CN105441068B - 一种识别钴离子荧光探针及其合成方法和应用 - Google Patents

一种识别钴离子荧光探针及其合成方法和应用 Download PDF

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CN105441068B
CN105441068B CN201510969475.6A CN201510969475A CN105441068B CN 105441068 B CN105441068 B CN 105441068B CN 201510969475 A CN201510969475 A CN 201510969475A CN 105441068 B CN105441068 B CN 105441068B
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钟克利
赵杰
曲秀莉
汤立军
励建荣
任欢欢
蔡克迪
许家胜
侯淑华
徐永霞
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Abstract

一种识别钴离子荧光探针及其合成方法和应用，该荧光探针L结构式如下：合成步骤是：以乙腈为溶剂，将原料8‑(2‑(2‑甲氧基乙氧基)乙氧基)喹啉‑2‑甲醛和吡啶‑2‑甲酰肼，加热回流反应后，减压旋出乙腈，得到的粗产物用硅胶柱色谱法进行纯化，用乙酸乙酯和石油醚作为洗脱剂进行分离，得到荧光探针L。该荧光探针合成方法简单，产物分离提纯过程容易，在水介质中即可实现对Co2+离子的定性识别和定量检测，具有特异选择性和灵敏性。

Description

一种识别钴离子荧光探针及其合成方法和应用
技术领域
本发明涉及一种基于8-羟基喹啉-2-甲醛吡啶-2’-甲酰腙衍生物识别钴离子(Co2 +)荧光探针及其合成方法和应用。
背景技术
钴是一种重要的元素，微量存在于所有多细胞生物体的氰钴胺素和金属蛋白中。海水中的钴含量可达0.5μg/L～1.2μg/L。人们在硬质金属工业、金刚石研磨和瓷器、化学及制药工业中都会接触到钴。钴也是人体必需的微量元素，在新陈代谢和血色素的合成中，主要以维生素B12及B12辅酶形式发挥其生物学作用和生理功能。Co2+的缺乏可引起心血管疾病，而Co2+过量存在于环境中，会导致人体肺部损伤、支气管敏感和肺纤维化等疾病。
尽管有很多种方法如分光光度法、化学方法等都能检测Co2+，但是这些方法一般都需要复杂的操作程序，并且存在灵敏度很低，费用很高等缺点。因此，找到一种操作简单方便，选择性专一，灵敏度高的快速检测方法是非常重要的，在医学、环境监测及食品安全等领域具有广泛的应用前景。
目前，已有文献报道了有关检测Co2+的荧光探针，如CN104316504A公开了“一种荧光探针的制备及其对Al3+、Co2+离子的快速检测方法”，该荧光探针与Al3+离子结合后在紫外灯照射下即可见其溶液显黄色，与Co2+离子结合后通过肉眼即可观察到溶液颜色由浅黄色变为酒红色，由于识别与Co2+离子时通过颜色变化，因此无法实现定量识别，并且，在识别过程中容易受到其他离子干扰。New Journal of Chemistry(2015),39(12),9293-9298；Sensors and Actuators,B:Chemical(2015),221,1223-1228；Sensors and Actuators,B:Chemical(2015),209,853-863；Journal of Materials Chemistry A:Materials forEnergy and Sustainability(2014),2(43),18488-18496；Neimenggu Shiyou Huagong(2014),40(2),1-4；European Journal of Inorganic Chemistry(2013),2013(35),6019-6027；Tetrahedron Letters(2013),54(48),6464-6468；Advanced Materials Research(2012),554-556；Analytical Chemistry(2012),84(19),8294-8300；Chemistry-AEuropean Journal(2008),14(26),8004-8012；但是这些文献都是对多种阳离子的检测，部分阳离子还存在干扰，没有实现对钴离子的专一识别。