CN107033331B - 一种侧链氨基质子化的荧光共轭高分子、制备方法及其应用 - Google Patents
一种侧链氨基质子化的荧光共轭高分子、制备方法及其应用 Download PDFInfo
- Publication number
- CN107033331B CN107033331B CN201710204311.3A CN201710204311A CN107033331B CN 107033331 B CN107033331 B CN 107033331B CN 201710204311 A CN201710204311 A CN 201710204311A CN 107033331 B CN107033331 B CN 107033331B
- Authority
- CN
- China
- Prior art keywords
- conjugated polymer
- parts
- amino group
- monomer
- 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.)
- Active
Links
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
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
- 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
- C08G2261/124—Copolymers alternating
-
- 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
- C08G2261/143—Side-chains containing nitrogen
-
- 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
- C08G2261/22—Molecular weight
- C08G2261/228—Polymers, i.e. more than 10 repeat 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
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3328—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms alkyne-based
-
- 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
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
-
- 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
- C08G2261/35—Macromonomers, i.e. comprising more than 10 repeat units
- C08G2261/352—Macromonomers, i.e. comprising more than 10 repeat units containing only carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Optics & Photonics (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
本发明公开了一种侧链氨基质子化的共轭高分子、制备方法及其应用。两种单体通过Sonogashira偶联反应合成得到一种共轭高分子(PPE‑NBoc),再经三氟乙酸脱除Boc保护基团,制备得到侧链氨基质子化的共轭高分子(PPE‑NH3 +)。本发明提供的共轭高分子PPE‑NH3 +可用于实现对水体系中部分醛类物质的选择性检测,尤其对常见医用消毒液中戊二醛的有效检测。本发明无需借助大型仪器的使用,可设计小型荧光检测器,进行定性或定量检测。
Description
技术领域
本发明涉及一种荧光传感材料,特别涉及一种侧链氨基质子化的共轭高分子、制备及其对于水体系中醛的传感检测。
背景技术
与传统传感材料相比,共轭高分子由于其分子导线作用可实现信号的放大效应,并且其结构易调节,可实现某种特定功能。通过修饰特定的官能团,可实现对某一类物质的特异性响应。
