CN113173883B - 一种8-羟基喹啉功能化柱[5]芳烃及其合成和在检测及吸附乙二胺中的应用 - Google Patents
一种8-羟基喹啉功能化柱[5]芳烃及其合成和在检测及吸附乙二胺中的应用 Download PDFInfo
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Abstract
本发明提供了一种8‑羟基喹啉功能化柱[5]芳烃,是乙腈为溶剂,以双边1.4‑二溴丁烷修饰的柱芳烃和8‑羟基喹啉为反应底物,在K2CO3和KI作用及N2保护下,于80~85℃下反应70~72h,反应结束后采用柱层析分离,得到的白色固体,即为8‑羟基喹啉功能化柱[5]芳烃PQ8。将PQ8固体粉末暴露在乙腈、二氯甲烷、氯仿、甲醛、吡啶、四氢呋喃、氨水、正丙胺、正丁胺、1.6‑己二胺、1.10‑癸二胺和乙二胺的蒸汽中,只有乙二胺的蒸汽可使8‑羟基喹啉功能化柱[5]芳烃的固体粉末的荧光颜色由蓝色变为淡黄色,因此可以实现对乙二胺的单一选择性检测;同时,PQ8可实现对乙二胺的吸附,对乙二胺的摩尔吸附率可达到176.19%。
Description
技术领域
本发明涉及一种8-羟基喹啉功能化柱[5]芳烃及其合成方法;本发明同时还涉及8-羟基喹啉功能化柱[5]芳烃在检测及吸附乙二胺中的应用,属于化学合成、VOCs检测和吸附领域。
背景技术
乙二胺(EDA,C2H6N2)是一种常见的挥发性有机化合物,主要应用于聚合物树脂、印染工业、电镀工业、农药工业以及医药生产中。该化合物蒸气对人体粘膜和皮肤有强烈刺激性,可引起结膜炎、支气管炎、肺炎、肺水肿和接触性皮炎,皮肤和眼直接接触其液体可致灼伤,严重则引起起肝、肾损害;而且该化合物还可引起职业性哮喘,并且对水体会造成严重污染。近年来,鲜有关于乙二胺吸附的报道,只有少数运用稀土金属有机框架对乙二胺进行吸附分离。然而,这些方法要么昂贵(使用稀土金属如La或Ce),要么需要特殊的解决方案,因此迫切需要构建通过荧光变化来检测吸附乙二胺的化学材料。目前,显色和荧光探针在化学材料领域有着巨大的发展潜力。
由于对挥发性有机化合物(VOCs)选择性检测和吸附分离对人类健康和环境保护至关重要。本发明设计了一种将8-羟基喹啉引入到柱芳烃结构中,可以选择性检测吸附乙二胺,具有专一选择性,对环境污染小的优点。
发明内容
本发明的目的是提供一种8-羟基喹啉功能化柱[5]芳烃及其合成方法;
本发明的另一个目的是提供8-羟基喹啉功能化柱[5]芳烃在检测及吸附乙二胺中的应用
一、8-羟基喹啉功能化柱[5]芳烃及其制备
本发明8-羟基喹啉功能化柱[5]芳烃,其分子式为C69H72N2O12,结构式如下:
本发明8-羟基喹啉功能化柱[5]芳烃的合成方法,是以乙腈为溶剂,以双边1.4-二溴丁烷修饰的柱芳烃和8-羟基喹啉为反应底物,在K2CO3和KI作用(K2CO3提供碱性环境,KI活化反应位点)及N2保护下,于80~85℃下反应70~72h,反应结束后采用硅胶柱层析法分离,得到的白色固体,即为8-羟基喹啉功能化柱[5]芳烃,标记为PQ8。其中,双边1.4-二溴丁烷修饰的柱芳烃和8-羟基喹啉的摩尔比为1:2~1:2.5;双边1.4-二溴丁烷修饰的柱芳烃与K2CO3的摩尔比为1:10~1:10.5;双边1.4-二溴丁烷修饰的柱芳烃与KI的摩尔比为1:2~1:2.5;双边1.4-二溴丁烷修饰的柱芳烃的结构式为:
