CN107417597A - 荧光化学传感器化合物及其制备方法和用途 - Google Patents
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Abstract
本发明公开了一类荧光化学传感器化合物及其制备方法和用途，将2‑[N,N‑二(2‑吡啶甲基)胺甲基]‑6‑醛基‑4‑取代(R)苯酚(R＝‑CH3，‑F，‑Cl，‑Br)、N‑(2‑氨基乙基)吗啉溶于一定量的醇溶剂中，加热回流一定时间后，除去溶剂，水洗，干燥后得到产物。该荧光化学传感器具有检测限低，灵敏度高，特异性强的特点，在分析化学、生命科学、环境科学等技术领域有着广泛的应用前景。
Description
技术领域
本发明属于分析化学、生命科学、环境科学等技术领域，具体涉及一类荧光化学传感器化合物及其制备方法和用途。
背景技术
典型的荧光化学传感器含有一个识别位点和一个与识别位点相连接的荧光团，当识别位点和金属离子结合后，荧光信号会发生变化。理想的荧光化学传感器必须满足两个条件：(1)荧光传感器和金属离子的结合力要强；(2)选择性要好，抗干扰能力强(参见：XuZ.C.等,Chem.Soc.Rev.,2010,39,1996.)。
根据发光机理的不同，荧光化学传感器主要分为两类：基于光诱导电子转移的比值型和基于分子内电荷转移的比率型。比值型荧光化学传感器是根据识别离子前后的荧光强度变化来检测离子；而比率型则是根据加入离子前后的荧光发射波长的位移变化来检测离子。为了提高的检测灵敏度，最好的荧光化学传感器应该是比值型和比率型的结合(参见：Silva A.D.等,Chem.Rev.,1997,97,1515.)。
目前的荧光化学传感器，绝大多数为单一的比值型或比率型，具有灵敏度低，不易观察等缺点。
发明内容
本发明的目的是为了改进现有技术的不足而提供了将比值型和比率型相结合的荧光化学传感器化合物，本发明的另一目的是提供一种方法简单、一步反应、成本低的制备上述化合物的方法，本发明还有一目的是提供上述荧光化学传感器化合物在检测锌离子中的应用。
本发明的技术方案为：荧光化学传感器化合物，其特征在于其结构通式为：
本发明还提供了一种制备上述化合物的方法，其具体的步骤为：将2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)和N-(2-氨基乙基)吗啉按比例混合后，溶于醇溶剂中，加热回流反应后，旋蒸去醇溶剂，然后用氯仿溶解后水洗，干燥后得到产物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)。
反应路线如下：
优选2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)和N-(2-氨基乙基)吗啉的摩尔比为1:(1～2)。
优选上述的醇溶剂为甲醇或乙醇。
优选2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)和溶剂的摩尔比为1：(200～500)。
优选加热回流反应的时间为6～12小时。
本发明还提供了上述的荧光化学传感器化合物在检测锌离子中的应用。
上述的荧光化学传感器化合物在检测锌离子中的应用方法如下：将该荧光化学传感器化合物配制成一定浓度的甲醇溶液，然后加入待检测的离子，通过荧光光度分光计分别检测空白溶液和已加入待检测离子溶液的荧光强度，其激发波长为365nm，如果加入待检测物质的荧光强度增加，则说明含有锌离子。
有益效果：
1、制备的荧光化学传感器具有低的锌离子检测限：0.62μm，荧光特异性强，抗干扰能力好。
2、制备方法简单：直接将原料混合加热回流即可，不需要惰性气体保护。
3、收率高：一般收率都高于85％，部分条件下超过90％。
附图说明
图1为实施例1所制备得到的2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚的红外图谱；
图2为实施例1所制备得到的2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚的1HNMR图谱；
图3为实施例1所制备得到的2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚的锌离子荧光滴定图；
图4为实施例2所制备得到的2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氯苯酚的1HNMR图谱；
图5为实施例3所制备得到的2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-溴苯酚的1HNMR图谱。
具体实施方式
下面通过实例对本发明作进一步说明，但不限制本发明的保护范围。
实施例1：一种用作锌离子荧光化学传感器的化合物：2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚的合成方法。
将340毫克(1毫摩尔)的2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-甲基苯酚和132毫克(1毫摩尔)的N-(2-氨基乙基)吗啉加入有10毫升(247毫摩尔)甲醇的茄形瓶中，加热回流8小时，旋蒸除去大部分溶剂，将剩余物溶于氯仿，水洗3次，除去氯仿，真空干燥后得产物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚392毫克，产率为：88％。由图1可知：在1633cm-1处为C＝N双键伸缩振动峰，说明得到了所合成的物质；1H NMR(CDCl3/400MHz)：δ(ppm),8.53(d,2H),8.34(s,1H),7.68(t,2H),7.64(t,2H),7.33(d,1H),7.15(t,2H),6.98(s,1H),3.88(s,4H),3.79(s,2H),3.75(t,2H),3.72(t,4H),2.70(t,2H),2.54(t,4H),2.29(s,3H)。由图2可知：在化学位移8.34ppm处的单峰归属为H-C＝N-的氢峰，进一步说明合成了目标产物。
