CN110590648B - 三足柱[5]芳烃的合成及其检测和吸附甲基紫精的应用 - Google Patents

三足柱[5]芳烃的合成及其检测和吸附甲基紫精的应用 Download PDF

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CN110590648B
CN110590648B CN201910924523.8A CN201910924523A CN110590648B CN 110590648 B CN110590648 B CN 110590648B CN 201910924523 A CN201910924523 A CN 201910924523A CN 110590648 B CN110590648 B CN 110590648B
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林奇
张云飞
江晓梅
魏太保
张有明
姚虹
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Abstract

本发明合成了一种三足柱[5]芳烃化合物QP5，是由柱[5]芳烃（P5）和三吡啶基三苯胺（TPA）在乙腈中回流而得。荧光光谱实验数据表明，当在QP5的DMSO溶液中加入甲基紫精时，QP5的荧光强度减弱，并且溶液的颜色由橙黄色变暗。核磁滴定实验表明，QP5与甲基紫精JG在DMSO中具有很好的络合作用，因此，在检测和去除环境中的甲基紫精方面具有很好的应用。

Description

三足柱[5]芳烃的合成及其检测和吸附甲基紫精的应用
技术领域
本发明涉及一种柱[5]芳烃，尤其涉及一种三足柱[5]芳烃及其合成；本发明同时涉及三足柱[5]芳烃在检测和吸附甲基紫精的应用，属于化学合成技术领域及阳离子盐检测技术领域。
背景技术
百草枯，化学名：N,N-二甲基-4-4-联吡啶阳离子盐，又名甲基紫精，简写为JG，其结构式：
Figure 100002_DEST_PATH_IMAGE001
百草枯是一种具有接触性和内吸附性的快速杀菌除草剂。它的有效成分对叶绿体层膜破坏力极强，使光合作用和叶绿素合成很快中止，接触土壤后迅速与土壤结合而钝化。同时，也可以被植物的绿色组织迅速吸收，导致其死亡。现如今随着农业的快速发展，除草剂和农作物产品在现代农业中是必不可少的。然而，它们的使用对人类、动物和环境都有潜在的风险。当它被用作杀虫剂时，它一定会对水资源造成威胁。因此，检测环境中百草枯具有十分重要的意义。
柱芳烃是继冠谜、环糊精、杯芳烃，葫芦脲之后的第五代大环主体分子，2008年由Ogoshi首次报道。柱芳烃作为一类新型的大环宿主分子，具有独特的结构和易于功能化的性质。由于其均匀的柱状结构、易于制备和功能化、刚性结构和富电子腔，这些独特的性质使柱芳烃成为一种优良的主体分子。并且在药物释放、细胞成像、分离吸附、相转移催化、荧光传感等领域受到越来越多的关注。
发明内容
本发明的目的是提供一种三足柱[5]芳烃及其合成方法；
本发明的目的另一目的是对上述三足柱[5]芳烃对百草枯的识别和吸附性能进行研究。
一、三足柱[5]芳烃的合成
将柱[5]芳烃（P5）与三吡啶基三苯胺（TPA）分散于乙腈中，于85 ℃~90℃回流反应84 h~96h；待反应结束后冷却至室温，抽滤，所得固体用乙腈洗涤3~5次，真空干燥，即得三足柱[5]芳烃，标记为QP5。
柱[5]芳烃（P5）与三吡啶基三苯胺（TPA）的摩尔比为3:1~3.5:1。
柱[5]芳烃（P5）的结构式如下：
Figure 286740DEST_PATH_IMAGE002
三吡啶基三苯胺（TPA）的结构式如下：
Figure 100002_DEST_PATH_IMAGE003
三足柱[5]芳烃的结构式如下：
Figure 735038DEST_PATH_IMAGE004
二、三足柱[5]芳烃与甲基紫精的络合作用
1、QP5对JG的荧光滴定
为了研究主体化合物QP5对甲基紫精JG的络合能力，我们进行了荧光滴定。移取2mL
