CN116283942A - 一种用于检测溶液中铬离子含量的有机化合物及其应用 - Google Patents
一种用于检测溶液中铬离子含量的有机化合物及其应用 Download PDFInfo
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- CN116283942A CN116283942A CN202310350194.7A CN202310350194A CN116283942A CN 116283942 A CN116283942 A CN 116283942A CN 202310350194 A CN202310350194 A CN 202310350194A CN 116283942 A CN116283942 A CN 116283942A
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- C07D405/14—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 three or more hetero rings
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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
- C07D401/14—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 three or more hetero rings
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- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
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- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
本发明涉及溶液中金属离子检测领域,尤其涉及一种用于检测溶液中铬离子含量的有机化合物及其应用。本发明提出一种采用亚乙基苯并哌嗪‑吡啶‑6‑甲酸作为离子络合体,与显色基团或荧光基团连接的有机化合物,是一种选择性铬离子络合剂,可用于铬离子的选择性消除和掩蔽,具有极高的选择性。通过引入显色基团,可用于各种介质中的铬离子选择性显色、分光光度测定、显色试纸的制备。通过引入荧光基团,也可成为铬离子荧光指示剂,从其荧光强度计算出每个溶液中铬离子的含量,大大提高了效率、灵敏度和重现性。
Description
技术领域
本发明涉及溶液中金属离子检测技术领域,尤其涉及一种用于检测溶液中铬离子含量的有机化合物及其应用。
背景技术
铬离子是继汞、铅、镉之后第四个有毒金属离子,其毒性对环境水质产生巨大影响。各国环境保护部门对其废水排放都有严格要求。但是,与前三个离子不同,三价铬离子又是生物体系内必要得微量元素之一,其含量过多或过少对生物体系有着非常重要得影响其中影响。传统的检测方法包括火焰原子吸收、电感耦合原子发射光谱(ICP-AES)、X-射线荧光光谱和电化学分析。这些方法对于微量的铬离子的含量的检测非常繁琐,而且只能在实验室进行,不能自动化检测,对于水质参数的检测和补偿措施的全程自动化很难实现。荧光探针法由于其方法简便,灵敏度高,而被广泛用于各个领域。目前铬离子荧光探针主要有以羧基吖啶酮、苯并咪唑、丹磺酰胺和哌嗪等作为离子络合体。但是该系列荧光探针对铬离子的选择性差,响应范围不能满足实际检测要求。而且那些分子不含可用于固定化的官能团,不能用于制作可逆的传感器,所以不能应用需要多次使用的各种样品中铬离子的连续检测。
为克服现有技术中的缺陷,本发明公开了一种用于检测溶液中铬离子含量的有机化合物及其应用。
发明内容
