CN110317175B - 一种萘衍生物及其合成方法和应用 - Google Patents
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Abstract
本发明提供了一种萘衍生物及其合成方法和应用，属于萘衍生物和镉离子的检测领域。萘衍生物的合成方法：将2，3‑二氨基萘和咪唑‑2‑甲醛在甲醇和乙醇的混合溶液(v/v＝1：1)中加热回流，抽滤，洗涤得到。本发明还提供了一种检测镉离子的方法：以萘衍生物为探针，在EtOH‑H2O(pH＝7.4)的溶液中定量检测Cd2+的含量。该检测方法可以高选择性、高灵敏性地检测水溶液中的镉离子，操作简单、方便、快捷。
Description
技术领域
本发明涉及镉离子检测试剂，具体涉及一种萘衍生物及其合成方法和在检测Cd2+中的应用。
背景技术
镉是一种剧毒的重金属，即使在低浓度下也会引起严重的健康问题。通过直接摄入受污染的水或食物或通过香烟烟雾暴露摄入Cd2+会对人体肾脏，肺脏，骨骼和神经系统产生毒性作用，导致肾功能不全，钙代谢紊乱和各种癌症发病率增加。但是，镉作为一种重要的天然元素已被广泛应用于采矿，冶金，军事，农业中含Cd的磷肥的应用，镍镉充电电池的生产等。所有这些应用都大大提高了环境污染的可能性，并可能导致镉暴露水平增加。由于其不可生物降解的性质和在人体中长的消除半衰期(10-30年)，镉被美国环境保护署(EPA)列为126种污染物之一。由世界卫生组织(WHO)和美国环境保护署(EPA)设定的饮用水中Cd2+的最大允许浓度分别为3μgL-1和5μgL-1。因此，在环境分析和生命科学领域非常需要高选择性和高灵敏度的荧光探针用于Cd2+的检测。
荧光光谱法具有灵敏度高，准确度较高，操作简便快速的特点，并且通常伴随着溶液颜色的变化，可以通过裸眼识别进行快速检测分析。比率荧光传感更有利，因为测量两个不同波长的发射强度比可以减少外部因素的影响，从而大大提高测量的可靠性。
发明内容
本发明的目的在于提供一种萘衍生物及其合成方法和在检测Cd2+中的应用。该萘衍生物能避免多种金属离子的干扰，可以通过光谱法高选择性、高灵敏性地检测水溶液中的镉离子，操作简单、方便、快捷，不需要特殊仪器设备和专业培训，易于推广，结果清晰易辩。
为实现上述目的，本发明提供的技术方案为：
一种萘衍生物，其结构式为：
一种萘衍生物的合成方法，包括如下步骤：将反应物2，3-二氨基萘和咪唑-2-甲醛在甲醇和乙醇的混合溶液(v/v＝1:1)加热回流，反应20-25小时，抽滤，洗涤得到萘衍生物NIS。
反应式如下：
作为优选，所述步骤中2，3-二氨基萘和咪唑-2-甲醛的摩尔比为1:2-2.2。
为了保证反应物能充分反应，得到纯净的产物，优选反应时间为24小时。
为了保证反应物能充分反应，得到纯净的产物，优选加热回流温度为80℃。
一种比率荧光光谱法用于检测镉离子的方法，包括如下步骤：
(1)配置10-3M萘衍生物的DMSO储备液，配置10-2M Cd2+的水溶液；
(2)取20μL萘衍生物储备液加入干净的比色管中，随着Cd2+浓度的增加，在荧光光度计上测定472nm处的荧光强度逐渐减弱，398nm处的荧光逐渐增强，体系在398nm的荧光强度I398nm和[Cd2+]浓度在0-30×10-6M的范围内呈现良好的线性关系(R2＝0.98306)，以Cd2+浓度为横坐标，以荧光强度I398nm为纵坐标作图，得到Cd2+浓度与荧光强度的线性方程：F＝3658.41667+131.40774[Cd2+]；
(3)取2.5mL含有4×10-6M萘衍生物的EtOH-水溶液加入干净的比色管中，取xμL待测样品溶液加入，在荧光分光光度计上检测，测得的荧光强度，带入步骤(2)的线性方程，得到[Cd2+]的浓度，待测样品[Cd2+]待测＝5000μL×[Cd2+]×10-6/xμL,即可求得Cd2+的浓度。
与现有技术相比，本发明具有以下优点和效果：
(1)方法经济：萘衍生物制备所需试剂价格便宜，产物收率高，检测成本低。
(2)特异性高：萘衍生物在水溶液中可高选择性地实现对镉离子的检测，不受其他共存阳离子的干扰，尤其不受具有相似结构Zn2+的影响。
(3)快捷：检测时间只需30-60s，完全能够满足紧急情况的检测需要。
(4)操作简单方便：只需通过荧光分光光度计进行检测，检测手段简便，结果清晰可辩。
附图说明
图1为本发明萘衍生物用于测定Cd2+的荧光光谱图；
图2为本发明萘衍生物测定Cd2+的工作曲线图；
图3为本发明萘衍生物用于测定Cd2+的紫外吸收光谱图；
图4为本发明实施例4共存金属离子对NIS-Cd2+体系的影响对比图。
具体实施方式
实施例1 2，3-二氨基萘衍生物的合成和表征
在50mL圆底烧瓶中，将2,3-二氨基萘(0.079g，0.5mmol)和咪唑-2-甲醛(0.1g，1.1mmol)溶解在混合的乙醇-甲醇溶剂中(20mL，v/v＝1：1)，然后加入2-3滴乙酸。将所得混合物加热回流(80℃)，将其连续搅拌24小时，然后冷却至室温。过滤出固体，用CH3OH洗涤并在真空下干燥，得到黄色固体，即为本技术所述萘衍生物。1H NMR(600MHz,DMSO-d6),δ(ppm):8.423(1H,s),8.199(1H,s),8.0045(2H,d),7.943(1H,s),7.915(1H,m),7.626(1H,s),7.467(1H,m),7.413(1H,s),7.378(2H,t),7.241(1H,s),13.468(1H,s),13.085(1H,s).13C NMR(DMSO-d6):δ148.669,144.566,138.750,135.711,130.813,130.416,130.251,128.411,127.884,124.279,123.555,120.482,115.304,107.351.HRMS(ESI):calcd.forC18H14N6(M+H)+315.13584,found 315.13480.