QP5(1×10﹣4mol/L)溶液中于荧光比色皿中，随着甲基紫精当量的增加，在λ= 560nm的发射峰逐渐降低，当加入58.75倍当量的JG时QP5荧光强度基本保持不变，说明QP5与甲基紫精JG完全发生络合作用，使QP5荧光发生猝灭（如图1所示），并且最低检测限为3.56×10-7M（如图2所示）。
2、核磁滴定实验
为了研究主客体识别机理，我们做了主客体的核磁滴定实验，向QP5的DMSO溶液中（2×10-4mol/L）分别加入1.0、2.0、3.0倍当量的甲基紫精的DMSO溶液，观察核磁氢谱中质子峰的移动。图3为QP5加入JG的核磁滴定（从下到上依次QP5，QP5+1.0 equiv. JG，QP5+2.0equiv. JG，QP5+3.0 equiv. JG，JG）。从核磁滴定实验中可以看出，随着客体JG的加入，JG的氢质子Ha，Hb，Hc均向低场移动，同时QP5的氢质子H1，H2，H3，H4也均向低场移动。上述现象均说明主体QP5和客体JG发生络合。
3、QP5和JG的络合比的确定
为了确定主体分子QP5和JG的络合比，将称取少量主体分子QP5与客体JG混合于1.5 mL离心管中加入DMSO溶液使其溶解，然后移取0.5 mL该溶液用乙腈溶液进行稀释至无色，对其络合比进行质谱分析。图4为QP5与JG络合后的质谱。通过图4的质谱数据，在4508.03处出现质谱峰，经过分析为[QP5+3JG-OH]-质谱峰，说明QP5和JG的络合比为1:3。
基于三足柱[5]芳烃QP5和客体JG发生络合的原理，QP5可以用于吸附和检测环境中甲基紫精。
4、QP5吸附JG的性能
称取1.1 mg的甲基紫精JG于比色管中，加入25mL的蒸馏水使其溶解，浓度为1×10﹣4mol/L，然后移取5mL于10mL离心管中，加入2mg主体化合物QP5，常温下搅拌，每隔30 min取清液并测量吸光度，直到吸光度保持不变。图5为 QP5吸附JG后的紫外吸收光谱。如图5所示，在没有加入QP5时，JG吸光度为2.723，加入QP5后，经过4 h后，JG吸光度降低到0.193且保持不变，通过计算残留在水溶液的JG浓度为9.9×10﹣6mol/L，说明在水溶液中主体化合物QP5可以高效的吸附客体JG。因此，三足柱[5]芳烃QP5对于水的JG具有很好的吸附作用。
5、QP5检测JG的性能
称取4.4mg的甲基紫精JG 于10 mL比色管中，加入10mL 蒸馏水使其完全溶解，其浓度为1×10﹣3mol/L，然后分别稀释浓度至8×10﹣5mol/L、6×10﹣5mol/L、4×10﹣5mol/L、2×10﹣5mol/L、1×10﹣5mol/L、8×10﹣6mol/L、6×10﹣6mol/L于10mL比色管中；然后，对其通过紫外可见光谱进行分析测量，在λ=254 nm处吸光度为纵坐标，浓度为横坐标绘制标准曲线。
图6为客体JG不同浓度绘制的标准曲线。由图6可知，在6×10﹣6 mol/L~8×10﹣5mol/L浓度范围内，环境中甲基紫精的浓度与三足柱[5]芳烃QP5呈如下线性关系：
Y=﹣0.05284+24.60652X，其中，横坐标X为浓度，单位：mmol/L；纵坐标Y为吸光度，单位：mol/g；相关系数R2=0.99845。
综上所述，本发明涉及合成了一种三足柱[5]芳烃主体化合物QP5，其与甲基紫精JG在DMSO溶液中具有很好的络合作用，因此在检测和去除环境中的甲基紫精方面具有很好的应用价值。
附图说明
图1 主体化合物QP5对JG的荧光滴定。
图2主体化合物QP5对JG的荧光最低检测限。
图3为QP5中加入JG的核磁滴定。
图4为QP5与JG络合后的质谱。
图5为QP5吸附JG后的紫外吸收光谱。
图6为JG在不同浓度绘制的标准曲线。
具体实施方式
下面通过具体实施例对本发明三足柱[5]芳烃QP5的合成及在检测和吸附JG的应用作进一步说明。
实施例1、QP5的合成
（1）三吡啶基三苯胺的合成：根据文献[H.C. Ma,M.Y. Yang, S. X. Zhang, P.Yin, T. Wang, Y. Yang,Z. Q. Lei, Y.C. Ma, Y.F. Qin and Z. M. Yang, Analyst,2019, 144, 536–542.]合成化合物三吡啶基三苯胺（TPA）；
