CN111423563B - 一种用于检测Fe3+的稠杂环共轭聚合物及其制备方法和应用 - Google Patents
一种用于检测Fe3+的稠杂环共轭聚合物及其制备方法和应用 Download PDFInfo
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- CN111423563B CN111423563B CN202010446544.6A CN202010446544A CN111423563B CN 111423563 B CN111423563 B CN 111423563B CN 202010446544 A CN202010446544 A CN 202010446544A CN 111423563 B CN111423563 B CN 111423563B
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- fused heterocyclic
- conjugated polymer
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- -1 carbomethoxy Chemical group 0.000 claims abstract description 3
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Abstract
本发明公开了一种用于检测Fe3+的稠杂环共轭聚合物及其制备方法和应用，该聚合物的结构单元为
R1代表
或
R2代表苯基、C1～C8烷基取代苯基、卤代苯基、C1～C3烷氧基取代苯基、甲酯基或乙酯基。本发明聚合物利用A3‑coupling反应合成，具有多组分反应的优点，如良好的原子利用率、产物多样性等。Fe3+离子对所合成的主链咪唑并[2,1‑b]噻唑结构的稠杂环共轭聚合物的四氢呋喃溶液的荧光具有明显的淬灭作用，可用于有机相中Fe3+离子的检测，且对Fe3+离子的选择性高、检出限低。
Description
技术领域
本发明属于高分子聚合物技术领域，具体涉及一种新型稠杂环共轭聚合物，具体的说是主链含咪唑并[2,1-b]噻唑稠杂环共轭聚合物，以及该聚合物的制备方法和在检测Fe3+中的应用。
背景技术
稠杂环共轭聚合物作为一种新型的先进功能高分子材料，由于其优异的光电活性吸引了科学家们的广泛关注。在过去的几十年中，已经开发并研究了一系列稠合杂环聚合物，例如含有苯并二吡咯、苯并呋喃、苯并噻吩、苯并噻二唑、苄基咔唑和萘并吡喃的聚合物，聚-(亚氨基香豆素)等。这些聚合物中独特的共轭稠合杂环结构赋予了聚合物优异的电子传输性能，使其能够广泛的应用于聚合物发光二极管、有机光伏电池、有机场效应晶体管、光学传感器等领域。
在众多稠合杂环结构中，咪唑并[2,1-b]噻唑因其广泛的应用而引起了我们的关注。咪唑[2,1-b]噻唑是一种含氮稠合杂环化合物，存在于许多天然产物和药物分子中，具有显著的生理和药理活性，如抗癌、抗菌、抗焦虑等。此外，这类化合物还广泛应用于染料、多功能材料、荧光探针等技术领域。然而，迄今为止，成功制备含咪唑并噻唑基团的聚合物还未见报道。
近些年来，由于过渡金属离子在生命体中的重要作用，以及其对环境的影响，它们的检测技术成为了人们关注的焦点。其中，铁(Fe)是一种人体必需的微量金属元素，其参与细胞和组织的多个生物学过程，尤其在血红蛋白合成、氧化还原反应和能量代谢等过程中扮演着重要的角色。铁缺乏最常见的是引起缺铁性贫血，导致血红素合成障碍，进而导致红细胞中血红蛋白含量下降和红细胞携氧能力的下降。铁过量之后，则可能导致铁在全身多个器官的沉积，如肝脏、心脏、大脑等，进而造成多个***的功能障碍。还有大量的研究表明，帕金森和阿尔茨海默病与铁密切相关。其次，Fe含量是检测饮用水的重要指标。根据世界卫生组织的规定，生活应用水中Fe含量应小于5.4μmol/L，因此如何快速、简便、灵敏、选择性的检测Fe3+的含量是人类研究的重要课题之一。目前，检测金属离子的方法有很多，如电化学分析法、原子光谱法、离子质谱法等。但这些传统的检测方法存在稳定性差、操作复杂、仪器设备昂贵等局限性，并且样品制备过程也相当繁杂。
发明内容
本发明的目的是提供一种用于检测Fe3+具有操作简单、响应时间短，并且具有较高的稳定性和选择性的稠杂环共轭聚合物，以及该聚合物的制备方法和应用。
