CN106496186B - 一种汞离子荧光传感器及其合成和在纯水中检测汞离子的应用 - Google Patents

一种汞离子荧光传感器及其合成和在纯水中检测汞离子的应用 Download PDF

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CN106496186B
CN106496186B CN201610910747.XA CN201610910747A CN106496186B CN 106496186 B CN106496186 B CN 106496186B CN 201610910747 A CN201610910747 A CN 201610910747A CN 106496186 B CN106496186 B CN 106496186B
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张有明
仲开鹏
林奇
姚虹
魏太保
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Abstract

本发明公开了一种以萘环为荧光信号报告基团，组氨酸为亲水基团的汞离子荧光传感器分子，其以DMF为溶剂，组氨酸和1,8‑萘二甲酸酐为底物，回流反应得到中间体N,N‑二(1,8‑萘二甲酰胺)组氨酸；再使中间体与氢氧化钠反应形成钠盐，即得汞离子荧光传感器分子。该传感器分子能够在纯水中专一选择性识别汞离子，识别过程具有很高的灵敏度（响应时间在5秒之内），而且这一识别过程不受其它阳离子的干扰。本发明同时制备了负载有该传感器分子的汞离子检测试纸，具有方便携带、现象明显、快速检测等优点。另外，本发明合成的传感器分子识别汞离子的过程是可逆的，能够循环利用，在阳离子检测领域具有很好的应用前景。