针对背景技术中存在的问题,提出一种用于检测溶液中铬离子含量的有机化合物及其应用。本发明提出一种采用亚乙基苯并哌嗪-吡啶-6-甲酸作为离子络合体,与显色基团或荧光基团连接的有机化合物,是一种选择性铬离子络合剂,可用于铬离子的选择性消除和掩蔽,具有极高的选择性。通过引入显色基团,可用于各种介质中的铬离子选择性显色、分光光度测定、显色试纸的制备。通过引入荧光基团,也可成为铬离子荧光指示剂,从其荧光强度计算出每个溶液中铬离子的含量,大大提高了效率、灵敏度和重现性。
本发明提出一种用于检测溶液中铬离子含量的有机化合物,该有机化合物采用亚乙基苯并哌嗪-吡啶-6-甲酸作为离子络合体,与显色基团或荧光基团连接,具有如下结构式:
优选的,上述的有机化合物中至少包括一个显色基团或一个荧光基团;显色基团或荧光基团选自:
优选的,其中R5’、R6、R7、R8、R8’、R9、R10、R11、R11’、R12、R13、R14、R15、R16、R17、R18、R19、R20独立地选自-H、-OH、C1-C6的直链或支链烷基、C1-C6的直链或支链烷氧基、C3-C6的环烷基、-F、-Cl、-Br、-I、-CN、-NO2、-NH2、
优选的,R1、R2、R3和R4分别选自-H、C1-C6的直链或支链烷基和C1-C6的直链或支链烷氧基。
优选的,R21、R22、R23、R24、R25、R26、R27、R28、R29、R30、R31分别选自-H、C1-C6的直链或支链烷基;R32、R33、R34分别选自-H、C1-C6的直链或支链烷基、C1-C6的直链或支链烷氧基、-COOH。
优选的,S、T分别选自:
优选的,S、T分别选自-H、-CH3和C2H5OCOCH2-,2-甲基吡啶-6-甲酸。
优选的,Y选自荧光基团:
本发明又提出一种用于检测水环境中金属离子含量的产品,包括上述的有机化合物;产品通过该有机化合物和作为载体的亲水高聚物制备而成半成品,再将半成品加入水凝胶涂布而成。
本发明又提出一种用于检测溶液中铬离子含量的有机化合物的应用,包括上述的产品,用于检测的金属离子为Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、Ag+、Hg2+、Mg2+、Mn2+、Ni2+、Pb2+、Sr2+、La3+、Eu3+和Er3+。
与现有技术相比,本发明具有如下有益的技术效果:
1、本发明提出一种采用亚乙基苯并哌嗪-吡啶-6-甲酸作为离子络合体,与显色基团或荧光基团连接的有机化合物,是一种选择性铬离子络合剂,可用于铬离子的选择性消除和掩蔽,具有极高的选择性。通过引入显色基团,可用于各种介质中的铬离子选择性显色、分光光度测定、显色试纸的制备。通过引入荧光基团,也可成为铬离子荧光指示剂,从其荧光强度计算出每个溶液中铬离子的含量,大大提高了效率、灵敏度和重现性。
2、本发明中的有机化合物通过固定在亲水高聚物表面制成产品,实现了对微量金属离子含量即时监测,使整个分析过程自动化,大大提高了效率。
3、本发明涉及的合成工艺路线和工艺参数,反应条件温和、安全,产品纯度可达到99.0%以上。
附图说明
图1为本发明制备中含铬离子络合基团的反应路线。
图2为本发明中铬离子荧光指示剂(图1中化合物11)荧光激发和发射光谱。
图3为本发明中铬离子荧光指示剂(图1中化合物11)在不同铬离子浓度下的荧光光谱。
图4为本发明中铬离子荧光指示剂(图1中化合物11)对铬离子的校正曲线。
图5为本发明中铬离子络合基团(图1中化合物8)在不同铬离子浓度下的紫外可见光谱。
图6为本发明中铬离子络合基团(图1中化合物8)在不同铬离子浓度下的紫外可见校正曲线。
图7为本发明中铬离子络合基团(图1中化合物11)在不同离子浓度下的荧光响应比值。
具体实施方式
本发明提出一种用于检测溶液中铬离子含量的有机化合物。该有机化合物采用亚乙基苯并哌嗪-吡啶-6-甲酸作为离子络合体,与显色基团或荧光基团连接,具有如下结构式:
下面以具体化合物为例显示了本发明中的金属离子载体化合物和显色或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。