针对上述目的，本发明所采用的稠杂环共轭聚合物的结构单元如下所示：
式中R1代表
中任意一种，R2代表为苯基、C1～C8烷基取代苯基、卤代苯基、C1～C3烷氧基取代苯基、甲酯基、乙酯基中任意一种。
本发明稠杂环共轭聚合物的制备方法为：将式Ⅰ所示的双吖嗪单体、式Ⅱ所示的含有两个醛基的单体、式Ⅲ所示的炔烃单体、铜盐、碱加入二甲基亚砜中，在惰性气体保护及70～90℃搅拌条件下进行聚合反应，反应结束后经萃取、干燥、透析，得到稠杂环共轭聚合物；
式Ⅲ中，R3代表氢或羧基。
上述制备方法中，所述的铜盐为氯化亚铜、碘化亚铜、溴化亚铜中任意一种；所述的碱为无水碳酸钾、无水碳酸钠中任意一种。
上述制备方法中，优选双吖嗪单体与含有两个醛基的单体、炔烃单体的摩尔比为1:1.0～3.0:2.0～5.0，双吖嗪单体与碘化亚铜、无水碳酸钾的摩尔比为1:0.02～ 0.5:2.0～5.0。
本发明稠杂环共轭聚合物在检测Fe3+中的应用，具体检测方法为：将稠杂环共轭聚合物溶于四氢呋喃或水中，配制成1.0×10-6mol/L的聚合物溶液；然后向其中加入不同浓度的Fe3+标准样品，检测体系的荧光强度，绘制不同浓度Fe3+对应体系的最大荧光强度随Fe3+浓度变化的标准曲线；然后测试加入待测Fe3+样品溶液时体系的荧光强度，根据荧光强度结合标准曲线方程即可确定Fe3+的含量。
本发明的有益效果如下：
1、本发明利用A3-Coupling偶联反应合成了一类稠杂环共轭聚合物，与传统方法如：Suzuki交叉偶联反应、Still反应、Kumada反应、Sonogashira反应、Sonogashira 反应等相比，本发明合成方法原料商品化，操作简单，无需经过多步反应及中间体纯化。
2、Fe3+离子对本发明所合成的稠杂环共轭聚合物的四氢呋喃溶液的荧光具有明显的淬灭作用，可用于有机相中Fe3+离子的检测，不仅操作简单、响应时间短，且对Fe3+离子的选择性高、检出限低。
附图说明
图1是聚合物P1的荧光强度随Fe3+浓度变化的荧光光谱图。
图2是聚合物P1的相对荧光强度随Fe3+浓度变化的线性关系图。
图3是聚合物P2的荧光强度随Fe3+浓度变化的荧光光谱图。
图4是聚合物P2的相对荧光强度随Fe3+浓度变化的线性关系图。
图5是聚合物P3的荧光强度随Fe3+浓度变化的荧光光谱图。
图6是聚合物P3的相对荧光强度随Fe3+浓度变化的线性关系图。
图7是聚合物P5的荧光强度随Fe3+浓度变化的荧光光谱图。
图8是聚合物P5的相对荧光强度随Fe3+浓度变化的线性关系图。
图9是聚合物P1在不同阳离子体系中的相对荧光强度对比图。
图10是聚合物P2在不同阳离子体系中的相对荧光强度对比图。
图11是聚合物P3在不同阳离子体系中的相对荧光强度对比图。
图12是聚合物P5在不同阳离子体系中的相对荧光强度对比图。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明，但本发明的保护范围不仅限于这些实施例。
实施例1
将0.2g(6.71×10-4mol)2,2’-二氨基-6,6’-联苯并双噻唑、0.099g(7.381×10- 4mol) 1,4-对苯二甲醛、0.0256g(1.34×10-4mol)CuI、0.206g(1.41×10-3mol)无水K2CO3加入到干燥的三口烧瓶中，进行抽真空充氩气，循环三次。再将0.263g(1.41×10-3 mol)1-乙炔基-4-己基苯溶解于6.7mL无水DMSO中，并用注射器将该所得溶液加到上述三口烧瓶中，加热至80℃，搅拌反应72h。反应结束后，冷却至室温，向反应液中加入100mL二氯甲烷，然后分别用50mL饱和食盐水和50mL饱和氯化铵水溶液洗涤3次，向有机层中加入无水硫酸镁干燥过夜，减压蒸馏得到粗产物。将得到的粗产物溶于四氢呋喃中，透析处理2天，最终以54.3％的收率得到黄褐色粉末状稠杂环共轭聚合物P1，其结构表征结果如下：
1H NMR(400MHz,CDCl3)δ(ppm)8.10-7.25(22H,ArH),4.29(s,4H,CH2), 2.69-2.65(m,8H,CH2),1.58-1.55(m,8H,CH2),1.32-1.24(m,8H,CH2),0.96-0.87(t,6H, CH3)；FT-IR(KBr)3031,2923,2852,2729,1604,1465,1207,1122,1014,817。
经凝胶渗透色谱测试，该聚合物的Mn＝5.7×104，Mw＝9.1×104，Mw/Mn＝1.59。
