CN105566331A - 一种能同时检测氟离子和二氧化碳的吲哚并咔唑类衍生物 - Google Patents

一种能同时检测氟离子和二氧化碳的吲哚并咔唑类衍生物 Download PDF

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CN105566331A
CN105566331A CN201610051388.7A CN201610051388A CN105566331A CN 105566331 A CN105566331 A CN 105566331A CN 201610051388 A CN201610051388 A CN 201610051388A CN 105566331 A CN105566331 A CN 105566331A
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陈善勇
姜山
于泓
李璐
金容�
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Abstract

本发明提供了一种能同时检测氟离子和二氧化碳的荧光探针分子。该类分子是以吲哚[3,2-b]咔唑为骨架，以苯基等芳香类基团或正己基等烷基类基团为取代基构建的。这类分子制备提纯简单、产率高、价格便宜。同时，该类分子对氟离子有很高的选择性和检测灵敏度，瞬时响应，检测限达0.6mg？L-1。在加入TBAF活化后，该类分子对二氧化碳也有很好的检测性能，其检测限达1*10-6M。本发明分子能同时检测氟离子和二氧化碳，简化了检测仪器的结构，具有较好的应用前景，可以在水污染、饮用水、大气等检测领域广泛应用。

Description

一种能同时检测氟离子和二氧化碳的吲哚并咔唑类衍生物
技术领域
本发明属于荧光探针领域，具体涉及一种能同时检测氟离子和二氧化碳的吲哚并咔唑类衍生物。
背景技术
氟离子和二氧化碳在人们的生活中发挥着重要作用。但是，只有含量恰当，它们才能产生有利的作用。例如，氟离子含量过高或过低均会引起牙齿与骨骼方面的疾病。而在相对密闭的场所(如冬天的北方房屋、地下室、煤矿和潜水器等)，高浓度的二氧化碳会导致人们头昏、头痛甚至死亡。但在蔬菜大棚，二氧化碳含量过低又会导致作物生长困难。因此，开发氟离子和二氧化碳的检测器以实时监测并保证它们的浓度在一个合理水平就很重要。
在前面的工作中，人们相继开发了电化学法、红外光谱法等手段来检测氟离子和二氧化碳(Anal.Chem.，2007，79，7005；Sens.Actuators，A，2005，119，584)。但是，这些检测方法灵敏度低、响应时间长、成本高并且需要大型复杂仪器作为支撑，因而实用性不强。为此，人们一直在寻找新的检测手段。经过不懈努力，人们发现荧光探针灵敏、便宜、快速并且简单，非常适合用来检测氟离子和二氧化碳(Chem.Commun.，2013，49，8229；Chem.Commun.，2014，50，320)。基于此，人们陆续开发了大量氟离子和二氧化碳荧光探针。但可惜的是，这些荧光探针在灵敏度、响应时间以及制备成本等方面还有诸多缺陷，导致其应用受到限制。因而，开发便宜、高性能的荧光探针就很必要。
发明内容
针对上述问题，本发明开发了一类新型荧光探针。该类分子仅需简单的一步反应即可制备，成本非常低。同时，该类探针检测灵敏、瞬时响应，这是其他荧光探针较少能达到的。并且，该类探针可以同时检测氟离子和二氧化碳，这在荧光探针领域是比较罕见的；
本发明提供一类可同时用于氟离子和二氧化碳检测的吲哚并咔唑类荧光探针化合物DAr-ICZ、DR-ICZ、ArR-ICZ。该类分子的结构通式如下：.
其中，Ar为蒽、吡嗪、萘啶、吖啶、苯、萘、吡啶等芳香基团及其衍生基团，R为1-30整数烷基链(直链或非直链)或三氟甲基等杂烷基链；
