CN106478602A - 一种基于萘酰亚胺衍生物的比色探针及其制备方法与应用 - Google Patents
一种基于萘酰亚胺衍生物的比色探针及其制备方法与应用 Download PDFInfo
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Abstract
本发明提供了一种基于萘酰亚胺衍生物的比色探针及其制备方法和应用,其中所述萘酰亚胺衍生物的化学结构式如下,本发明的萘酰亚胺衍生物能选择性的与二价铜离子作用,由红色变为无色,具有比色减弱效应,可实现裸眼辨别检测,特别是作为比色探针方便检测水样中铜离子的应用。
Description
技术领域
本发明属于有机合成领域,具体涉及萘酰亚胺衍生物及其制备方法和应用。
背景技术
铜是人体重要的微量元素,在线粒体的呼吸、铁的吸收、酶的氧化还原等不同的生理过程中起着十分重要的作用。但若体内的铜离子代谢平衡遭到破坏,有可能引起代谢紊乱和诸多疾病,如胆固醇升高,动脉弹性降低,血压升高。此外,由于铜离子大量地开采和广泛地使用,使得铜也成为一个重要的金属污染物。鉴于其对生命和环境的重要性,科学家们一直致力于采用选择性比色和荧光传感探针实现对铜离子在生物和环境系统中检测的研究。
发明内容
本发明的目的是提供一种可检测二价铜离子的灵敏度高、选择性好的金属离子比色探针;另一目的是提供该探针的制备方法和应用。
本发明的技术方案是,一种基于萘酰亚胺衍生物的比色探针,所述萘酰亚胺衍生物具有如下结构式:
本发明还提供了一种基于萘酰亚胺衍生物的比色探针的制备方法,其步骤如下:
S1:将5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯首先用乙腈溶解,再加入N-羟乙基-4-肼基萘酰亚胺;
S2:将S1所得混合物在常压下70-90 ℃回流,反应时间1-3h;
S3:将S2所得溶液冷却至室温后,有红色固体析出,减压过滤,取滤渣;
S4:将S3所得滤渣用乙腈重结晶,得到基于萘酰亚胺衍生物的荧光探针。
所述S1中, 5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯与N-羟乙基-4-肼基萘酰亚胺的物质的量之比为1:1。
所述的基于萘酰亚胺衍生物的比色探针的制备方法:将0.001-0.01mol的5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯溶于10-50ml无水乙醇中,再加入0.001-0.01mol的N-羟乙基-4-肼基萘酰亚胺,常压下回流搅拌1-3h,冷却至室温后析出固体,减压过滤,将滤渣用乙腈重结晶得到基于萘酰亚胺衍生物的比色探针。
所述的萘酰亚胺衍生物作为比色探针方便检测水样中铜离子的应用。
一种用于检测水样中二价铜离子的比色探针,所述比色探针主要由权利要求1所述的萘酰亚胺衍生物组成。
本发明通过用吡咯修饰改性萘酰亚胺制备萘酰亚胺类比色探针,合成简单,原料易得,在多种常见金属离子中,对二价铜离子表现出较高的选择性和识别性能,使含有二价铜离子的溶液由红色变为无色,可实现裸眼辨别检测,更为重要的是也可用于水样中铜离子的检测,具有快速、简便、灵敏度高、选择性强的特点,以及广泛的潜在应用价值。
附图说明
图1为本发明实施例1制得的萘酰亚胺衍生物比色探针的结构;
图2为本发明实施例1制得的萘酰亚胺衍生物比色探针的核磁氢谱谱图;
图3为本发明实施例1制得的萘酰亚胺衍生物比色探针的质谱谱图;
图4为本发明实施例1制得的萘酰亚胺衍生物比色探针的乙腈/水(体积比9:1)溶液(5×10-6 mol/L)对5当量不同金属离子(Ag+,Al3+,Ca2+,Cd2+,Co2+,Cr3+,Cu2+,Fe3+,Hg2+,K+,Mg2 +, Mn2+,Na+,Ni2+,Pb2+,Zn2+,5×10-6 mol/L)的紫外吸收光谱图;
