CN106366041A - 一种连续识别钯离子、co的荧光探针及应用 - Google Patents
一种连续识别钯离子、co的荧光探针及应用 Download PDFInfo
- Publication number
- CN106366041A CN106366041A CN201610801733.4A CN201610801733A CN106366041A CN 106366041 A CN106366041 A CN 106366041A CN 201610801733 A CN201610801733 A CN 201610801733A CN 106366041 A CN106366041 A CN 106366041A
- Authority
- CN
- China
- Prior art keywords
- fluorescent probe
- fluorescence
- probe
- pipd
- palladium ion
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring 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
- 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
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
本发明提供了一种连续识别钯离子、CO的荧光探针,其为1‑4‑(1氢‑菲醌[9,10‑d]咪唑‑2‑乙基)苯基N,N‑二甲基甲胺,简称PIPD,本发明还公开了所述荧光探针可以在水相中专一识别二价钯离子的应用。本发明的钯离子荧光探针能在水相中选择性检测钯离子并发生荧光淬灭,当遇到生物CO试剂时荧光再次淬灭。本发明所述荧光探针的AIE特性对于检测生物体具有突出优点,并在激光激发荧光生物标记领域具有潜在的应用价值。
Description
技术领域
本发明涉及一种新型的荧光染料及其应用,尤其涉及一种应用AIE机理在水相/有机相中荧光增强的菲醌-咪唑类化合物荧光探针及其应用,此类化合物对钯离 子、CO有连续识别性质;属于有机小分子荧光探针领域。
背景技术
在过去的几十年中,荧光材料因其具有的多功能性,如发光效率高,很好的运输能力等,在许多领域如电致发光器件、生物成像、荧光探针等领域受到越来越多的关注。然而,对于绝大多数传统的有机发光材料,当处于聚集态时,会出现荧光猝灭的现象,我们称之为聚集荧光淬灭效应(aggregation-caused quenching, ACQ)。因为传统的发光团通常是平面盘状的芳香环分子,具有大的π-共轭性,以单分子形态溶解在稀溶液中发出强烈的荧光。然而,在固态或聚集状态,分子紧密排列,分子间存在强烈的π-π作用,导致强烈的ACQ效应。这种荧光猝灭效应大大限制了发光材料的应用。
现有技术中采取了各种各样的化学、物理和工程上的方法阻止分子间的聚集。2001年,由香港科技大学的唐本忠教授课题组发现了一种与ACQ效应完全相反的发光效应。他们发现一种噻咯(1-methyl-1,2,3,4,5-pentaphenylsilole, silole)衍生物在稀溶液中基本 是不发光的,然而当其分子处于聚集态,即在浓溶液或者制成固体膜的时候表现出了很强的荧光。这是因为在稀溶液里面,它的5个苯基转子进行动态的分子内旋转,而在聚集状态下,由于空间限制,这种分子内旋转受到了很大阻碍,非辐射能量衰减受到抑制,激发态分子只能通过辐射跃迁形式回到基态,从而使荧光显著增强。由于这种现象是通过自聚作用诱导产生的,所以把它命名为自聚诱导荧光(aggregation-induced emission,AIE)。
虽然对传统的有机发光材料的研究已经在实验室里面试验了许多年,但是从事研究具有AIE活性荧光材料的还相对较少。除了唐本忠教授发现的最具有代表性的Silole类化合物以外,迄今为止国内外已经发现的AIE化合物也在陆续增多。这些化合物在有机电致发光器件、有机激光器、太阳能电池及光学传感器等诸多领域都有着很好的应用前景。然而,应用AIE发光材料来特异性检测的探针分子还是很少见的,特别是有机小分子。基于此,开发新型的具有AIE特性的小分子化合物,并能检测离子的荧光探针,有着重要的研究价值。
发明内容
针对现有技术的不足,本发明提供了一种简单合成的并且在水相中连续识别二价钯离子、CO的菲醌-咪唑类化合物荧光探针及其应用。
本发明所述的适于在水相中连续识别二价钯离子、CO的荧光探针,其特征在于:它是小分子化合物的1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺,简称PIPD,其化学结构式如式(1)所示:
()
上述1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺(简称PIPD)的制备方法是:将4-溴甲基苯甲醛1与二甲胺的水溶液2和K2CO3、KI在乙腈做溶剂条件下生成化合物2,然后将化合物2与菲醌发生反应得到终产物:1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺PIPD,其NMR谱图见图1-2。
上述PIPD的制备反应式如下:
上述适于水相/有机相中具有AIE效应、连续识别二价钯离子、CO的荧光探针的应用。
上述的应用中:所述荧光探针是在水相/有机相中以荧光聚集诱导发光的方式实现AIE特征。
上述荧光探针在水相中能高选择性识别二价钯离子,该探针本身由于AIE荧光强度高,当钯离子配位后,荧光淬灭;当加入CO后荧光继续淬灭。
