CN111620904A - 基于羟基脱保护反应的喹啉偶氮衍生物传感器及其制备与应用 - Google Patents
基于羟基脱保护反应的喹啉偶氮衍生物传感器及其制备与应用 Download PDFInfo
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Abstract
本发明公开了基于羟基脱保护反应的喹啉偶氮衍生物传感器及其制备与应用。本发明以对硝基苯胺、叔丁基二甲基氯硅烷及8‑羟基喹啉等为原料,制备叔丁基二甲基‑对硝基苯胺偶氮8‑羟基喹啉,记为P‑TB。采用红外光谱仪、紫外‑可见分光光度计和荧光光谱仪对产物进行结构及性能表征,探究其谱学变化规律及对阴离子的识别行为。结果表明:P‑TB乙腈溶液能识别甲醇及水溶液中的F‑。本发明拓展了氟离子光化学识别方法,该传感器制备方法新颖,简单,对离子识别设备简单,操作方便,大大减少了此类光化学识别离子的操作步骤,可应用于医学、环境及水体等领域中氟离子的检测,大大节约了检测成本,保护了环境,具有良好的经济和社会效益。
Description
技术领域
本发明涉及化学分析测试领域,具体涉及基于羟基脱保护反应的喹啉偶氮衍生物传感 器及其制备与应用。
背景技术
阴离子极广泛存在于生物中,生命体中大多数酶的反应都需要阴离子参与。因此,人 们投入了大量精力研究阴离子的配位和识别问题。而受体分子的设计受许多限制,如阴离 子半径、几何构型、酸碱敏感度、溶剂效应等。氟是人体必需的微量元素,在形成牙齿釉质以及钙磷方面,氟起着十分重要的作用。氟还是冷冻机、橡胶及特种塑料中的重要元素。由于氟特殊的化学特点,氟在化学应用上有着重要的作用。
生色阴离子主体的设计是阴离子识别研究的关键环节之一,比色法具有操作简单、方 便等优势,已被广泛应用于分子识别研究中,生色阴离子主体主要包括两部分:阴离子识 别基团和生色团,它们之间常以共价键直接相连,其中氢键是阴离子识别研究中应用最为 广泛的作用力之一。含偶氮基团的化合物,在基态时可发生分子内电荷转移,具有较大的 偶极矩对介质环境极为敏感并且是良好的生色基团。
8-羟基喹啉偶氮衍生物中含有生色团,可通过偶联形成的共扼延伸体系可作为阴离子 识别主体。制备一种可以识别氟离子的传感器具有重要意义。
发明内容
本发明目的在于提供基于羟基脱保护反应的喹啉偶氮衍生物传感器及其制备,通过合 成系列8-羟基喹啉偶氮类衍生物,通过取代基团推拉电子能力的改变从而调控主体分子对 阴离子客体的亲合力,筛选出选择性好的阴离子识别主体,探索出对氟离子有识别的喹啉 偶氮类衍生物并研究其在不同溶剂下的识别行为。
基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,包括以下步骤:
1)将对硝基苯胺溶于乙醇溶液,加入浓盐酸溶液并于冰浴中搅拌,然后加入亚硝酸钠 溶液,反应得到混合液,反应式如下:
2)将8-羟基喹啉用氢氧化钠热溶液溶解,加到上述混合液中,调节pH为8~10,反应得偶氮溶液,然后抽滤,纯化,干燥得到4-硝基苯胺偶氮8-羟基喹啉,记为PNQ,反应 式如下:
3)将PNQ溶于乙腈,再加入叔丁基二甲基氯硅烷于55-60℃回流48-52h,进行减压蒸馏,干燥得叔丁基二甲基-对硝基苯胺偶氮8-羟基喹啉,记为P-TB,反应式如下:
步骤1)的反应温度为0~5℃,反应时间为1-1.2小时。
步骤1)中,所述对硝基苯胺与乙醇溶液的用量比为1.384g∶80-100mL。
步骤2)中,控制温度为0~5℃,反应时间为2-2.5h。
所述8-羟基喹啉与对硝基苯胺的质量比为1.445-1.465∶1.384,优选为为1.457∶1.384。
步骤3)中,所述叔丁基二甲基氯硅烷与PNQ的质量比为0.715-0.735:0.285,优选为 0.727:0.285。
本发明采用以上技术方案,以对硝基苯胺、叔丁基二甲基氯硅烷及8-羟基喹啉等为原 料,制备叔丁基二甲基-对硝基苯胺偶氮8-羟基喹啉(P-TB)。采用红外光谱仪、紫外-可见 分光光度计和荧光光谱仪对产物进行结构及性能表征,探究其谱学变化规律及对阴离子的 识别行为。结果表明:P-TB乙腈溶液能识别甲醇及水溶液中的F-,拓展了氟离子光化学识 别方法,该传感器制备方法新颖,简单,对离子识别设备简单,操作方便,大大减少了此 类光化学识别离子的操作步骤,可应用于医学、环境及水体等领域中氟离子的检测,大大 节约了检测成本,保护了环境,具有良好的经济和社会效益。
附图说明
