CN112608276A - 对光气、三光气响应的荧光探针及其制备方法与应用 - Google Patents
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Abstract
本发明公开了一种对光气、三光气响应的荧光探针及其制备方法与应用。本发明的光气、三光气荧光探针，其结构式如下：
Description
技术领域
本发明公开了一种能检测光气、三光气的荧光探针，属于荧光分析技术领域。具体涉及一种高灵敏度快速检出光气、三光气的荧光探针及其合成方法与应用。
背景技术
光气,又称碳酰氯,剧毒,微溶于水,较易溶于苯、甲苯等。由一氧化碳和氯气的混合物通过活性炭制得。光气常温下为无色气体,有腐草味,化学性质不稳定,遇水迅速水解,生成氯化氢，是氯塑料高温热解产物之一。用作有机合成、农药、药物、染料及其他化工制品的中间体。环境中的光气主要来自染料、农药、制药等生产工艺。光气是剧烈窒息性毒气。毒性比氯气约大10倍,但在体内无蓄积作用。三光气，即双(三氯甲基)碳酸酯，俗称固体光气。有类似光气的气味，遇水分解，但水解很慢，加热或加碱能使水解加速。主要用作光气的替代品，具有毒性低，使用安全方便，应用于医药、农药和有机合成等领域中。
光气在第一次世界大战期间被用作化学武器剂(CWA)。过度吸入光气会导致严重的肺部并发症，如肺水肿和肺气肿，在没有及时的医疗干预的情况下是致命的。光气可能在恐怖袭击中作为化学武器释放，也可能在工业事故中意外泄漏。它对公众健康和安全构成潜在的严重威胁，也对环境产生了严重的影响。因此，高效可靠的光气释放监测方法对工业安全和环境保护具有重要意义。光气检测有许多的分析方法，包括电化学方法、色谱-质谱方法、拉曼色谱，但是这些方法弊端明显，如设备昂贵，携带不便，操作复杂等缺点。与之相比，采用荧光探针或比色法具有灵敏度高，可靠性高，操作简单，实时检测等优点，受到广泛的关注。
发明内容
本发明所述的一种能检测光气、三光气的荧光探针，并进一步提供了探针的制备方法和应用。分子式为C14H17N3O，命名为QK，结构式如下所示：
名称：QK。
本发明所述的一种能检测光气、三光气的荧光探针，上述的荧光探针的合成路线如下：
本发明所述的能检测光气、三光气的荧光探针，通过如下方法实现：
将6-(二乙基氨基)喹啉-2-甲醛和盐酸羟胺加入至反应瓶中，加入干燥的乙醇作为溶剂，然后加入三乙胺，室温搅拌2.5小时，有黄色固体析出，抽滤得到目标产物。
6-(二乙基氨基)喹啉-2-甲醛、盐酸羟胺、三乙胺的摩尔比为1：1-2：2-3。作为优选方案，6-(二乙基氨基)喹啉-2-甲醛、盐酸羟胺、三乙胺的摩尔比为1：2：2。
本发明的优点，探针的合成只需要一步就可以完成，且后处理过程简单。探针的选择性好，灵敏度高，检测时间快，稳定性强。显示出对光气有良好的选择性。
附图说明
图1是实施例1中探针QK的1HNMR图谱。
图2是实施例7中探针QK检测光气浓度的荧光光谱。
图3是实施例8中探针QK检测光气、三光气的选择性荧光光谱。
图4是实施例9中探针QK检测光气浓度的紫外光谱。
具体实施方式
实施例1
将115mg(0.5mmol)化合物1和68.4mg(0.98mmol)盐酸羟胺加至反应瓶中，同时加入4ml干燥乙醇作为溶剂，再在室温条件下加入三乙胺101mg(0.99mmol)搅拌反应2.5小时，减压抽滤得到目标产物，产率为67.4％，反应式如下：
实施例2
将57.5mg(0.25mmol)化合物1和34.7mg(0.5mmol)盐酸羟胺加至反应瓶中，同时加入2ml干燥乙醇作为溶剂，再在室温条件下加入三乙胺60.7mg(0.6mmol)搅拌反应2.5小时，减压抽滤得到目标产物，产率为60.8％。
实施例3
将57.5mg(0.25mmol)化合物1和34.7mg(0.5mmol)盐酸羟胺加至反应瓶中，同时加入4ml干燥乙醇作为溶剂，再在室温条件下加入三乙胺60.7mg(0.6mmol)搅拌反应2.5小时，减压抽滤得到目标产物，产率为53.8％。
实施例4
将57.5mg(0.25mmol)化合物1和34.7mg(0.5mmol)盐酸羟胺加至反应瓶中，同时加入2ml干燥乙醇作为溶剂，再在室温条件下加入三乙胺50.6mg(0.5mmol)搅拌反应2.5小时，减压抽滤得到目标产物，产率为69.4％。
实施例5
将57.5mg(0.25mmol)化合物1和26.1mg(0.375mmol)盐酸羟胺加至反应瓶中，同时加入2ml干燥乙醇作为溶剂，再在室温条件下加入三乙胺50.6mg(0.5mmol)搅拌反应2.5小时，减压抽滤得到目标产物，产率为63.5％。
