CN110003175A - 一种用于检测水中金属离子含量的化合物及其应用 - Google Patents
一种用于检测水中金属离子含量的化合物及其应用 Download PDFInfo
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- CN110003175A CN110003175A CN201910236301.7A CN201910236301A CN110003175A CN 110003175 A CN110003175 A CN 110003175A CN 201910236301 A CN201910236301 A CN 201910236301A CN 110003175 A CN110003175 A CN 110003175A
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
本发明公开了一种用于金属离子含量检测的有机化合物，所述化合物以N‑乙氧基乙酸基‑N‑甲基吡啶苯胺作为金属离子络合体，在其分子中引入生色基团或荧光基团，生成金属离子特别是锌离子的显色指示剂或荧光指示剂。本发明的化合物还可以被固定在亲水高聚物上，利用生色基团或荧光基团的特性制成可以多次使用的可逆金属离子荧光探针，能够适用于各种环境中的金属离子浓度的连续检测，尤其是水中对锌离子浓度的连续测定。
Description
技术领域
本发明属于有机化合物领域，尤其涉及一种可用于水中金属离子含量检测的有机化合物及其相关应用。
背景技术
水是人类发展不可缺少的自然资源，也是人类与一切生物赖以生存的物质基础。随着我国经济发展快速，人们过分依赖水资源的投入，出现大量水资源的浪费和水体污染。工业、农业、居民生活用水需求量大大增加，有些城市用水量超过当地水资源的供水能力，城市用水紧张。尤其是工业发展的多样化，复杂的污染物导致水污染状况加剧。面临水资源的严重缺乏和污染，我们必须采取措施保护和可持续利用水资源，那么污水处理任务重大，对于水质检测工作提出了更高的要求。
锌是人体必需的微量元素之一，在人体生长发育、生殖遗传、免疫、内分泌等重要生理过程中起着极其重要的作用[1]。锌是脑中含量最多的微量元素，是维持脑的正常功能所必需的，锌的含量要在一定的正常范围内，过多或者过少都会引起疾病。饮用水被锌污染后，可造成过量的锌进入人体。慢性锌中毒主要以恶心、胃部不适为主要症状，也可引起免疫功能低下，降低高密度或低密度脂蛋白胆固醇，降低铜蓝蛋白亚铁氧化酶活性，最终导致动脉粥样硬化、高血压、冠心病等。当水中锌含量为1mg·L-1时，对水体生物氧化过程有轻微抑制作用；含锌量在3mg·L-1～5mg·L-1时，在煮沸后水会呈现乳白色，放置一段时间后出现一层油脂状薄膜；含锌量超过5mg·L-1时，水中有苦涩味。
铅、汞、镉等一系列剧毒重金属被广泛用于工业生产流程中，它们大都最终转化成为阳离子而被排放到自然界。这些重金属离子在生物体内不可降解，而且可以通过食物链在生物组织里富集，从而对人和自然界造成巨大的危害。镉被广泛用于工业生产(如电池工业)，在磷肥中也大量存在，这使得环境中镉的含量近年来有了明显的增加。长期接触镉，能引起多种癌症发病率的增加。Hg单质及Hg2+在排人环境后，可以被水生微生物转化为甲基汞，甲基汞通过食物链在生物体内富集，达到人体后，使人产生严重的恶心、呕吐、腹痛以及肾功能损伤，危害极大。环境中的铅大都以Pb2+的形式存在。铅能引起消化系统、神经系统以及心脏的病变。铅对儿童的危害更为严重，可以导致儿童的智力障碍。
因此，水质检测重金属研究成为了科学研究领域中一个重要的科研课题。目前水质检测金属离子的方法中，最广泛应用的方法有电感耦合等离子发射光谱法、流动注射分析和电化学法等[2]。