（2）化合物P5的合成；根据文献[T. Ogoshi, T. A. Yamagishi and Y.Nakamoto, Chem Rev., 2016, 116, 7937−8002.]合成化合物P5；
（3）三足柱[5]芳烃QP5的合成：于100mL的圆底烧瓶中加入0.4374 g（0.4860mmol）柱[5]芳烃（P5），加入30mL乙腈作为溶剂搅拌溶解；将0.045g（0.081 mmol）TPA加入20mL乙腈中超声使完全分散，然后逐滴滴入到上述溶液中，在油浴90℃加热回流84 h ~ 96h；待反应停止并冷却至室温，抽滤，所得固体用乙腈洗涤3~5次，真空干燥箱中烘干，得到橙黄色固体（0.10g），即为化合物QP5，产率：35%。(M.P.: 212-214℃)，1H NNR (600 MHZ,DMSO-d 6 ),8.87(s, 6H), 8.42(s, 6H), 8.12-8.13(d,J=8.13 Hz,6H), 7.34-7.36(d,J=7.35 Hz, 6H), 6.71- 6.81(m, 30H), 4.32-4.35(d,J=4.34Hz, 6H), 3.59-3.82(t,J=3.62Hz,111H), 1.95(s, 6H), 1.79(s,6H),1.73(s, 6H), 1.50(s,6H), 1.02-1.04(m,6H)。
实施例2、QP5检测环境中甲基紫精浓度
（1）样品溶液的配制：称取4.4 mg甲基紫精JG于10mL比色管中，再加入10mL蒸馏水使其完全溶解，浓度为1×10﹣3mol/L，然后移取1mL该溶液稀释至10mL，得到浓度为1×10﹣ 4mol/L的甲基紫精溶液。
（2）检测方法：通过荧光发射光谱法检测甲基紫精，在荧光发射光谱中，移取2 mL
QP5(1×10﹣4mol/L)溶液中于荧光比色皿中，随着甲基紫精当量的增加，在λ= 560nm的发射峰逐渐降低，当加入58.75倍当量JG时，在λ=560 nm的发射峰不再变化，说明QP5与甲基紫精完全络合，即通过荧光验证QP5对JG的吸附能力；同时通过紫外可见分光光度法检测水溶液中残留的JG浓度，移取5mL的JG（1×10﹣4mol/L）溶液于10mL离心管中，加入2mg主体化合物QP5，常温下搅拌，每隔30min 测量吸光度，直到吸光度保持不变，根据浓度和吸光度绘制标准曲线，通过标准曲线即可计算出水溶液中残留的JG浓度。
（3）检测结果：根据标准曲线计算出样品溶液中甲基紫精的浓度为1.1×10﹣4mol/L。
实施例3、QP5对甲基紫精的吸附实验
称取0.0011g甲基紫精JG于比色管中，加入25mL的蒸馏水使其溶解，浓度为1×10﹣ 4mol/L，然后移取5mL于10mL离心管中，加入2mg主体化合物QP5，常温下搅拌，每隔30 min取清液并测量吸光度，直到吸光度保持不变，确定吸附后甲基紫精的残余浓度为9.9×10﹣ 6mol/L。通过计算，主体化合物QP5对甲基紫精的吸附率为90.10%。

Claims (4)

1.一种三足柱[5]芳烃化合物，其结构式如下：
Figure DEST_PATH_IMAGE001
。
2.如权利要求1所述一种三足柱[5]芳烃化合物的合成方法，是将柱[5]芳烃与三吡啶基三苯胺分散于乙腈中，于85℃~90℃回流反应84h~96h；待反应结束后冷却至室温，抽滤，所得固体用乙腈洗涤3~5次，真空干燥，即得三足柱[5]芳烃；
所述柱[5]芳烃的结构式如下：
Figure 899105DEST_PATH_IMAGE002
所述三吡啶基三苯胺的结构式如下：
Figure DEST_PATH_IMAGE003
。
3.如权利要求2所述一种三足柱[5]芳烃化合物的合成方法，其特征在于：柱[5]芳烃与三吡啶基三苯胺的摩尔比为3:1~3.5:1。
4.如权利要求1所述一种三足柱[5]芳烃化合物在检测吸附环境溶液中甲基紫精的应用，其特征在于：在6×10﹣6 mol/L~8×10﹣5 mol/L浓度范围内，环境中甲基紫精的浓度与三足柱[5]芳烃QP5呈如下线性关系：Y=﹣0.05284+24.60652X。
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