CN108912037B - 一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器及其制备方法 - Google Patents
一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器及其制备方法 Download PDFInfo
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Abstract
本发明涉及一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器，其制备方法，包括步骤：将磺酸基苯肼和异戊酮合成磺酸基吲哚，磺酸基吲哚与靛红合成磺酸基吲哚类靛红衍生物化合物。本发明的有益效果是：合成过程较为简单，反应条件容易控制，制备的磺酸基吲哚类靛红衍生物具有优良的光学性能和光学稳定性。磺酸基吲哚类靛红衍生物在对铜离子识别过程中，除吸收光谱发生变化外，溶液颜色也发生变化，具有比色识别功能，有利于对铜离子进行检测。此外，该化学传感器对铜离子的识别具有良好的选择性和抗干扰性。
Description
技术领域
本发明具体涉及一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器及其制备方法，属于化学分析测试领域。
背景技术
铜离子是人体丰度三大必须微量元素之一。在细胞内的生化过程起着至关重要的作用，如增强蛋白质的结构和功能、基因的表达，也是人体神经系统所必须元素。如果人体铜离子水平过高，会导致威尔森氏症、胃肠功能紊乱和肾脏损害等。相反，铜元素缺乏也可能会导致多种疾病。更重要的是，随着社会经济的快速发展，人类生产活动对环境的干扰破坏日益严峻，农业和工业生产活动常导致土壤和水体的铜污染，铜已经成为环境重金属污染的主要因素之一。因此，对铜离子的检测无论是对于生物体的健康发展还是对自然环境的保护都具有重大意义。常规的铜离子检测方法有原子吸收光谱法、电感耦合等离子体原子发射光谱以及伏安法等.虽然这些方法能进行定量的检测，但是由于仪器设备操作复杂、样品预处理过程繁琐和测试费用昂贵大大降低了它们的应用价值。因此，研究和开发高选择性和高灵敏度且肉眼可见的铜离子化学传感器具有十分重要的意义。
目前，基于不同光调控机理识别铜离子的荧光比色化学传感器已有大量文献报道，但其中大部分受其他金属离子如Ag+和Fe3+的干扰。因此，研究对铜离子具有高效选择性和灵敏度的新型化学传感器仍然具有挑战性。
靛红类衍生物作为一种新型的有机功能染料，其在近红外吸收波长位于紫外可见区域，且该类染料的光、热稳定性好，因此在光学记录与存贮、液晶显示等领域显示出优异的应用性能。在以往合成的錠红衍生物中，多数是在読红苯环上进行一个位置取代基衍生合成和苯环上多位置取代靛红的合成，而对吡咯环上氧原子的取代的研究报道较少，本发明设计合成了在靛红的吡咯环上的氧原子取代的衍生物。由于靛红衍生物含有碳杂原子(如：N、O)，具有潜在的识别金属离子的活性位点，所以靛红衍生物具有识别金属离子的特性。
本发明具体涉及一种新型的可用于Cu2+检测的靛红衍生物化学传感器，其合成的方法比较简单，反应条件容易控制，并且反应结束后经过简单的处理就能够得到纯的产物，此外作为Cu2+的检测的化学传感器，此靛红衍生物的优点是具有很高的灵敏度和选择性。
发明内容
本发明要解决的技术问题是：本发明为了解决现有探针对Cu2+检测的化学传感器的不足，提供了一种能够高效识别Cu2+的磺酸基吲哚类靛红衍生物染料及其制备方法。
本发明解决其技术问题所采用的一个技术方案是：一种用于识别Cu2+的磺酸基吲哚类靛红衍生物染料，其结构如下所示：
本发明所述的一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器的制备方法，包括如下步骤：