图1显示了本发明的一种优选分子结构(亦可称为铬离子载体)即亚乙基苯并哌嗪吡啶-6-甲酸做为铬离子络合剂的合成路线。以化合物(1)2,6-吡啶二甲酸为原料,在浓硫酸催化下与甲醇反应形成二甲酯化合物(2)。然后与硼氢化钠单还原为2-羟甲基吡啶-6-甲酸甲酯化合物(3),再与氯化亚砜得到化合物(4)。以化合物(5)邻苯二胺为原料,与氯乙酸反应关环的化合物(6),再用氢化铝锂还原酰胺生成苯并哌嗪化合物(7)。再与化合物(4)烷基化得得化合物(8)。再与DMF反应形成醛基化合物(9),最后与4-氯间苯二酚缩合形成二氯荧光素衍生物化合物(10),再用碱水解二甲酯得到最终产物化合物(11)。
下面按照图1所描述的反应过程制备本发明所提到的各种化合物,做出具体的实施例:
实施例1
化合物2的合成
称量化合物1(167g,1mol,1eq)放入2000mL三口烧瓶中,加入甲醇(2000ml)和浓硫酸(50mL),升温至回流,搅拌过夜反应16h。溶液澄清,薄层色谱TLC(DCM:MeOH=5:1)显示反应完毕。将反应液浓缩至200mL,降温搅拌30分钟,过滤,滤饼用少量甲醇洗涤后干燥,得产品化合物2(156g,80%)。1H NMR(CDCl3)δ=3.90(s,6H),8.60(m,1H)。8.90-8.95(m,2H)。
化合物3的合成
称量化合物2(19.5g,0.1mol,1eq)放入500mL三口瓶中,加入300mL无水THF/MeOH(5:1 300mL),降温至0度,分批加入硼氢化钠(3.8g,0.1mol),加完后升温至室温,反应4h。薄层色谱TLC(PE:EA=3:1)显示反应完毕。加饱和氯化铵淬灭,旋干溶剂,用乙酸乙酯萃取(300mL*3),有机相合并后用饱和食盐水(500mL*1),有机相用无水硫酸钠干燥后旋干得到化合物3(12g,72%)灰白色固体。1H NMR(CDCl3)δ=3.80(s,3H),5.15(d,2H),6.70(t,1H),8.10(m,1H),8.35-8.40(m,2H)。
化合物4的合成
称量化合物3(8.4g,50mmol,1eq)放入250mL三口瓶中,加入100mL氯化亚砜,室温搅拌过夜,薄层色谱TLC(PE:EA=3:1)显示反应完毕。浓缩反应液,得到化合物4(8.9g,100%),直接用于下一步。1H NMR(CDCl3)δ=3.85(s,3H),5.25(d,2H),8.15(m,1H),8.45-8.50(m,2H)。
化合物6的合成
称取化合物5(10.8g,100mmol)溶于二甲基甲酰胺(DMF,100mL)于250mL三口瓶中,加入氯乙酸(11g,120mmol)和碳酸钾(25.6g,200mmol),室温搅拌过夜,后升温到100度反应过夜。TLC(PE:EA=1:1)检测反应完全。浓缩反应液,加入水(300mL),用乙酸乙酯萃取(300mL*3),无水硫酸钠干燥后旋干有机相得粗品,柱层析得到化合物6(11.5g,78%)。1HNMR(CDCl3)δ=3.99(s,2H),4.80(br,1H),6.75(m,1H),6.80(m,1H),6.90(m,1H),9.55(br,1H)。
化合物7的合成
称取化合物6(7.4g,50mmol)溶于无水THF(150mL)于250mL三口瓶中,零度下分批加入氢化铝锂(3.8g,100mmol),升温到80度反应过夜。TLC(PE:EA=3:1)检测反应完成。零度下用15%的氢氧化钠(4mL)淬灭反应,过滤,滤饼用四氢呋喃洗涤两次,合并有机相后旋干溶剂得产物5g(75%)。1HNMR(CDCl3)δ=3.25(s,4H),6.55(m,2H),6.65(m,2H),7.55(br,2H)。
化合物8的合成
称取化合物7(1.34g,10mmol)溶于二甲基甲酰胺(DMF,50mL)于250mL三口瓶中,加入化合物4(4.1g,22mmol)和碳酸钾(4.16g,30mmol),加热至80度反应18小时。TLC(PE:EA=1:1)检测反应完全。反应液加水(200mL),用100ml乙酸乙酯萃取3次,合并有机相后用饱和食盐水洗涤一次,用无水硫酸钠干燥,浓缩有机相,得到粗品6.7g,柱层析(淋洗剂:二氯甲烷,DCM)得到产物1.5g(35%)。1H NMR(CDCl3)δ=3.45(s,4H),3.65(s,6H),4.95(s,4H),6.35(m,2H),6.49(m,2H),7.85(m,2H),8.10(m,2H),8.25(m,2H)。