图5为本发明实施例1制得的萘酰亚胺衍生物比色探针的乙腈/水(体积比9:1)溶液(5×10-6 mol/L)滴定不同浓度Cu2+的紫外吸收光谱图;
图6为在二次水中,萘酰亚胺衍生物比色探针试纸与Cu2+的比色图:将试纸于萘酰亚胺衍生物比色探针溶液(1×10-3 mol/L)中浸泡1分钟,真空避光干燥24小时。于二次水中添加不同浓度的二价铜离子,分别将试纸浸泡1分钟后自然风干。铜离子浓度分别为: (1) 10-2 mol/L, (2) 10-3 mol/L, (3) 10-4 mol/L, (4) 10-5 mol/L, (5) 10-6 mol/L, (6) 10-7mol/L, and (7) 0 mol/L。
具体实施方式
下面结合附图和具体实施例进一步详细说明本发明,本发明实施例采用的试剂和原料为常规市场购买或参考文献合成得到。
实施例1
萘酰亚胺衍生物的合成
将0.195 g 5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯溶于10mL无水乙醇中,再加入0.271g N-羟乙基-4-肼基萘酰亚胺,常压下78℃回流搅拌3h,冷却至室温后析出大量固体,减压过滤,将滤渣用乙腈重结晶得到红色固体即为目标产物,目标产物的产率为78.2%。
萘酰亚胺衍生物核磁共振分析结果如下:
1H NMR (400 MHz, DMSO-d 6 ), δ (ppm): 11.62 (s, 1H, OH), 11.25 (s, 1H, NH),8.73-8.75 (d, 1H, Aryl-H), 8.47-8.49 (d, 1H, Aryl-H), 8.40 (s, 1H, CH=N),8.33-8.35 (d, 1H, Aryl-H), 7.76-7.84 (m, 2H, Aryl-H), 4.79-4.82 (t, 1H, OH),4.13-4.20 (m, 4H, 2CH2), 3.59-3.63 (q, 2H, CH2), 2.33 (s, 3H, CH3), 1.29-1.31(t, 3H, CH3).
单晶结构:萘酰亚胺衍生物晶体结构图见图1;
质谱:ESI-MS: m/z = 449.1764 for [M+H]+.具体质谱谱图见图2。
实施例2
所述的基于萘酰亚胺衍生物的比色探针的制备方法:将0.001 mol的5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯溶于50ml无水乙醇中,再加入0.01mol的N-羟乙基-4-肼基萘酰亚胺,常压下70℃回流搅拌1h,冷却至室温后析出固体,减压过滤,将滤渣用乙腈重结晶得到基于萘酰亚胺衍生物的比色探针。
实施例3
所述的基于萘酰亚胺衍生物的比色探针的制备方法:将0.01mol的5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯溶于10 ml无水乙醇中,再加入0.001的N-羟乙基-4-肼基萘酰亚胺,常压下90℃回流搅拌3h,冷却至室温后析出固体,减压过滤,将滤渣用乙腈重结晶得到基于萘酰亚胺衍生物的比色探针。
实施例4
所述的基于萘酰亚胺衍生物的比色探针的制备方法:将0.01mol的5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯溶于50ml无水乙醇中,再加入0.01mol的N-羟乙基-4-肼基萘酰亚胺,常压下80℃回流搅拌2h,冷却至室温后析出固体,减压过滤,将滤渣用乙腈重结晶得到基于萘酰亚胺衍生物的比色探针。
萘酰亚胺衍生物对二价铜离子的光学性质测定
