CN115304750A - 一种共价有机框架材料、配体、荧光传感器及其应用 - Google Patents

一种共价有机框架材料、配体、荧光传感器及其应用 Download PDF

Info

Publication number
CN115304750A
CN115304750A CN202211237214.1A CN202211237214A CN115304750A CN 115304750 A CN115304750 A CN 115304750A CN 202211237214 A CN202211237214 A CN 202211237214A CN 115304750 A CN115304750 A CN 115304750A
Authority
CN
China
Prior art keywords
organic framework
covalent organic
framework material
ligand
preparation
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.)
Withdrawn
Application number
CN202211237214.1A
Other languages
English (en)
Inventor
赵礼义
曹宇
许名飞
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.)
Jilin China Science And Technology Co ltd
Original Assignee
Jilin China Science And Technology Co ltd
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 Jilin China Science And Technology Co ltd filed Critical Jilin China Science And Technology Co ltd
Priority to CN202211237214.1A priority Critical patent/CN115304750A/zh
Publication of CN115304750A publication Critical patent/CN115304750A/zh
Withdrawn legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • 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"
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/312—Non-condensed aromatic systems, e.g. benzene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/52—Luminescence
    • C08G2261/522—Luminescence fluorescent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/94—Applications in sensors, e.g. biosensors
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—Non-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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • 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)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

一种共价有机框架材料、配体、荧光传感器及其应用，涉及环境检测用材料技术领域，解决了共价有机框架材料检测金属离子种类少的问题，应用于金属离子检测荧光传感器中。共价有机框架材料制备：将配体和3,4,9,10‑四羧酸酐混合后研磨，升温后煅烧。原料1制备：将2‑甲基‑4‑氰基苯硼酸、蒸馏水、聚乙二醇400、4‑溴苯胺、二氯化钯和碳酸钾混合后搅拌；用乙醚反复萃取后合并有机相，用硫酸镁干燥再旋干，用石油醚/乙酸乙酯混合溶液作为洗脱剂进行硅胶柱层析。配体制备：原料1加入二氯甲烷中搅拌得混合溶液，特定温度下滴加三氟甲磺酸，氮气保护下搅拌；加入蒸馏水后用饱和NaOH溶液将pH调至7，抽滤后用蒸馏水冲洗干燥。