由于上述测试方法的几点劣势(仪器贵重，耗时，步骤复杂，专业性强)，荧光传感器检测金属离子的方法以其独特的优点引起了人们广泛关注和极大兴趣，并在近些年得到了较大的发展。荧光传感器离子检测拥有众多的优点，有望替代此前描述的传统方法。比如，测试过程快捷方便，价格低廉，“裸眼”可视化检测，选择性好，灵敏度高，分子结构易于修饰优化。
目前，虽然文献报道了很多重金属离子识别载体，但是目前所用的重金属离子识别载体只能用于单次测定，无法连续使用也就无法实现自动化检测。
发明内容
针对现有技术的上述及其他缺陷，本申请的发明人通过大量创造性的研究工作，发明了一种效率高、灵敏度好及重现性好的用于水中的金属离子尤其是锌镉汞铅等重金属离子含量检测的有机化合物，该化合物可固定在亲水的高聚物上，可制成多次使用的可逆的离子荧光探针，适用于各种环境中的离子浓度的连续检测。
为实现上述及其他目的，本发明提供如下技术方案。
在本发明第一方面，提供一种用于水质中金属离子含量检测的有机化合物，所述化合物包含取代或未取代的N-乙氧基乙酸基-N-甲基吡啶苯胺作为金属离子络合体，并在N-乙氧基乙酸基-N-甲基吡啶苯胺的对位引入了生色基团或荧光基团。
一种优选实施方式中，所述化合物具有如下结构式：
其中R9独立地选自1至4个碳原子的烷基；R1～R8独立地为任意基团，只要这些基团不影响所述化合物的离子络合以及显色或荧光性能；Y为生色基团或荧光基团。
更优选的实施方式中，R1～R8独立地选自氢；R9独立地选自1至4个碳原子的烷基。一种优选实施方式中，R1～R8独立地选自氢，R9为乙基。
另一种优选实施方式中，所述生色基团选自下述结构：
仍然另一种优选实施方式中，所述荧光基团选自下述结构：
一种优选实施方式中，可用本发明化合物检测的金属离子选自锌、镉、汞、铅离子。
在本发明第二方面，提供用于水中金属离子含量检测的产品，所述产品包含本发明上述有机化合物和作为载体的亲水高聚物。所述产品可以是检测试剂盒的形式。常见的亲水高聚物均可用于本发明，优选高聚物为氨基纤维素或水凝胶。一种优选实施方式中，将本发明化合物加入水凝胶涂布成薄膜作为荧光探针。另一种优选实施方式中，所述金属离子选自锌、镉、汞、铅离子。
在本发明第三方面，提供本发明化合物在水中金属离子含量检测中的应用。一种优选实施方式中，所述金属离子选自锌、镉、汞、铅离子。另一种优选实施方式中，所述检测为荧光检测，连续检测。
本发明的有机化合物作为金属离子探针具有如下突出的技术优势：
1、本发明在N-乙氧基乙酸基-N-甲基吡啶苯胺中引入生色基团，可以制备出一系列金属离子(尤其是锌、镉、汞、铅离子)显色指示剂。反应条件温和、安全，产品纯度可达到99.0％以上。
2、通过在所述苯胺中引入荧光基团，可以制备出一系列金属离子(尤其是锌、镉、汞、铅离子)荧光指示剂。当金属离子含量改变时，荧光强度随着改变，可从其荧光强度计算出溶液中金属离子的含量。
3、还可利用分子另一端的络合基团，将本发明的探针固定在高聚物表面，实现微量金属离子含量的分析，大大提高了效率、灵敏度和重现性。
附图说明
图1为本发明制备荧光型金属离子染料的反应路线。
图2为本发明锌离子检测荧光探针络合锌离子的原理图。
图3为本发明金属离子检测荧光探针对不同离子的荧光光谱图。
图4为本发明金属离子检测荧光探针对不同离子的荧光强度柱形图。
图5为本发明锌离子检测荧光探针络合不同浓度锌离子的荧光发射光谱图。
图6为本发明锌离子检测荧光探针络合锌离子的荧光光谱图。
具体实施方式
本发明通过使用N-乙氧基乙酸基-N-甲基吡啶苯胺结构，可络合多种金属离子，从而可用于实现微量离子含量的分析。申请人在长期的研发过程中对本发明化合物结构可络合的金属离子进行了广泛检测，发现其对Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、Hg2+、K+、Mg2+、Mn2+、Na+、Ni2+、Pb2+、Zn2+及镧系金属离子等均具有一定的结合能力，在这之中，尤其是对锌、镉、汞、铅离子具有较好的络合能力，最优的是对锌离子具有显著的、特异性结合的络合能力，可以作为锌离子的有效载体。通过在上述苯胺结构的对位引入生色或荧光基团，基于光致诱导电子转移原理，当离子含量改变时，其显色或荧光强度随之改变，由此可从紫外吸收值或荧光强度计算出溶液中离子的含量。