目前,关于侧链含有氨基基团或侧链氨基质子化的共轭高分子的合成及应用已有报道,(参见文献:Adv. Mater. 2013, 25, 1203-1208; Chem. Commun. 2015, 51, 4036-4039; Anal. Chem. 2016, 88, 2985-2988; Angew. Chem. Int. Ed. 2007, 46, 4667-4670; Chem. Commun. 2013, 49, 6048-6050.)有的主链结构相同,但侧链与之不同;有的侧链结构类似,但主链骨架又完全不同;例如Moon及其合作者设计了一种共轭高分子,通过酸化处理,使氨基质子化,制备成纳米粒子,而目前这一共轭高分子也仅仅应用于生物领域,例如:生物成像,DNA、RNA检测等。(参见文献:Chem. Commun. 2011, 47, 8370-8372;Angew. Chem. Int. Ed. 2007, 46, 8223-8225; Adv. Mater. 2009, 21, 3492-3496.)而对生活用水或医用废水中醛的检测尚未报道。
目前关于醛类检测的技术主要基于一些大型仪器,利用高效液相色谱、气相色谱、分光光度法等,已有报道利用有机荧光小分子用于甲醛的检测,而利用共轭高分子对醛的检测尚未见报道。
发明内容
本发明针对现有技术对废水中醛的检测存在的不足,提供一种制备简单,对废水中醛类具有明显的选择性的侧链氨基质子化的共轭高分子、制备方法及其应用。
实现本发明目的的技术方案是提供一种侧链氨基质子化的共轭高分子,结构式如下:
。
本发明技术方案还包括如上所述的侧链氨基质子化的共轭高分子的制备方法,步骤如下:
1、单体1的制备:按摩尔计,将1份2,5-二溴对苯二酚,2~3份2-([叔丁氧羰基]氨基)乙基4-甲基苯磺酸酯,5~15份无水碳酸钾和150~250份N,N-二甲基甲酰胺混合,在温度为60~90℃的条件下反应,混合物经提纯即为单体1;
2、组分1的制备:无水无氧状态下,按摩尔计,将1份单体1,0.025~0.1份CuI,0.025~0.1份 (PPh3)2PdCl2,2.5~3.5份三甲基乙炔基硅以及60~150份四氢呋喃和20~50份二异丙胺混合,在温度为55~65℃的条件下反应,得到的混合物经提纯即为组分1;
3、单体2的制备:无水无氧状态下,按摩尔计,将1份组分1,0.25~0.75份无水碳酸钾和200~300份无水甲醇混合,常温下反应,混合物经提纯即为单体2;
4、前驱体的制备:按摩尔计,将一份单体1,一份单体2,0.05~0.15份(PPh3)2PdCl2, 0.025~0.75份CuI以及 150~300份四氢呋喃和20~50份二异丙胺混合,在温度为55~65 ℃的条件下反应,混合物经提纯即为前驱体;
5、按摩尔计,将一份前驱体,10~100份三氟乙酸,400~1000份二氯甲烷 ,在常温条件下反应,混合物经提纯即为一种侧链氨基质子化的共轭高分子。
本发明提供的侧链氨基质子化的共轭高分子,将其用于对水中醛的选择性检测。
本发明所述的醛包括甲醛、戊二醛。
本发明的机理是:侧链氨基可与醛基进行特异性结合,氨基质子化,可提供弱酸性环境,更利于两者之间的相互作用,从而实现对水环境中醛的特征检测。
与现有技术相比,本发明的有益效果在于:
1、本发明提供的共轭高分子侧链可提供氨基反应基团,同时,氨基质子化之后可提供弱酸性环境,使醛基(-CHO)与氨基(-NH2)的反应更易进行,具有高灵敏,低检测限。
2、本发明提供的荧光共轭高分子可实现水体系中醛类的选择性检测,对于农产品,医用废水中等水环境中有害醛类的检测,具有很好的应用前景。
3、本发明无需借助大型仪器的使用,可设计小型荧光检测器,进行定性或定量检测。
附图说明
图1是本发明实施例制备荧光共轭高分子各步骤所需单体的合成路线图;
图2是本发明实施例制备共轭高分子合成路线图;
图3是本发明实施例制备的共轭高分子的光物理数据图;
图4是本发明提供的选择性检测结果数据图;
图5是本发明实施例提供的甲醛检测荧光数据图;
图6是本发明实施例提供的戊二醛检测荧光数据图。
具体实施方式
下面结合附图和实施例对本发明技术方案作进一步的阐述
实施例1
用于合成共轭高分子的两种单体的制备主要包括以下几个主要步骤:
参见附图1,单体1(M1)的制备:氩气保护下,烧瓶中依次加入2,5-二溴对苯二酚(0.80 g, 3.00 mmol)、2-([叔丁氧羰基]氨基)乙基4-甲基苯磺酸酯(2.13 g, 6.75mmol)、无水碳酸钾(4.15 g, 30.0 mmol), 15 mL N,N-二甲基甲酰胺,加热至70 ℃,回流搅拌24 h。冷却至室温,加入200 mL去离子水,充分搅拌后,抽滤得固体,粗产物经干燥后,用少量乙酸乙酯溶解,以乙酸乙酯/正己烷(1:2)为淋洗剂过硅胶柱,收集产物并去除溶剂,得到的产物乙酸乙酯/正己烷重结晶,得白色絮状晶体,干燥。产量1.22 g (74%)。1H NMR(400 MHz, CDCl3, δ): 1.46(s, 18H), 3.55(q, 4H), 4.02(t, 4H), 5.05(br, 2H),7.10(s, 2H). Calcd for C20H30O6N2Br2(%): C, 43.34; H, 5.46; N, 5.05; found: C,43.21; H, 5.53; N, 4.84.
