CN110885448A - 一种镉配合物合成及作为荧光探针、光降解催化剂的应用 - Google Patents
一种镉配合物合成及作为荧光探针、光降解催化剂的应用 Download PDFInfo
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Abstract
本发明提供一种镉金属配合物制备及其在荧光探针、光降解催化剂的应用。所述配合物的化学式为[Cd4(L)3(DMF)Cl2·H2O]n；其中，H2L＝1，1′‑(4‑羧基苯基)‑2，2′‑联咪唑。所述镉金属配合物为镉离子通过L2‑配体自组装而成三维结构。该镉配合物对三价铁离子、重铬酸根离子、抗生素呋喃西林和呋喃妥因表现出明显的荧光猝灭效应，可作为其荧光探针，在环境监测和生命科学领域具有潜在的应用价值。此外该镉配合物具有稳定和高效的催化光降解染料性质：在可见光的条件下，100分钟内亚甲基蓝基本降解完全，且易分离并可多次循环使用。
Description
关于资助研究或开发的声明：本发明是在江苏省政策引导类计划(产学研合作)-前瞻性联合研究项目(Grant no.BY2016066-08)的资助下进行的。
技术领域
本发明属于有机合成和金属有机化学技术领域，具体涉及到一种以1，1′-(4-羧基苯基)-2，2′-联咪唑为配体的三维镉配位聚合物的制备及作为三价铁离子(Fe3+)、重铬酸根离子(Cr2O7 2-)、呋喃西林(NZF)以及呋喃妥因(NFT)抗生素荧光探针并且可以有效降解亚甲基蓝(MB)染料的镉配合物的应用。
背景技术
相比于传统发光材料，配合物荧光材料因同时具有无机材料高化学稳定性和有机材料高量子产率而备受关注。配合物荧光性能受自身金属离子的电子构型和能级、配位构型和配位环境，配体以及外界条件如溶剂(溶液荧光)、温度等因素影响。特别是结构中具有孔道、裸露金属位点、具有路易斯酸或者碱性位点的活性有机基团的配合物，他们能够有效与客体分子(包含阴离子、金属阳离子和有机小分子)进行主客体相互作用，并将作用结果直接反映在该物质荧光变化中，使其在有机物检测、金属离子检测、温度探针、pH探针和活性探针等方面表现出良好的应用价值。一系列的荧光探针配合物已被报道，但是能同时检测多种客体分子的荧光探针配合物报道比较少。
金属离子的存在与现代人类的生活密切相关：一方面，随着现代工业的迅速发展，采矿、工业废气、废水排放等环境污染问题日趋严重，并使重金属离子进入生物体内，造成生物体的慢性中毒。另一方面，金属离子也是生物和人体必不可少的组成元素。因此，快速、方便、准确检测金属离子非常重要的。
铁是一种生物体中微量的过渡金属元素，在人体内参与多种酶和免疫系统的组成，也是血红蛋白的主要组成部分，体内铁元素不足或者过量将引起诸多疾病，影响人体健康。但是如果人体内的铁含量过剩，则会导致人体脏器的结构发生变化导致病变；如肝纤维化等，严重者会危及生命。铬是人类必须的微量元素之一，同时也是重金属污染物之一。自然界中的铬一般以三价和六价两种形式存在，但其毒性相差很大，六价铬的毒性超过三价铬100倍，是一种剧毒的环境污染物，容易进入人体细胞，对肝、肾等内脏器官和DNA造成损伤，在人体内蓄积具有致癌性并可能诱发基因突变。因此，快速、方便、准确检测三价铁离子和重铬酸根离子非常重要的。