实验证实:检测环境是水相时,由本发明所述的荧光探针的溶剂化效应显示,在水中和PBS缓冲液中探针的荧光强度相对较弱(图3),量子产率约为0.1(参见表1:1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺的光物理性质),而在有机相中,如MeOH、EtOH 和MeCN,其荧光强度相对较大,量子产率增加。这是因为水是稳定的极性溶剂,而MeOH、 EtOH 和MeCN等有机溶剂在极性上有差别。有机小分子往往在有机溶液中表现出好的溶解性。因此,本实验选用水/DMF作为检测AIE效应的溶剂(图4)。系统的改变混合物水和DMF的极性,来研究化合物在溶剂混合物的发射光谱。在纯的DMF中,探针的荧光强度相对较弱,当加入少量水时,荧光强度增强但改变不大。当水的百分比增大到50%时,荧光强度迅速增强,直至水的含量高达90%。配制含水百分比不同的DMF溶液,加入等量的探针,在365nm光照下可明显观察到光强的变化。该现象符合典型的AIE行为。
在钯离子滴定实验中(图5),在钯离子加入量ncu=0~500 PIPD当量的条件下,荧光发生淬灭,加入300当量的钯离子时,荧光几乎完全淬灭。,随着钯离子浓度的增加,荧光趋于减弱。在各种离子存在的情况下,钯离子同样荧光强度趋于淬灭,表明本发明所述的钯离子荧光探针在水相中排除了其他例子的干扰(图6),当在淬灭的体系中加入CO时,荧光趋于逐渐淬灭至平衡的趋势(图7)。
基于上述实验结果,可以证明本发明所述的菲醌-咪唑类化合物荧光探针是一类新型的小分子型AIE特征的高选择性钯离子荧光探针分子,通过含水百分比实验可以证实该探针符合AIE特征。钯离子与探针的配位作用使探针本身的机制受到破坏,使荧光淬灭;当加入生物CO时,结构改变使荧光继续淬灭。其识别反应式如通式(II)所示:
(II)
本发明提供的新型菲醌-咪唑类化合物荧光探针与其功能相近的AIE荧光探针比具有显著优势,由于该化合物的分子量小,可以随着孵育时间的延长慢慢进入细胞内部,在细胞膜上可观察到发光情况。且本发明所述菲醌-咪唑类化合物在水相中的选择性和合成手段也具有新颖性和简便性。基于本发明提供的识别二价钯离子的菲醌类化合物荧光探针在溶剂中具有高的荧光量子产率,并且当加入生物CO后荧光变化的结果及现象,为生物学成像应用奠定了理论基础,预示其在激光激发荧光生物标记领域具有潜在的应用价值。
附图说明
图1:PIPD 1H NMR (400 MHz, MeOD)
图2:PIPD 13C NMR(100 MHz, DMSO-d6)
图3:探针在不同溶剂下的溶剂化效应。
图4:探针在不同百分比的水/DMF中的强度变化。其中激发波长为365 nm;探针PIPD母液的浓度:10-3M,稀释5ml进行测试。水/DMF中水的含量范围为0%~90%。
图5:钯离子的滴定实验;其中激发波长为365 nm;探针PIPD母液的浓度:10-3M,稀释5ml进行测试;钯离子为0~500当量。
图6:探针在各离子存在的情况下对钯离子的竞争实验。其中激发波长为365 nm;探针PIPD的浓度:10-3M;选择性例子(图示离子)的浓度为4.5x10-5 M。
图7:生物CO的反滴定实验。其中激发波长为365 nm;探针PIPD母液的浓度:10-3M,稀释5ml进行测试;CO为250当量。
具体实施方式
下面结合实施例对本发明作进一步的说明。
实施例1
4-(二甲胺基)甲基苯甲醛(2)的合成:
将0.2 g (1 mmol) 4-溴甲基苯甲醛,0.276g (2 mmol)K2CO3,0.332g (2 mmol)KI和33%二甲胺水溶液(3 g) 混合到100毫升圆底烧瓶中,然后加入乙腈20毫升做溶剂。混合液在氮气保护下加热回流10 h。反应结束后冷却至室温,将液体倒入100mL的冰水中,用CH2Cl2萃取,用盐水洗有机层,然后用Na2SO4干燥、真空旋干,产品用硅胶柱层析法纯化得到黄色的液体状化合物1。产率:85%。
1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺(PIPD)的合成:
将0.21 g(1 mmol)的菲醌,化合物1(1 mmol),1.54g醋酸铵和10mL冰醋酸混合在50mL的圆底烧瓶中,在氮气保护下加热回流8h,反应体系由黄色变为红褐色。反应结束后冷却至室温,将液体倒入100mL的冰水中,用CH2Cl2萃取,用盐水洗有机层,然后用Na2SO4干燥、真空旋干,产品用硅胶柱层析法纯化得到黄色的固体化合物PIPD。产率:83%。
1H NMR (400 MHz, MeOD) δ 8.80 (d, J = 8.2 Hz, 1H), 8.55 (s, 1H), 8.31(d, J = 8.3 Hz, 1H), 7.75 – 7.61 (m, 3H), 4.12 (s, 1H), 2.72 (s, 3H).详见图1.13C NMR (100 MHz, DMSO-d6): 193.09, 148.17, 136.53, 135.91, 130.71, 127.77,126.96, 29.50, 29.04, 27.01, 22.57, 14.43, 7.65. 详见图2. HRMS (m/z): [M+2H]+calcd for C24H21N3: 353.17; found, 353.16.
实施例2
1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺(PIPD)的溶剂化效应