ChemPhysChem(2014),15(18),3933-3937；ACS Sustainable Chemistry&Engineering(2013),1(12),1600-1608；ACS AppliedMaterials & Interfaces(2012),4(10),5217-5226；这些文献虽然能专一识别钴离子，但是合成复杂，需要制备成复合粒子或材料才有效果，成本较高。CN102735663B；AnalyticaChimica Acta(2006),580(2),143-148；这些文献报道的探针能在水介质中识别钴离子，但受体本身水溶性差，识别灵敏度低，合成路线较长。为发展一种经济实用、可以定性、定量专一检测Co2+的荧光探针，我们设计合成了新颖的、可在水介质中识别Co2+的荧光探针，并在实际水样中实现了对Co2+的快速、定量检测。
发明内容
本发明要解决的技术问题是提供一种识别钴离子荧光探针及其合成方法和应用，该荧光探针合成方法简单，产物分离提纯过程容易，在水介质中即可实现对Co2+离子的定性识别和定量检测，具有特异选择性和灵敏性。
本发明的技术方案是：
一种识别钴离子荧光探针,该荧光探针L是基于8-羟基喹啉-2-甲醛吡啶-2’-甲酰腙衍生物，结构式如下：
一种识别钴离子荧光探针的合成方法，其具体步骤如下：
以乙腈为溶剂，将原料8-(2-(2-甲氧基乙氧基)乙氧基)喹啉-2-甲醛()和吡啶-2-甲酰肼()按照摩尔比1:1～1:1.3进行投料，加热进行回流反应，回流反应时间为2h～8h，减压旋出乙腈，得到的粗产物用硅胶柱色谱法进行纯化，用乙酸乙酯和石油醚作为洗脱剂进行分离，得到荧光探针8-(2-(2-甲氧基乙氧基)乙氧基)喹啉-2-甲醛吡啶-2’-甲酰腙()。
所述乙酸乙酯和石油醚的体积比为1:1～1:5。
所述回流反应时间为2.5h～5h。
一种识别钴离子荧光探针的应用，在pH＝7～11、体积比为1:1的HEPES与乙腈的缓冲溶液中对钴离子进行检测。
一种识别钴离子荧光探针的应用，在体积比为1:1的实际水样与乙腈混合溶液中对钴离子进行定量检测。
本发明的有益效果：
(1)合成荧光探针原料易得，合成方法简单，产物分离提纯过程容易；荧光探针可以在水介质中识别钴离子，具有高度的选择性和良好的灵敏度，并可应用到实际水样中定量检测钴离子。
(2)以8-羟基喹啉-2-甲醛为底物，通过引入醚链来增加水溶性，引入2-吡啶甲酰肼来提供更多的配位原子，设计合成的荧光探针在实际水样中，与Co2+结合后，溶液绿色荧光褪去，仅借助手提式紫外灯即可完成定性检测，可以实现对Co2+浓度在1μmol/L～9μmol/L的范围内的定量检测，检测限达到10-6mol/L。
附图说明
图1是本发明荧光探针L的1H NMR谱图；
图2是本发明荧光探针L的13C NMR谱图；
图3是本发明荧光探针L的质谱谱图；
图4是本发明荧光探针L与Ni2+,Hg2+,Ca2+,Ba2+,Mg2+,K+,Al3+,Mn2+,Pb2+,Na+,Sr2+,Co2+,Cr3+,Ag+,Fe2+,Fe3+,Cu2+,Zn2+,Cd2+作用前后的荧光发射光谱图；
图5是本发明荧光探针L分别加入Ni2+,Hg2+,Ca2+,Ba2+,Mg2+,K+,Al3+,Mn2+,Pb2+,Na+,Sr2+,Co2+,Cr3+,Ag+,Fe2+,Fe3+,Cu2+,Zn2+,Cd2+离子后365nm紫外光照射的光学照片；
图6是本发明荧光探针L对Co2+识别时抗其它金属离子干扰的荧光检测图；