实施例2 2，3-二氨基萘衍生物用于Cd2+的荧光光谱测定
用DMSO配置1mM的萘衍生物储备液，用蒸馏水配置0.01M的Cd2+溶液，并配置pH＝7.4、浓度为0.025M的HEPES缓冲溶液；取20μL的萘衍生物储备液加入干净的比色管中，分别加入不同体积的Cd2+(2μL、4μL、6μL、8μL、10μL、12μL、14μL)，0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在荧光分光光度计上检测，随着Cd2+的加入，472nm处的荧光强度逐渐减弱，398nm处的荧光逐渐增强。荧光光谱图见图1。
实施例3萘衍生物测定Cd2+的线性关系
取20μL的萘衍生物储备液加入干净的比色管中，分别加入不同体积的Cd2+(2μL、4μL、6μL、8μL、10μL、12μL、14μL)，0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在荧光分光光度计上检测，随着Cd2+的加入，472nm处的荧光强度逐渐减弱，398nm处的荧光逐渐增强。体系在398nm的荧光强度I398nm和[Cd2+]浓度在0-30×10-6M的范围内呈现良好的线性关系(R2＝0.98306)，以Cd2+浓度为横坐标，以荧光强度I398nm为纵坐标作图，得到Cd2+浓度与荧光强度的线性方程：F＝3658.41667+131.40774[Cd2+]，[Cd2+]的单位为10-6mol/L；工作线性图见图2。
实施例4萘衍生物用于Cd2+的紫外吸收测定
取100μL的萘衍生物储备液加入干净的比色管中，分别加入不同体积的Cd2+(2μL、4μL、6μL、8μL、10μL、15μL、20μL、25μL、30μL、40μL、50μL、60μL、70μL)，加入0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在紫外可见分光光度计上检测，随着Cd2+的加入，在272nm处的吸收峰逐渐减弱，283nm处的吸收峰逐渐减弱，并且342nm处的吸收峰发生红移至347nm，365nm处出现肩峰。紫外光谱吸收图见图3。
实施例5共存阳离子对Cd2+的干扰性的荧光测定
取20μL的萘衍生物储备液加入干净的比色管中，分别加入20μL的Cd2+，14μL的其他各种阳离子(K+,Ca2+,Na+,Mg2+,Al3+,Zn2+,Hg2+,Ag+,Pb2+,Co2+,Ni2+,Cr3+,Hg2+,Fe3+)，0.5mLHEPES缓冲，用乙醇定容至5mL，摇匀后取2.5mL加到干净的比色皿中，在荧光分光光度计上检测。共存阳离子对NIS-Cd2+的荧光强度的干扰见图4。
实验证明，其它常见阳离子不干扰体系对Cd2+的测定。
Claims (7)
1.一种萘衍生物，其特征在于，结构式为：
2.如权利要求1所述的萘衍生物的合成方法，其特征在于，包括如下步骤：将反应物2，3-二氨基萘和咪唑-2-甲醛在体积比1：1的甲醇和乙醇的混合溶液中加热回流，反应20-25小时，抽滤，洗涤得到萘衍生物。
3.如权利要求2所述的萘衍生物的合成方法，其特征在于，所述2，3-二氨基萘和咪唑-2-甲醛的摩尔比为1:2-2.2。
4.如权利要求2所述的萘衍生物的合成方法，其特征在于，所述的反应时间为24小时。
5.如权利要求2所述的萘衍生物的合成方法，其特征在于，所述加热回流温度为80℃。
6.如权利要求1所述的萘衍生物在制备检测Cd2+试剂中的应用。
7.一种比率荧光光谱测定Cd2+的方法，其特征在于，包括如下步骤：
（1）用DMSO配置1mM的如权利要求1所述的萘衍生物的储备液，用蒸馏水配置10-2M的Cd2+溶液，并配置pH=7.4、浓度为25mM的HEPES的缓冲溶液；
（2）取20μL 萘衍生物储备液加入干净的比色管中，随着Cd2+浓度的增加，在荧光光度计上测定472nm处的荧光强度逐渐减弱，398nm处的荧光强度逐渐增强，体系在398nm的荧光强度I398nm和[Cd2+]浓度在0-30×10-6M的范围内呈现良好的线性关系R2=0.98306，以Cd2+浓度为横坐标，以荧光强度I398nm为纵坐标作图，得到Cd2+浓度与荧光强度的线性方程：F=3658.41667+131.40774[Cd2+]；
（3）取2.5mL含有4×10-6M萘衍生物的EtOH-水溶液加入干净的比色管中，取xμL待测样品溶液加入，在荧光分光光度计上检测，测得的荧光强度，带入步骤（2）的线性方程，得到[Cd2+]的浓度，待测样品[Cd2+]待测=5000μL×[Cd2+]×10-6/xμL，即可求得Cd2+的浓度。
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