图1为PNQ红外光谱图;
图2为P-TB红外光谱图;
图3为阴离子甲醇溶液对P-TB甲醇溶液的UV-Vis吸收光谱影响;
图4为阴离子水溶液对P-TB甲醇溶液的UV-Vis吸收光谱影响;
图5为阴离子甲醇溶液对P-TB乙腈溶液的UV-Vis吸收光谱影响;
图6为F-甲醇溶液用量对P-TB乙腈溶液的UV-Vis吸收光谱影响;
图7为F-甲醇溶液用量与P-TB乙腈溶液吸光度线性关系;
图8为阴离子水溶液对P-TB乙腈溶液的UV-Vis吸收光谱影响;
图9为F-水溶液用量对P-TB乙腈溶液的UV-Vis吸收光谱影响;
图10为F-水溶液用量与P-TB乙腈溶液吸光度线性关系;
图11为P-TB甲醇溶液荧光光谱;
图12为P-TB乙腈溶液荧光光谱;
图13为F-水溶液对P-TB甲醇溶液荧光光谱影响;
图14为F-甲醇溶液对P-TB甲醇溶液荧光光谱的影响;
图15为F-水溶液对P-TB乙腈溶液荧光光谱的影响;
图16为F-甲醇溶液对P-TB乙腈溶液荧光光谱的影响。
具体实施方式
以下结合附图和具体实施例对本发明作进一步详细的说明:
实施例1
叔丁基二甲基-对硝基苯胺偶氮8-羟基喹啉(P-TB)的制备
称1.384g对硝基苯胺溶于80mL乙醇溶液,加入3mL浓盐酸溶液并于冰浴中搅拌。加入亚硝酸钠溶液,反应1h,反应式如下:
称取1.457g 8-羟基喹啉并用氢氧化钠热溶液溶解,控温0~5℃,加到上述溶液中, 调pH约8~10,反应2h得偶氮溶液,抽滤,纯化,干燥4-硝基苯胺偶氮8-羟基喹啉(PNQ),反应式如下:
取0.285g的PNQ溶于110mL乙腈,再加入0.727g叔丁基二甲基氯硅烷于56℃左 右回流48h,进行减压蒸馏,干燥得P-TB,反应式如下:
实施例2
1.性能检测
1.1FI-IR表征
利用傅里叶型红外光谱仪,在波数范围为4000~400cm-1下表征合成的产品。
1.2UV-Vis检测
将产品分别配制成10-4mol·L-1乙腈和甲醇溶液,置于UV-Vis可见吸收分光光度计 中,在波长为800~200nm下检测合成的产品。
1.3离子识别行为分析
将产品分别溶于甲醇溶液和乙腈溶液,另分别配制不同阴离子水溶液和不同阴离子甲 醇溶液,将不同溶剂下的阴离子溶液加入到不同溶剂下的产品溶液中,并利用UV-Vis检 测并分析其光谱变化规律。
1.4荧光光谱分析
将合成物质溶于乙腈和甲醇溶液中,分别加入不同溶剂状态下的F-溶液,在激发波长 为190~550nm下扫描,找出最佳激发波长并在此波长下检测其光谱变化规律。
2结果与分析
2.1FI-IR谱图分析
图1为4-硝基苯胺偶氮8-羟基喹啉(PNQ)的红外谱图。据图可知,产品中含有酚羟基(342342cm-1)、偶氮基团(13367cm-1)、硝基(1196cm-1)、苯环(3111cm-1、1510 cm-1),800cm-1处为PNQ苯环的对位二取代上的C-H键弯曲振动峰。据此,PNQ已经 成功合成。
图2为叔丁基二甲基-对硝基苯胺偶氮8-羟基喹啉(P-TB)的红外谱图,据图可知,产品中含有硝基(1043cm-1)、偶氮基团(1337cm-1)、-C(CH3)3(1238cm-1)以及-Si-O-(1196cm-1),1599cm-1处为P-AB苯环的骨架变形振动峰。据此,P-TB已经成功合成。
2.2UV-Vis光化学传感器研究
2.2..1阴离子甲醇溶液对P-TB甲醇溶液的UV-Vis吸收光谱影响
图3为阴离子甲醇溶液对P-TB甲醇溶液的UV-Vis吸收光谱影响。由图可知,CO3 2-、HPO4 2-、OH-三种阴离子甲醇溶液对P-TB甲醇溶液UV-Vis吸收影响明显。CO3 2-在460n m附近峰值减小。HPO4 2-在450nm附近峰值减小。OH-在460nm附近峰值减小。其它离 子无明显识别,故不作讨论。
2.2..2阴离子水溶液对P-TB甲醇溶液的UV-Vis吸收光谱影响
图4为阴离子水溶液对P-TB甲醇的UV-Vis吸收光谱影响。由图可知,HCO3 -、HP O4 2-、OH-三种阴离子水溶液对P-TB甲醇溶液UV-Vis吸收光谱影响明显。CO3 2-在460n m附近峰值减小。HPO4 2-在565nm附近峰值变大。OH-在565nm左右处峰值增大。其它 离子无明显识别,故不作讨论。
2.2.2.3阴离子甲醇溶液对P-TB乙腈溶液的UV-Vis吸收光谱影响