这类分子的具体制备步骤为：
向一5L的双口瓶中加入234g吲哚(2mol)、芳基甲醛或烷基甲醛(2mol)和2L乙腈，体系真空氮气置换至氮气环境。氮气下向瓶中加入75mlHI(45％)(0.4mol)。回流反应14h后，点板发现反应完全。冷至0℃，抽滤，用冷乙腈洗，得白色固体。将白色固体加入到一5L双口瓶中，加入2L乙腈，氮气下加入200g碘。回流反应10h，点板检测反应完全。旋干滤液，加入硫代硫酸钠溶液搅拌20min后，抽滤。滤饼至石油醚中超声处理，抽滤后，将滤饼置于乙醚中加热回流，趁热抽滤，旋干滤液，可得较纯的产物。然后将粗产品柱层析，得到淡黄色的纯产品；
在各种阴离子中，该类分子对其他干扰离子基本无响应或者响应很弱，而对氟离子则有很强的响应。加入氟离子后，该类分子在蓝光区的发射峰急剧下降到检测不到，而在黄光区则出现新的荧光峰。这种荧光颜色和强度同时变化的分子在荧光探针中是比较少的。相对于其他分子，这类分子的更大优点在于其加入氟离子后是瞬时响应，而其他分子则可能需要几分钟到几个小时。最后，该分子的合成极其简单便宜，使其具有应用潜力。因此，本发明荧光探针分子在检测氟离子方面更快更灵敏更便宜；
四丁基氟化铵(TBAF)活化后，本发明分子对二氧化碳也有很高的检测灵敏度，检测限能到1*10-6M。二氧化碳能将该类分子的原有荧光峰恢复，是检测氟离子的反过程，其荧光变化也非常剧烈；
本发明分子能同时检测氟离子和二氧化碳，简化了检测仪器的结构，具有较好的应用潜力，可在水污染、饮用水、大气等检测领域广泛应用。
附图说明
图1：DP-ICZ分子结构；
图2：在DP-ICZ乙腈溶液(1毫摩尔每升)中加入10倍量的四丁基铵盐(氟，氯，溴，碘，硫酸氢根，高氯酸根)后，其荧光光谱变化(激发波长为365纳米)；
图3：在DP-ICZ乙腈溶液(1毫摩尔每升)中加入10倍量的四丁基铵盐(氟，氯，溴，碘，硫酸氢根，高氯酸根)后，不同离子带来的荧光强度变化对比(I/I0＝变化后的荧光强度/初始荧光强度)；
图4：在DP-ICZ乙腈溶液(1毫摩尔每升)中加入不同量的四丁基氟化铵(0.5，1.0，1.5，2.0，2.5，3.0，3.5，4.0，5.0，6.0，7.0，8.0，10.0倍量)后，化合物荧光光谱的变化；
图5：在DP-ICZ乙腈溶液(1毫摩尔每升)中加入4倍量的四丁基氟化铵后，再通入不同量的二氧化碳(0.1ml，0.2ml，0.3ml，0.4ml，0.6ml，1.0ml，1.5ml，2ml，3ml，4ml，6ml，10ml)，其荧光光谱变化。
具体实施方式
实施例1：化合物DP-ICZ的合成
向一5L双口瓶中加入234g吲哚、210g苯甲醛和2L乙腈，体系真空氮气置换至氮气环境。氮气下向瓶中加入75mlHI(45％)。回流反应14h后，点板发现反应完全。冷至0℃，抽滤，用冷乙腈洗，得白色固体。将这个白色固体加入至一5L双口瓶中，加入2L乙腈，氮气下加入200g碘。回流反应10h，点板检测反应完全。旋干滤液，加入硫代硫酸钠溶液搅拌20min后，抽滤。滤饼至石油醚中超声处理，抽滤后，将滤饼置于乙醚中加热回流，趁热抽滤，旋干滤液，可得较纯的产物。然后用二氯甲烷∶石油醚＝10∶1的溶剂为洗脱剂、200-300目硅胶为柱体柱层析，得到淡黄色的纯产物。产率60％。核磁氢谱(500MHz，DMSO-d6)：6.81(2H，t，ArH)，7.05(2H，d，ArH)，7.24(2H，t，ArH)，7.44(2H，d，ArH)，7.65-7.60(10H，m，ArH)，10.53(2H，s，NH)。质谱：408.10(理论：408.16)。
实施例2：化合物DN-ICZ的合成
