CN116789638A - 一种吲哚吡啶类酸性指示剂、制备方法及其应用 - Google Patents
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Abstract
本发明提供了一种吲哚吡啶类酸性指示剂、制备方法及其应用，属于指示剂合成技术领域。该酸性指示剂为吲哚吡啶衍生物。具有酸性条件下由无色变黄色的指示剂性能。该指示剂变色范围是pH小于7.0，并且在水和有机溶剂中都具有较好的溶解性。该指示剂合成简单，显色清晰，检测灵敏，具有可逆检测的特性。该指示剂还可以在紫外和荧光分光光度计中使用，化合物的细胞毒性小，是一种多功能，安全灵敏的强碱性指示剂，具有很好的实用性。
Description
技术领域
本发明属于指示剂合成技术领域，涉及一种吲哚吡啶类酸性指示剂、制备方法及其应用。
背景技术
酸指示剂是检验溶液碱性的常用化学试剂，在实验室和工业生产中均可发挥重要的作用。目前最为流行和简便的pH检测方法是使用玻璃电极的pH计，但是玻璃电极受周围环境的影响，存在较大的误差，此外便携性和易用性都限制其应用。基于紫外和荧光光谱的新型pH指示剂能够消除玻璃电极的误差，而被广泛关注。
发明内容
本发明的第一个目的是提供一种酸性指示剂，该指示剂为吲哚吡啶衍生物指示剂，具有制备简单、显色清晰、检测灵敏、具有可逆检测等优点。
所述吲哚吡啶盐衍生物选自式(I)所示的化合物中的一种或者多种组合：
其中R1、R2、R3、R4可以是H、F、Cl、Br、I、NO2、OH、CHO等。R2、R3自身或者与毗邻的取代基相连形成3-7元饱和或不饱和的环烷基或杂环烷基。
所述的指示剂溶质为吲哚吡啶化合物，溶剂为水或有机溶剂。
有机溶剂为甲醇、乙醇、丙酮、二氯甲烷、三氯甲烷、石油醚、乙酸乙酯、乙腈、N,N-二甲基甲酰胺、二甲亚砜中的一种或多种的组合。
作为本发明的第二个目的，提供一种酸性指示剂的制备方法，包括如下步骤：量取干燥乙腈(15-50mL)置于100mL圆底烧瓶中，称取芦竹碱(2-10mmol)溶解入上述反应瓶中，再取4-醛基吡啶(4-20mmol)和正三丁基膦(4-20mmol)常温下加入上述反应瓶中，80℃加热回流反应8h。硅胶板检测反应进程。旋干有机溶剂，得褐色油状物质，经硅胶柱层析分离纯化，得淡黄色固体，产率为51％。其中芦竹碱：4-醛基吡啶：正三丁基膦：的摩尔比为1:2:2。
作为其应用，所述的pH指示剂为酸性pH指示剂，当然，也可以负载到定性滤纸上得到酸性pH试纸。
pH值检测方法包括在不同pH条件下使用该指示剂进行紫外吸收光谱、荧光光谱的分析。
本发明所涉及的吲哚吡啶衍生物，是一种活性生物小分子，被广泛用于医药领域，但其作为酸性指示剂的报道还没有被发现。该指示剂具有制备简单、显色清晰、检测灵敏、具有可逆检测等优点。
附图说明
图1是化合物的合成路线；
图2是化合物1的核磁图谱(氢谱)；
图3是化合物1的核磁图谱(碳谱)；
图4吲哚吡啶化合物的在不同pH条件下的发射和吸收光谱；
图5吲哚吡啶化合物的可见光下的颜色变化；
图6吲哚吡啶化合物的紫外光下的颜色变化；
图7吲哚吡啶化合物优化后的构型；
图8吲哚吡啶化合物荧光响应机理；
图9吲哚吡啶化合物质子化前后的HOMO/LUMO。
具体实施方式
以下是本发明的具体实施例并结合附图，对本发明的技术方案作进一步的描述，但本发明并不限于这些实施例。
实施例一：
如图1所示，一种碱指示剂的制备方法，化合物的制备方法：量取15ml干燥乙腈置于50ml圆底烧瓶中，称取芦竹碱2mmol溶解入上述反应瓶中，再取4-醛基吡啶4mmol和正三丁基膦4mmol常温下加入上述反应瓶中，800C加热回流反应8h。硅胶板检测反应进程。旋干有机溶剂，得褐色油状物质，经硅胶柱层析分离纯化，得淡黄色固体(化合物1)，产率为51％。其中芦竹碱：4-醛基吡啶：正三丁基膦：的摩尔比为1:2:2。图2为化合物1的核磁图谱(氢谱)，图3为化合物1的核磁图谱(碳谱)。
1H NMR(400MHz,DMSO-d6)δ11.50(s,1H),8.47(d,J＝4.6Hz,2H),8.05(d,J＝7.7Hz,1H),7.73(d,J＝15.5Hz,2H),7.52(d,J＝4.5Hz,2H),7.46(d,J＝7.9Hz,1H),7.18(dd,J＝9.6,7.7Hz,2H),7.07(d,J＝16.6Hz,1H).13C NMR(100MHz,DMSO-d6)δ149.71,145.84,137.12,127.87,127.28,125.03,122.02,120.22,120.04,119.91,119.86,113.18,112.03.