图5为阴离子甲醇溶液对P-TB乙腈溶液的UV-Vis吸收光谱影响。由图可知,F-、O H-两种阴离子甲醇溶液对P-TB乙腈溶液UV-Vis吸收光谱影响明显。OH-在460nm附近 峰值增大。F-在410nm附近峰值减小,在545nm左右处峰值增大。其它离子无明显识别, 故不作讨论。
图6为F-(C=1×10-4mol·L-1)甲醇溶液不同用量对P-TB的UV-Vis吸收光谱影响。由 图得,F-含量不断升高,P-TB在555nm附近峰值增大,说明加入F-甲醇溶液至P-TB乙 腈溶液有增色效应产生。这是由于加入F-后引发体系里面的Si-O键断裂,形成F-Si键, 从而实现对F-选择性识别。使氢键作用增强。图7为F-甲醇溶液用量与P-TB乙腈溶液紫 外吸光度线性图。由图得,在用量为150μL~300μL之间,线性较好。
2.2..3阴离子水溶液对P-TB乙腈溶液的UV-Vis吸收光谱影响
图8为阴离子水溶液对P-TB乙腈溶液的UV-Vis吸收光谱影响。由图可知,F-、ClO-、NO2 -、HCO3 -四种阴离子水溶液对P-TB乙腈溶液UV-Vis吸收光谱影响明显。F-在545n m附近峰值增大。ClO-在450nm附近峰值减小。HCO3 -在545nm附近峰值增大。NO2 -在545nm附近峰值增大。其它离子无明显识别,故不作讨论。
图9为F-(C=1×10-4mol·L-1)水溶液不同用量对P-TB乙腈溶液光谱影响。由图9得, 随着F-含量不断增多,P-TB在545nm附近峰值增大,说明加入F-水溶液至P-TB乙腈溶 液有增色效应产生。这是由于加入F-后引发体系里面的Si-O键断裂,形成了F-Si键,进 而实现对F-选择性识别。图10为F-水溶液用量与P-TB乙腈溶液紫外吸光度线性图。由图 得,在用量为50μL~290μL之间,线性较好。
2.3荧光光谱分析
2.3.1荧光峰检测
图11为P-TB甲醇溶液荧光光谱,图12为P-TB乙腈溶液荧光光谱。由图11得,在 激发峰为220nm,狭缝宽度为5nm条件下,P-TB甲醇溶液有较强的荧光峰吸收,峰值为 292nm、579nm。由图12得,在激发峰为230nm,狭缝宽度为10nm条件下,P-TB乙腈 溶液有较强的荧光峰吸收,峰值为305nm、330nm。
2.3.2不同F-溶液对荧光峰影响
图13为F-水溶液对P-TB甲醇溶液荧光光谱影响,图14为F-甲醇溶液对P-TB甲醇溶液荧光光谱的影响,图15为F-水溶液对P-TB乙腈溶液荧光光谱的影响,图16为F-甲醇 溶液对P-TB乙腈溶液荧光光谱的影响。由图12-16知,加入F-甲醇溶液,P-TB乙腈溶液 荧光峰强度均增强。加入F-水溶液,P-TB乙腈溶液荧光峰强度均增强,说明本发明制备的 P-TB可实现对F-的识别。
Claims (10)
2.根据权利要求1所述的基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,其特征在于:步骤1)的反应温度为0~5℃,反应时间为1-1.2小时。
3.根据权利要求1所述的基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,其特征在于:步骤1)中,所述对硝基苯胺与乙醇溶液的用量比为1.384g∶80-100mL。
4.根据权利要求1所述的基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,其特征在于:步骤2)中,控制温度为0~5℃,反应时间为2-2.5h。
5.根据权利要求1所述的基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,其特征在于:所述8-羟基喹啉与对硝基苯胺的质量比为1.445-1.465∶1.384。
6.根据权利要求1所述的基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,其特征在于:所述8-羟基喹啉与对硝基苯胺的质量比为1.457∶1.384。
7.根据权利要求1所述的基于羟基脱保护反应的喹啉偶氮衍生物传感器的制备方法,其特征在于:骤3)中,所述叔丁基二甲基氯硅烷与PNQ的质量比为0.715-0.735:0.285。
8.根据权利要求1-7任一制备方法得到的喹啉偶氮衍生物传感器。
9.如权利要求8所述的喹啉偶氮衍生物传感器在阴离子识别中的应用。
10.根据权利要求8所述的应用,其特征在于;所述阴离子为氟离子。
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