通俗地讲，抗生素就是用于治疗各种非病毒感染的药物。呋喃西林(NZF)是一种人工合成的抗菌药，它可以干扰细菌糖代谢的早期阶段，导致细菌代谢紊乱而死亡，其抗菌谱较广，体外能抑制一般的细菌，高浓度时可杀菌，外用冲洗或湿敷可以处理体表感染和皮肤疾病，但是呋喃西林在动物源性食品中的残留可以通过食物链传递给人类，长期摄入会引起各种疾病，对人体有致癌、致畸胎等副作用。呋喃妥因(NFT)是国家基本药物，有广谱抗菌作用，可有效地杀灭下尿路感染的革兰阳性菌和革兰阴性菌。临床上主要用于敏感菌引起的急性下尿路感染、慢性菌尿症及反复发作的慢性尿路感染。呋喃妥因的不良反应涉及多个器官系统，包括消化系统：恶心、呕吐、腹泻等；呼吸系统：急性肺炎、肺间质纤维化等；神经系统：三叉神经痛、周围神经病变以及血液系统：溶血、慢性溶血性贫血；全身的高敏反应：皮疹、发热、黄疸、肝损伤等。国外已有国家如美国已经禁止临床使用呋喃妥因片剂，可见人们对其安全性的担忧和警惕。基于上述原因，实现对呋喃西林、呋喃妥因的选择性荧光识别很有研究价值。
除此之外，工业的快速发展带来了日趋严峻的生态环境问题，人类的生存环境不断遭到破坏，使得水污染问题日趋严重。目前，我国水体污染的主要来源是工业废水，其中印染废水占工业废水的比重已超过35％。印染废水具有废水量大、色度高、毒性大、水质复杂等特点，属于高浓度难降解有机废水。亚甲基蓝(MB)、甲基橙(MO)等偶氮型染料在水体中的危害极大，不但严重危害河流、海洋的生态平衡，而且还会通过皮肤吸收进入人体内，导致头痛、呕吐，甚至照成多种器官不可逆的伤害乃至致癌。因此，高效处理水体中偶氮型染料污染物是一个重要课题。
传统的水处理工艺因具有易产生二次污染、耗能高、效率低等一系列弊端而不断被革新，由单纯传统处理工艺的改革逐渐转变为水处理的新材料研发。利用环境净化材料催化光降解染料废水的方法可以降解许多难生物降解的复杂大分子，在染料废水处理领域越来越引起人们的关注。因此，设计合成环境友好的、合成方法简单的、具有优异光催化性能的环境净化材料是一个重要的挑战。
与传统用于光降解的半导体材料相比，配合物在光降解染料方面具有许多优势：(1)晶体结构的精准有利于研究配合物光降解染料的结构与性质之间的关系；(2)可调谐的活性位点促进了配合物光降解染料，高效的利用太阳能；(3)配合物的多孔性和较大比表面积能够允许染料分子快速的通过通道，这对提高光催化降解的效率是十分有效的；(4)配合物的金属离子和配体的相互作用可以有效分离光生电子和空穴，从而提高光催化活性。因此，配合物具有高的光催化活性和化学稳定性，且合成方法简单，是一种理想的光反应的催化剂。
1，1′-(4-羧基苯基)-2，2′-联咪唑是配位能力较强的桥连配体：在这个配体的两端具有两个羧酸基，两个苯环之间通过联咪唑连接，有利于配合物的合成；它可以部分或完全去质子化，允许与金属离子有不同的配位模型，易合成具有不同维数的金属配合物，而合成不同维数的结构是完成器件化至关重要的一步。
本发明属于有机合成和金属有机化学技术领域，涉及具有三维镉金属荧光配合物的合成，更具体的说是以1，1′-(4-羧基苯基)-2，2′-联咪唑为配体的镉配位聚合物的合成及其作为荧光探针、光降解催化剂应用。本发明分别采用二价镉离子作为主体，以1，1′-(4-羧基苯基)-2，2′-联咪唑为配体，探究不同溶剂分子对金属配合物的荧光性能影响，同时具有三维结构的镉荧光配合物对三价铁离子、重铬酸根离子和抗生素都表现出明显的荧光淬灭效应，作为荧光探针材料可以应用在金属离子、抗生素分子检测和分析研究，具有一个广阔的应用前景。此外，在本发明中，我们合成的配合物对于亚甲基蓝染料具有明显的光降解性质：在可见光的条件下，100分钟内亚甲基蓝染料基本降解完全，且易于分离并多次循环使用，催化效率基本保持不变。