实施例二：
我们研究了不同pH值下PVI在B-R缓冲溶液中的吸收和发射光谱(图4)。如图4所示，弱酸条件下(pH＝7.00-4.00)，PVI的最大吸收峰位于414nm处，荧光强度在酸性条件下随着pH值的减小而逐渐升高。在pH大于4时，荧光强度的增幅开始减缓。同时溶液颜色逐渐由无色变为黄色。化合物吸光度的变化是由于质子化后的PVI分子整体Π成键轨道与Π反键轨道能级缩小，跃迁概率增大所致。与此同时，在该吸收光波长上激发出的最大荧光发射峰位于527nm处，且荧光强度随着pH的减小而逐渐升高。这可能是因为质子化后的PVI分子的ICT效应受到阻碍，导致荧光增强。
实施例三：
如图5、6所示，一种吲哚吡啶衍生物的应用，为进一步研究化合物的光物理性质，究了化合物在不同pH环境下的光学性质。在可见光和紫外灯的照射下，探针的荧光强度和颜色发生改变。可见光条件下，在pH大于7的条件下，探针的颜色由黄色变为无色。紫外光条件下，在pH大于7的条件下，探针的的绿色荧光逐渐消失。
实施例四：
为了探究荧光响应对pH的潜在机制，对PVI质子化前后的分子构型和HOMO/LUMO能级分布进行了密度泛函(DFT)分析。如图7所示，PVI是一个大共轭平面。其中吲哚环上的氮原子的孤对电子也参与共轭体系的构建，而吡啶环则不然。吲哚环上的氮原子比吡啶环上的氮更容易被质子化，所以吲哚环上的氮原子先被质子化。随后，研究了相应结构的HOMO/LUMO能级分布(图9)。质子化后PVI的HOMO和LUMO在分子中分布较多，导致ICT效应被抑制使荧光增强(图8)。PVI质子化后的HOMO和LUMO轨道之间的能量间隙(Eg)逐渐减小，这与它们的荧光发射峰红移的结果一致。
本文中所描述的具体实施例仅是对本发明精神作举例说明。本发明所属技术领域的技术人员可以对所描述的具体实施例，做修改或补充或采用类似的方式替代，但并不会偏离本发明的精神或者超越所附权利要求书所定义的范围。
Claims (8)
1.一种吲哚吡啶类酸性指示剂，其特征在于，吲哚吡啶类酸性指示剂为式(I)所示的化合物中的一种或者多种组合：
其中R1、R2、R3、R4可以是H、F、Cl、Br、I、NO2、OH、CHO；
R2、R3自身或者与毗邻的取代基相连形成3-7元饱和或不饱和的环烷基或杂环烷基。
2.根据权利要求1所述一种吲哚吡啶类酸性指示剂，其特征在于，所述吲哚吡啶类酸性指示剂溶质为式(I)所示的化合物，溶剂为水或有机溶剂。
3.根据权利要求2所述一种吲哚吡啶类酸性指示剂，其特征在于，有机溶剂为甲醇、乙醇、丙酮、二氯甲烷、三氯甲烷、石油醚、乙酸乙酯、乙腈、N,N-二甲基甲酰胺、二甲亚砜中的一种或多种的组合。
4.一种制备权利要求1-3任意项所述吲哚吡啶类酸性指示剂的方法，其特征在于，包括如下步骤：量取干燥乙腈(15-50mL)置于100mL圆底烧瓶中，称取芦竹碱(2-10mmol)溶解入上述反应瓶中，再取4-醛基吡啶(4-20mmol)和正三丁基膦(4-20mmol)常温下加入上述反应瓶中，800C加热回流反应8h；硅胶板检测反应进程；旋干有机溶剂，得褐色油状物质，经硅胶柱层析分离纯化，得淡黄色固体。
5.根据权利要求4所述一种吲哚吡啶类酸性指示剂的制备方法，其特征在于，芦竹碱：4-醛基吡啶：正三丁基膦：的摩尔比为1:2:2。
6.一种吲哚吡啶类酸性指示剂的应用，其特征在于，将如权利要求1-3任意项所述的吲哚吡啶类酸性指示剂作为酸性pH指示剂。
7.一种吲哚吡啶类酸性指示剂的应用，其特征在于，将如权利要求1-3任意项所述的吲哚吡啶类酸性指示剂负载到定性滤纸上得到酸性pH试纸。
8.根据权利要求6所述一种吲哚吡啶类酸性指示剂的应用，其特征在于，pH值检测方法包括在不同pH条件下使用该指示剂进行紫外吸收光谱、荧光光谱的分析。
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