CN114149367A - 一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用 - Google Patents

一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用 Download PDF

Info

Publication number
CN114149367A
CN114149367A CN202111517251.3A CN202111517251A CN114149367A CN 114149367 A CN114149367 A CN 114149367A CN 202111517251 A CN202111517251 A CN 202111517251A CN 114149367 A CN114149367 A CN 114149367A
Authority
CN
China
Prior art keywords
gel
hydrazine
metal coordination
hydrazine hydrate
quinoline
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
CN202111517251.3A
Other languages
English (en)
Other versions
CN114149367B (zh
Inventor
林奇
贾钰
魏太保
张有明
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 CN202111517251.3A priority Critical patent/CN114149367B/zh
Publication of CN114149367A publication Critical patent/CN114149367A/zh
Application granted granted Critical
Publication of CN114149367B publication Critical patent/CN114149367B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • 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
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • 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"
    • G01N2021/6432—Quenching

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • General Physics & Mathematics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Dispersion Chemistry (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

本发明提供了一种基于喹啉功能化柱[5]芳烃金属配位凝胶，是将5‑羟基喹啉功能化柱[5]芳烃与与银离子配位形成金属凝胶PQ‑AG，该金属凝胶可多通道，超灵敏检测肼/水合肼。将该凝胶充分暴露在肼/水合肼蒸汽中，PQ‑AG的荧光颜色由蓝色到荧光猝灭，裸眼条件下PQ‑AG由白色凝胶变为黑色凝胶。这是由于肼/水合肼接触金属凝胶后破坏了PQ5与Ag+的配位作用，导致凝胶塌陷，荧光颜色及裸眼下凝胶颜色发生变化，从而实现对肼/水合肼的超灵敏检测，检测限可达到2.68×10‑8M。