Description

一种汞离子荧光传感器及其合成和在纯水中检测汞离子的 应用
技术领域
本发明属于阳离子检测领域，涉及一种荧光识别汞离子的传感器，尤其涉及一种以萘环为荧光信号报告基团，组氨酸为亲水基团的汞离子荧光传感器分子及其制备方法；本发明同时还涉及该汞离子荧光传感器分子在纯水中检测汞离子的应用。
背景技术
汞目前被大量的应用在化工原料、电气设备、银汞合金以及电池中，在自然状态下的汞以及汞的氧化物对人体和自然环境具有很大的危害性。为了能够检测和监测各种情况下的汞，就需要一种有效的方法。在各种检测汞离子的方法中，荧光探针法具有高灵敏度、容易操作的特征，已经越来越受到人们的关注。
到目前为止，一方面许多对汞离子的荧光探针已经被合成，但是大部分的传感器都含有硫原子，硫原子与汞容易形成Hg–S键，并且使得识别过程不可逆，难以循环。并且大部分含硫的传感器在富硫环境中都很容易受到干扰和影响，难以发挥检测汞离子的作用。另一方面，在生物和环境系统中，汞离子经常出现在水溶液中，但是大部分传感器都不溶于水，难以检测水溶液中的汞离子。因此，合成一种能够在水溶液中检测汞离子的荧光传感器具有十分重要的意义。
发明内容
本发明的目的是针对现有技术存在的问题，提供一种能够在纯水中检测的汞离子荧光传感器分子；
本发明的另一目的是提供一种上述汞离子荧光传感器分子的制备方法；
本发明还有一个目的，就是提供上述汞离子荧光传感器分子在纯水中检测汞离子的应用。
一、汞离子荧光传感器分子
该荧光传感器可以高效，快速的检测纯水中汞离子。
本发明的汞离子荧光传感器分子，是以萘环为荧光信号报告基团，组氨酸的钠盐为亲水基团的化合物，其化学命名为N,N-二(1,8-萘二甲酰胺)组氨酸钠（盐）。其中中间体N,N-二(1,8-萘二甲酰胺)组氨酸（H1）的结构式为：
由于中间体（H1）组氨酸上的羧基可以形成钠盐，所以制成了钠盐的荧光传感器，记为（H）；的结构式为：
由于荧光传感器H羧基上的氧原子能够与汞离子配位，从而可实现对汞离子的单一选择性识别。
二、汞离子荧光传感器的制备
本发明汞离子荧光传感器的制备，是以DMF为溶剂，组氨酸和1,8-萘二甲酸酐为底物进行回流反应；反应结束后冷却至室温，加水析出，抽滤，洗涤，得到中间体白色固体产物——中间体N,N-二(1,8-萘二甲酰胺)组氨酸（H1）；再使中间体H1与氢氧化钠反应形成钠盐，即为荧光传感器分子H。
1,8-萘二甲酸酐与组氨酸的摩尔比为1:1~1:1.2；回流反应的温度为130~140℃，回流反应时间为20~24h。
中间体H1与氢氧化钠摩尔比为1:1，在室温下就可形成钠盐。
三、汞离子荧光传感器对阳离子的识别性能
1、传感器对阳离子离子识别性能
分别移取0.5 mL传感器分子H的水溶液(2×10-4 mol·L-1)于一系列10 mL 比色管中，分别加入Fe3+，Hg2+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2+，Zn2+，Cr3+，Mg2+的水溶液(0.004mol·L-1)0.25 mL，用pH=7.2的缓冲稀释至5mL，此时受体浓度为2×10-5mol·L-1，阳离子浓度为受体浓度的10倍，观察传感器分子对各阳离子的响应。
结果发现，当在传感器分子H的水溶液中加入上述阳离子的水溶液时，荧光发射谱中，只有Hg2+的加入使传感器分子在384nm处的发射峰消失且在480nm出有新的吸收峰(图1)，而其余阳离子的加入对传感器分子水溶液的荧光光谱无明显影响。相应的，Hg2+的加入使传感器分子水溶液的荧光猝灭并红移，而其余阳离子的加入对传感器分子水溶液的荧光没有影响。
2、传感器分子的滴定实验
移取2.0mL传感器分子 H的水溶液（2.0×10-5mol/L）于石英池中，用累积加样法逐渐加入Hg2+ 的水溶液，于15℃测其荧光发射光谱（图2）。滴定实验说明H的荧光强度受到汞离子浓度的影响，伴随着汞离子浓度的增加而减弱。并且根据滴定实验得到了H对汞离子的荧光光谱的检测限为1.815×10-7mol/L。
图3为不同浓度的Hg2+ (0~8倍) 存在下传感器分子H的散点图，该散点图能够清晰明了的反映H的荧光强度在0~8倍汞离子浓度范围内的变化趋势。并且可以发现汞离子在0.8~4.4倍当量时与传感器分子H的荧光强度呈较好的线性关系，继而进一步计算得到了H对汞离子的荧光光谱的检测限为1.815×10−7mol/L，检测过程具有很高的灵敏度。
3、抗干扰性能检测
为了测定传感器分子H对Hg2+的检测效果，我们又进行了如下测试：取两组10ml比色管分别加入0.5mL该传感器分子的水溶液，再分别加入0.25mL各种阳离子的水溶液(4×10-3mol·L−1)，然后用pH=7.2的缓冲稀释至5mL刻度，另外一组中再分别加0.25mL Hg2+，在每一个比色管中分别加入0.25mL其它十一种阳离子（Fe3+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2 +，Zn2+，Cr3+，Mg2+），然后用pH=7.2的缓冲稀释至5mL刻度。将上述溶液混合均匀后进行观察。
上述溶液静置后于15℃测其荧光发射光谱。结果发现，加入十一种阳离子后，传感器分子H在384nm处的荧光猝灭，这与Hg2+对传感器分子的影响是一致的。从而说明该传感器分子检测Hg2+不受其它阳离子的干扰（见图4）。
4、传感器H识别Hg2+的循环可逆性
很多识别阳离子的过程是不可逆的，难以进行循环利用，因此通过滴加阴离子来确定它的可逆性。向加入10倍Hg2+的溶液中继续加入20倍的Br-，溴离子与汞离子形成了溴化汞，使得受体H被释放出来，溶液回复原有的黄色荧光，这样反复多次，可以至少循环5次（图5）。
5、传感器H对Hg2+的响应速度
该传感器分子对于识别汞离子的响应时间在5秒之内，因此该传感器对于汞离子的识别过程具有很高的灵敏度。
6、机理的探讨
图6为传感器分子H与Hg2+配合物的质谱图。该图中550.60的出峰表明H1与Hg2+的络合后得到的峰。图7为传感器分子H的红外及H与Hg2+配合物的红外谱图。图7中红外羧基峰的消失，以及图6中络合物的新峰说明了该荧光传感器H上的羧基与汞离子发生了配位，且是1:1配位的。
三、汞离子检测试纸
为了方便快捷的检测环境体系中的汞离子，利用该传感器分子制作成的汞离子的响应检测试纸。
检测试纸的制作：将传感器H配制成1×10-3 mol·L−1的水溶液。将经处理过的滤纸烘干后剪取长约4cm，宽约1cm的滤纸两张，分别浸润在上述的两个比色管中10分钟左右，使传感器分子H负载于滤纸上，然后取出晾干。将检滤纸在荧光灯照射下，负载有H的滤纸呈黄色荧光。当在负载有H的滤纸上滴加汞离子时，滤纸原来的黄色荧光发生猝灭，而其它阳离子的滴加，对检测滤纸的荧光没有影响。
综上所述，本发明合成的汞离子荧光传感器分子H，能够在纯水中快速选择性识别汞离子，而且这一识别过程不受其它阳离子的干扰，而且识别过程具有很高的灵敏度（响应时间在5s之内）。另外，本发明合成的传感器分子识别汞离子的过程是可逆的，能够循环利用，在阳离子检测领域具有很好的应用前景。
附图说明
图1为传感器H以及其加入10倍的阳离子时的荧光光谱（激发波长：343nm，发射波长384nm）。
图2为不同浓度的Hg2+ (0~8倍) 存在下受体H的荧光光谱。
图3为不同浓度的Hg2+ (0~8 倍) 存在下受体H的散点图。
图4为H对汞离子识别的抗干扰性能图。
图5为传感器H对汞离子识别的荧光可逆性实验。
图6为传感器H与Hg2+配合物的的质谱图。
图7为传感器H与Hg2+的红外图谱。
具体实施方式
下面通过具体实施例对本发明传感器分子H的合成，以及在检测水中Hg2+的应用作进一步说明。
一、传感器分子H的合成
将10mmol 1,8-萘二甲酸酐和10mmol 组氨酸置于100 mL圆底烧瓶中，加入15mLDMF，在油浴上140℃加热回流反应24h，待反应停止冷却至室温，加水析出后，抽滤干燥；所得固体用加热的DMF洗涤，干燥的白色固体——N,N-二(1,8-萘二甲酰胺)组氨酸（H1），产率：40%。
取5mmol中间体H1，5mmol氢氧化钠，置于50 mL圆底烧瓶中，加入25mL 水，在室温下搅拌30分钟，待反应结束后旋干溶剂得产物；即N,N-二(1,8-萘二甲酰胺)组氨酸的钠盐，即为传感器分子H。
1: m.p: 300°C以上; 1H NMR (600 MHz, d6-DMSO) δ 8.47~8.45 (m, 4H), 7.88~7.85 (m, 2H), 7.36 (s, 1H), 6.56 (s, 1H), 5.79~5.77 (m, 1H), 3.43~3.32 (m,1H); 13C NMR (151MHz, d6-DMSO) δ 170.89, 163.30, 135.06, 131.66, 127.85,121.99, 53.79, 26.64; IR (KBr, cm-1) v: 3400, (-NH),2900,(-OH)2800,(C=O)1641,(C=N),1100,(-C=O); ESI-MSm/z: (M-H)+ Calcd for C18H13N3O4334.1412; Found334.1412; Anal. Calcd for C18H13N3O4: C, 64.47; H, 3.91; N, 12.53; O,19.09;Found C, 64.47; H, 3.91; N, 12.53; O,19.09。
荧光传感器分子H的合成路线如下：
。
二、Hg2+的检测
1、荧光检测
分别移取0.5 mL传感器分子H的水溶液(2×10-4 mol·L-1)于一系列10 mL 比色管中，分别加入Fe3+，Hg2+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2+，Zn2+，Cr3+，Mg2+的水溶液(0.004mol·L-1)。若H的水溶液荧光猝灭，则加入的是Hg2+，若H水溶液的荧光没有发生变化，则加入不是Hg2+。
2、试纸检测
检测试纸的制作：将传感器分子H配制成1×10-3 mol·L−1的水溶液。将经处理过的滤纸烘干后剪取长约4cm×1cm的滤纸若干张，浸润在上述水溶液中10分钟左右，使传感器分子H负载于滤纸上，然后取出晾干即得。该检测试纸在荧光灯照射下呈黄色荧光。
Hg2+的检测：分别在滤纸上滴加Fe3+，Hg2+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2+，Zn2+，Cr3+，Mg2+的水溶液，若滤纸原来的黄色荧光消失了，说明滴加的是Hg2+的水溶液，若滤纸的荧光没有变化，则说明滴加是其它阳离子水溶液。

