CN113698353B - 一种用于水溶液中铜（ii）粒子检测的咪唑基希夫碱荧光传感器及其合成方法 - Google Patents
一种用于水溶液中铜（ii）粒子检测的咪唑基希夫碱荧光传感器及其合成方法 Download PDFInfo
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Abstract
本发明公开一种用于水溶液中铜(II)粒子检测的咪唑基希夫碱荧光传感器及其合成方法，其化学结构式为：
所述咪唑基希夫碱荧光传感器是通过4‑硝基邻苯二胺与水杨醛反应生成苯并咪唑环，通过还原硝基得到氨基，最后通过其氨基与水杨醛反应，合成了一种用于水溶液中铜(II)粒子检测的咪唑基希夫碱荧光传感器。本发明的咪唑基希夫碱荧光传感器对水中的铜(II)粒子具有高的选择性和灵敏度，以及较低的检出限，可应用于纸色谱中定性检测水样中的铜(II)粒子,应用前景广泛。
Description
技术领域
本发明涉及有机小分子荧光传感器领域，尤其涉及一种用于水溶液中铜(II)粒子检测的“关闭”型咪唑基希夫碱荧光传感器及其合成方法。
背景技术
铜元素是人体内第三大必需的微量元素，参与人体重要的生理过程，在生理活动中发挥着至关重要的作用。人血液中铜(II)粒子浓度约为15.7-23.6μM。当人体内铜(II)粒子浓度超过正常值时，会导致人体内生理过程失衡，甚至可能导致严重的神经系统疾病。世界卫生组织规定饮用水中铜(II)粒子的最大允许浓度为20μM。因此，开发一种灵敏度高、检出限低的化学传感器来检测铜(II)粒子，具有重要的意义。在众多检测方法中，荧光传感器简单快速且被广泛应用，这使得开发一种绿色环保的荧光传感器用于实际水样的实时监测成为了可能。
发明内容
为此，本发明提供了一种用于水溶液中铜(II)粒子检测的咪唑基希夫碱荧光传感器及其合成方法。
本发明用于水溶液中铜(II)粒子检测的咪唑基希夫碱荧光传感器，其化学结构如下：
本发明提供一种用于水溶液中铜(II)粒子检测的咪唑基希夫碱荧光传感器的合成路线如下：
所述合成步骤包括以下三步：
第一步：以4-硝基邻苯二胺与水杨醛为原料，所述4-硝基邻苯二胺与水杨醛发生缩合反应，生成2-(6-硝基-1H-苯并咪唑-2-基)苯酚(即化合物1)。
第二步：将第一步所得化合物2-(6-硝基-1H-苯并咪唑-2-基)苯酚(即化合物1)进行还原反应，生成2-(6-氨基-1H-苯并咪唑-2-基)苯酚(即化合物2)。
第三步：将第二步所得化合物2-(6-氨基-1H-苯并咪唑-2-基)苯酚(即化合物2)与水杨醛进行缩合反应，生成咪唑基希夫碱荧光传感器(即化合物3)。
本发明通过设计合成咪唑基希夫碱荧光传感器，并成功用于水溶液中铜(II)粒子检测，咪唑基希夫碱荧光传感器3具有高的选择性和灵敏度，而且具有较低的检出限(77.01nM)。
附图说明
图1：化合物(3)10μM的PBS缓冲溶液(0.2M,pH 8.0)中不同金属阳离子的荧光强度变化比例柱状图；
图2：化合物(3)10μM的PBS缓冲溶液(0.2M,pH 8.0)中进行铜(II)粒子标准品溶液的荧光滴定图；
图3：化合物(3)10μM的PBS缓冲溶液(0.2M,pH 8.0)中响应持续时间折线图。
具体实施方式
以下实施例中所涉及的试剂未特别说明，则为商业化产品，纯度为化学级。为了更加清楚的解释本发明所解决的技术问题及技术方案，以下所述的具体实施例对本发明进行了进一步详细说明。此处所述的具体实施列仅用于解释本发明，并不用于限定本发明。
实施例1
化合物1的制备
在100mL圆底烧瓶中，加入1.53g 4-硝基邻苯二胺，1.05mL水杨醛和20mL无水乙醇，室温搅拌5h，过滤，滤饼用无水乙醇洗涤，干燥，得2.40g黄色固体(即化合物1)，收率94％。
HRMS(ESI)C13H9N3O3calcd.for[M+H]+256.0722；found:256.2604。
化合物2的制备
在250mL圆底烧瓶中，加入50mL 50％乙酸,缓慢加入1.02g化合物1，60℃下搅拌混合物，加入1.12g铁粉，机械搅拌30min，反应结束后，将反应混合物倒入50mL乙酸乙酯中，过滤，滤液用NaOH溶液调节pH＝8，分液，有机相用饱和食盐水洗涤，无水硫酸钠干燥，过滤，浓缩，以石油醚/乙酸乙酯为洗脱剂，柱层析纯化，得到0.45g黄褐色固体(化合物2)，收率51％。
H HRMS(ESI)m/z calcd.for C13H11N3O([M+H]+):226.0980；found:226.0946。
化合物3的制备
在50mL圆底烧瓶中，加入0.090g化合物2,42μL水杨醛和15mL无水甲醇，室温搅拌5h，过滤，滤饼用无水甲醇洗涤，干燥，得0.12g黄色固体(即化合物3)，收率94％。
HRMS(ESI)m/z calcd.for C20H15N3O2([M+H]+):330.1243；found:330.1205。
实例2