Description

一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与 应用
技术领域
本发明涉及一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备方法；本发明同时涉及该金属配位凝胶在检测肼/水合肼中的应用，属于化学合成领域及有毒气体检测领域。
背景技术
肼/水合肼作为一种重要的精细化工原料，主要用于合成发泡剂；也用作锅炉和反应釜的脱氧和脱二氧化碳的清洗处理剂；在医药工业中用于生产抗结核、抗糖尿病的药物；在农药工业中用于生产除草剂、植物生长调和剂和杀菌、杀虫、杀鼠药；此外它还可用于生产火箭燃料、重氮燃料、橡胶助剂等。但肼/水合肼不仅会造成水体污染，而且接触肼/水合肼蒸气，刺激呼吸道，引起头晕、恶心和中枢神经系统兴奋，刺激眼睛可致永久性损害，并且具有致癌性。目前，关于检测肼/水合肼检测方法的报道有气相色谱法、荧光分析法、希夫碱反应法等。常用的仪器检测方法价格昂贵，操作不便；而且，已经开发出了用于检测肼/水合肼的检测方法，大多数只能在溶液中进行检测。因此，迫切需要开发多种方法同时检测肼/水合肼的新型材料。近年来，随着刺激响应凝胶的发展，特别是金属凝胶因其作为生物和化学探针以及在许多其他领域的潜在应用而受到广泛关注。
由于对有毒气体的检测人类健康和环境保护至关重要。本发明报道了一种将喹啉功能化柱[5]芳烃与银离子配位形成金属凝胶。该凝胶可以通过裸眼，荧光检测肼/水合肼，具有方便快捷，且检测限低的优点。
发明内容
本发明的目的是提供一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备方法；
本发明的另一目的是提供该金属配位凝胶在检测肼/水合肼中的应用。
一、金属配位凝胶
本发明基于喹啉功能化柱[5]芳烃的金属配位凝胶，分子式为[AgC69H72N2O12]+ n，其结构式为：
Figure 100002_DEST_PATH_IMAGE001
该金属配位凝胶是依靠弱相互作用力形成的配位聚合物凝胶，是一个无限链结构。
本发明基于喹啉功能化柱[5]芳烃的金属配位凝胶的制备方法，是将主体分子5-羟基喹啉功能化柱[5]芳烃PQ5加入DMSO和H2O混合液中，再加入Ag+，加热至120℃，静5分钟，冷却至室温，即得到白色的金属配位凝胶PQ-AG。其中，5-羟基喹啉功能化柱[5]芳烃和Ag+的摩尔比为1:1.5~1:2.5。DMSO和H2O混合液中，水的体积含量为15%~25%。
5-羟基喹啉功能化柱[5]芳烃的结构式为：
Figure DEST_PATH_IMAGE002
5-羟基喹啉功能化柱[5]芳烃的合成参考文献：Y. Jia, J. - P. Hu, L.-R.Dang, H. Yao, B. B. Shi, Y.-M. Zhang, T.-B. Wei, and Q. Lin, ACS Sustainable Chem. Eng. 2021, 9, 48, 16203-16209。
图1为本发明金属配位凝胶基本单元[AgC69H72N2O12]+ n的高分辨质谱图，说明PQ5与Ag+配位比为1:2。
图2为本发明金属配位凝胶PQ-AG溶胶-凝胶的相变图，由主体分子PQ5与Ag+可制备出金属配位凝胶PQ-AG.
二、金属配位凝胶对肼/水合肼的检测
分别制备200μL的金属配位凝胶，将PQ-AG凝胶充分暴露在肼/水合肼蒸汽中，将金属配位凝胶PQ-AG分别暴露在肼/水合肼、氨水、乙二胺、甲醛、乙醛和吡啶的蒸汽中，只有肼/水合肼蒸汽能使金属配位凝胶PQ-AG的蓝色荧光猝灭，其他蒸汽均不能使金属配位凝胶PQ-AG的蓝色荧光猝灭（图3）。
将金属配位凝胶PQ-AG分别暴露在肼/水合肼、氨水、乙二胺、甲醛、乙醛和吡啶的蒸汽中，裸眼条件下只有肼/水合肼能使金属配位凝胶PQ-AG由白色凝胶变为黑色凝胶（图3、图4）。
图5为金属配位凝胶PQ-AG的荧光滴定谱图。图5的结果显示，随着肼/水合肼的滴入，金属配位凝胶PQ-AG的荧光颜色由蓝色到荧光猝灭。因此，金属配位凝胶PQ-AG能够检测肼/水合肼。图6为金属配位凝胶PQ-AG荧光检测肼/水合肼最低检测限图， PQ-AG对肼/水合肼最低检测限为2.68×10-8M，表明可以实现对肼/水合肼的超灵敏检测。
图7为本发明金属配位凝胶主体分子PQ5加入Ag+，及PQ-AG加入肼/水合肼后的核磁滴定图（a为主体分子PQ5，b为PQ5中加入2倍当量的Ag+、c为继续加入2倍当量肼/水合肼）。在一定浓度(9 mM)的PQ5的溶液中加入2当量的Ag+后，PQ5的喹啉环上的质子信号Ha、Hb、Hc、Hd、He和Hf均呈下场偏移说明PQ5的喹啉基团与Ag+之间为金属配位作用，而在金属配位凝胶中PQ-AG加入肼/水合肼后PQ5的喹啉环上的质子信号Ha、Hb、Hc、Hd、He和Hf均呈高场偏移，说明加入肼/水合肼后破坏了PQ5与Ag+之间为金属配位作用从而实现对肼/水合肼的检测。因此主体分子PQ5通过配位作用固定Ag+形成金属凝胶，接触肼/水合肼后进而导致破坏了PQ5与Ag+之间为金属配位作用从而实现对肼/水合肼的检测，表现出荧光变色以及裸眼下凝胶变色现象。
附图说明
图1为本发明金属配位凝胶基本单元[AgC69H72N2O12]+ n的高分辨质谱图；
图2为本发明的金属配位凝胶溶胶-凝胶相变图；
图3为本发明的金属配位凝胶PQ-AG分别暴露在不同有机化合物蒸汽中的荧光及裸眼变化图；
图4为本发明金属配位凝胶暴露肼/水合肼蒸汽中30s后的裸眼颜色变化图；
图5为本发明金属配位凝胶荧光检测肼/水合肼荧光猝灭滴定图；
图6为本发明金属配位凝胶荧光检测肼/水合肼最低检测限图；
图7为本发明金属配位凝胶主体分子PQ5加入Ag+，及PQ-AG加入肼/水合肼后的核磁滴定图。
具体实施方式
下面通过具体实例对本发明金属配位凝胶PQ-AG的制备和检测肼/水合肼的应用做进一步说明。
实施例1金属配位凝胶PQ-AG的制备
金属配位凝胶PQ-AG的制备：将PQ5 (0.0200g，1.78×10-5 mol)加入160μL的DMSO和H2O混合液（水的体积含量为20%）中，再加入3.56×10-5mol Ag+（Ag+来源于AgNO3溶液。），加热至120℃静置5分钟，冷却至室温即可得到白色的金属配位凝胶PQ-AG。
实施例2 金属配位凝胶PQ-AG对肼/水合肼的荧光检测
制备200μL金属配位凝胶PQ-AG平铺在玻璃板上，将其分别暴露在肼/水合肼、氨水、乙二胺、甲醛、乙醛和吡啶的蒸汽中，若金属配位凝胶PQ-AG的蓝色荧光猝灭，说明为肼/水合肼蒸汽；若金属配位凝胶PQ-AG的蓝色荧光没有发生变化，说明是其他蒸汽。
实施例3 金属配位凝胶PQ-AG对肼/水合肼的裸眼检测
制备200μL金属配位凝胶PQ-AG平铺在玻璃板上，将其分别暴露在肼/水合肼、氨水、乙二胺、甲醛、乙醛和吡啶的蒸汽中，若金属配位凝胶PQ-AG由白色凝胶变为黑色凝胶，说明是肼/水合肼蒸汽；若金属配位凝胶PQ-AG的凝胶颜色没有变为黑色凝胶，说明是其他蒸汽。

