CN110746329A - 一种功能化三柱[5]芳烃化合物及其合成和应用 - Google Patents

一种功能化三柱[5]芳烃化合物及其合成和应用 Download PDF

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CN110746329A
CN110746329A CN201911031040.1A CN201911031040A CN110746329A CN 110746329 A CN110746329 A CN 110746329A CN 201911031040 A CN201911031040 A CN 201911031040A CN 110746329 A CN110746329 A CN 110746329A
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林奇
王中会
孙小文
魏太保
张有明
姚虹
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Abstract

本发明公开了一种功能化三柱[5]芳烃化合物制备方法，是由水合肼功能化的柱[5]芳烃和对羟基苯甲醛功能化的柱[5]芳烃在DMF中反应，再经过分离提纯而得。核磁滴定实验表明，本发明制备的功能化三柱[5]芳烃化合物在d6‑DMSO中和甲基紫精发生络合，从而实现了其对甲基紫精的吸附，因此用吸附去除环境中甲基紫精，吸附率达到91.2%。紫外吸收光谱表明，在2×10‑3 mmol/L~2×10‑2 mmol/L的浓度范围内，功能化三柱[5]芳烃化合物溶液的紫外吸光度与甲基紫精浓度呈线性关系，因此实现了对水样中甲基紫精含量的定量监测。