Claims (8)

1.一种汞离子荧光传感器分子，其结构式如下：
。
2.如权利要求1所述汞离子荧光传感器分子的合成方法，先以DMF为溶剂，组氨酸和1,8-萘二甲酸酐为底物进行回流反应；反应结束后冷却至室温，加水析出，抽滤，洗涤，得到中间体N,N-二(1,8-萘二甲酰胺)组氨酸；再使中间体与氢氧化钠室温反应形成钠盐，即得荧光传感器分子；所述中间体N,N-二(1,8-萘二甲酰胺)组氨酸的结构式为：
。
3.如权利要求2所述汞离子荧光传感器分子的合成方法，其特征在于：1,8-萘二甲酸酐与组氨酸的摩尔比为1:1~1:1.2。
4.如权利要求2所述汞离子荧光传感器分子的合成方法，其特征在于：回流反应的温度为130~140℃，回流反应时间为20~24h。
5.如权利要求2所述汞离子荧光传感器分子的合成方法，其特征在于：中间体与氢氧化钠的摩尔比为1:1。
6.如权利要求1所述汞离子荧光传感器分子在纯水中检测汞离子的应用，其特征在于：在汞离子荧光传感器分子的水溶液中，分别加入Fe3+，Hg2+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2+，Zn2+，Cr3+，Mg2+的水溶液，当传感器分子水溶液的黄色荧光猝灭，说明加入的是Hg2+，当传感器分子水溶液的荧光没有发生变化，则加入不是Hg2+。
7.一种负载有如权利要求1所述汞离子荧光传感器分子的汞离子检测试纸。
8.如权利要求7所述汞离子检测试纸用于荧光识别汞离子，其特征在于：在汞离子检测试纸滤纸上滴加Fe3+，Hg2+，Ag+，Ca2+，Cu2+，Co2+，Ni2+，Cd2+，Pb2+，Zn2+，Cr3+，Mg2+的水溶液，当滤纸原来的黄色荧光消失了，说明滴加的是Hg2+，当滤纸的荧光没有变化，则滴加是其它阳离子水溶液。
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