙酰甲胺磷农药的荧光纳米CdSe量子点探针及其应用
CN105842235B (zh) 高灵敏度、可裸眼检测易挥发性有机胺的荧光试纸及制备
CN110964515A (zh) 一种双席夫碱铝离子荧光探针、其合成方法及其应用
CN106518900A (zh) 基于bodipy染料的次氯酸根荧光探针的合成及应用
CN106483240A (zh) 简化定量香稻香味特征物质2‑乙酰‑1‑吡咯啉含量的气相质谱联用方法
Li et al. Furfural and organic acid targeted carbon dot sensor array for the accurate identification of Chinese baijiu
CN110698407B (zh) 一种裸眼或荧光Al3+探针及其制备方法和应用
Mahmoud et al. Ultrasensitive and selective determination of naringin using eggplant peel-derived nitrogen doped-carbon dots after extraction with Amberlite IRA-400: Evaluation the bitterness of grapefruit juice
CN109422667B (zh) 一种萘甲腈类硫化氢荧光探针
CN108218881B (zh) 基于罗丹明b的汞离子荧光探针及其制备方法与应用
CN113087651B (zh) 一种含有吲哚基团的化合物及其制备方法和应用
CN109422669B (zh) 一种萘酚类硫化氢荧光探针
CN109422721B (zh) 一种硫化氢荧光探针
Tsivileva et al. Antioxidant properties of the Artist's Conk medicinal mushroom, Ganoderma applanatum (Agaricomycetes), upon cultivation with para-substituted phenolic compounds and tea leaf extracts
CN109422738A (zh) 一种香豆素类硫化氢荧光探针
CN115490700B (zh) 一种快速检测亚硝酸根离子的荧光探针及其应用
CN107589204B (zh) 气相色谱-质谱法测定葡萄酒中邻氨基苯甲酸酯类葡萄香精的方法
CN107831165A (zh) 一种双通道铜离子检测试纸及其制备方法

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