Description

一种共价有机框架材料、配体、荧光传感器及其应用
技术领域
本发明涉及环境检测用材料技术领域，具体涉及一种共价有机框架材料、配体、荧光传感器及其应用。
背景技术
随着经济的高速发展，人类生活水平得到了大幅度的提升，可环境污染问题也越来越严重，特别是重金属污染。一方面，重金属会破坏植物的一些组织和功能，从而降低植物的产量和品质，例如土壤中镉含量过高会破坏植物叶片的叶绿素结构最终导致植物死亡。另一方面，重金属会通过食物链在植物体内富集，研究表明随着表层土壤镉污染的加重，水稻籽粒中的镉含量逐步提高。除此之外，土壤中的重金属还会经雨水淋滤及地表径流作用转移进入地表水系统，进而通过地表水和地下水的交互作用污染地下水体，对饮用水安全构成威胁。为了能有针对性地对不同种类、不同类型的重金属污染事件选择合适的修复方法，迫切需要开发一种广谱检测金属离子的敏感平台。
在过去的几十年里，人们建立了各种检测金属离子的方法，例如原子吸收光谱法、原子荧光光谱法、毛细管电泳、电喷雾离子化质谱以及表面增强拉曼光谱等，这些检测方法具有较高的灵敏度和准确度，但是成本高昂、设备复杂。相比于这些检测方法，荧光检测法具有样品处理简单、检测操作简便、低成本等优点，且在使用过程中无需大型设备，只需紫外灯即可实现检测。因此，荧光检测近年来在金属检测相关领域收到了广泛关注，研发一种成本低廉、合成条件温和、易于调控且适合大批量工业生产的荧光探针材料是当前的研究热点之一。
共价有机框架材料（Covalent Organic Farmeworks，COFs）是一类的多孔有机纳米材料，其具有高比表面积、结构可调性强以及成本低廉等多种优势。与传统的探针材料相比，共价有机框架材料不但具有堆叠的结构和丰富的π电子，使其体系具有较强的荧光发射，而且共价有机框架材料在高温强酸、强碱等苛刻条件下依然能保持框架结构的稳定，这赋予了共价有机框架材料作为荧光探针材料的优秀应用前景。但是目前已知的共价有机框架材料能够检测的金属离子种类较少，这降低了重金属检测的广泛度和准确度。
发明内容
为了解决现有共价有机框架材料检测的金属离子种类较少的问题，本发明提出了一种共价有机框架材料、配体、荧光传感器及其应用。
本发明的技术方案如下：
一种共价有机框架材料，所述共价有机框架材料的结构式如下：
Figure 49481DEST_PATH_IMAGE001
，所述共价有机框架材料命名为COF-ET25。
一种制备共价有机框架材料用配体，用于制备如上所述的共价有机框架材料，所述配体的结构式如下：
Figure 890922DEST_PATH_IMAGE002
。
本发明还提供了一种荧光传感器，包括如上所述的共价有机框架材料。
本发明还提供了一种如上所述的共价有机框架材料或荧光传感器在金属离子检测中的应用。
与现有技术相比，本发明解决了共价有机框架材料检测的金属离子种类较少的问题，具体有益效果为：
1、本发明提供的共价有机框架材料，其原料来源广泛、成本低廉、合成工艺简单，且具有良好的荧光稳定性能，能够在水中和DMF（二甲基甲酰胺）中荧光强度在25h内几乎保持不变；
2、Fe2+、Fe3+、Cd2+、Co2+、Cr2+、Ni2+、Zn2+、Pb2+和Mn2+等多种金属离子对本发明所述的共价有机框架材料会产生明显的荧光淬灭现象，这是目前已知共价有机框架材料用于金属离子检测种类的最大数量，在金属离子检测中展现了优异的性能和良好的应用前景。
附图说明
图1为本发明提供的共价有机框架材料的红外表征；
图2为本发明提供的共价有机框架材料对不同金属离子荧光发射强度图谱；
图3为本发明提供的共价有机框架材料在水和DMF中的荧光稳定性图谱。
具体实施方式
为使本发明的技术方案更加清楚，下面将结合本发明的说明书附图，对本发明实施例中的技术方案进行清楚、完整地描述，需要说明的是，以下实施例仅用于更好地理解本发明的技术方案，而不应理解为对本发明的限制。
本实施例中使用的2-甲基-4-氰基苯硼酸（CAS：313546-18-8）、4-溴苯胺（CAS：106-40-1）、3,4,9,10-四羧酸酐（CAS：128-69-8）均从市面直接采购获得。
以下描述本发明所述的共价有机框架材料的制备过程和表征结果：
第一步、制备原料1：
向50mL三口瓶中依次加入2-甲基-4-氰基苯硼酸（3g，18.63mmol）、蒸馏水3.5mL、聚乙二醇400 3.5mL、4-溴苯胺（3.82g，22.35mmol）、二氯化钯（16mg，0.09mmol）和碳酸钾（0.91g，6.59mmol），在25℃下搅拌8h，混合物用乙醚萃取三次，每次用25mL乙醚，萃取后合并有机相，将有机相用硫酸镁干燥然后旋干得到粗产物；用体积比为1:4的石油醚/乙酸乙酯混合溶液作为洗脱剂对粗产物进行硅胶柱层析，得到白色固体3.02g，即原料1，收率78%。
对获得的原料1分别做核磁共振氢谱分析、碳谱分析、质谱分析和元素分析测试，结果如下：
氢谱1H NMR (400 MHz, DMSO) ：
δ 7.94 (s, 1 H), 7.72 (d, 2 H), 7.43 (m, 2 H), 6.60 (m, 2 H), 5.32(s, 2H), 2.56 (s, 2 H)；
碳谱13C NMR (100 MHz, DMSO)：
δ 150.86, 142.32, 140.07, 135.35, 134.76, 130.66, 130.03, 129.50,119.39, 118.60, 116.37, 21.23；