参见附图1,组分1的制备:烧瓶中依次加入单体M1(1.12 g, 2.00 mmol)、CuI(20mg, 0.10 mmol)、(PPh3)2PdCl2 (70 mg, 0.10 mmol),加入15 mL无水四氢呋喃和10 mL无水二异丙胺,在氩气保护下,逐滴滴加三甲基乙炔基硅(0.8 mL, 5.60 mmol),常温下搅拌1h后60 ºC回流搅拌12 h。冷却至室温,抽滤,收集滤液并除去溶剂,溶于少量乙酸乙酯,以乙酸乙酯/正己烷(1:4)为淋洗剂过硅胶柱,收集产物并除去溶剂,得到的产物乙酸乙酯/正己烷重结晶,得银灰色固体,干燥。产量0.88 g (75%)。1H NMR (400 MHz, CDCl3, δ): 0.27(s, 18H), 1.45(s, 18H), 3.53(q, 4H), 4.03(t, 4H), 5.11(br, 2H), 6.91(s, 2H).
参见附图1,单体M2的制备:将组分1(0.88 g, 1.50 mmol)、无水碳酸钾(0.10 g,0.75 mmol)加入至50 mL烧瓶中,氩气保护下,加入15 mL无水甲醇,常温下搅拌12 h。抽滤,收集滤液并除去溶剂,以乙酸乙酯/正己烷(2:5)为淋洗剂过硅胶柱,再将产物以乙酸乙酯/正己烷重结晶,得到淡黄色絮状晶体,干燥。产量0.53 g (80%)。1H NMR (400 MHz, CDCl3,δ): 1.45(s, 18H), 3.36(s, 2H), 3.54(q, 4H), 4.04(t, 4H), 5.10(br. 2H), 6.97(s, 2H). Calcd for C24H32O6N2(%): C, 64.85; H, 7.26; N, 6.30; found: C, 64.54;H, 7.29; N, 6.21.
实施例2
参见附图2,它是制备两种荧光共轭高分子所需的单体的结构及合成路线;用于检测的共轭高分子的合成包括以下几个主要步骤:
参见附图2,前驱体PPE-NBoc的制备:将单体M1(0.277 g, 0.50 mmol)、单体M2(0.222 g, 0.50 mmol)、(PPh3)2PdCl2(35 mg, 0.050 mmol)、CuI(5 mg, 0.025 mmol) 加入到预先烘干、除氧的烧瓶中,通氩气状态下,加入8 mL无水四氢呋喃和2 mL无水二异丙胺。氩气保护下60℃回流搅拌14 h。反应结束后,冷却至室温,反应液用0.22 μm的滤头过滤,滴加至200 mL冰冷的***中沉淀,经离心得固体,最后真空干燥箱干燥,得到橙红色固体0.212 g (51%)。1H NMR (400 MHz, CDCl3, δ): 1.38 (br, 18H), 3.54 (br, 4H),4.17 (br, 4H), 5.09-5.43 (br, 2H), 7.17 (br, 2H). Calcd for C22H30O6N2(%): C,63.14; H, 7.22; N, 6.69; found: C, 62.49; H, 7.40; N, 5.67. GPC: =37.0kDa;=18.0 kDa; PDI=2.06. UV-vis λmax: 429 nm. Emission λmax: 496 nm. Φf = 21% in THF, 光物理图谱参见附图3(a)。
参见附图2,PPE-NH3 +的制备:将PPE-NBoc(100 mg, 0.24 mmol)加入至10 mL二氯甲烷中,充分搅拌,待完全溶解后加入三氟乙酸(1 mL, 13.5 mmol),氩气氛围下,常温下反应24 h。反应结束后,旋转蒸发除去溶剂,少量DMF溶解,滴加至冰冷的氯仿中析出,经离心得固体,真空干燥得到橘色固体78 mg (73%),即为共轭高分子PPE-NH3 +。1H NMR (400 MHz,DMSO-d6, δ): 3.58 (s, 4H), 4.28 (br, 4H), 7.35 (br, 2H), 8.30 (br, 6H). 1HNMR (400 MHz, D2O, δ): 3.44 (s, 4H), 4.39 (br, 4H), 7.36 (br, 2H). 19F NMR(600 MHz, DMSO-d6, δ): -75.7 ppm. Calcd for C16H16F6O6N2 (%): C, 43.06; H, 3.61;N, 6.28; found: C, 42.17; H, 4.17; N, 5.94. Φf=0.8 % in H2O, Φf = 2.4 % inDMF, 光物理图谱参见附图3(b)。
实施例3
用实施例2中的共轭高分子PPE-NH3 +配制溶液检测水环境中醛。