预先准备1份10 mL的 10-3 M探针PIPD的N, N-二甲基甲酰胺溶液,然后分别取10μL加入六个相同的5mL容量瓶中,分别用DMF、乙腈、PBS、水、甲醇、乙醇、氯仿稀释到5mL,然后进行荧光检测,结果见图3。
实施例3
根据实施例2数据计算探针PIPD在各溶剂内的量子产率。
上述计算公式如下:
其中,和 分别代表样品和参比的单光子荧光量子产率,和 分别代表样品 和 所选参比的吸光度数值, 和分别代表样品和参比分子的荧光强度,∫Fs和∫Fr分别代表探针分子和参比的单光子荧光积分面积。理想的参比一般是与激发波长无关(见表 1)。
表1:1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺(PIPD)在不同溶剂中的光物理性质
。
实施例4
1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺的AIE特性
配制10 mL不同百分比的水/DMF溶液及探针PIPD母液的浓度为10-3M作为备用。
向各百分比的溶液中加入10μL探针母液,摇匀后进行荧光检测(λEx= 365 nm, λEm= 420 nm),计算各体系中荧光强度,建立荧光强度与溶液百分比的曲线图 ,结果见图4。
实施例 5
钯离子的滴定
配制45 mL浓度为4.5x10-5 M钯离子的水溶液及探针PIPD母液的浓度为10-3M作为备用。钯离子浓度从0当量滴定到500当量并进行荧光检测(λEx= 365 nm, λEm= 420 nm),计算各体系中荧光强度,建立荧光强度与钯离子浓度标准曲线,标准曲线(见图5)。
实施例6
竞争实验
配制45 mL浓度为4.5x10-5 M各种离子的水溶液及探针PIPD母液的浓度为10-3M作为备用。
取10μL探针和250当量的钯离子溶液,然后用其他各离子的水溶液稀释到5mL进行荧光检测(λEx= 365 nm, λEm= 420 nm),建立荧光强度与各种离子的柱状图 (见图6)。
实施例7
CO的反滴定
配制45 mL浓度为4.5x10-5 M钯离子的水溶液及探针PIPD母液的浓度为10-3M作为备用。
取10μL探针母液加入和250当量的钯离子母液加入5mL容量瓶,然后加入CO试剂从0-500当量反滴定上述体系建立荧光强度与CO浓度标准曲线 (见图7)。
Claims (3)
1.一种连续识别钯离子、CO的荧光探针,其特征在于:其化学名称为:1-4-(1氢-菲醌[9,10-d]咪唑-2-乙基)苯基N,N-二甲基甲胺,简称PIPD,其化学结构式如下式(1)所示:
()。
2.根据权利要求1所述的荧光探针,其特征在于,由以下方法制备而成:将4-溴甲基苯甲醛、二甲胺的水溶液和K2CO3、KI在乙腈做溶剂条件下反应,然后再与菲醌发生反应得到终产物。
3.一种权利要求1或2所述的荧光探针在连续识别钯离子、CO中的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610801733.4A CN106366041B (zh) | 2016-09-05 | 2016-09-05 | 一种连续识别钯离子、co的荧光探针及应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610801733.4A CN106366041B (zh) | 2016-09-05 | 2016-09-05 | 一种连续识别钯离子、co的荧光探针及应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106366041A true CN106366041A (zh) | 2017-02-01 |
CN106366041B CN106366041B (zh) | 2019-02-19 |
Family
ID=57899014
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610801733.4A Expired - Fee Related CN106366041B (zh) | 2016-09-05 | 2016-09-05 | 一种连续识别钯离子、co的荧光探针及应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106366041B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106957267A (zh) * | 2017-03-28 | 2017-07-18 | 济南大学 | 一种新型检测钯的可逆比色比率苯并咪唑类荧光分子探针 |
CN108148572A (zh) * | 2018-01-12 | 2018-06-12 | 济南大学 | 一种脂滴荧光探针及其合成方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100253208A1 (en) * | 2009-04-02 | 2010-10-07 | Chien-Hong Cheng | Bis-phenanthroimidazolyl compound and electroluminescent device using the same |
CN103965865A (zh) * | 2014-05-05 | 2014-08-06 | 吉林大学 | 一种压致变色材料其制备方法及应用 |
CN104099084A (zh) * | 2014-06-25 | 2014-10-15 | 吉林大学 | 一种蓝色有机电致荧光材料其制备方法及应用 |