PQ8的质谱和氢谱谱图见图1、图2。
二、8-羟基喹啉功能化柱[5]芳烃对乙二胺的检测及吸附
1、PQ8对乙二胺的检测
称取10mg PQ8的固体粉末,分别暴露在有机挥发性化合物乙腈、二氯甲烷、氯仿、甲醛、吡啶、四氢呋喃、氨水、正丙胺、正丁胺、1.6-己二胺、1.10-癸二胺和乙二胺的蒸汽中,观察固体粉末荧光颜色的变化。
图3为本发明PQ8固体粉末中分别暴露在有机挥发蒸汽中12h后的荧光谱图。图3的结果显示,只有暴露在乙二胺蒸汽中后,才能使PQ8的荧光颜色由蓝色变为淡黄色,而暴露在其他有机蒸汽中后不能使PQ8的荧光发生变化。因此,PQ8在固体状态下能够单一选择性检测乙二胺。
图4为PQ8的可回收利用性,将暴露在乙二胺蒸汽中后的PQ8固体粉末溶解于氯仿溶剂中,以石油醚重结晶得到白色沉淀,其荧光颜色得到恢复,表明PQ8固体粉末可实现重复使用。
2、PQ8对乙二胺的吸附
图5为PQ8(左)和PQ8暴露于乙二胺蒸汽中吸附乙二胺(右)后的热重分析谱图,结果表明PQ8固体粉末失重开始于140.0℃左右,而PQ8吸附EDA后的固体粉末失重开始于40.6℃左右,有力支持了PQ8晶体对己二腈的吸附。同时也说明EDA的解吸温度为40.6℃。
图6为PQ8吸附EDA后的高分辨质谱图,结果表明PQ8与EDA的主客体络合比为1:2。
图7为PQ8吸附EDA前后重量变化图,将0.0395g PQ8(与称量瓶共重7.8441g)暴露于EDA蒸汽48h后,PQ8与称量瓶共重7.8478g。结果表明PQ8暴露于EDA蒸汽48h后增重0.0037g,实现了对EDA蒸汽的吸附,PQ8对EDA的摩尔吸附率可达到176.19%。
3、PQ8对乙二胺的检测吸附机理分析
图8为本发明主体PQ8和客体EDA的核磁滴定图,其中(a) PQ8; (b) PQ8中加入EDA;(c) EDA。在一定浓度(9 mM, 0.5mL)的PQ8的溶液中加入3.0μL EDA后,H1和H2质子在EDA上的共振呈上场偏移,PQ8上的信号质子Hg、Hh和Hf质子呈下场偏移。同时,PQ8的8-羟基喹啉基团上的Ha-e质子的信号也出现了上移。以上结果表明,客体分子EDA与主体分子PQ8上的喹啉环、烷基链及空腔上的甲氧基之间形成了C-H…O和C-H…N,因此主体PQ8通过氢键作用捕获EDA分子,实现了对EDA的吸附,并导致PQ8在接触乙二胺蒸汽后出现荧光变色,实现了对EDA的检测。
附图说明
图1为本发明PQ8的质谱图;
图2为本发明PQ8的氢谱图;
图3为本发明PQ8固体粉末暴露在有机挥发性化合物蒸汽中的固体荧光谱图(λex=310 nm);
图4为本发明PQ8固体粉末吸附乙二胺后,通过氯仿和石油醚重结晶后得到得的PQ8固体粉末的荧光谱图(λex=310 nm);
图5为本发明PQ8(左)PQ8吸附EDA后(右)的热重分析谱图;
图6为本发明PQ8吸附EDA后的高分辨质谱图;
图7为PQ8吸附EDA前后重量变化图;
图8为本发明主体PQ8和客体EDA的核磁滴定图。
具体实施方式
下面通过具体实例对PQ8的制备和应用做进一步说明。
实施例1 PQ8的合成