聚合物溶液浓度为2×10-5 M(按重复单元),先配置两种不同浓度的待测物初始溶液0,1 M与0.5 M,每个样品均取2ml的聚合物溶液,均加入20 μL各待测物溶液,最终保证两组实验中各待测物在混合溶液中的有效浓度分别为1 mM和5 mM,混合后,震荡5 min,再放置25 min之后逐个进行荧光测试,所有样品现配现用,每组数据重复三遍,荧光谱图中最大发射处的荧光强度变化,即为响应。按该方法得到数据图,参见附图4。结果表明,共轭高分子对甲醛、戊二醛、乙二醛有较好的检测性,并且表现出对戊二醛极好的选择性,即使在其他所有醛的干扰下,依然表现出极佳的淬灭效果。
聚合物溶液浓度为2×10-5 M(按重复单元),一定浓度的初始甲醛和戊二醛溶液,每个样品均取2ml的聚合物溶液,每个样品中通过滴加不同体积的初始待测物溶液和水(两者共计20 μL),以保证聚合物浓度相同,待测物浓度依次增加。混合后,震荡5 min,再放置25 min之后逐个进行荧光测试,所有样品现配现用,每组数据重复三遍,荧光谱图中最大发射处的荧光强度变化,即为响应。按上述方法得到的数据参见附图5和附图6。图5为甲醛的检测效果图,结果表明共轭高分子对甲醛有较好的检测效果,其对甲醛检测限可达8 μM,图6为戊二醛检测效果图,结果表明共轭高分子系对戊二醛的检测效果要更加明显,表现为显著的荧光淬灭,并且检测限在这一条件下可达350 nM。
Claims (4)
1.一种侧链氨基质子化的共轭高分子,其特征在于它的结构式为:
。
2.一种如权利要求1所述的侧链氨基质子化的共轭高分子的制备方法,其特征在于包括如下步骤:
(1)单体1的制备:按摩尔计,将1份2,5-二溴对苯二酚,2~3份2-([叔丁氧羰基]氨基)乙基4-甲基苯磺酸酯,5~15份无水碳酸钾和150~250份N,N-二甲基甲酰胺混合,在温度为60~90℃的条件下反应,混合物经提纯即为单体1;
(2)组分1的制备:无水无氧状态下,按摩尔计,将1份单体1,0.025~0.1份CuI, 0.025~0.1份 (PPh3)2PdCl2,2.5~3.5份三甲基乙炔基硅以及60~150份四氢呋喃和20~50份二异丙胺混合,在温度为55~65℃的条件下反应,得到的混合物经提纯即为组分1;
(3)单体2的制备:无水无氧状态下,按摩尔计,将1份组分1,0.25~0.75份无水碳酸钾和200~300份无水甲醇混合,常温下反应,混合物经提纯即为单体2;
(4)前驱体的制备:按摩尔计,将一份单体1,一份单体2,0.05~0.15份(PPh3)2PdCl2,0.025~0.75份CuI以及 150~300份四氢呋喃和20~50份二异丙胺混合,在温度为55~65℃的条件下反应,混合物经提纯即为前驱体;
(5)按摩尔计,将一份前驱体,10~100份三氟乙酸,400~1000份二氯甲烷 ,在常温条件下反应,混合物经提纯即为一种侧链氨基质子化的共轭高分子。
3.一种如权利要求1所述的侧链氨基质子化的共轭高分子的应用,其特征在于将其用于对水中醛的选择性检测。
4.根据权利要求3所述的侧链氨基质子化的共轭高分子的应用,其特征在于:所述醛包括甲醛、戊二醛。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710204311.3A CN107033331B (zh) | 2017-03-30 | 2017-03-30 | 一种侧链氨基质子化的荧光共轭高分子、制备方法及其应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710204311.3A CN107033331B (zh) | 2017-03-30 | 2017-03-30 | 一种侧链氨基质子化的荧光共轭高分子、制备方法及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107033331A CN107033331A (zh) | 2017-08-11 |
CN107033331B true CN107033331B (zh) | 2018-10-12 |
Family
ID=59533941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710204311.3A Active CN107033331B (zh) | 2017-03-30 | 2017-03-30 | 一种侧链氨基质子化的荧光共轭高分子、制备方法及其应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107033331B (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107573488B (zh) * | 2017-09-13 | 2019-05-24 | 中国科学院化学研究所 | 聚芴苯类聚合物及其制备方法和应用 |
CN107586378B (zh) * | 2017-09-13 | 2019-05-24 | 中国科学院化学研究所 | 聚芴苯类聚合物及其制备方法和应用 |
CN115304749B (zh) * | 2022-08-31 | 2023-12-22 | 苏州大学 | 一种含邻苯二酚侧基的荧光共轭高分子及其制备方法 |