总结来说，具有荧光和光降解的配合物已经分别有了大量报道，但是能同时具有对Fe3+、Cr2O7 2-、NZF及NFT都有响应且具有明显光降解性质的配合物的报道是非常少的。在本发明中，我们合成的金属配合物具有成本低、效率高、重现性好、检测灵敏、易于分离、收益高的优点，在Fe3+、Cr2O7 2-、NZF及NFT检测和亚甲基蓝染料降解方面具有一个广阔的应用前景。
发明内容
本发明旨在提供一种用作三价铁离子、重铬酸根离子、呋喃西林和呋喃妥因荧光探针并有效催化降解含偶氮类有机染料亚甲基蓝的三维镉配合物及其制备方法。本发明选用1，1′-(4-羧基苯基)-2，2′-联咪唑配体和氯化镉构筑镉配位聚合物。该化合物对三价铁离子、重铬酸根离子、抗生素呋喃西林、抗生素呋喃妥因有荧光识别的功能，能检测水溶液中微量三价铁离子、重铬酸根离子、抗生素呋喃西林和呋喃妥因的存在，且能够高效降解亚甲基蓝有机染料并能保证优异的催化活性及重复性。该化合物合成工艺简单、成本低、效率高、重现性好、检测灵敏、易于分离、收益高，可应用于工业化生产，在环境监测、生命科学及污染物降解领域具有潜在的应用前景。
本发明所涉及的用作三价铁离子、重铬酸根离子、抗生素呋喃西林和呋喃妥因荧光探针的镉配合物的化学式为：[Cd4(L)3(DMF)Cl2·H2O]n，其中，H2L＝1，1′-(4-羧基苯基)-2，2′-联咪唑。H2L的结构式如下：
本发明所涉及的用作三价铁离子、重铬酸根离子、抗生素呋喃西林和呋喃妥因荧光探针及偶氮类有机染料亚甲基蓝光降解催化剂的三维镉配合物结构如图1(a)所示，它的基本结构参数为：
本发明的镉配合物的晶体属于六方晶系，空间群为P61，晶胞参数为：
α＝β＝90°，γ＝120°。中心离子镉为五配位的四方锥、六配位的八面体构型；镉离子与1，1′-(4-羧基苯基)-2，2′-联咪唑羧基氧原子、咪唑基氮原子原子配位，形成了复杂的三维镉配位聚合物，如图1(b)所示。
本发明所涉及的镉配合物的制备方法包括下述步骤：
(1)将9.2mg的氯化镉(CdCl2)、18.7mg的1，1′-(4-羧基苯基)-2，2′-联咪唑(H2L)放入水热25mL反应釜的聚四氟乙烯内胆中混合，再加入浓度为0.15mol·L-1的HCl溶液调节pH至1.2，调节后的水溶液体积至10mL，常温搅拌30分钟后，得到混合液；
(2)将上述混合液在120℃下烘制72小时，取出产物后将固体分离；
(3)用乙醇将上述固体洗涤三次，得到无色透明块状晶体。
进一步地，本发明提供上述镉配合物用作三价铁离子、重铬酸根离子、抗生素呋喃西林和呋喃妥因荧光探针的应用，用于监测环境和生物体中的三价铁离子、重铬酸根离子、呋喃西林和呋喃妥因。除此之外，本发明还提供上述镉配合物用作催化光降解去除水中亚甲基蓝染料的应用，用于治理自然水体中的亚甲基蓝染料废水。
本发明的优点是：该制备方法工艺简单，产率高、易于分离、重现性好、灵敏度高、催化效率好、收率高，可以得到单一晶型、高纯度的晶体材料，易工业化生产；该产品对三价铁离子、重铬酸根离子、呋喃西林和呋喃妥因具有荧光识别的功能，可以用于水溶液中微量三价铁离子、重铬酸根离子、呋喃西林和呋喃妥因的检测，与传统的检测法相比，该方法具有定性、快速、灵敏、高效、操作简便等优点；该产品在可见光下能够有效的催化降解亚甲基蓝，且多次循环使用而催化效率基本保持不变；该产品具有较高的热稳定性，温度高于180℃时才会分解，优于常见的荧光探针材料。