化合物9的合成
称取化合物8(0.43g,1mmol)溶于DMF(5mL)于100mL三口瓶中,氩气保护下加入三氯氧磷(1mL),升温到60度反应过夜。薄层色谱TLC(PE:EA=3:1)检测反应完全后,加入50mL水,用乙酸乙酯(EA,50mL)萃取三次,混合有机相后用水洗三次,分液,有机相用无水硫酸钠干燥后旋干,得粗品,柱层析纯化得到产物320mg(70%)。1H NMR(CDCl3)δ=3.47(s,4H),3.68(s,6H),4.90(s,4H),6.38(m,2H),6.53(m,2H),7.80(m,2H),8.15(m,2H),8.35(m,2H)。9.80(s,1H)。
化合物10的合成
称取化合物9(0.23g,0.5mmol),间苯二酚(0.22g,1mmol)溶于二氯甲烷(15mL)于50mL三口瓶中,加入对甲磺酸(0.1mL,cat),室温反应过夜。TLC(石油醚:乙酸乙酯,PE:EA=1:1)检测反应完全后,加入3ml三乙胺和DDQ(680mg,3mmol),室温搅拌过夜,旋干有机相,制备板分离得到化合物1050mg(16%)。1H NMR(CDCl3)δ=3.50(s,4H),3.70(s,6H),4.90(s,4H),6.42(m,2H),6.28(m,2H),6.58(m,2H),6.78(m,2H),7.85(m,2H),8.17(m,2H),8.38(m,2H)。
化合物11的合成
称取化合物10(25mg)溶于甲醇(2mL)于50mL三口瓶中,加入15%氢氧化钠溶液(1mL),室温反应过夜。反应液直接用于测试。
化合物11的测试
取化合物5溶液(40μl),用10mlHEPES缓冲溶液稀释,配制成40μM的pH=7.4的HEPES缓冲溶液用于测试。该溶液对铬离子的响应紫外-可见吸收光谱的测试结果见图2。
图2显示了铬离子荧光指示剂化合物11得荧光激发和发射光谱。指示剂浓度为0.1毫摩尔,在pH为7.0的10毫摩尔TRIS-HCl缓冲溶液中。与母体一样,该化合物几乎保持了二氯荧光素得所有光学性质,最大激发在470纳米处,非常适合市售蓝色发光二极管,最大发射在530纳米,适合蓝光滤光片。
图3为本发明铬离子荧光指示剂(图1中化合物11)在不同铬离子浓度下的荧光发射光谱。指示剂浓度为0.1毫摩尔,在pH为7.0的10毫摩尔TRIS-HCl缓冲溶液中,激发波长为470纳米。荧光强度随着铬离子浓度的增加而降低,在800-1200微摩尔铬离子浓度区间信号变化最快。
图4为本发明铬离子荧光指示剂(图1中化合物11)在不同铬离子浓度下的荧光校正曲线。在0-1600微摩尔铬离子浓度区间有响应,最大斜率在800微摩尔附近,可以用于环境水中的铬离子浓度的样品的测定。
图5为本发明铬离子头(图1中化合物8)在不同铬离子浓度下的紫外-可见吸收光谱。离子头浓度为0.1毫摩尔,在pH为7.0的10毫摩尔TRIS-HCl缓冲溶液中。随着镉离子浓度增加,最大吸收峰在247纳米的吸光度增加,而在320纳米处的吸光度在减少,在300纳米附近存在一个等吸光点。这组数据证明,铬离子头与铬离子发生络合作用,影响了离子头的电子云的分布,从而引起紫外-可见吸收光谱的相应变化。最大吸光度变化发生在600微摩尔铬离子浓度区间。
图6为本发明铬离子头(图1中化合物8)在不同铬离子浓度下的紫外-可见吸收光谱所形成的相应校正曲线。离子头浓度为0.1毫摩尔,在pH为7.0的10毫摩尔TRIS-HCl缓冲溶液中。以最大吸收峰在247纳米的吸光度对铬离子浓度做图,最大信号变化发生在600微摩尔铬离子浓度区间。
