CN105349135A - 一种检测铅离子的荧光探针及制备方法 - Google Patents
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Abstract
本发明公开了一种罗丹明6G类铅离子荧光探针，结构如式I所示：
Description
技术领域
本发明属于荧光探针及其制备领域，具体涉及一种检测铅离子的荧光探针及其制备方法。
背景技术
随着冶金、电镀、机械加工、重金属化工等行业的蓬勃发展，重金属元素的污染问题日益严重。以铅、汞、镉等重金属离子为代表的有毒重金属污染是目前环境污染中面临的重大污染源之一。铅对人体的所有器官都能够造成损害，主要损害神经、消化、免疫和生殖系统等。为此研究出快速、简便、低成本、高灵敏度的铅离子检测手段具有十分重要的意义。
荧光探针法具有简单、快速、灵敏度高、选择性好和易于实现自动化与可视化成像等特点而备受关注。近年来基于小分子荧光探针法检测铅离子已有文献报道。罗丹明类化合物由于具有吸收波长和发射波长比较长、荧光量子产率较高、光稳定性良好等光谱性质，一直是科学家在设计和合成荧光探针的研究热点，基于其分子内螺环开-关机理的荧光探针得到了广泛研究，其中罗丹明B、丁基罗丹明B和罗丹明6G为比较最常用的罗丹明类荧光团。已报道的罗丹明衍生物荧光探针主要用于检测汞离子、铜离子、铬离子、铁离子及银离子等。罗丹明衍生物荧光探针检测铅离子的文献报道较少。本发明所涉及的荧光探针未见文献报道，通过连接两个罗丹明6G酰胺分子形成对称的双罗丹明6G席夫碱荧光探针，其可应用于环境水溶液中铅离子的高选择性检测。
发明内容
本发明的目的是提供一种结构新颖的双罗丹明6G类式I化合物，可用于铅离子的荧光检测和可视化检测。本发明制备的荧光探针可用于环境水溶液中铅离子的高选择性检测，溶液中共存的其他金属离子不干扰铅离子的检测，双罗丹明6G类式I化合物的溶液中加入Pb2+离子后颜色由淡黄色变为粉红色，具有对铅离子可视化检测的应用前景。
一种检测铅离子的荧光探针，结构如式I所示：
本发明荧光探针是通过有机合成技术制备的，合成该化合物的方法包括以下步骤：
1)在有机溶剂介质中，氧化剂氧化2-羟基-5-甲基-1,3苯二甲醇制备2,6-二甲酰-4-甲基苯酚，氧化剂指的是二氧化锰或三氧化铬或过氧化氢或是高锰酸钾，反应温度为70～140℃；
2)在有机溶剂介质中，2,6-二甲酰-4-甲基苯酚与罗丹明6G乙二胺衍生物反应制备化合物(I)，溶剂为极性有机溶剂，反应温度为50～100℃。
本发明的有益效果：本发明的荧光探针结构中含有荧光基团和识别基团，识别基团选择性识别铅离子，其他重金属离子不被识别，不干扰测定；荧光基团罗丹明6G类化合物荧光量子产率高、光稳定性好，利用此荧光探针可实现对环境水溶液中铅离子的高选择性荧光检测；铅离子与该化合物反应后溶液颜色由淡黄色变为粉红色，利用溶液颜色的变化可实现对铅离子的可视化检测。探针溶液的荧光强度与铅离子浓度在1.0×10-8～1.0×10-7M范围内，呈现良好的线性关系，检测限为2.7×10-9M，可用于水体中铅离子浓度的定量检测。
附图说明
图1干扰离子对铅离子测定的影响。实验条件：激发光波长528nm，发射光波长554nm，实验中铅离子浓度为1.0×10-7M；干扰离子Cu2+、Co2+、Cd2+、Ca2+、Fe3+、Hg2+、Mg2+、Mn2+、K+、Na+、Zn2+、Sn4+的浓度均为2.0×10-7M，缓冲溶液为0.01MHEPES，pH7.4。
图2荧光探针检测铅离子的线性关系图(R2＝0.9929)。实验条件：激发波长528nm，发射波长554nm，缓冲溶液为0.01MHEPES，pH7.4，铅离子浓度从1.0×10-8M至1.0×10-7M。
具体实施方式
下面通过实施例具体说明本发明，但本发明不受下述实施例的限定。
实施例1：荧光探针的合成路线
1)2,6-二甲酰-4-甲基苯酚的合成
向250mL三口烧瓶中加入6.0g2-羟基-5-甲基-1,3苯二甲醇(35.7mmol)和46.6gMnO2(535.5mmol)，150mL1,4-二氧六环，搅拌升温至100℃，搅拌反应18h。薄层色谱跟踪反应，待原料点消失后，停止反应。砂芯漏斗过滤，滤液经柱层析分离(淋洗剂，石油醚:乙酸乙酯＝15:1)，得2,6-二甲酰-4-甲基苯酚。
1HNMR(400MHz,CDCl3)δ/ppm：11.45(s,1H),10.21(s,2H),7.77(s,2H),2.39(s,3H).