Claims (7)

1.一种基于喹啉功能化柱[5]芳烃的金属配位凝胶，其结构式为：
Figure DEST_PATH_IMAGE001
。
2.如权利要求1所述基于喹啉功能化柱[5]芳烃的金属配位凝胶的制备方法，是将主体分子5-羟基喹啉功能化柱[5]芳烃加入DMSO和H2O混合液中，再加入Ag+，加热至120~130℃，静置5分钟，冷却至室温，即得到白色的金属配位凝胶PQ-AG。
3.如权利要求2所述基于喹啉功能化柱[5]芳烃的金属配位凝胶的制备方法，其特征在于：5-羟基喹啉功能化柱[5]芳烃和Ag+的摩尔比为1:1.5~1:2.5。
4.如权利要求2所述基于喹啉功能化柱[5]芳烃的金属配位凝胶的制备方法，其特征在于：DMSO和H2O混合液中，水的体积含量为15%~25%。
5.如权利要求1所述基于喹啉功能化柱[5]芳烃的金属配位凝胶在检测肼/水合肼中的应用。
6.如权利要求5所述基于喹啉功能化柱[5]芳烃的金属配位凝胶在检测肼/水合肼中的应用，其特征在于：将金属配位凝胶PQ-AG分别暴露在肼/水合肼、氨水、乙二胺、甲醛、乙醛和吡啶的蒸汽中，只有肼/水合肼蒸汽能使金属配位凝胶PQ-AG的蓝色荧光猝灭。
7.如权利要求5所述基于喹啉功能化柱[5]芳烃的金属配位凝胶在检测肼/水合肼中的应用，其特征在于：将金属配位凝胶PQ-AG分别暴露在肼/水合肼、氨水、乙二胺、甲醛、乙醛和吡啶的蒸汽中，裸眼条件下只有肼/水合肼能使属配位凝胶PQ-AG由白色凝胶变为黑色凝胶。
CN202111517251.3A 2021-12-13 2021-12-13 一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用 Active CN114149367B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111517251.3A CN114149367B (zh) 2021-12-13 2021-12-13 一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111517251.3A CN114149367B (zh) 2021-12-13 2021-12-13 一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用

Publications (2)

Publication Number Publication Date
CN114149367A true CN114149367A (zh) 2022-03-08
CN114149367B CN114149367B (zh) 2023-06-23

Family

ID=80450402

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111517251.3A Active CN114149367B (zh) 2021-12-13 2021-12-13 一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用

Country Status (1)

Country Link
CN (1) CN114149367B (zh)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108610287A (zh) * 2018-05-11 2018-10-02 西北师范大学 一种8-羟基喹啉功能化柱[5]芳烃的制备及有机框架的构建和应用
CN108774168A (zh) * 2018-06-20 2018-11-09 西北师范大学 一种喹啉化超分子传感器及其合成和荧光识别汞离子和氰根的应用
CN109187472A (zh) * 2018-09-12 2019-01-11 西北师范大学 一种基于主客体自组装的超分子传感器及其制备和应用
CN109824589A (zh) * 2019-04-09 2019-05-31 西北师范大学 一种基于双边8-羟基喹啉功能化柱[5]芳烃的金属有机凝胶及其合成和应用
CN113173883A (zh) * 2021-05-11 2021-07-27 西北师范大学 一种8-羟基喹啉功能化柱[5]芳烃及其合成和在检测及吸附乙二胺中的应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108610287A (zh) * 2018-05-11 2018-10-02 西北师范大学 一种8-羟基喹啉功能化柱[5]芳烃的制备及有机框架的构建和应用
CN108774168A (zh) * 2018-06-20 2018-11-09 西北师范大学 一种喹啉化超分子传感器及其合成和荧光识别汞离子和氰根的应用
CN109187472A (zh) * 2018-09-12 2019-01-11 西北师范大学 一种基于主客体自组装的超分子传感器及其制备和应用
CN109824589A (zh) * 2019-04-09 2019-05-31 西北师范大学 一种基于双边8-羟基喹啉功能化柱[5]芳烃的金属有机凝胶及其合成和应用
CN113173883A (zh) * 2021-05-11 2021-07-27 西北师范大学 一种8-羟基喹啉功能化柱[5]芳烃及其合成和在检测及吸附乙二胺中的应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YU JIA等: "Rational Tuning of Binding Properties of Pillar[5]arene-Based Crystalline Material by Synergistic Effect and Its Application for Fluorescent Detection and Adsorption of 1,2-Ethylenediamine", pages 16203 *