CN104962278A (zh) * | 2015-05-18 | 2015-10-07 | 华东理工大学 | 一种钯离子荧光探针及其制备方法和应用 |
-
2016
- 2016-09-05 CN CN201610801733.4A patent/CN106366041B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100253208A1 (en) * | 2009-04-02 | 2010-10-07 | Chien-Hong Cheng | Bis-phenanthroimidazolyl compound and electroluminescent device using the same |
CN103965865A (zh) * | 2014-05-05 | 2014-08-06 | 吉林大学 | 一种压致变色材料其制备方法及应用 |
CN104099084A (zh) * | 2014-06-25 | 2014-10-15 | 吉林大学 | 一种蓝色有机电致荧光材料其制备方法及应用 |
CN104962278A (zh) * | 2015-05-18 | 2015-10-07 | 华东理工大学 | 一种钯离子荧光探针及其制备方法和应用 |
Non-Patent Citations (3)
Title |
---|
YOSHIDA, KATSUHIRA,等: "Fluorescence sensing behavior of crystals of an imidazole-type clathrate host upon contact with gaseous carboxylic acids", 《CHEMISTRY LETTERS》 * |
孙亮: "《STN》", 2 April 2018 * |
赵鑫,等: "新型菲并咪唑衍生物的合成及其光物理性能", 《石油化工》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106957267A (zh) * | 2017-03-28 | 2017-07-18 | 济南大学 | 一种新型检测钯的可逆比色比率苯并咪唑类荧光分子探针 |
CN106957267B (zh) * | 2017-03-28 | 2019-05-07 | 济南大学 | 一种新型检测钯的可逆比色比率菲并咪唑类荧光分子探针 |
CN108148572A (zh) * | 2018-01-12 | 2018-06-12 | 济南大学 | 一种脂滴荧光探针及其合成方法和应用 |
CN108148572B (zh) * | 2018-01-12 | 2019-04-16 | 济南大学 | 一种脂滴荧光探针及其合成方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN106366041B (zh) | 2019-02-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Xu et al. | A carbazole-functionalized metal–organic framework for efficient detection of antibiotics, pesticides and nitroaromatic compounds | |
Su et al. | Hydrazone-based switches, metallo-assemblies and sensors | |
Qiu et al. | An unusual AIE fluorescent sensor for sequentially detecting Co2+-Hg2+-Cu2+ based on diphenylacrylonitrile Schiff-base derivative | |
Li et al. | Supersensitive detection of explosives by recyclable AIE luminogen-functionalized mesoporous materials | |
Wang et al. | Improving covalent organic frameworks fluorescence by triethylamine pinpoint surgery as selective biomarker sensor for diabetes mellitus diagnosis | |
Wang et al. | Highly sensitive and selective fluorometric off–on K+ probe constructed via host–guest molecular recognition and aggregation-induced emission | |
Chen et al. | Ultrasensitive water sensors based on fluorenone-tetraphenylethene AIE luminogens | |
Zhang et al. | Non-conjugated fluorescent molecular cages of salicylaldehyde-based tri-Schiff bases: AIE, enantiomers, mechanochromism, anion hosts/probes, and cell imaging properties | |