(1)M4(名称)的合成:将对苯二酚(2.20g, 20mmol)、KI(6.64g, 40mmol)、K2CO3(13.82 g, 100 mmol)和1.4-二溴丁烷(17.27g, 80mmol)依次加入到丙酮(250.0 mL)溶液中。反应混合物在氮气气氛下,于85℃回流72 h。然后在减压下除去溶剂。目标化合物采用柱层析分离(洗脱剂:石油醚/乙酸乙酯= 50:1,v/v)。最终目标产物M4为白色固体。产率:55%,熔点: 83~85℃。
(2)双边1.4-二溴丁烷修饰的柱芳烃的合成:M4(1.90g, 5mmol)、1.4-二甲氧基苯(6.90g, 20mmol)和多聚甲醛(2.50g, 25mmol)加入1.2-二氯乙烷(250.0 mL)溶液中。于30℃搅拌30min后滴加BF3O.(C2H5)2, 共滴加6.5mL。溶液颜色变化至墨绿色后加入100.0mL水常温搅拌2h,以50.0mL二氯甲烷和50.0mL水对溶液进行萃取,取下层二氯甲烷层加入无水Na2SO4除去水分,然后在减压下除去溶剂。目标化合物采用柱层析分离(洗脱剂:石油醚/二氯甲烷:乙酸乙酯= 100:50:1,v/v/v)。最终目标化合物双边1.4-二溴丁烷修饰的柱芳烃(P5)为白色固体。产率:50%,熔点:187~189 °C。
(3)PQ8的合成:将K2CO3(1.38 g, 10 mmol)、双边1.4-二溴丁烷修饰的柱芳烃(0.99 g, 1 mmol)、KI (0.33g, 2 mmol)和8-羟基喹啉(0.36 g, 2.5 mmol)依次加入到乙腈(60.0 mL)溶液中。反应混合物在氮气气氛下,于85℃下回流反应72 h。然后在减压下除去溶剂,采用柱层析分离(洗脱剂:石油醚/乙酸乙酯= 5:1,v/v),得到的白色固体PQ8。产率:40%,熔点: 85~86℃。
PQ8合成路线为:
实施例2 PQ8对EDA的检测
称取10mg PQ8的固体粉末,分别暴露在有机挥发性化合物乙腈、二氯甲烷、氯仿、甲醛、吡啶、四氢呋喃、氨水、正丙胺、正丁胺、1.6-己二胺、1.10-癸二胺和乙二胺的蒸汽中,若PQ8的荧光颜色由蓝色变成淡黄色,则说明该有机挥发性化合物为乙二胺;若PQ8的荧光颜色无明显变化,则说明为其他有机挥发性化合物。
Claims (7)
3.如权利要求1所述一种8-羟基喹啉功能化柱[5]芳烃在检测乙二胺中的应用,其特征在于:8-羟基喹啉功能化柱[5]芳烃的合成方法为:以乙腈为溶剂,以双边1.4-二溴丁烷修饰的柱芳烃和8-羟基喹啉为反应底物,在K2CO3和KI作用及N2保护下,于80~85℃下反应70~72h,反应结束后采用柱层析分离,得到的白色固体,即为8-羟基喹啉功能化柱[5]芳烃。
5.如权利要求3所述一种8-羟基喹啉功能化柱[5]芳烃在检测乙二胺中的应用,其特征在于:双边1.4-二溴丁烷修饰的柱芳烃和8-羟基喹啉的摩尔比为1:2~1:2.5。
6.如权利要求3所述一种8-羟基喹啉功能化柱[5]芳烃在检测乙二胺中的应用,其特征在于:双边1.4-二溴丁烷修饰的柱芳烃与K2CO3的摩尔比为1:10~1:10.5。
7.如权利要求3所述一种8-羟基喹啉功能化柱[5]芳烃在检测乙二胺中的应用,其特征在于:双边1.4-二溴丁烷修饰的柱芳烃与KI的摩尔比为1:2~1:2.5。
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