Also Published As

Publication number Publication date
CN114149367B (zh) 2023-06-23

Similar Documents

Publication Publication Date Title
Buchanan et al. Emerging use of isotope ratio mass spectrometry as a tool for discrimination of 3, 4-methylenedioxymethamphetamine by synthetic route
CN104833743B (zh) 一种液质联用分析生物样品中卡西酮、甲卡西酮、4-甲基甲卡西酮的方法
CN107935926A (zh) 能够识别芳香酸异构体的凝胶因子及其超分子聚合物凝胶的制备和应用
CN113607709B (zh) 一种荧光碳量子点在检测环烷酸中的应用及环烷酸的检测方法
CN108658862A (zh) 基于萘二甲酰亚胺衍生物的传感器分子及其合成和应用
Baheri et al. Application of HKUST‐1 metal‐organic framework as coating for headspace solid‐phase microextraction of some addictive drugs
Zhou et al. [2] Pseudorotaxane‐Based Supramolecular Optical Indicator for the Visual Detection of Cellular Cyanide Excretion
Xu et al. Fluorescent Recognition of 1, 2‐Diamines by a 1, 1′‐Binaphthyl‐Based Trifluoromethyl Ketone
Monteleone et al. Peek–wc-based mixed matrix membranes containing polyimine cages for gas separation
Gao et al. Highly selective fluorescence detection of Cu2+ based on Schiff base functionalized periodic mesoporous organosilicas
Bożejewicz et al. 2, 6-Bis ((benzoyl-R) amino) pyridine (R= H, 4-Me, and 4-NMe2) Derivatives for the Removal of Cu (II), Ni (II), Co (II), and Zn (II) Ions from aqueous solutions in classic solvent extraction and a membrane extraction
Karakücük et al. Polymer supported calix [4] arene schiff bases: a novel chelating resin for Hg2+ and dichromate anions
Ilktaç et al. Magnetite-molecularly imprinted polymer based highly sensitive chromatographic method for preconcentration and determination of pirimicarb
Li Nanoporous silica-dye microspheres for enhanced colorimetric detection of cyclohexanone
CN114149367A (zh) 一种基于喹啉功能化柱[5]芳烃的金属配位凝胶及其制备与应用
Song et al. Rosebengal-Loaded Nanoporous Structure Based on Rare Earth Metal-Organic-Framework: Synthesis, Characterization and Photophysical Performance
Kumari et al. Hydrogen bond mediated turn-on sensor: Ultra-sensitive and label free barium-MOF for probing malathion an organophosphate pesticide
Abel et al. Ruthenium (II) Complexes with (3-Polyamino) phenanthrolines: Synthesis and Application in Sensing of Cu (II) Ions
Havelková et al. Combining polymerization and templating toward hyper-cross-linked poly (propargyl aldehyde) s and poly (propargyl alcohol) s for reversible H2O and CO2 capture and construction of porous chiral networks
Milli et al. Turning Around the L‐Phe‐D‐Oxd Moiety for a Versatile Low‐Molecular‐Weight Gelator
CN107402206B (zh) 一种汞离子比色传感器及其制备方法和应用
CN108507993B (zh) 一种内修饰分子管为化学传感器检测违禁药物的方法
Emandi et al. Triptycene scaffolds: Synthesis and properties of triptycene-derived Schiff base compounds for the selective and sensitive detection of CN− and Cu2+
CN111077196A (zh) 纳米材料复合物的加工方法及在双酚a检测中的应用
Al-Ithawi et al. Mechanosynthesis of Diaminobiphenyls-Based Schiff’s Bases as Simple Probes for the Naked-Eye Detection of Cyanide Ion

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