(1)将磺酸基苯肼和异戊酮按照摩尔比1:1.5加入到圆底烧瓶中，加入冰乙酸，加热回流条件下过夜搅拌，溶液慢慢从混浊变为澄清，且颜色由淡黄色变成深红色。待反应结束后，停止加热和搅拌，用旋转蒸发仪旋蒸出溶剂。以二氯甲烷和甲醇混合溶剂(体积比为5:1)为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到黄色的磺酸基吲哚。
(2)将步骤(1)制备得到的磺酸基吲哚与靛红按照摩尔比1:1加入到圆底烧瓶中，加入正丁醇和甲苯混合溶剂(体积比为1:1)，连接冷凝管和斯托克分水器，通入氮气，在110-140℃下加热回流6-9小时，溶液由淡红色变为深红色，反应中生成的水用分水器分出。反应结束后，待其自然冷却至室温，减压条件下用旋转蒸发仪旋去溶剂。以二氯甲烷和甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到深红色的磺酸基吲哚类靛红衍生物。
进一步地，所述步骤(1)中二氯甲烷和甲醇的体积比为10:1。
进一步地，所述步骤(2)中二氯甲烷和甲醇的体积比为5:1。
基于磺酸基吲哚类靛红衍生物化学传感器的应用，化学传感器可用于识别溶液中的铜离子。
本发明的有益效果是：(1)本发明的磺酸基吲哚类靛红衍生物合成过程较为简单，反应条件容易控制，通过简单的后处理就能够得到纯的产物。此外，制备的磺酸基吲哚类靛红衍生物染料具有优良的光学性能和光学稳定性。(2) 本发明的磺酸基吲哚类靛红衍生物染料在对铜离子识别过程中，除吸收光谱发生变化外，溶液颜色也发生变化，具有比色识别功能，有利于对铜离子进行检测。(3)本发明的磺酸基吲哚类靛红衍生物染料对铜离子的识别具有良好的选择性和抗干扰性。
附图说明
下面结合附图和实施例对本发明做进一步说明：
图1为实施例1制备的磺酸基吲哚类靛红衍生物对金属离子铜离子识别的紫外吸收图；
图2为实施例1制备的磺酸基吲哚类靛红衍生物在其他金属离子存在的条件下对铜离子识别竞争的紫外吸收图；
具体实施方式
为了更好地理解本发明，下面结合实施例和应用例进一步阐明本发明的内容，但本发明的内容不仅仅局限于以下的实施例和应用例。
实施例1
将0.376g磺酸基苯肼(约0.002mol)和0.258g异戊酮(约0.003mol)加入到圆底烧瓶中，加入50ml冰醋酸，加入冰乙酸，加热回流条件下过夜搅拌，溶液慢慢从混浊变为澄清，且颜色由淡黄色变成深红色。待反应结束后，停止加热和搅拌，用旋转蒸发仪旋蒸出溶剂。以200ml的二氯甲烷和20ml的甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到黄色的磺酸基吲哚。
称取0.279g的靛红(约0.0019mol)和0.474g的磺酸基吲哚(约0.0019mol) 加入到圆底烧瓶中，加入20mL甲苯与20mL正丁醇,连接冷凝管和斯托克分水器，110℃下加热回流搅拌9个小时，溶液由淡红色变为深红色，反应中生成的水用分水器分出。反应结束后，待其自然冷却至室温，减压条件下用旋转蒸发仪旋去溶剂。以400ml的二氯甲烷和80ml的甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到深红色的磺酸基吲哚类靛红衍生物。
实施例2
将0.941g磺酸基苯肼(约0.005mol)和0.646g异戊酮(约0.0075mol)加入到圆底烧瓶中，加入60ml冰醋酸，加入冰乙酸，加热回流条件下过夜搅拌，溶液慢慢从混浊变为澄清，且颜色由淡黄色变成深红色。待反应结束后，停止加热和搅拌，用旋转蒸发仪旋蒸出溶剂。以200ml的二氯甲烷和20ml的甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到黄色的磺酸基吲哚。
称取0.558g的靛红(约0.0038mol)和0.948g的磺酸基吲哚(约0.0038mol) 加入到圆底烧瓶中，加入30mL甲苯与30mL正丁醇,连接冷凝管和斯托克分水器，140℃下加热回流搅拌9个小时，溶液由淡红色变为深红色，反应中生成的水用分水器分出。反应结束后，待其自然冷却至室温，减压条件下用旋转蒸发仪旋去溶剂。以400ml的二氯甲烷和80ml的甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到深红色的磺酸基吲哚类靛红衍生物。