图7为本发明PET型铬离子荧光指示剂(图1中化合物11)在不同金属离子溶液中的荧光发射光谱(所测金属离子为Ag+、Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Er3+、Eu3+、Fe2+、Fe3+、Hg2+、La3 +、Mg2+、Mn2+、Na+、Ni2+、Pb2+、Sr2+、Zn2+)。数据显示,该分子对铬离子的荧光增强最为显著,其次为稀土离子Er3+和Eu3+离子,对指示剂略有淬灭作用,其它离子的荧光强度几乎不变。这些数据表明,该指示剂对铬离子具有较好的选择性。
以上数据表明,对取代亚乙基苯并哌嗪引入各种取代基,可以得到一系列新的离子载体,这些载体也可以与不同的荧光基团连接,产生一系列新的荧光传感器,满足各种不同的需求。具有本领域专业知识的一般技术人员,利用不同取代基的组合,举一反三,制备出金属离子特别是铬离子的一系列显色剂和荧光指示剂。
通过实施例1可知,在本发明的技术方案中,设置离子载体亚乙基苯并哌嗪的取代苯基的结构中引入显色基团,生成一系列分子可对金属离子尤其是铬离子产生颜色响应。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。在本发明的离子载体中引入荧光基团,生成一系列分子可对金属离子尤其是铬离子产生荧光响应。此类分子在不同的铬离子浓度的样品中能产生不同强度的荧光,可用荧光仪检测。因此本发明的有机化合物中至少包括一个显色基团或一个荧光基团,当U为显色基团或荧光基团时,Y可以为其他基团;当Y为荧光基团或显色基团时,U可以为其他基团,或者U与Y成环形成至少一个荧光或显色基团,只要保证该化合物中至少存在一个显色基团或一个荧光基团即可。
实施例二
本发明提供一种用于检测溶液中铬离子含量的产品,所述产品通过实施例1中的化合物和作为载体的亲水高聚物制备,再加入水凝胶涂布而成。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。
在具体实施方式中,产品为荧光探针或敏感膜。
在具体实施方式中,产品可以做成检测试剂盒。
在具体实施方式中,检测为连续检测。
实施例三
本发明提供一种用于检测溶液中铬离子含量的有机化合物的应用,所述产品可以用于检测下列金属离子:Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、Ag+、Hg2+、Mg2+、Mn2+、Ni2+、Pb2+、Sr2+、La3+、Eu3+、Er3+。
上面结合附图对本发明的实施方式作了详细说明,但是本发明并不限于此,在所属技术领域的技术人员所具备的知识范围内,在不脱离本发明宗旨的前提下还可以作出各种变化。
Claims (10)
2.根据权利要求1所述的一种用于检测溶液中铬离子含量的有机化合物,其特征在于,R1、R2、R3和R4分别选自-H、C1-C6的直链或支链烷基和C1-C6的直链或支链烷氧基。
5.根据权利要求3或4所述的一种用于检测溶液中铬离子含量的有机化合物,其特征在于,R21、R22、R23、R24、R25、R26、R27、R28、R29、R30、R31分别选自-H、C1-C6的直链或支链烷基;R32、R33、R34分别选自-H、C1-C6的直链或支链烷基、C1-C6的直链或支链烷氧基、-COOH。
7.根据权利要求5所述的一种用于检测溶液中铬离子含量的有机化合物,其特征在于,S、T分别选自-H、-CH3和C2H5OCOCH2-,2-甲基吡啶-6-甲酸。
9.一种用于检测水环境中金属离子含量的产品,其特征在于,包括权利要求1所述的有机化合物;产品通过该有机化合物和作为载体的亲水高聚物制备而成半成品,再将半成品加入水凝胶涂布而成。
10.一种用于检测溶液中铬离子含量的有机化合物的应用,其特征在于,包括权利要求9所述的产品,用于检测的金属离子为Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Fe2+、Fe3+、Ag+、Hg2+、Mg2+、Mn2 +、Ni2+、Pb2+、Sr2+、La3+、Eu3+和Er3+。
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