Sathiyan et al. | A multibranched carbazole linked triazine based fluorescent molecule for the selective detection of picric acid | |
CN104151326B (zh) | 一种苝二酰亚胺-罗丹明荧光探针及其制备方法和应用 | |
Zhang et al. | Two novel AIEE-active imidazole/α-cyanostilbene derivatives: photophysical properties, reversible fluorescence switching, and detection of explosives | |
Gupta et al. | Design and synthesis of novel V-shaped AIEE active quinoxalines for acidochromic applications | |
Li et al. | Chemical sensing failed by aggregation-caused quenching? A case study enables liquid/solid two-phase determination of N2H4 | |
Zhou et al. | Spectroscopic analysis and in vitro imaging applications of a pH responsive AIE sensor with a two-input inhibit function | |
Jiang et al. | Dimethoxy triarylamine-derived terpyridine–zinc complex: A fluorescence light-up sensor for citrate detection based on aggregation-induced emission | |
Nie et al. | Two novel six-coordinated cadmium (II) and zinc (II) complexes from carbazate β-diketonate: crystal structures, enhanced two-photon absorption and biological imaging application | |
Xu et al. | Recent advances of covalent organic frameworks in chemical sensing | |
WO2020253756A1 (en) | Fluorescent red-emissive compounds for cellular organelle imaging | |
Kong et al. | A novel DA type terpyridine-based carbazole Zn (II) complex with enhanced two-photon absorption and its bioimaging application | |
Martin et al. | Solvent switchable dual emission from a bichromophoric ruthenium–BODIPY complex | |
Jiang et al. | Tetraphenylethene end-capped [1, 2, 5] thiadiazolo [3, 4-c] pyridine with aggregation-induced emission and large two-photon absorption cross-sections | |
CN106478458B (zh) | 基于四苯基乙烯和马来腈的希夫碱化合物及其制备方法和应用 | |
Degirmenci et al. | Synthesis, chemiluminescence and energy transfer efficiency of 2, 3-dihydrophthalazine-1, 4-dione and BODIPY dyad | |
Wang et al. | The synthesis and highly sensitive detection of water content in THF using a novel solvatochromic AIE polymer containing diketopyrrolopyrrole and triphenylamine | |
Yin et al. | Thermosensitivity and luminescent properties of new tetraphenylethylene derivatives bearing peripheral oligo (ethylene glycol) chains |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | 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 | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190219 Termination date: 20200905 |