本发明化合物中可包含取代或未取代的N-乙氧基乙酸基-N-甲基吡啶苯胺结构。本领域技术人员不难确定可进行哪些取代而不影响本发明化合物络合金属离子并显色或显示荧光的能力。优选实施方式中，“取代的”是指被选自以下的取代基取代：1至4个碳原子的烷基；1至4个碳原子的烷氧基；卤素，包括氟、氯、溴、碘；卤代烷基；氰基；硝基；氨基；和苯基。
在本申请上下文中，“烷基”指1至4个碳原子的直链或支链烷基，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基。“烷氧基”指具有1至4个碳原子的烷氧基，例如甲氧基、乙氧基、丙氧基、丁氧基。
利用显色原理或荧光均可实现对离子浓度的连续检测，尤其是对锌离子浓度的检测。本领域常用的生色基团或荧光基团均可用于本发明。
一方面，在本发明离子载体即苯胺结构中引入生色基团以后，所生成的一系列分子可对金属离子尤其是锌离子产生颜色响应。此类分子在不同离子浓度的样品中能产生不同颜色，可用光度计或者肉眼检测。申请人在实验中证实了上述效果。数据显示，该分子可以作为锌离子显色指示剂。
另一方面，在本发明的离子载体中引入荧光基团以后，所生成的一系列分子可对金属离子尤其是锌离子产生荧光响应。此类分子在不同的锌离子浓度的样品中能产生不同强度的荧光，可用荧光分光光度计检测。申请人在实验中证实了上述效果，荧光强度随着样品中锌离子浓度的增加而增加，增加幅度能达十几倍。由于络合结构对于不同金属离子的结合能力有差异，考虑到实际的检测应用需要，本发明的有机化合物最适合的检测对象是锌离子；也可检测镉、汞、铅离子，包括但不限于Ca2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、K+、Mg2+、Mn2+、Na+、Ni2+、Zn2+，尤其可用于科学研究用途。
为便于工业应用，还可将本发明的离子检测化合物结合于亲水高聚物载体制成用于检测水质中金属离子含量的产品，所述产品例如是试剂盒的形式。常见的亲水高聚物均可用于本发明，优选高聚物为氨基纤维素或水凝胶。一种优选实施方式中，将本发明化合物加入水凝胶涂布成薄膜作为荧光探针。
附图1以具体化合物为例显示了本发明离子载体化合物和荧光指示剂的合成路线。需要注意的是，此处使用具体化合物只是出于方便理解的目的，本领域技术人员可根据这些具体化合物的合成路线进行必要的改动来制备可用于本发明的其他离子载体化合物和指示剂。
参考附图1所示，显示了本发明的一种优选分子结构(亦可称为锌离子载体)即N-乙氧基乙酸基-N-甲基吡啶苯胺以及锌离子荧光指示剂的合成路线。
本说明书上文中结合具体实施方式对本发明进行了阐释，但应理解，这些描述和阐释只是为了更好地理解本发明，而不构成对本发明的任何限定。本领域技术人员在阅读了本申请说明书之后可对本发明的具体实施方式进行必要的改动而不脱离本发明的精神和范围。本发明的保护范围由所附的权利要求书限定，并且涵盖了权利要求的等同变换。
下面结合实施例对本发明进行进一步的说明。在下述实施例中，提供了具体的化合物结构以说明本发明化合物的结构类型、制备方法、及其作为锌离子浓度检测探针的检测性能。所提供的实施例仅用于说明本发明可如何实施，并不构成特别限定。具有本领域专业知识的一般技术人员，可通过下面所举的具体例子，举一反三，制备出金属离子特别是锌离子的一系列显色剂和荧光指示剂。
除非本申请上下文中另有其他说明，否则本申请中所用技术术语及缩写均具有本领域技术人员所知的常规含义；除非另有说明，否则下述实施例中所用原料化合物均为商购获得。
按照图1所描述的反应过程制备本发明所提到的各种化合物，每个步骤的反应的具体步骤如下：
化合物1的制备参照文献[3].