实施例6
将57.5mg(0.25mmol)化合物1和34.7mg(0.5mmol)盐酸羟胺加至反应瓶中，同时加入2ml二氯甲烷作为溶剂，再在室温条件下加入三乙胺50.6mg(0.5mmol)搅拌反应2.5小时，减压抽滤得到目标产物，产率为35.4％。
实施例7
探针对光气的浓度荧光检测
取实施例1制备的荧光探针化合物，溶解到DMSO溶液中，配置成500μM的探针母液。
将三乙胺加入到乙腈中，配置成20μM的三乙胺母液。
将三光气溶解到乙腈中(三光气和三乙胺在乙腈中生产光气)，配置成50mM的三光气母液。
在试管中加入乙腈，每根试管3mL，从探针母液中取出60μL(10μM)加入到每根试管当中，接着加入不同体积的三光气母液于试管中，再加入配置的三乙胺母液2.7μL(1μM)。反应1分钟后，采用380nm的激发波长，用荧光光谱仪测试探针与不同浓度三光气(0、10、20、30、40、50、60、70、80、90、100、120μM)反应的荧光光谱变化。荧光光谱变化情况如图2所示，图中从上到下的检测光谱线依次为0、10、20、30、40、50、60、70、80、90、100、120μM。随着光气浓度的逐渐增加，在467nm处荧光发射逐渐减弱。右上图的插入图(左图)：10μM探针(包含1μM三乙胺)分别加入0μM，120μM的三光气后探针的可见光照射下图片，由图可见溶液颜色由肉眼可见的淡黄色变为橙色；右图：10μM(包含1μM三乙胺)探针加入0μM和120μM的光气后探针溶液在365nm紫外光照射下的荧光图片，未加光气时，溶液呈蓝色荧光，由图可见在加入了120μM的光气后，溶液荧光颜色产生了明显的猝灭现象。
实施例8
探针对光气的选择性检测
取实施例1制备的荧光探针化合物，溶解到DMSO溶液中，配置成500μM的探针母液，配置10种选择物母液(1、三乙胺2、三氟乙酸3、乙酰氯4、氯乙酰氯5、草酰氯6、盐酸7、甲磺酰氯8、苯磺酰氯9、光气10、三光气)。配置乙腈，每根试管3mL。从探针母液中取出60μL(10μM)加入到每根试管当中，取相同浓度的不同选择物母液15μL(120μM)于前述盛有3mL探针的试管中。反应1分钟后，采用380nm的激发波长，用荧光光谱仪测试探针与相同浓度的不同选择物的荧光光谱变化情况，如图3所示，图中从左到右的样品1到11，依次是空白、三乙胺、三氟乙酸、乙酰氯、氯乙酰氯、草酰氯、盐酸、甲基磺酰氯、苯磺酰氯、光气(三光气+三乙胺)、三光气。随着加入相同浓度的不同选择物后，图中看到只有光气和三光气对探针产生了强烈的荧光猝灭效果，得到只有光气和三光气对探针有较高的响应性。
实施例9
探针对光气的浓度紫外响应
取实施例1制备的荧光探针化合物，溶解到DMSO溶液中，配置成500μM的探针母液，将三乙胺加入到乙腈中，配置成1.1mM的三乙胺母液。将三光气溶解到乙腈中(三光气和三乙胺在乙腈中产生光气)，配置成50mM的三光气母液。配置乙腈，每根试管3mL。从探针母液中取出30μL(5μM)加入到每根试管当中，取不同体积的三光气母液于前述盛有探针的3mL试管中，加入三乙胺母液2.7μL(1μM)。反应1分钟后，用紫外可见吸收光谱仪测试探针与不同浓度三光气(图4中从上到下依次为0、10、20、30、40、50、60、70μM)反应的紫外可见吸收光谱变化。紫外可见吸收光谱变化情况如图4所示。随着光气浓度的逐渐增加，产生一个新的红移吸收峰，且随光气浓度增加，吸收强度增加。
Claims (5)
1.对光气、三光气响应的荧光探针，其特征在于，其分子式为：C14H17N3O；其结构式如下：
2.根据权利要求1所述的对光气、三光气响应的荧光探针的合成方法，其特征在于，步骤如下：
将6-(二乙基氨基)喹啉-2-甲醛和盐酸羟胺加入至反应瓶中，加入干燥的乙醇作为溶剂，然后加入三乙胺，室温搅拌进行反应，此时看到有固体析出，抽滤得到目标产物。
3.根据权利要求2所述的对光气、三光气响应的荧光探针的合成方法，其特征在于，6-(二乙基氨基)喹啉-2-甲醛、盐酸羟胺、三乙胺的摩尔比为1：1～2：2～3。
4.根据权利要求2所述的对光气、三光气响应的荧光探针的合成方法，其特征在于，6-(二乙基氨基)喹啉-2-甲醛、盐酸羟胺、三乙胺的摩尔比为1：2：2。
5.根据权利要求1所述的荧光探针在选择性检测光气和/或三光气上的应用。
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