将上述实施例1制得的萘酰亚胺衍生物作为探针在乙腈/水(体积比9:1)介质中配制成摩尔浓度为5×10-6 mol/L的溶液,分别在含摩尔浓度为5×10-6 mol/L的Ag+,Al3+,Ca2+,Cd2 +,Co2+,Cr3+,Cu2+,Fe3+,Hg2+,K+,Mg2+, Mn2+,Na+,Ni2+,Pb2+,Zn2+等金属离子的溶液中加入等量的上述探针溶液,采用紫外可见光光度计对实施例1制得的萘酰亚胺衍生物进行紫外吸收光谱分析,所得的紫外吸收光谱图见图3。本发明实施例1制得的萘酰亚胺衍生物与二价铜离子作用在480 nm处的吸收峰明显下降,同时产生肉眼明显可见红色到无色颜色变化,可用于二价铜离子的快速检测。而本发明制得的萘酰亚胺衍生物对其它金属离子如Ag+,Al3+,Ca2+,Cd2+,Co2+,Cr3+, Fe3+,Hg2+,K+,Mg2+, Mn2+,Na+,Ni2+,Pb2+,Zn2+等无明显紫外吸收响应。
浓度为5×10-6 mol/L的萘酰亚胺衍生物作为荧光探针的乙腈/水(体积比9:1)溶液中分别加入浓度为0 mol/L,1×10-6 mol/L,2×10-6 mol/L,3×10-6 mol/L,4×10-6 mol/L,5×10-6 mol/L,6×10-6 mol/L,7.5×10-6 mol/L,1×10-5 mol/L,1.5×10-5 mol/L,2×10-5 mol/L的二价铜离子,采用紫外-可见分光光度计对其分别进行吸收光谱分析,记录480nm处的吸收强度值,所得的吸收光谱图见图4。通过附图4可以看出,随着铜离子浓度增加,萘酰亚胺衍生物比色探针在480 nm处的吸收逐渐减弱,且吸收峰强度与铜离子离子浓度在0-4×10-5 mol/L范围内线性相关,检测限为1.09×10-6 mol/L。
萘酰亚胺衍生物比色探针在水样中铜离子的检测实验
将试纸于萘酰亚胺衍生物比色探针溶液(1×10-3 mol/L)中浸泡1分钟,真空避光干燥24小时。于二次水中添加不同浓度的二价铜离子,分别将试纸浸泡1分钟后自然风干,得到比色卡。可以看出,随着铜离子浓度的增加,试纸红色逐渐消褪,浓度达到1×10-3 mol/L至无色,最低响应浓度为1×10-7 mol/L。
以上所述实施例仅是为充分说明本发明而所举的较佳的实施例,其保护范围不限于此。本技术领域的技术人员在本发明基础上所作的等同替代或变换,均在本发明的保护范围之内,本发明的保护范围以权利要求书为准。
Claims (6)
1.一种基于萘酰亚胺衍生物的比色探针,其特征在于,所述萘酰亚胺衍生物具有如下结构式:
。
2.根据权利要求1所述的基于萘酰亚胺衍生物的比色探针的制备方法,其特征在于,包括如下步骤:
S1:将5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯首先用乙腈溶解,再加入N-羟乙基-4-肼基萘酰亚胺;
S2:将S1所得混合物在常压下70-90 ℃回流,反应时间1-3h;
S3:将S2所得溶液冷却至室温后,有红色固体析出,减压过滤,取滤渣;
S4:将S3所得滤渣用乙腈重结晶,得到基于萘酰亚胺衍生物的荧光探针。
3.根据权利要求2所述的基于萘酰亚胺衍生物的比色探针的制备方法,其特征在于,S1中, 5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯与N-羟乙基-4-肼基萘酰亚胺的物质的量之比为1:1。
4.根据权利要求2所述的基于萘酰亚胺衍生物的比色探针的制备方法,其特征在于,将0.001-0.01mol的5-甲酰-2,4-二甲基吡咯-3-甲酸乙酯溶于10-50ml无水乙醇中,再加入0.001-0.01mol的N-羟乙基-4-肼基萘酰亚胺,常压下回流搅拌1-3h,冷却至室温后析出固体,减压过滤,将滤渣用乙腈重结晶得到基于萘酰亚胺衍生物的比色探针。
5.根据权利要求1所述的萘酰亚胺衍生物作为比色探针方便检测水样中铜离子的应用。
6.一种用于检测水样中二价铜离子的比色探针,其特征在于,所述比色探针主要由权利要求1所述的萘酰亚胺衍生物组成。
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