质谱表征结果：
ESI（m/z）：[M+H]＋calcd. for C14H12N2,226.0801；found, 227.1625；
元素分析测试结果：
Calcd. for C13H11BO3 C, 69.08; H, 4.91; O, 21.23. Found: C, 70.23; H,3.65; O, 21.66。
根据以上分析数据可以证明，得到的原料1为：
Figure 873922DEST_PATH_IMAGE003
。
第二步、制备配体：
向250mL三口瓶中依次加入85mL二氯甲烷和原料1（2g，9.61mmol）后进行充分搅拌，随后在0℃下缓慢滴加三氟甲磺酸（4.33g，28.83mmol），得到的混合物在氮气保护下，100℃搅拌反应12h；向反应体系中加入120mL蒸馏水，随后用饱和的氢氧化钠溶液将体系的pH值调至7。抽滤后用蒸馏水冲洗干燥，得到淡黄色固体5.1g，即为制备共价有机框架材料用配体，收率为85%。
对获得的配体分别做核磁共振氢谱分析、碳谱分析、质谱分析和元素分析测试，结果如下：
氢谱1H NMR (400 MHz, DMSO)：
δ 8.02 (m, 6 H), 7.50 (m, 6 H), 7.31 (m, 3 H), 6.60 (m, 6 H), 5.41(s, 6 H), 2.75 (s, 1 H)；
碳谱13C NMR (100 MHz, CDCl3)：
δ150.86, 149.04, 141.51, 140.77, 140.47, 140.41, 140.05, 139.54,139.43, 138.58, 136.42, 134.40, 131.17, 130.74, 130.54, 130.03, 129.89,129.37, 129.17, 128.67, 128.17, 118.60, 117.03, 116.74, 21.40, 21.31；
质谱表征结果：
ESI（m/z）：[M+H]＋calcd. for C42H36N6, 624.3001；found, 625.2546；
元素分析测试结果：
Calcd. for C42H36N6 C, 80.74; H, 5.81; N, 13.45. Found: C, 80.03; H,5.72; N, 13.21。
根据以上分析数据可以证明，得到的配体结构式为：
Figure 331448DEST_PATH_IMAGE004
。
第三步、共价有机框架材料的合成：
将制备共价有机框架材料用配体（2g，3.2mmol）、3,4,9,10-四羧酸酐（1.26g，3.2mmol）放到玛瑙研钵中研磨30min，随后将得到的混合物转移到氧化铝坩埚中，以5℃/min的加热速率进行加热，加热到325℃，在此温度下煅烧4h，得到固体7.96g，即为共价有机框架材料，收率为43%。
对获得的共价有机框架材料分别做质谱分析和元素分析测试，结果如下：
元素分析测试结果：
Calcd. for C408H240N18O24 C, 84.81; H, 4.19; N, 4.36; O, 6.64. Found: C,84.85; H, 4.16; N, 4.38; O, 6.59；
质谱表征结果：
ESI（m/z）：[M+H]＋Calcd. for C408H240N18O24, 5777.8247；found, 5778.6585。
对获得的共价有机框架材料和制备用配体进行红外表征，测试仪器为IRAffinity-1傅里叶变换红外分光光度计，KBr压片，测试结果如图1所示。由图中可知，在共价有机框架材料中，配体中原有的N-H（3331 cm-1、3469 cm-1）伸缩振动消失，3,4,9,10-四羧酸酐中原有的C-O（1264 cm-1、1025 cm-1）伸缩振动减弱，出现了新的键连C=C（1592 cm-1）和C-N-C（1233 cm-1），这证明了共价有机框架材料分子的成功构建，所述共价有机框架材料称为COF-ET25。
接下来对共价有机框架材料COF-ET25进行荧光性能的测试，测试均在25℃下通过F-7100荧光分光光度计进行。测试过程中，设定荧光激发波长为369 nm、发射波长范围为470 nm-590 nm、激发、发射狭缝为10 nm。
本实施例还测试了14种金属离子对共价有机框架材料COF-ET25荧光强度的影响：分别配置5×10-4 mol/L Ba2+、Cr2+、Cd2+、Co2+、Fe2+、Fe3+、Al3+、Mn2+、Na+、Ni2+、K+、Cu2+、Zn2+、Pb2+的水溶液，按照1:9体积比与共价有机框架材料COF-ET25溶液混合，超声分散均匀，放置12h，保证荧光强度稳定后，检测其荧光性能，测试结果见图2所示。由图可知，多种金属离子可以极大地淬灭共价有机框材料COF-ET25的荧光，例如Fe2+、Fe3+、Cd2+、Co2+、Cr2+、Ni2+、Zn2+、Pb2+、Cu2＋和Mn2+。
此外，本实施例测试了共价有机框材料COF-ET25在水中和DMF中的荧光稳定性能，结果见图3，可以证明在水中和DMF中的荧光强度在25h内几乎保持不变，这表明共价有机框材料COF-ET25在应用中具有良好的稳定性。
需要说明的是，以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等，均应包含在本发明的保护范围之内。