实施例2
本实施例中，用等摩尔2,5-噻吩二甲醛替换实施例1中的1,4-对苯二甲醛，其他步骤与实施例1相同，最终以58.9％的收率得到黄褐色固体稠杂环共轭聚合物P2，其结构表征结果如下：
1H NMR(400MHz,CDCl3)δ(ppm)8.03-7.06(18H,ArH),4.62(s,4H,CH2), 2.63-2.55(m,8H,CH2),1.55-1.51(m,8H,CH2),1.23-1.19(m,8H,CH2),0.81-0.77(t,6H, CH3)；FT-IR(KBr)2930,2862,2725,1701,1606,1465,1261,1099,1018,833。
经凝胶渗透色谱测试，该聚合物的Mn＝6.8×104，Mw＝12.4×104，Mw/Mn＝1.81。
实施例3
本实施例中，用等摩尔丙炔酸乙酯替换实施例1中的1-乙炔基-4-己基苯，反应结束后将反应液倒入100mL冷水中，静置30min，过滤得到粗产物，其他步骤与实施例1相同，最终以45.5％的收率得到黄色固体稠杂环共轭聚合物P3，其结构表征结果如下：
1H NMR(400MHz,CDCl3)δ(ppm)8.13-7.29(14H,ArH),4.32(s,4H,CH2), 4.13-4.09(m,4H,CH2),1.22-1.18(t,6H,CH3)；FT-IR(KBr)2985,2902,2827,2735,1720, 1607,1271,1219,1166,1039,985,825。
经凝胶渗透色谱测试，该聚合物的Mn＝1.9×104，Mw＝3.7×104，Mw/Mn＝1.88。
实施例4
本实施例中，用等摩尔2,5-噻吩二甲醛替换实施例3中的1,4-对苯二甲醛，其他步骤与实施例3相同，最终以47.3％的收率得到黄色固体稠杂环共轭聚合物P4，其结构表征结果如下：
1H NMR(400MHz,CDCl3)δ(ppm)8.41-7.30(10H,ArH),4.32(s,4H,CH2), 4.23-4.18(m,4H,CH2),1.22-1.88(t,6H,CH3)；FT-IR(KBr)2979,2933,2862,1722,1637, 1537,1444,1373,1205,1026,810。
经凝胶渗透色谱测试，该聚合物的Mn＝1.8×104，Mw＝3.3×104，Mw/Mn＝1.78。
实施例5
本实施例中，用等摩尔苯丙炔酸替换实施例3中的丙炔酸乙酯，其他步骤与实施例3相同，最终以44.9％的收率得到黄色固体稠杂环共轭聚合物P5，其结构表征结果如下：
1H NMR(400MHz,CDCl3)δ(ppm)7.91-7.22(24H,ArH),4.02(s,4H,CH2)；FT-IR(KBr)3080,2920,1701,1625,1446,1299,1186,1107,1107,817。
经凝胶渗透色谱测试，该聚合物的Mn＝0.8×104，Mw＝1.7×104，Mw/Mn＝2.01。
实施例6
本实施例中，用等摩尔2,5-噻吩二甲醛替换实施例5中的1,4-对苯二甲醛，其他步骤与实施例5相同，最终以47.7％的收率得到黄色固体稠杂环共轭聚合物P6，其结构表征结果如下：
1H NMR(400MHz,CDCl3)δ(ppm)8.02-7.18(20H,ArH),4.12(s,4H,CH2)；FT-IR(KBr)2962,2921,2852,1718,1604,1244,1174,1107,1020,833。
经凝胶渗透色谱测试，该聚合物的Mn＝1.1×104，Mw＝2.1×104，Mw/Mn＝1.89。
实施例7
实施例1制备的稠杂环共轭聚合物P1在检测Fe3+中的应用，具体方法如下：
将稠杂环共轭聚合物P1溶于四氢呋喃中，配制成1.0×10-6mol/L P1的四氢呋喃溶液；将3mL 10-6mol/L P1的四氢呋喃溶液加入比色皿中，向其中加入Fe3+标准样品，分别使所得混合液中Fe3+的浓度为0、3.33、6.67、10、13.3、16.67、20μmol/L，采用荧光光谱仪测量不同浓度Fe3+对应体系的荧光光谱(见图1)，并绘制在440nm 处不同浓度Fe3+对应体系的相对荧光强度随Fe3+浓度变化的标准曲线。
由图1可见，P1的荧光强度受Fe3+浓度的影响变化很明显，伴随着Fe3+浓度的增加，体系的荧光强度逐渐减小。由图2可见，Fe3+的浓度在0～20μmol/L时，相对荧光强度随Fe3+浓度线性增加，线性方程为：
