CN111233709A - 一种比率型樟脑基镓离子荧光探针及其制备方法和应用 - Google Patents
一种比率型樟脑基镓离子荧光探针及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种比率型樟脑基镓离子荧光探针及其制备方法与应用。本发明利用3‑(3‑甲酰基‑4‑羟基苯亚甲基)樟脑为原料,与2,3‑二氨基顺丁烯二腈进行缩合反应得到2‑氨基‑3‑(2‑羟基‑5‑(3‑樟脑亚甲基)苯亚甲氨基)顺丁烯腈。该化合物能够专一性的识别水溶液中的镓离子,在365nm紫外光照射下,溶液荧光由红色变为亮黄绿色,因此该化合物可作为检测镓离子的荧光探针,具有很好的应用价值。
Description
技术领域
本发明属精细有机合成技术领域,涉及一种比率型樟脑基镓离子荧光探针及其制备方法和应用。
背景技术
镓是一种非常重要的稀有金属元素,在金属催化剂、半导体、太阳能电池等多种领域中都有非常广泛的应用。柠檬酸镓也常被用作磁共振成像的造影剂。但镓类化合物在工业生产中的频繁使用也不可避免对生态环境造成一定的危害。针对环境中镓离子的定性和定量检测非常重要。
相比于传统的分析检测手段,有机荧光探针技术具有选择性好、灵敏度高、操作简单、反应迅速等许多优点,也逐渐引起了越来越多研究者的注意。利用3-(3-甲酰基-4-羟基苯亚甲基)樟脑为原料合成新型的镓离子荧光探针,暂无相关报道。
发明内容
针对现有技术中存在的不足,本发明所要解决的技术问题是提供一种比率型樟脑基镓离子荧光探针2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈,能满足使用需求。本发明所要解决的另一技术问题是提供2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈的制备方法。本发明还要解决一个技术问题是提供一种上述比率型樟脑基镓离子荧光探针的应用。
为实现解决上述技术问题,本发明采用的技术方案为:
比率型樟脑基镓离子为2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈,其结构式为:
所述的2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈的制备方法:3-(3-甲酰基-4-羟基苯亚甲基)樟脑与2,3-二氨基顺丁烯二腈进行缩合反应,得到2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈;
在浓硫酸的作用下3-(3-甲酰基-4-羟基苯亚甲基)樟脑与2,3-二氨基顺丁烯二腈进行反应,得到2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈,具体的制备方法包括:
(1)将0.15mol 3-(3-甲酰基-4-羟基苯亚甲基)樟脑、0.15~0.25mol 2,3-二氨基顺丁烯二腈、0.01~0.05mol浓硫酸和10~20L无水乙醇依次加入配有搅拌器的三口烧瓶中,在室温条件下反应4~5h,用TLC跟踪监测反应,直至原料点消失,停止反应;
(2)将反应液浓缩至4~6L,抽滤、洗涤、干燥得到黄色粉末2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈。
所述的2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈在检测镓离子中的应用。
所述的2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈为比率型樟脑基镓离子荧光探针,能够专一性的识别水溶液中的镓离子,在365nm紫外光照射下,溶液荧光由红色变为亮黄绿色。
有益效果:与现有技术相比,本发明利用3-(3-甲酰基-4-羟基苯亚甲基)樟脑为起始原料,制备出新型的2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈,能专一性的识别镓离子,在365nm紫外光照射下,溶液的荧光由红色变为亮黄绿色,作为检测镓离子的荧光探针具有合成简单、识别专一、灵敏度高、响应迅速等优点,具有良好的应用前景。
附图说明
图1是2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈与不同金属离子作用的荧光光谱图;
图2是2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈与不同浓度镓离子作用的荧光光谱图。
具体实施方式
下面结合具体实施例对本发明做进一步的说明。
实施例1
2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈的制备方法,制备过程为:
具体步骤如下:
2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈的制备:
将1mmol 3-(3-甲酰基-4-羟基苯亚甲基)樟脑、1.5mmol 2,3-二氨基顺丁烯二腈、0.5mmol浓硫酸、15mL乙醇依次配有搅拌器的三口烧瓶中,在室温条件下进行反应,反应4h左右至3-(3-甲酰基-4-羟基苯亚甲基)樟脑完全消失(TLC跟踪监测)。将反应液浓缩至5mL,抽滤、洗涤得到黄色粉末2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈,得率为81.2%,纯度为99.4%,熔点为211.3-211.8℃。1H NMR(400MHz,DMSO-d6)δ:10.86(s,1H),8.57(s,1H),8.28(s,1H),7.93(s,2H),7.60(d,J=12Hz,1H),7.11(s,1H),7.03(d,J=12Hz,1H),3.15(d,J=6Hz,1H),2.12-2.17(m,1H),1.75-1.79(m,1H),1.45-1.49(m,1H),1.34-1.38(m,1H),0.97(s,3H),0.92(s,3H),0.73(s,3H);13C NMR(100MHz,DMSO-d6)δ:207.25,159.16,151.63,140.33,133.39,132.16,127.03,126.90,126.82,122.22,117.54,114.93,114.32,103.66,56.78,48.87,46.76,30.64,26.08,20.63,18.45,9.76;HRMS(m/z):[M+H]+calcd for C22H22N4O2+H+,375.1821;found,375.1819。
实施例2
将2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈溶于PBS缓冲溶液中配制成1×10-5M的溶液,同样将不同金属离子溶于PBS缓冲液中配成浓度为1×10-4M的溶液。采用荧光光谱滴定法在荧光分光光度计上测得不同金属离子对2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈的荧光发射光谱,如图1所示。结果表明,镓离子的加入能使水溶液体系的红色荧光消失而绿色荧光增强,而加入其他金属离子如Li+,Zn2+,Cd2+,Co2+,Ni2+,Mg2+,Ba2+,Na+,K+,Ag+,Ca2+,Cr3+,Pb2+,Fe3+,Hg2+,Al3+,In3+等对比参照观察,溶液的荧光光谱并没有发生显著的变化。由此说明,该化合物可以作为专一性识别镓离子的荧光探针。
实施例3
将2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈溶于PBS缓冲溶液配制成1×10-5M的溶液,将镓离子分别溶于PBS缓冲液中配成浓度为0、0.5、1.0、1.5、2.0、2.5、3.0、4.0、5.0、6.0、7.0、8.0、9.0、10.0、15.0、20.0、25.0、30.0、35.0、40.0、45.0、50.0μM的溶液。采用荧光光谱滴定法在荧光分光光度计上测得不同浓度的镓离子对2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈的荧光发射光谱,如图2所示。结果表明,在365nm紫外光照射下,随着水溶液中镓离子浓度的逐渐增加,溶液的红色荧光逐渐消失,绿色荧光逐渐增强。由此说明,该化合物可作为灵敏性检测镓离子的荧光探针。
Claims (6)
2.权利要求1所述的比率型樟脑基镓离子荧光探针的制备方法,其特征在于:3-(3-甲酰基-4-羟基苯亚甲基)樟脑与2,3-二氨基顺丁烯二腈进行缩合反应,得到2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈。
3.根据权利要求2所述的比率型樟脑基镓离子荧光探针的制备方法,其特征在于,在浓硫酸作用下3-(3-甲酰基-4-羟基苯亚甲基)樟脑与2,3-二氨基顺丁烯二腈进行缩合反应,得到2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈。
4.根据权利要求2或3所述的比率型樟脑基镓离子荧光探针的制备方法,其特征在于,具体步骤如下:
(1)将0.15mol 3-(3-甲酰基-4-羟基苯亚甲基)樟脑、0.15~0.25mol 2,3-二氨基顺丁烯二腈、0.01~0.05mol浓硫酸和10~20L无水乙醇依次加入配有搅拌器的三口烧瓶中,在室温条件下反应4~5h,用TLC跟踪监测反应,直至原料点消失,停止反应;
(2)将乙醇反应液浓缩至4~6L,抽滤、洗涤、干燥得到黄色粉末2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈。
5.权利要求1所述的2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈在检测镓离子中的应用。
6.根据权利要求5所述的应用,其特征在于,所述的2-氨基-3-(2-羟基-5-(3-樟脑亚甲基)苯亚甲氨基)顺丁烯腈为比率型樟脑基镓离子荧光探针,能够专一性的识别水溶液中的镓离子,在365nm紫外光照射下,溶液荧光由红色变为亮黄绿色。
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