图7是本发明荧光探针L与0μmol/L～15μmol/L Co2+作用前后的荧光发射光谱变化图；
图8是本发明荧光探针L的荧光比值(Imax-I)/(Imax-Imin)对log[Co2+]的线性关系图；
图9是本发明荧光探针L与Co2+的Job’s plot图；
图10是本发明荧光探针L-Co2+配合物的质谱谱图；
图11是本发明荧光探针L识别钴离子的原理图；
图12是本发明荧光探针L在实际水样中与1μmol/L～9μmol/L Co2+作用后的变化图。
具体实施方式
下面结合具体实施例对本发明的技术方案作进一步详细地说明。
实施例1
(1)合成一种基于8-羟基喹啉-2-甲醛吡啶-2’-甲酰腙衍生物荧光探针，其结构式如下：
(2)该荧光探针L的具体合成步骤如下：
称量吡啶-2-甲酰肼343mg(2.5mmol)，溶解于20mL乙腈，加入8-(2-(2-甲氧基乙氧基)乙氧基)喹啉-2-甲醛630mg(2.5mmol)，加热回流3小时，自然冷却至室温，减压蒸出无水乙醇，获得褐色粗产物，用硅胶柱色谱法进行纯化，用乙酸乙酯和石油醚＝1:1(v/v)作为洗脱剂进行分离，得到810mg淡黄色固体化合物L，产率为82％。
实施例2
称量吡啶-2-甲酰肼301mg(2.2mmol)，溶解于20mL乙腈，加入8-(2-(2-甲氧基乙氧基)乙氧基)喹啉-2-甲醛504mg(2.0mmol)，加热回流2.5小时，冷却至室温，减压蒸出无水乙醇，获得褐色粗产物，用硅胶柱色谱法进行纯化，用乙酸乙酯和石油醚＝1:3(v/v)作为洗脱剂进行分离，得到680mg淡黄色固体化合物L，产率为85％。
实施例3
称量吡啶-2-甲酰肼840mg(6.5mmol)，溶解于40mL乙腈，加入8-(2-(2-甲氧基乙氧基)乙氧基)喹啉-2-甲醛1.26g(5.0mmol)，加热回流5小时，冷却至室温，减压蒸出无水乙醇，获得褐色粗产物，用硅胶柱色谱法进行纯化，用乙酸乙酯和石油醚＝1:5(v/v)作为洗脱剂进行分离，得到1.82g淡黄色固体化合物L，产率为91％。
本发明实施例1～实施例3的基本数据：
1H NMR(400MHz,CDCl3)δ11.27(d,J＝6.4Hz,1H),8.63–8.58(m,2H),8.41(d,J＝8.6Hz,1H),8.33(d,J＝7.8Hz,1H),8.16(d,J＝8.6Hz,1H),7.91(dd,J＝7.7,1.2Hz,1H),7.44(dd,J＝17.9,7.7Hz,2H),7.1–7.09(m,1H),4.42(d,J＝5.5Hz,2H),4.11–4.06(m,2H),3.82(dd,J＝5.4,3.8Hz,2H),3.64–3.60(m,2H),3.41(s,3H),3.13(s,1H)，如图1；
13C NMR(100MHz,CDCl3)δ160.34,154.51,152.22,149.15,148.79,148.20,139.64,137.61,136.43,129.74,127.65,126.94,123.02,119.93,119.13,109.53,71.87,70.72,69.51,68.15,59.11，如图2；
高分辨质谱(电喷雾，正模式)：荧光探针L的计算值[L+H]+:395.16，实测值395.1718，如图3。
利用实施例3的荧光探针L对Co2+选择性的检测：
10μmol/L的荧光探针L的HEPES:CH3CN＝1:1(v/v,pH＝7.4)缓冲溶液，向其中分别加入15μmol/L的金属阳离子(Ni2+,Hg2+,Ba2+,Mg2+,K+,Al3+,Mn2+,Pb2+,Na+,Sr2+,Co2+,Cr3+,Ag+,Fe2+,Fe3+,Cu2+,Zn2+,Cd2+)，检测溶液的荧光发射光谱变化，如图4所示。从图4中可以看出，当加入Co2+时，只有Co2+可以引起荧光强度显著变化，即加入Co2+后505nm处的荧光强度原位猝灭，而其他金属阳离子的加入对荧光强度没有明显影响，只有Cd2+引起荧光强度稍微降低，但不明显，由此可知，荧光探针L对Co2+有很好的选择性。从荧光探针L加入离子后365nm紫外光照射的光学照片(如图5所示)也可看出，加入Co2+后探针L荧光完全淬灭，其他离子没有变化，也说明荧光探针L对Co2+有高度的选择性。