化合物2的合成
0.4g(0.76mmol)化合物1，154mg(0.92mmol)氯乙氧基乙酸乙酯，0.26mL(1.54mmol)N，N-二异丙基乙胺(DIEA)和0.26g(1.54mmol)碘化钾加入到10ml DMF中，80℃反应过夜，TLC检测反应完全，冷却后倒入水中，析出油状粘稠物，倾去水相，二氯甲烷重新溶解，无水硫酸钠干燥，旋干，粗品柱层析提纯得到195mg。1HNMR(CDCl3)δ8.50(d，J＝7.3Hz，1H)，8.42(d，J＝8.4Hz，1H)，7.89(d，J＝8.2Hz，3H)，7.50(dd，J＝16.7，8.1Hz，3H)，7.06(d，J＝8.3Hz，2H)，6.70(d，J＝8.5Hz，1H)，6.62(d，J＝8.3Hz，2H)，5.46-5.39(t，J＝8.2Hz，1H)，5.37(s，2H)，4.35(s，1H)，4.22(dd，J＝14.3，7.1Hz，2H)，4.11(s，2H)，3.77(t，J＝5.0Hz，2H)，3.57(dd，J＝11.9，6.4Hz，2H)，3.31(t，J＝5.0Hz，2H)，2.95(t，J＝6.7Hz，2H)，1.54(s，9H)，1.28(t，J＝7.2Hz，3H).13C NMR(CDCl3)δ170.786，165.894，164.836，164.189，149.748，147.425，142.726，135.034，131.567，131.050，130.059，129.765，128.584，126.736，126.423，124.886，122.956，120.433，113.687，109.985，104.686，81.014，77.756，77.332，76.908，70.438，68.450，61.298，44.877，43.912，43.322，34.034，28.401，14.466.MS(+ESI)：Calc.for MH+，652.29；Found，652.3.
化合物3的合成
100mg(163.21μmol)化合物2，110mg(592.40μmol)氯甲基吡啶盐酸盐，0.2mL(1.18mmol)N，N-二异丙基乙胺DIEA以及99mg(592.4μmol)碘化钾加入到2mL DMF中，110℃加热搅拌20小时。TLC(PE∶EA＝1∶2)检测反应完全后，将反应液逐滴慢慢滴加到I级水中，二氯甲烷萃取，无水硫酸钠干燥，过滤，将溶剂旋干，制备板分离提纯得到10mg产品.1H NMR(300MHz，CDCl3)δ8.48-8.44(m)，8.35(d，J＝8.4Hz)，7.92-7.88(m)，7.85-7.78(m)，7.62(t，J＝7.8Hz)，7.45(t，J＝8.2Hz)，7.29(d，J＝7.8Hz)，6.99(d，J＝8.6Hz)，6.61(dd，J＝16.1，8.6Hz)，5.28(d，J＝13.1Hz)，4.74(s)，4.10(q，J＝7.1Hz)，3.98(s)，3.95(s)，3.71(dd，J＝6.4，3.8Hz)，3.50(dd，J＝11.8，6.5Hz)，2.88(t，J＝6.6Hz)，1.47(s)，1.16(d，J＝7.1Hz).MS(+ESI)：Calc.for MH+，801.34；MNa+，823.34；Found，823.4。
化合物4的合成
10mg(12.49μmol)化合物3溶于4mL二氯甲烷中，慢慢滴加0.5mL三氟乙酸，室温搅拌反应。TLC检测反应完全后，旋干。然后再加入二氯甲烷溶剂旋干，反复操作3次，以便将三氟乙酸完全除去。得到9mg黄色固体产品可直接用于下一步反应。