附图内容
图1(a)本发明镉配合物的晶体结构图；图1(b)本发明镉配合物的三维结构图。
图2为本发明镉配合物的固体荧光图。
图3为本发明镉配合物对不同溶剂的荧光强度图。
图4(a)为本发明镉配合物对不同金属溶液的荧光发射强度图；图4(b)为本发明镉配合物对不同浓度三价铁离子溶液的荧光强度图和荧光淬灭拟合图。
图5(a)为本发明镉配合物对不同阴离子溶液的荧光发射强度图；图5(b)为本发明镉配合物对不同浓度重铬酸根离子溶液的荧光强度图和荧光淬灭拟合图。
图6(a)为本发明镉配合物对不同种类抗生素溶液的荧光发射强度图；图6(b)为本发明镉配合物对不同浓度的呋喃西林溶液荧光发射强度图和荧光淬灭拟合图。
图7为本发明镉配合物对亚甲基蓝的光催化降解图。
图8为本发明镉配合物对亚甲基蓝的光催化循环降解图。
图9为本发明镉配合物的热分解图。
具体实施方式
为了更好的理解本发明，下面结合实施实例进一步阐述本发明的内容，但本发明的内容不仅仅局限于下面的实施例。本发明的所述原料均有市售。
实施例中的所用原料均可从市场获得。氯化镉，分析纯，国药集团；1，1′-(4-羧基苯基)-2，2′-联咪唑，济南恒化。
实施例1配合物的合成：
将9.2mg的氯化镉(CdCl2)、18.71mg的1，1′-(4-羧基苯基)-2，2′-联咪唑(H2L)溶于10mL水中，搅拌半小时，转移至25mL水热反应釜的聚四氟乙烯内胆中，在120℃温度条件下反应72小时，所得产物用乙醇洗涤三次(2mL/次)，得到无色透明块状晶体。基于金属Cd计算的产率45.2％。
实施例2配合物的结构表征：
晶体结构采用Bruker Smart CCD X-射线单晶衍射仪，在296(2)K下，挑选尺寸为0.35×0.15×0.12mm的晶体，使用经过石墨单色化的MoKα射线(λ＝0.07107nm)为入射辐射光源，以ω/2θ扫描方式收集衍射点，晶胞参数经最小二乘法精修，用SADABS程序对收集到的数据进行吸收校正。用直接法解出配合物的结构，运用全矩阵最小二乘法对非氢原子坐标和各向异性温度因子进行精修，用SHELXTL程序完成全部计算。详细的晶体学参数列于表1。[Cd4(L)3(DMF)Cl2·H2O]n的晶体结构图及三维结构图如图1(a)和图1(b)所示。
表1配合物的晶体学数据
实施例3配合物的荧光性质：
采用LS-55型荧光光谱仪，在室温下测试配合物的荧光性质。图2为实施例1所制备镉配合物的固体荧光图，表明材料具有较强的荧光性质。如图3所示，该配合物在水溶液中表现出很强的发光性能。
从图4(a)可以看出，在所选金属离子水溶液中，实施例1所制备镉配合物的荧光强度表现出对金属离子的依赖性，对Fe3+表现出完全的荧光淬灭效果，有望成为Fe3+的荧光探针。
从图5(a)可以看出，在所选阴离子水溶液中，实施例1所制备镉配合物的荧光强度表现出对阴离子类型的依赖性，只有Cr2O7 2-表现出完全的荧光淬灭效果，有望成为Cr2O7 2-的荧光探针。
从图6(a)可以看出，在所选抗生素水溶液中，实施例1所制备镉配合物的荧光强度表现出对抗生素类型的依赖性，呋喃西林、呋喃妥因表现出完全的荧光淬灭效果，可望成为呋喃西林和呋喃妥因的荧光探针。
据我们所知，这是首例基于镉配合物的Fe3+、Cr2O7 2-、NZF和NFT荧光探针。