荧光探针L识别Co2+的抗干扰检测：
10μmol/L的荧光探针L的HEPES:CH3CN＝1:1(v/v,pH＝7.4)溶液，分别加入15μmol/L的金属阳离子(Ni2+,Hg2+,Ba2+,Mg2+,K+,Al3+,Mn2+,Pb2+,Na+,Sr2+,Co2+,Cr3+,Ag+,Fe2+,Fe3+,Cu2+,Zn2+,Cd2+)，检测溶液的荧光发射光谱,然后向以上各个含有金属离子的溶液中再分别加入15μmol/L的Co2+，检测溶液的荧光发射光谱，取最大发射波长所对应的值作图，如图6所示。由图6可知，即使有其它金属阳离子存在时，Co2+也能导致探针L荧光淬灭，说明荧光探针L只对Co2+有结合，不受其它金属阳离子的干扰。
荧光探针L对Co2+的滴定测试：
10μmol/L的荧光探针L的HEPES:CH3CN＝1:1(pH＝7.4)缓冲溶液，分别加入0μmol/L～15μmol/L的Co2+，检测溶液的荧光发射光谱变化，如图7所示。从图7中可以看出，随着Co2 +不断加入，在505nm处的发射峰逐渐降低，当加入15μmol/L的Co2+时，在505nm处的发射峰不再降低，说明此时达到了饱和。由此可见，荧光探针L只需1.5倍的Co2+即可完成检测，说明具有良好的灵敏度。
探针L对Co2+的检测限测试：
利用图7中的滴定数据，取505nm处的强度做成点图，用Origin软件作线性拟合，获得一条线性相关系数为0.99的直线Y＝1.90+0.32X，从而计算得到检测限数值为1.15×10- 6M(如图8所示)，已经达到了微摩尔级，说明可以在水溶液中检测出微量钴离子。
探针L与Co2+的结合比测试：
通过完成等摩尔连续测定实验，根据实验结果绘制了Job’s plot图，如图9所示。两条直线相交在0.5处，说明荧光探针L与Co2+的摩尔分数都是0.5，也就是1:1结合的。然后用高分辨质谱测量L-Co2+配合物的分子量，如图10所示。[L+Co2+-H+]+配合物的质谱峰理论值为452.1，实测值为452.0880，说明探针L只结合了一个Co2+，这个结果与Job’s实验得出的结果是一致的。荧光探针L识别钴离子的原理如图11所示。
荧光探针L在实际水样中检测Co2+：
(1)实际水样的处理
取湖水、河水水样，先过滤除去其中的不溶性杂质，然后再用有机溶剂萃取除去其中的有机物，萃取后的水样及自来水都加热煮沸15分钟，冷却，过滤杂质，清液用作后续水样测试；
(2)在实际水样中检测Co2+离子
用处理后的实际水样与乙腈按体积比(CH3CN:H2O＝1:1)制备成10μmol/L的荧光探针L水溶液，分别加入0μmol/L～20μmol/L的钴离子，2小时后检测溶液的荧光发射光谱变化(如图12所示)，由图12可以看出在加入1μmol/L～9μmol/L Co2+的范围内，荧光强度与加入Co2+的浓度呈线性关系，说明当实际水样中的Co2+浓度在1μmol/L～9μmol/L的范围内，可实现对Co2+的定量检测。
以上仅为本发明的具体实施例而已，并不用于限制本发明，对于本领域的技术人员来说，本发明可以有各种更改和变化。凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (3)

1.一种识别钴离子荧光探针,其特征是：
该荧光探针结构式如下：
2.如权利要求1所述的识别钴离子荧光探针的应用，其特征是：在pH＝7～11、体积比为1:1的HEPES与乙腈的缓冲溶液中对钴离子进行检测。
3.如权利要求1所述的识别钴离子荧光探针的应用，其特征是：在体积比为1:1的实际水样与乙腈混合溶液中对钴离子进行定量检测。
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