CN116082534B (zh) * | 2022-12-26 | 2024-05-28 | 临沂大学 | 一种海藻酸衍生物、海藻酸衍生物铵盐/石墨烯复合材料及其制备方法和应用 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104198451B (zh) * | 2014-09-02 | 2016-08-24 | 深圳市坤健创新药物研究院 | 一种传感器阵列及其在金属离子辅助鉴定中的应用 |
CN106518762A (zh) * | 2016-11-02 | 2017-03-22 | 济南大学 | 一种检测细胞内质网中甲醛的荧光探针 |
-
2017
- 2017-03-30 CN CN201710204311.3A patent/CN107033331B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN107033331A (zh) | 2017-08-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107033331B (zh) | 一种侧链氨基质子化的荧光共轭高分子、制备方法及其应用 | |
CN106478576B (zh) | 一种用于检测羧酸酯酶的荧光探针及其制备方法与应用 | |
CN108218923A (zh) | 一种检测pH的水溶性磷光聚合物及其制备方法和应用 | |
Zhou et al. | Ratiometric fluorescent Zn2+ chemosensor constructed by appending a pair of carboxamidoquinoline on 1, 2-diaminocyclohexane scaffold | |
CN112209871B (zh) | 一种基于四苯乙烯的锌离子荧光探针及其制备方法与应用 | |
CN109867611A (zh) | 一种用于红酒和活体内硫化氢检测的水溶性双光子硫化氢荧光探针及其制备方法和应用 | |
CN105588824B (zh) | 双层静电纺丝薄膜传感器在硝基芳烃类物质检测中的应用 | |
Li et al. | A fluorescent detection pen for sensitive, specific, and real-time detection of phosgene based on a novel rhodamine probe | |
CN113214144B (zh) | 基于偶极有机配体的金属有机框架材料、合成方法及其应用 | |
CN110092773A (zh) | 一种氧杂蒽类衍生物及其制备方法和应用 | |
CN106397743B (zh) | 一种水溶性荧光共轭聚合物在硝基芳烃检测中的应用 | |
CN105503831B (zh) | 一种具有极酸性pH响应的近红外荧光探针及其制备方法和应用 | |
CN115261015B (zh) | 一种基于ICT原理检测N2H4和Cu2+的双通道荧光探针及其制备方法和应用 | |
CN109369569A (zh) | 一类检测丙酮醛的荧光探针及其制备方法和应用 | |
CN106496239B (zh) | 一种溶酶体内pH比率荧光探针的制备与应用 | |
CN113121541B (zh) | 一种同时区分金离子Au3+与钯的荧光探针的合成及应用 | |
CN109912501A (zh) | 一种高选择性且大Stokes位移的酯滴探针及其制备方法和应用 | |
CN111925316B (zh) | 一种基于4-氟苯乙炔基的双光子荧光极性探针及其制备方法和用途 | |
Kou et al. | Coumarin functionalized cellulose-based fluorescent probe for detection of hydrazine and its applications in environmental analysis | |
CN106543058A (zh) | 一种手性硒脲类化合物及其制备与应用 | |
CN110105280B (zh) | 一种基于1,8-萘二甲酰亚胺的水溶性荧光探针及其制备方法和应用 | |
CN109265429B (zh) | 萘衍生物类荧光染料及其制备方法和用途 | |
CN114716401B (zh) | 一种有机小分子荧光探针及其制备方法和应用 | |
CN105732766A (zh) | 一种生物分子荧光标记方法及得到的荧光标记的生物分子及其应用 | |
CN112521620B (zh) | 一种用于磺胺二甲嘧啶检测的超分子磷光探针试剂及其制备方法 |
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 |