Sensor Zn的合成(即水解化合物4)
9mg(12.49μmol)化合物4溶于1mL甲醇中，加入氢氧化钠溶液(47mg，1.16mmol氢氧化钠溶于2mL I级水)40℃水解，TLC(DCM∶MeOH＝5∶1)检测反应完全后，直接用于下一步的性质响应实验测试。本发明通过对N-乙氧基乙酸基-N-甲基吡啶苯胺引入生色基团或荧光基团，使得该分子在与金属离子络合时产生颜色变化或荧光强度的变化，从而实现了微量金属离子可视化检测或自动化检测。该分子与金属离子络合后的颜色变化或荧光强度的变化与溶液中金属离子的浓度直接相关，因而可根据该分子的颜色变化或荧光强度而计算出溶液中金属离子的含量，实现对金属离子含量的快速准确检测。
图3及图4显示了锌离子载体对不同离子的荧光发射光谱及其柱状图。
图5显示了加入不同浓度的锌离子溶液，Sensor Zn的浓度滴定荧光强度响应变化曲线，随着加入锌离子浓度逐渐增加，Sensor Zn的荧光逐渐增强，直至锌离子浓度增加到25μM时荧光强度达到最大值不再变化，取最大发射波长550nm处所对应的荧光强度响应变化相对值对锌离子浓度做浓度滴定曲线如图6所示。
本领域技术人员都能根据本说明书所提供的思路和合成方法，制备出具有络合能力的锌离子指示剂，此处不予赘述。
综合上述实验结果可知，本发明的有机化合物对于锌离子浓度的增加有良好的响应，在没有锌离子或锌离子含量很低的样品中，荧光很弱，或几乎没有荧光。
参考文献：
[1]侯振江，张宗英，李月秋，微量元素与健康研究，2002，19(4)，65.
[2]陈正，王彬彬，科技创新与应用，2016，5，155.
[3]Huarui He，Kenneth Jenkins，Chao Lin，A fluorescent chemosensor forcalcium with excellent storage stability in water，Anal.Chim.Acta，2008，611，197-204.
Claims (10)
1.一种用于水中金属离子含量检测的荧光有机化合物，所述化合物包含取代或未取代的N-乙氧基乙酸基-N-甲基吡啶苯胺作为金属离子络合体，并在其分子的对位引入生色基团或荧光基团。
2.根据权利要求1所述的有机化合物，其特征在于所述化合物具有如下结构式：
其中R9独立地选自1至4个碳原子的烷基；R1～R8独立地为任意基团，只要这些基团不影响所述化合物的离子络合以及显色或荧光性能；Y为生色基团或荧光基团。
3.根据权利要求2所述的有机化合物，其特征在于R1～R8独立地选自氢、R9独立地选自1至4个碳原子的烷基。
4.根据权利要求1至3中任一项所述的有机化合物，其特征在于所述生色基团选自：
所述荧光基团选自：
5.一种用于水中金属离子含量检测的产品，该产品包含权利要求1至4中任一项所述的有机化合物和作为载体的亲水高聚物。
6.根据权利要求5所述的产品，其特征在于所述亲水高聚物选自氨基纤维素或水凝胶。
7.根据权利要求5所述的产品，其特征在于所述产品为试剂盒。
8.权利要求1至4中任一项所述的有机化合物在水质中金属离子含量检测中的应用。
9.根据权利要求8所述的应用，其特征在于所述金属离子选自重金属锌离子、镉离子、汞离子、铅离子。
10.根据权利要求8所述的应用，其特征在于所述检测为荧光检测，连续检测。
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