应用例
为了检测实施例1制备的磺酸基吲哚类靛红衍生物探针对铜离子的识别，以纯水作溶剂，将合成的磺酸基吲哚类靛红衍生物配制成浓度为1×10-4mol/L，分别取10mL配好的溶液于15只试管中，标号1-15。依次加入1mL 1×10-2mol/L 的Zn2+、K+、Na+、Ba2+、Mg2+、Ni2+、Ca2+、Ag+、Cu2+、Cr3+、Fe3+、Co2+、Pb2+、 Al3+、Cd2+溶液，分别测定其紫外吸收，如图1所示，磺酸基吲哚类靛红衍生物 -Cu2+曲线的吸光度发生了明显的降低，且溶液由黄色变为无色，而磺酸基吲哚类靛红衍生物-其它金属离子曲线没有发生变化，这证明了所制备磺酸基吲哚类靛红衍生物染料对Cu2+有独特的识别性能。
为了进一步检测磺酸基吲哚类靛红衍生物探针对铜离子的识别性能，以纯水的作溶剂，将合成的磺酸基吲哚类靛红衍生物染料配制成浓度为1×10-4mol/L 的溶液，分别取10mL配好的溶液于14只试管中，标号1-14。依次加入1mL 1×10-2mol/L的Zn2+、K+、Na+、Ba2+、Mg2+、Ni2+、Ca2+、Ag+、Cr3+、Fe3+、Co2+、 Pb2+、Al3+、Cd2+溶液，再分别取1ml的1×10-2mol/L的铜离子溶液14份，分别加入到上述试管中，利用紫外-可见光分度计依次测定其吸收光谱的变化，其吸收光谱如图2所示。由图可以看出，磺酸基吲哚类靛红衍生物染料对铜离子识别的吸收光谱在存在其他金属离子与不存在其他金属离子相比，没有发生明显变化，这进一步证明了磺酸基吲哚类靛红衍生物染料对Cu2+有很好的识别效果。
以本发明的实施例为启示，根据上述的说明内容，相关工作人员可以在不偏离本项发明技术思想的范围内，进行多样的变更和修改。本项发明的技术性范围并不局限于以上的内容，必须要根据权利要求范围来确定其技术性范围。
Claims (5)
1.一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器，其特征是：磺酸基吲哚类靛红衍生物化学传感器的结构式如图I所示：
2.权利要求1所述的一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器的制备方法，其特征是：包括以下步骤：
(1)将磺酸基苯肼和异戊酮按照摩尔比1:1.5加入到圆底烧瓶中，加入冰乙酸，加热回流条件下过夜搅拌，溶液慢慢从混浊变为澄清，且颜色由淡黄色变成深红色，待反应结束后，停止加热和搅拌，用旋转蒸发仪旋蒸出溶剂，以二氯甲烷和甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到黄色的磺酸基吲哚；
(2)将步骤(1)制备得到的磺酸基吲哚与靛红按照摩尔比1:1加入到圆底烧瓶中，加入正丁醇和甲苯混合溶剂，连接冷凝管和斯托克分水器，通入氮气，在110-140℃下加热回流6-9小时，溶液由淡红色变为深红色，反应中生成的水用分水器分出，反应结束后，待其自然冷却至室温，减压条件下用旋转蒸发仪旋去溶剂，以二氯甲烷和甲醇混合溶剂为洗脱剂，采用硅胶色谱柱进行分离，分离得到的产品用旋转蒸发仪进行悬蒸出洗脱剂，将悬蒸出的产品放入蒸发皿中，置于烘箱60℃下干燥后得到深红色的磺酸基吲哚类靛红衍生物。
3.根据权利要求2所述的一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器的制备方法，其特征是：所述的步骤(1)中洗脱剂二氯甲烷和甲醇的体积比为10:1。
4.权利要求2所述的一种识别Cu2+的磺酸基吲哚类靛红衍生物化学传感器的制备方法，其特征是：所述的步骤(2)中正丁醇和甲苯的体积比为1:1，洗脱剂二氯甲烷和甲醇的体积比为5:1。
5.权利要求1所述的磺酸基吲哚类靛红衍生物化学传感器，其特征是：所述的化学传感器能用于识别水溶液中的Cu2+。
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