y＝0.3604x1+1
式中y为相对荧光强度，x1为Fe3+浓度，相关系数R2为0.9861。由此可见相对荧光强度与Fe3+浓度的线性关系很好。利用最低检出限的公式计算最低检出限，P1对 Fe3+的检测灵敏度很高，检出限为9.483×10-6mol/L。
实施例8
实施例2制备的稠杂环共轭聚合物(P2)在检测Fe3+中的应用，具体方法与实施例7相同。由图3可见，P2的荧光强度受Fe3+浓度的影响变化很明显，伴随着 Fe3+浓度的增加，体系的荧光强度逐渐减小。由图4可见，Fe3+的浓度在0～20μmol/L 时，相对荧光强度随Fe3+浓度线性增加，线性方程为：
y＝0.3259x2+1
式中y为相对荧光强度，x2为Fe3+浓度，相关系数R2为0.9914。由此可见相对荧光强度与Fe3+浓度的线性关系很好。利用最低检出限的公式计算最低检出限，P2对 Fe3+的检测灵敏度很高，检出限为5.860×10-6mol/L。
实施例9
实施例3制备的稠杂环共轭聚合物P3在检测Fe3+中的应用，具体方法与实施例7相同。由图5可见，P3的荧光强度受Fe3+浓度的影响变化很明显，伴随着Fe3+浓度的增加，体系的荧光强度逐渐减小。由图6可见，Fe3+的浓度在0～20μmol/L 时，相对荧光强度随Fe3+浓度线性增加，线性方程为：
y＝0.3499x3+1
式中y为相对荧光强度，x3为Fe3+浓度，相关系数R2为0.9633。由此可见相对荧光强度与Fe3+浓度的线性关系很好。利用最低检出限的公式计算最低检出限，P3对 Fe3+的检测灵敏度很高，检出限为8.377×10-6mol/L。
实施例10
实施例5制备的稠杂环共轭聚合物P5在检测Fe3+中的应用，具体方法与实施例7相同。由图7可见，P1的荧光强度受Fe3+浓度的影响变化很明显，伴随着Fe3+浓度的增加，体系的荧光强度逐渐减小。由图8可见，Fe3+的浓度在0～20μmol/L 时，相对荧光强度随Fe3+浓度线性增加，线性方程为：
y＝0.2119x4+1
式中y为相对荧光强度，x4为Fe3+浓度，相关系数R2为0.9676。由此可见相对荧光强度与Fe3+浓度的线性关系很好。利用最低检出限的公式计算最低检出限，P5对 Fe3+的检测灵敏度很高，检出限为1.18×10-6mol/L。
为了证明本发明稠杂环共轭聚合物对Fe3+检测的选择性，发明人分别采用实施例1、2、3、5的稠杂环共轭聚合物对Ag+、Ba2+、Ca2+、Cd2+、Cu2+、Mg2+、Mn2+、 Ni2+、Pd2+、Zn2+、Hg2+、Al3+以及Fe3+这13种重金属阳离子(其中聚合物浓度为 1.0×10-6mol/L，以四氢呋喃为溶剂配制而成，检测体系中金属离子浓度为1.0×10-4 mol/L)进行了测试，结果见图9～12。由图可见，当加入Fe3+时，检测体系的荧光淬灭效应最强，而其他离子几乎无荧光淬灭效应，说明本发明该稠杂环共轭聚合物能够高选择性的检测Fe3+。
Claims (7)
1.一种用于检测Fe3+的稠杂环共轭聚合物，其特征在于该聚合物的结构单元如下所示：
式中R1代表
中任意一种，R2代表为苯基、C1～C8烷基取代苯基、卤代苯基、C1～C3烷氧基取代苯基、甲酯基、乙酯基中任意一种。
2.权利要求1所述的稠杂环共轭聚合物的制备方法，其特征在于：将式Ⅰ所示的双吖嗪单体、式Ⅱ所示的含有两个醛基的单体、式Ⅲ所示的炔烃单体、铜盐、碱加入二甲基亚砜中，在惰性气体保护及70～90℃搅拌条件下进行聚合反应，反应结束后经萃取、干燥、透析，得到稠杂环共轭聚合物；
式Ⅲ中，R3代表氢或羧基。
3.根据权利要求2所述的稠杂环共轭聚合物的制备方法，其特征在于：所述的铜盐为氯化亚铜、碘化亚铜、溴化亚铜中任意一种。
4.根据权利要求2所述的稠杂环共轭聚合物的制备方法，其特征在于：所述的碱为无水碳酸钾、无水碳酸钠中任意一种。
5.根据权利要求2～4任意一项所述的稠杂环共轭聚合物的制备方法，其特征在于：所述双吖嗪单体与含有两个醛基的单体、炔烃单体的摩尔比为1:1.0～3.0:2.0～5.0。
6.根据权利要求2～4任意一项所述的稠杂环共轭聚合物的制备方法，其特征在于：所述双吖嗪单体与铜盐、碱的摩尔比为1:0.02～0.5:2.0～5.0。
7.权利要求1所述的稠杂环共轭聚合物在检测Fe3+中的应用。
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