Claims (5)

1.一种共价有机框架材料，其特征在于，所述共价有机框架材料的结构式如下：
Figure 293800DEST_PATH_IMAGE001
，所述共价有机框架材料命名为COF-ET25。
2.一种制备共价有机框架材料用配体，其特征在于，用于制备如权利要求1所述的共价有机框架材料，所述配体的结构式如下：
Figure 913000DEST_PATH_IMAGE002
。
3.一种荧光传感器，其特征在于，包括如权利要求1所述的共价有机框架材料。
4.一种如权利要求1所述的共价有机框架材料在金属离子检测中的应用。
5.一种如权利要求3所述的荧光传感器在金属离子检测中的应用。
CN202211237214.1A 2022-10-11 2022-10-11 一种共价有机框架材料、配体、荧光传感器及其应用 Withdrawn CN115304750A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211237214.1A CN115304750A (zh) 2022-10-11 2022-10-11 一种共价有机框架材料、配体、荧光传感器及其应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211237214.1A CN115304750A (zh) 2022-10-11 2022-10-11 一种共价有机框架材料、配体、荧光传感器及其应用

Publications (1)

Publication Number Publication Date
CN115304750A true CN115304750A (zh) 2022-11-08

Family

ID=83867922

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211237214.1A Withdrawn CN115304750A (zh) 2022-10-11 2022-10-11 一种共价有机框架材料、配体、荧光传感器及其应用

Country Status (1)

Country Link
CN (1) CN115304750A (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116496497A (zh) * 2023-06-21 2023-07-28 吉林省卓材新研科技有限公司 一种共价有机框架材料、配体和在Fe3+检测中的应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483746A (zh) * 2019-09-03 2019-11-22 西北师范大学 一种新型共价有机框架材料的合成及其在金属离子识别和染料吸附中的应用

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483746A (zh) * 2019-09-03 2019-11-22 西北师范大学 一种新型共价有机框架材料的合成及其在金属离子识别和染料吸附中的应用

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
KIM, HONG MO: "Comparative study of the synthetic methods for perylene-based covalent triazine polyimides", 《DYES AND PIGMENTS》 *
MASCHITA, JOHANNES: "Ionothermal Synthesis of Imide-Linked Covalent Organic Frameworks", 《ANGEWANDTE CHEMIE, INTERNATIONAL EDITION》 *
WU, SHAOFEI: "A rational construction of microporous imide-bridged covalent-organic polytriazines for high-enthalpy small gas absorption", 《JOURNAL OF MATERIALS CHEMISTRY A》 *
姚婵等: "基于有机多孔聚合物的荧光探针", 《高分子通报》 *
李玉森等: "固态发光多孔有机聚合物的研究进展", 《高分子通报》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116496497A (zh) * 2023-06-21 2023-07-28 吉林省卓材新研科技有限公司 一种共价有机框架材料、配体和在Fe3+检测中的应用
CN116496497B (zh) * 2023-06-21 2023-10-20 吉林省卓材新研科技有限公司 一种共价有机框架材料、配体和在Fe3+检测中的应用

Similar Documents

Publication Publication Date Title
Yue et al. A Bodipy-based derivative for selective fluorescence sensing of homocysteine and cysteine
Zhao et al. Highly thermostable lanthanide metal–organic frameworks exhibiting unique selectivity for nitro explosives
Li et al. A large Stokes shift, sequential, colorimetric fluorescent probe for sensing Cu2+/S2-and its applications
CN111393461B (zh) 一种基于bodipy的钯离子荧光探针化合物及其合成方法
Liu et al. Fluorescein-based fluorescent sensor with high selectivity for mercury and its imaging in living cells
CN115304750A (zh) 一种共价有机框架材料、配体、荧光传感器及其应用
Yang et al. Two novel pyrazole-based chemosensors:“naked-eye” colorimetric recognition of Ni 2+ and Al 3+ in alcohol and aqueous DMF media
Chen et al. A novel single-fluorophore-based ratiometric fluorescent probe for detection of formaldehyde in air
CN108864159B (zh) 一种可用于检测酸性环境下Fe3+的吡咯-苯硼氟荧光化合物及其制备方法
CN109503604B (zh) 苯并咪唑并咪唑衍生物及其合成方法
CN107337670A (zh) 吩嗪类金属富勒烯衍生物、制法及激发态寿命的调控方法
CN114853656B (zh) 具有aee特性的咔唑类衍生物、制备方法及应用
CN111100153A (zh) 一种氟硼二吡咯甲川衍生物染料配体及其制备方法
CN113201132B (zh) 一种基于单分散四臂聚乙二醇的罗丹明b衍生物荧光探针分子及其制备方法
CN113121469B (zh) 一种红光材料及其制备方法和应用
CN113185458B (zh) 一种三聚茚基共轭8-苄氧基喹啉衍生物的制备方法及应用
De Xu et al. Reduction of 4-azidonaphthalimide with different phosphine ligands and exploration of their spectroscopic properties
CN110128455B (zh) 一种冰片酯基苯乙炔基BODIPY类pH荧光探针的制备方法
Yuan et al. Development and cell imaging applications of a novel fluorescent probe for Cu 2+
Tamiaki et al. Chemosensitive chlorophyll derivatives: optical detection of various amines by synthetic 3-trifluoroacetyl-131-deoxo-pyropheophorbides in solution
CN116496497B (zh) 一种共价有机框架材料、配体和在Fe3+检测中的应用
Jiang et al. Two new isomerous fluorescent chemosensors for Al3+ based on photoinduced electron transfer
CN112679459A (zh) 一种近红外的肼荧光传感器及其制备方法和应用
CN108003157B (zh) 一种苝二酰亚胺化合物，其合成方法及其在Fe3+检测中的应用
Sakata et al. Preparation and Characterization of 7, 16-Dibenzoylated Tetraaza [14] Annulene Copper (II) Complexes

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
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20221108