检测锌离子的条件为：首先将4.6毫克的2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚溶于1升的甲醇中，然后取3毫升该溶液，加入物质的量分别为2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚的0,0.2,0.4,0.6,0.8,1.0,1.2,1.4,1.6,1.8,2.0,3.0,4.0倍的锌离子，检测加入锌离子后溶液的荧光发射强度，结果如图3所示，从图中可以看出：未加入锌离子的溶液几乎没有荧光，随着锌离子的加入，溶液的荧光强度逐渐增大，当锌离子的加入量是2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-甲基苯酚物质的量的两倍时，溶液荧光强度达到最大。
实施例2：一种用作锌离子荧光化学传感器的化合物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氯苯酚的合成方法。
将366毫克(1毫摩尔)的2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-氯苯酚和198毫克(1.5毫摩尔)的N-(2-氨基乙基)吗啉加入有10毫升(247毫摩尔)甲醇的茄形瓶中，加热回流12小时，旋蒸除去大部分溶剂，将剩余物溶于氯仿，水洗3次，除去氯仿，真空干燥后得产物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氯苯酚449毫克，产率为：94％。1H NMR(CDCl3/400MHz)：δ(ppm),8.51(d,2H),8.33(s,1H),7.64(t,4H),7.33(s,1H),7.11(q,2H),6.98(s,1H),3.87(s,4H),3.79(s,2H),3.71(t,2H),2.71(t,4H),2.67(t,2H),2.53(s,4H)。由图4可知：8.33ppm处出现的单峰归属为H-C＝N-的氢峰，说明合成了目标产物。
2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氯苯酚用于锌离子检测的条件和实施例1相同，结果和实施例1相似：随着锌离子的逐渐加入，溶液的荧光强度逐渐增大，当加入的锌离子的量是2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氯苯酚物质的量的两倍时，荧光强度达到最大。
实施例3：一种用作锌离子荧光化学传感器的化合物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-溴苯酚的合成方法。
将410毫克(1毫摩尔)的2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-溴苯酚和198毫克(1.5毫摩尔)的N-(2-氨基乙基)吗啉加入有20毫升(340毫摩尔)乙醇的茄形瓶中，加热回流10小时，旋蒸除去大部分溶剂，将剩余物溶于氯仿，水洗3次，除去氯仿，真空干燥后得产物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-溴苯酚475毫克，产率为：91％。1H NMR(CDCl3/400MHz)：δ(ppm),8.52(d,2H),8.34(s,1H),7.62(t,4H),7.33(s,1H),7.12(t,2H),6.98(s,1H),3.85(s,4H),3.79(s,2H),3.71(t,6H),2.68(t,2H),2.54(s,4H)。由图5可知：8.34ppm处出现的单峰归属为H-C＝N-氢的峰，说明合成了目标产物。
2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-溴苯酚用于锌离子检测的条件和实施例1相同，结果和实施例1相似：随着锌离子的逐渐加入，溶液的荧光强度逐渐增大，当加入的锌离子的量是2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-溴苯酚物质的量的两倍时，荧光强度达到最大。
实施例4：一种用作锌离子荧光化学传感器的化合物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氟苯酚的合成方法
将351毫克(1毫摩尔)的2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-氟苯酚和264毫克(2毫摩尔)的N-(2-氨基乙基)吗啉加入有20毫升(340毫摩尔)乙醇的茄形瓶中，加热回流10小时，旋蒸除去大部分溶剂，将剩余物溶于氯仿，水洗3次，除去氯仿，真空干燥后得产物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氟苯酚436毫克，产率为：94％。
2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氟苯酚用于锌离子检测的条件和实施例1相同，结果和实施例1相似：随着锌离子的逐渐加入，溶液的荧光强度逐渐增大，当加入的锌离子的量是2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-氟苯酚物质的量的两倍时，荧光强度达到最大。
Claims (7)
1.荧光化学传感器化合物，其特征在于其结构通式为：
2.一种制备如权利要求1所述化合物的方法，其具体的步骤为：将2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)和N-(2-氨基乙基)吗啉按比例混合后，溶于醇溶剂中，加热回流反应后，旋蒸去醇溶剂，然后用氯仿溶解后水洗，干燥后得到产物2-[N,N-二(2-吡啶甲基)胺甲基]-6-[(2-(N-吗啉基)乙基)亚胺甲基]-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)。
3.根据权利要求2所述方法，其特征是2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)和N-(2-氨基乙基)吗啉的摩尔比为1:(1～2)。
4.根据权利要求2所述方法，其特征是所述的醇溶剂为甲醇或乙醇。
5.根据权利要求2所述方法，其特征是2-[N,N-二(2-吡啶甲基)胺甲基]-6-醛基-4-取代(R)苯酚(R＝-CH3，-F，-Cl，-Br)和溶剂的摩尔比为1：(200～500)。
6.根据权利要求2所述方法，其特征是加热回流反应的时间为6～12小时。
7.一种如权利要求1所述的荧光化学传感器化合物在检测锌离子中的应用。
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