CN112538051A - 一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法 - Google Patents

一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法 Download PDF

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CN112538051A
CN112538051A CN202011490670.8A CN202011490670A CN112538051A CN 112538051 A CN112538051 A CN 112538051A CN 202011490670 A CN202011490670 A CN 202011490670A CN 112538051 A CN112538051 A CN 112538051A
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fluorescent probe
trifluralin
benzimidazole
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侯士立
王俊杰
夏天姿
蓝珍妮
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Abstract

本发明公开一种用于氟乐灵检测的苯并咪唑荧光探针，化学结构式为：
Figure DDA0002840600320000011
所述苯并咪唑荧光探针是通过邻苯二胺与香草醛反应生成苯并咪唑环，通过N,N‑二苯基氯甲酰胺与其酚羟基作用，合成了一种用于氟乐灵检测的苯并咪唑荧光探针。本发明的苯并咪唑荧光探针对氟乐灵除草剂具有高的选择性和高的灵敏度，以及较低的检出限，应用前景广泛。

Description

一种用于氟乐灵检测的苯并咪唑荧光探针及其合成方法
技术领域
本发明涉及有机小分子荧光探针领域，尤其涉及一种用于氟乐灵检测的苯并咪唑荧光探针其合成方法。
背景技术
氟乐灵是一种廉价而有效的二硝基除草剂，广泛应用于大豆、棉花、花生和向日葵等多种作物的除草。其除草机理是通过抑制杂草的根、芽细胞分裂和发育来控制萌发。氟乐灵除草剂的结构如下所示。2017年10月27日，世界卫生组织国际癌症研究机构公布的致癌清单初步整理参考，氟乐灵在3类致癌物清单中。因此，开发有效的氟乐灵监测方法具有重要意义。在众多检测中，荧光检测简单快速且广泛被应用，然而目前对氟乐灵的荧光检测方法少之甚少。氟乐灵的结构式如下：
Figure BDA0002840600300000011
发明内容
为此，本发明提供了一种用于氟乐灵检测的苯并咪唑荧光探针。
本发明用于氟乐灵检测的苯并咪唑荧光探针，其化学结构如下：
Figure BDA0002840600300000012
本发明提供一种用于氟乐灵检测的苯并咪唑荧光探针的合成路线如下：
Figure BDA0002840600300000021
所述苯并咪唑荧光探针的合成步骤包括以下两步：
第一步：以邻苯二胺与香草醛为原料，所述邻苯二胺与香草醛发生缩合反应，生成4-(1-(4-羟基-3-甲氧基苯基)-1H-苯并[d]咪唑-2-基)-2-甲氧基苯酚(即化合物1)。
第二步：将第一步所得化合物4-(1-(4-羟基-3-甲氧基苯基)-1H-苯并[d]咪唑-2-基)-2-甲氧基苯酚(即化合物1)与N,N-二苯基氯甲酰胺发生取代反应，生成苯并咪唑荧光探针(即化合物2)。
本发明通过设计合成苯并咪唑荧光探针，并成功用于氟乐灵检测，苯并咪唑荧光探针2具有高的选择性和高的灵敏度，而且具有较低的检出限(4.817μM)。
附图说明
图1：化合物(2)10-5M的甲醇溶液中不同有机化合物的荧光强度变化比例柱状图；
图2：化合物(2)10-5M的甲醇溶液中进行氟乐灵标准品溶液的荧光滴定图；
图3：化合物(2)10-5M的甲醇溶液中进行实际土壤样中氟乐灵溶液的荧光滴定图。
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
Figure BDA0002840600300000031
在100mL圆底烧瓶中，加入3.12g香兰素，1.08g邻苯二胺和25mL无水甲醇，加热回流6h，降温至室温，体系析出固体，过滤，滤饼用无水甲醇洗涤，干燥，得1.88g白色固体(即化合物1)，收率50％。
HRMS(ESI)C22H20N2O4 calcd.for[M+H]+377.1501；found 377.1482。
化合物2的制备
Figure BDA0002840600300000032
在50mL圆底烧瓶中，加入0.37g化合物(1)，0.69g N,N-二苯基酰氯甲酰胺和20mL吡啶，在60℃下搅拌12h，用TLC板监测反应。反应完成后，依次用稀HCl和饱和NaCl溶液洗涤混合物，然后用二氯甲烷萃取三次。将有机层结合，有机相用无水硫酸钠干燥，过滤，浓缩，以二氯甲烷/甲醇(10/1)为洗脱剂，柱层析对产物进行纯化，干燥得0.74g白色固体(化合物2)，收率97％。
HRMS(ESI)C48H38N4O6 calcd.for[M+H]+767.2869；found 767.2880。
实例2
在化合物2 10-5M的甲醇溶液中分别加入10当量的次氯酸，双氧水，甲醛，吡啶和氟乐灵，测其在292nm荧光发射强度变化。发现在加入10当量不同有机物后，化合物2对氟乐灵具有良好的选择性，在350nm下荧光发生猝灭，如图1和图2所示。
在化合物2 10-5M的甲醇溶液中分别加入不同浓度的氟乐灵标准品溶液和土样中浸取得氟乐灵土壤样溶液进行荧光滴定实验，对比发现，化合物2作为氟乐灵检测荧光探针具有现实可行性，如图2和图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)

1.一种用于氟乐灵检测的苯并咪唑荧光探针，其特征在于，该苯并咪唑荧光探针的化学结构式如下：
Figure FDA0002840600290000011
2.根据权利要求1所述的苯并咪唑荧光探针的合成方法,其特征在于,合成路线如下：
Figure FDA0002840600290000012
所述合成步骤包括以下两步：
第一步：以邻苯二胺与香草醛为原料，所述邻苯二胺与香草醛发生缩合反应，生成4-(1-(4-羟基-3-甲氧基苯基)-1H-苯并[d]咪唑-2-基)-2-甲氧基苯酚，即化合物1；
第二步：将第一步所得化合物4-(1-(4-羟基-3-甲氧基苯基)-1H-苯并[d]咪唑-2-基)-2-甲氧基苯酚，即化合物1；与N,N-二苯基氯甲酰胺发生取代反应，生成苯并咪唑荧光探针，即化合物2。
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CN115636792B (zh) * 2022-10-26 2024-03-01 福建师范大学 一种用于检测氯氟吡氧乙酸异辛酯的aie荧光探针及其合成方法

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