在化合物3 10μM的PBS缓冲溶液(0.2M,pH 8.0)中分别加入1当量的不同金属阳离子溶液，测其在360nm荧光发射强度变化；发现在加入1当量不同金属阳离子溶液，化合物3对铜(II)粒子具有良好的选择性；当在以上溶液中分别加入1当量的铜(II)粒子后，传感器可排除干扰，正常检测水溶液中的铜(II)粒子，如图1所示。
在化合物3 10μM的PBS缓冲溶液(0.2M,pH 8.0)中加入不同浓度铜(II)粒子溶液进行荧光滴定实验；对比发现，化合物3作为识别铜(II)粒子的荧光传感器具有现实可行性，如图2所示。
将化合物3 10μM滴入PBS缓冲溶液(0.2M,pH 8.0)中，以及将铜(II)粒子10μM溶液滴入化合物3 10μΜ的PBS缓冲溶液(0.2M,pH 8.0)中；对比发现，化合物3传感器对铜(II)粒子的识别在4min达到稳定且持续3h没有发生荧光波动，如图3所示。
以上所述仅为本发明优选实施例，并不用于限制本发明，凡在本发明的原则和精神之内所作的任何改动，等同替换和改进等，均包含在本发明的保护范围之内。
Claims (2)
1.一种用于水溶液中铜(II)粒子检测的咪唑基希夫碱荧光传感器，其特征在于，该咪唑基希夫碱荧光传感器的化学结构式如下：
2.根据权利要求1所述的咪唑基希夫碱荧光传感器的合成方法,其特征在于,合成路线如下：
所述合成步骤包括以下三步：
第一步：以4-硝基邻苯二胺与水杨醛为原料，所述4-硝基邻苯二胺与水杨醛发生缩合反应，生成2-(6-硝基-1H-苯并咪唑-2-基)苯酚，即化合物1；
第二步：将第一步所得化合物2-(6-硝基-1H-苯并咪唑-2-基)苯酚，即化合物1，发生还原反应，生成2-(6-氨基-1H-苯并咪唑-2-基)苯酚，即化合物2；
第三步：将第二步所得化合物2-(6-氨基-1H-苯并咪唑-2-基)苯酚，即化合物2，与水杨醛发生缩合反应，生成咪唑基希夫碱荧光传感器，即化合物3。
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103320118A (zh) * | 2013-05-08 | 2013-09-25 | 济南大学 | 一种希夫碱铜离子荧光探针及其制备方法 |
| CN108586382A (zh) * | 2018-04-08 | 2018-09-28 | 山西大学 | 一种希夫碱化合物及其制备和在铜离子检测中的应用 |
| KR20190025788A (ko) * | 2017-09-01 | 2019-03-12 | 삼성디스플레이 주식회사 | 벤즈아졸 유도체를 리간드로 하는 유기 금속 착물 및 이를 포함한 유기 전계발광 소자 |
| CN112812075A (zh) * | 2020-12-30 | 2021-05-18 | 山西大学 | 一种基于苯并噻唑类希夫碱荧光探针的制备方法及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103320118A (zh) * | 2013-05-08 | 2013-09-25 | 济南大学 | 一种希夫碱铜离子荧光探针及其制备方法 |
| KR20190025788A (ko) * | 2017-09-01 | 2019-03-12 | 삼성디스플레이 주식회사 | 벤즈아졸 유도체를 리간드로 하는 유기 금속 착물 및 이를 포함한 유기 전계발광 소자 |
| CN108586382A (zh) * | 2018-04-08 | 2018-09-28 | 山西大学 | 一种希夫碱化合物及其制备和在铜离子检测中的应用 |
| CN112812075A (zh) * | 2020-12-30 | 2021-05-18 | 山西大学 | 一种基于苯并噻唑类希夫碱荧光探针的制备方法及应用 |
Non-Patent Citations (2)
| Title |
|---|
| Masahiro Muto et al..Tripodal Trimanganese(III) Complexes of New Unsymmetrical Pentadentate Ligands Derived from 2-(Salicylideneamino)phenol: Syntheses, Crystal Structures and Properties.Eur. J. Inorg. Chem..2007,第3701–3709页. * |
| Rajasekhar Yerrasani et al..Thermal, optical and Photophysical behaviour of some Mesogenic Benzimidazole-based Schiff-bases.Journal of Molecular Liquids.2017,第248卷第214-218页. * |
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