2)罗丹明6G类荧光探针的合成
将0.55g罗丹明6G乙二胺衍生物(1.2mmol)和0.10g2,6-二甲酰-4-甲基苯酚(0.6mmol)加入到100mL三口烧瓶中，加入30mL乙醇，搅拌加热回流3h。薄层色谱跟踪反应，待原料点消失后，停止反应。过滤得粗品，乙醇重结晶制得精品，为淡黄色晶体。
荧光探针的基本数据：
IR(KBr)：1682cm-1(C＝O伸缩振动)，1519cm-1(C＝N伸缩振动)，1012cm-1(C-N-C伸缩振动)。
1HNMR(400MHz,CDCl3)δ/ppm：8.2(s,1H)7.97-7.85(m,2H),7.55-7.34(m,4H),7.09-6.92(m,2H),6.34(s,4H),6.20(s,4H),3.46(dd,8H),3.47-3.41(m,4H),3.34(t,J＝7.1Hz,4H),3.19(q,J＝6.9Hz,8H),2.21(s,3H),1.84(s,12H),1.31(t,J＝7.1Hz,12H)
TOFMS(ESI：C65H68N8O5)：m/z，1041.5(M+1)
元素分析(C65H68N8O5，％)：计算值：C74.97，H6.58，N10.76；测定值：C75.19，H6.63，N10.39
实施例2：荧光探针在铅离子检测中的应用
荧光探针溶液的配制:准确取荧光探针52mg，用乙腈和去离子水(体积比1:1)溶解后，转移至500mL的容量瓶中定容，配制浓度为1.0×10-4的荧光探针储备液(4℃下，避光保存)，使用时稀释至所需浓度。
荧光光谱的测定：激发光波长设定为528.0nm，发射光波长设为538.0～600.0nm，扫描速度为240nm/min，激发光源狭缝为5.0nm，发射光源狭缝为5.0nm，测试电压700V，响应时间为0.1s，测试条件为常温。
荧光探针的应用范围取决于探针对金属离子的选择识别性能，在实际应用中，荧光探针的高选择性尤为重要，实验考察了探针对金属离子的选择性识别，实验激发波长为528nm，发射波长为538～600nm。加入Pb2+离子后，荧光探针在554nm左右的发射峰强度明显增加，在加入两倍铅离子浓度的其它金属离子后，荧光强度变化很小或不发生变化(如图1所示)。说明其它金属离子对铅离子的测定无干扰，荧光探针对于铅离子的检测具有良好的选择性。加入铅离子前后溶液颜色发生明显变化，由淡黄色变为粉红色，可实现铅离子的可视化检测。
在HEPES缓冲溶液体系(0.010M，pH＝7.4)中，随着Pb2+离子浓度的增加，荧光发射光谱强度逐渐增加，在1.0×10-8～1.0×10-7M浓度范围内，荧光强度与Pb2+离子浓度呈现良好的线性关系(如图2所示)，可用于水体中铅离子浓度的定量检测。
Claims (3)
1.一种罗丹明6G类铅离子荧光探针，结构如式I所示：
按照权利要求I的化合物的制备方法，该方法包括以下步骤：
1)在有机溶剂介质中，氧化剂氧化2-羟基-5-甲基-1,3苯二甲醇制备2,6-二甲酰-4-甲基苯酚，氧化剂指的是二氧化锰或三氧化铬或过氧化氢或是高锰酸钾，反应温度为70～140℃；
2)在有机溶剂介质中，2,6-二甲酰-4-甲基苯酚与罗丹明6G乙二胺衍生物反应制备化合物I，溶剂为极性有机溶剂，反应温度为50～100℃。
2.含有权利要求1所述化合物的铅离子荧光探针。
3.含有权利要求1所述化合物用于铅离子的检测。
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| CN106854215A (zh) * | 2017-01-09 | 2017-06-16 | 济南大学 | 一种新型比率型二价铅离子荧光探针及其制备方法与应用 |
| TWI607972B (zh) * | 2016-07-22 | 2017-12-11 | 國立臺北科技大學 | 金屬離子感測化合物、包含其之多重感測共聚物及其纖維 |
| CN108276360A (zh) * | 2018-01-19 | 2018-07-13 | 青海大学 | 一种检测铅离子的新型荧光分子探针pp的合成方法 |
| CN111848543A (zh) * | 2020-07-27 | 2020-10-30 | 吉林大学 | 一种用于检测二价铅离子的比率型荧光探针及其制备方法 |
| CN111896507A (zh) * | 2020-06-30 | 2020-11-06 | 陕西科技大学 | 一种利用罗丹明类化合物在水溶液中特异性检测银离子的方法及其应用 |
| CN114761796A (zh) * | 2019-12-20 | 2022-07-15 | 罗伯特·博世有限公司 | 具有含硫的离子载体的化学传感器 |
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| CN114761796A (zh) * | 2019-12-20 | 2022-07-15 | 罗伯特·博世有限公司 | 具有含硫的离子载体的化学传感器 |
| CN114761796B (zh) * | 2019-12-20 | 2024-04-12 | 罗伯特·博世有限公司 | 具有含硫的离子载体的化学传感器 |
| CN111896507A (zh) * | 2020-06-30 | 2020-11-06 | 陕西科技大学 | 一种利用罗丹明类化合物在水溶液中特异性检测银离子的方法及其应用 |
| CN111848543A (zh) * | 2020-07-27 | 2020-10-30 | 吉林大学 | 一种用于检测二价铅离子的比率型荧光探针及其制备方法 |
| CN111848543B (zh) * | 2020-07-27 | 2022-04-01 | 吉林大学 | 一种用于检测二价铅离子的比率型荧光探针及其制备方法 |
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