为了研究实施例1所制备镉配合物识别水溶液中Fe3+、Cr2O7 2-、NZF和NFT的灵敏度，把Fe3+、Cr2O7 2-、NZF和NFT加入到该材料的水悬浊液中，配制成不同浓度的悬浊液，记录其荧光强度的变化。如图4、5和6所示，荧光强度随着Fe3+、Cr2O7 2-、NZF和NFT的浓度增大依然呈现下降趋势。当Fe3+、Cr2O7 2-、NZF和NFT的的浓度分别为在9.90×10-5mmol·L-1、9.90×10- 5mmol·L-1、8.26×10-5mmol·L-1、8.26×10-5mmol·L-1时，配合物的荧光就基本被完全淬灭了，表明该配合物在水溶液检测Fe3+、Cr2O7 2-、NZF和NFT的过程中具有很高的灵敏度。
实施例4配合物的光降解：
称量30mg本发明合成的镉配合物加入到50mL的亚甲基蓝水溶液(10mg/L)，然后加入5uL的H2O2，黑暗下搅拌30min使配合物表面达到吸附-脱附平衡，然后边搅拌的同时边用可见灯照射，每5min取1mL的亚甲基蓝水溶液，立即测试吸光度的变化(如图7)。光降解的结果显示，该配合物100min内对于亚甲基蓝的降解率分别高达95.2％，且可以多次循环使用(如图8)。
Claims (3)
1.一种用作三价铁离子、重铬酸根离子、抗生素呋喃西林和呋喃妥因荧光探针且可有效降解亚甲基蓝的镉配合物，其特征在于，其化学式为[Cd4(L)3(DMF)Cl2·H2O]n，其中，H2L＝1，1′-(4-羧基苯基)-2，2′-联咪唑；所述的镉配合物的晶体属于六方晶系，空间群为P6l，晶胞参数为：
α＝β＝90°，γ＝120°；中心离子镉为五配位的四方锥、六配位的八面体构型，与1，1′-(4-羧基苯基)-2，2′-联咪唑羧基氧原子、咪唑基氮原子原子配位，形成了复杂的三维镉配位聚合物。
2.根据权利要求1所述的镉金属的制备方法，其特征在于，步骤如下：在密封条件下，有机配体1，1′-(4-羧基苯基)-2，2′-联咪唑与氯化镉在水溶液中，经由水热反应得到晶体结构的镉配合物。
3.根据权利要求2所述的制备方法，其特征在于，其中：1，1′-(4-羧基苯基)-2，2′-联咪唑和氯化镉的摩尔比为1∶1，每0.05mmol的氯化镉对应10mL的去离子水，热反应的条件为120℃，反应时间为三天。
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| CN111548505A (zh) * | 2020-04-21 | 2020-08-18 | 安徽国防科技职业学院 | 三核锌簇微孔化合物的合成及高灵敏和选择性检测毒死蜱 |
| CN116135911A (zh) * | 2023-02-28 | 2023-05-19 | 安庆师范大学 | 一种噻菌灵类镉金属有机配合物及其制备方法与应用 |
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| CN111548505B (zh) * | 2020-04-21 | 2021-01-12 | 安徽国防科技职业学院 | 三核锌簇微孔化合物的合成及高灵敏和选择性检测毒死蜱 |
| CN116135911A (zh) * | 2023-02-28 | 2023-05-19 | 安庆师范大学 | 一种噻菌灵类镉金属有机配合物及其制备方法与应用 |
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