化合物DN-ICZ的合成和化合物DP-ICZ类似。但由于化合物DN-ICZ的溶解性要好很多，所以化合物DN-ICZ的后处理不一样。在用硫代硫酸钠溶液处理后，用二氯甲烷萃取。然后旋蒸除去二氯甲烷，得到的固体在乙醚中重结晶即可得到微黄色化合物DN-ICZ。然后用二氯甲烷∶石油醚＝10∶1的溶剂为洗脱剂、200-300目硅胶为柱体柱层析，得到淡黄色的纯产物。产率：70％。核磁氢谱(300MHz，CDCl3，δ)：8.89(s，2H；-NH)，6.57-8.17(m，22H；ArH)。质谱：508.33(理论：508.19)。
实施例3：化合物DP-ICZ对不同阴离子的响应实验
在7个10ml容量瓶中分别加入4.08mg(0.01mmol)的DP-ICZ，然后分别配制成10ml的DP-ICZ乙腈溶液。向其中六个瓶中加入四丁基铵盐(F-，Cl-，Br-，I-，HSO4 -和ClO4 -)(0.01mmol，10倍量)，观察瓶中颜色和荧光变化。结果显示，除F-外，其他离子不能带来DP-ICZ溶液颜色和荧光的变化。而氟离子加入后，DP-ICZ溶液立即从几乎无色变为棕黄色，而荧光则从强烈的蓝色变为暗淡的黄色，变化非常明显。进一步测试7瓶溶液的吸收光谱和发射光谱。结果发现，其他离子基本不对DP-ICZ的光谱产生影响，而氟离子的加入则导致其原有的450nm荧光峰急剧下降到消失，而在562nm黄光区则出现一个新峰，其强度相比之前有很大降低，详见附图2。由此，我们对比了DP-ICZ对不同离子的响应，详见附图3。结果显示，DP-ICZ对氟离子有高度灵敏的响应，对其他离子有强大的抗干扰能力。
实施例4：化合物DP-ICZ对不同氟离子含量的响应实验
分别配制1mM的DP-ICZ乙腈溶液和10mM的四丁基氟化铵(TBAF)乙腈溶液。接着分别向14个5ml瓶中加入1mlDP-ICZ溶液，然后分别向这些瓶中加入0.05ml，0.10ml，0.15ml，0.20ml，0.25ml，0.30ml，0.35ml，0.40ml，0.50ml，0.60ml，0.70ml，0.80ml，1.00mlTBAF溶液。分别测试每个瓶中的吸收光谱和发射光谱，结果如附图4。可以看出，随着TBAF含量的增加，450nm处的荧光强度急剧降低至消失，而562nm处的荧光则先增强后减弱，但总体效果是荧光强度逐渐降低。计算得到DP-ICZ对氟离子的检测限为1.5μM(600ppm，0.6mgL-1)，满足美国卫生部对氟离子的检测范围要求。
实施例5：化合物DP-ICZ对不同含量二氧化碳的响应实验
配制10mllmM的DP-ICZ乙腈溶液，然后加入4倍量的TBAF，混合均匀。接着向瓶中通入二氧化碳，观察溶液荧光随着二氧化碳含量的增加(0.1ml，0.2ml，0.3ml，0.4ml，0.6ml，1.0ml，1.5ml，2ml，3ml，4ml，6ml，10ml)的变化，结果如附图5所示。可以看出，随着二氧化碳的加入，562nm处的荧光逐渐消失，而450nm处的荧光逐渐增强，表明DP-ICZ分子结构的恢复。通过荧光强度的变化，我们能传感不同含量的二氧化碳，实现荧光探针的功能。
以上详细描述了本发明的较佳实施例。应当理解，本领域的普通技术人员无需创造性劳动就可以根据本发明的构思做出诸多修改和变化。凡本技术领域中技术人员依本发明的构思在现有技术的基础上通过逻辑分析、推理或者有限的实验可以得到的实验与技术方案，皆应在由权利要求书所确定的保护范围内。

Claims (3)

1.一种能同时检测氟离子和二氧化碳的吲哚并咔唑类衍生物，其特征在于，其分子结构通式如下：
其中，Ar为蒽、吡嗪、萘啶、吖啶、苯、萘、吡啶等芳香基团及其衍生基团，R为1-30整数的烷基链(直链或非直链)或三氟甲基等杂烷基链。
2.根据权利要求1所述，该类分子对氟离子有很高的选择性和检测灵敏度，其检测限为0.6mgL-1。
3.根据权利要求1所述，在加入TBAF活化后，该类分子对二氧化碳的检测限达1*10-6M。
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