Description

一种功能化三柱[5]芳烃化合物及其合成和应用
技术领域
本发明涉及一种双酰腙功能化柱[5]芳烃，尤其涉及水合肼功能化的柱[5]芳烃、对羟基苯甲醛功能化柱[5]芳烃，本发明同时还涉及双酰腙功能化柱[5]芳烃在溶液中单一选择性荧光识别甲基紫精，属于超分子有机科研领域。
背景技术
随着社会的发展，人们对于农药的利用越来多，所以也出现了各种各样的问题，例如，对环境的污染，有农药对人体的危害等。所以实现对残留农药的降解或者吸附是非常有必要的。甲基紫精（BCK），又名百草枯，是一种快速灭生性除草剂，具有触杀作用和一定内吸作用，能迅速被植物绿色组织吸收，使其枯死而，对非绿色组织没有作用。在土壤中迅速与土壤结合而钝化，对植物根部及多年生地下茎及宿根无效。百草枯对人毒性极大，且无特效解毒药，口服中毒死亡率极高。因此，对甲基紫精检测和吸附处理具有极高的利用价值。
发明内容
本发明的目的是提供一种功能化三柱[5]芳烃化合物的结构和制备方法；
本发明的另一目的是提供上述功能化三柱[5]芳烃化合物在检测和吸附环境中甲基紫精的应用。
一、功能化三柱[5]芳烃及其合成
功能化三柱[5]芳烃化合物的合成：以冰醋酸作催化剂，在DMF溶剂中，水合肼功能化的柱[5]芳烃与对羟基苯甲醛功能化柱[5]芳烃以1:2的摩尔比，于100 ml的圆底烧瓶中140回流反应70~72h；反应停止后冷却至室温，抽滤，柱层析分离纯化，得到淡黄色产物即为功能化三柱[5]芳烃化合物。
水合肼功能化的柱[5]芳烃的合成参见文献[ACS Sustainable Chem Eng. 2018,6, 8775-8781.]标记为TP2；其结构式为：
Figure DEST_PATH_IMAGE002
对羟基苯甲醛功能化柱[5]芳烃的合成参见文献[New J Chem, 2018,42, 1271-1275.]标记为I；其结构式为：
Figure DEST_PATH_IMAGE004
所得功能化三柱[5]芳烃化合物标记为TP2-I，其结构式为：
Figure DEST_PATH_IMAGE006
催化剂冰醋酸的用量为两种功能化柱[5]芳烃总摩尔量的0.05~0.06倍。
二、功能化三柱[5]芳烃化合物的对甲基紫精的识别和吸附性能
1、对甲基紫精的荧光识别性能
移取一定量的主体TP2-I，配置成d6-DMSO 溶液中（c=10mg/ml）。当向主体溶液中加入60.75倍当量甲基紫精DMSO溶液（1×10-4 mol·L-1）时，主体TP2-I溶液的荧光猝灭（如图1所示），而且TP2-I溶液的颜色变为红色。
荧光滴定实验表明，当向主体TP2-I溶液中加入甲基紫精时，随着甲基紫精浓度的不断增加，荧光强度逐渐下降，当加到60.75倍当量时荧光强度基本保持不变（如图2所示），并且最低检测限为9.33×10-7 M（如图3所示）。
主客体的核磁滴定：向TP2-I的d6-DMSO 溶液中（c=10mg/ml）分别加入1.5倍当量的甲基紫精，并观察核磁氢谱峰的移动。从核磁滴定我们可以看出，随着甲基紫精的加入羟基上的氢质子H1，H2，H3，向低场移动，同时，芳环上的氢质子Ha，Hb向高场移动（如图4所示）。上述现象说明了主体TP2-I和甲基紫精发生络合。基于此原理，主体TP2-I可用于环境中甲基紫精的吸附去除。
2、对甲基紫精的吸附性能
移取1mg 主体TP2-I的固体置于比色管中，然后取甲基紫精的水溶液（1×10-4 mol·L-1）5ml于10ml离心管磁力搅拌器上进行搅拌，每隔五分钟取清液测一次吸光度。直到吸光度保持不变。随着时间的推移，甲基紫精的水溶液的吸光度逐渐降低，说明主体分子TP2-I对客体分子（BCK）发生了吸附作用。
图5为TP2-I吸附BCK后的紫外吸收光谱。由图5可知，在吸附前后，随着时间的推移，甲基紫精溶液吸光度从1.3下降到0.3，说明TP2-I对甲基紫精有吸附作用。
3、TP2-I检测水样中甲基紫精浓度
首先，依次配制不同浓度梯度的标准溶液，并测量出相应浓度下溶液的吸光度，当紫外吸收光谱中最后一条线所对应的吸光度能够落在所配制的标准溶液对应的吸光度范围之内，然后对不同浓度梯度的标准溶液做线性曲线，所得到方程就是所对应的线性方程。
图6为客体BCK不同浓度绘制的标准曲线。图6表明，在0.001mmol/L~0.04mmol/L的浓度范围内，主体TP2-I溶液的紫外吸光度与甲基紫精浓度呈如下线性关系：
y=0.00429+30.807x，R2=0.9998
x——BCK的浓度，单位：mmol/L
Y——TP2-I吸附BCK后的紫外吸光度。
附图说明
图1主体化合物TP2-I对BCK的荧光识别；
图2主体化合物TP2-I对BCK的荧光滴定；
图3主体化合物TP2-I对BCK的荧光最低检测限；
图4为TP2-I加入甲基紫精的核磁滴定；
图5为TP2-I吸附BCK后的紫外吸收光谱；
图6为客体BCK不同浓度绘制的标准曲线。
具体实施方式
实施例1、TP2-I的合成
将0.1g（0.1mmol）水合肼功能化的柱[5]芳烃（TP2）置于100mL的圆底烧瓶中，加入50mL DMF作溶剂，搅拌下缓慢加入0.18g（2mmol）对羟基苯甲醛功能化柱[5]芳烃I，并加入1mL冰醋酸作催化剂，在油浴上加热至140℃回流反应72h。待反应停止后冷却至室温，抽滤，加硅胶拌样，旋干，用柱层析法纯化（石油醚:乙酸乙酯= 20:1），得到的淡黄色产物即为TP2-I。产率：21%。
TP2-I: (m.p. 大于133℃), 1H NNR (600 MHZ, d 6 -DMSO), δ/ppm: 11.27 (s,2H),8.13 (s,1H), 7.93 (s,2H), 7.61 (m, 3H),6.96 (m, 4H), 6.78 (m, 30H), 4.00(m, 12H), 3.64 (s,108H), 3.30 (s, 4H), 2.71 (s, 4H), 1.86 (m, 16H)。
实施例2、TP2-I吸附去除水样中甲基紫精
移取1mg TP2-I的固体置于比色管中，然后取甲基紫精的水溶液（1×10-4 mol·L-1）5ml于10ml离心管磁力搅拌器上进行搅拌，每隔五分钟取清液测一次吸光度。直到吸光度保持不变。确定吸附后甲基紫精的残余浓度。通过计算化合物对甲基紫精的吸附率为91.2%。
实施例3、TP2-I检测水样中甲基紫精的浓度
样品溶液的配制：取一定量甲基紫精，用水配置成浓度1×10-4 mol·L-1的水溶液；
甲基紫精的浓度的检测：移取1mg 主体TP2-I固体置于比色管中；取含有甲基紫精的样品溶液（1×10-4 mol·L-1）5ml，加入比色管中，于磁力搅拌器上进行搅拌，每隔五分钟取清液测一次吸光度，直到吸光度保持不变。根据主体TP2-I溶液的紫外吸光度与甲基紫精浓度的线性关系计算甲基紫精残余浓度，为8.87×10-5mol·L-1，吸附剂所吸附的甲基紫精浓度为1.12×10-5 mol·L-1。吸附浓度和残余浓度之和恰好为样品溶液中甲基紫精的浓度。

Claims (8)

1.一种功能化三柱[5]芳烃化合物，其结构式为：
Figure 886608DEST_PATH_IMAGE002
。
2.如权利要求1所述功能化三柱[5]芳烃化合物的合成方法，是以冰醋酸作催化剂，在DMF溶剂中，水合肼功能化的柱[5]芳烃与对羟基苯甲醛功能化柱[5]芳烃以1:2的摩尔比，于100 ml的圆底烧瓶中140℃回流反应70~72h；反应停止后冷却至室温，抽滤，柱层析分离纯化，得到淡黄色产物即为功能化三柱[5]芳烃化合物。
3.如权利要求2所述功能化三柱[5]芳烃化合物的合成方法，其特征在于：水合肼功能化的柱[5]芳烃的结构式为：
Figure 69328DEST_PATH_IMAGE004
。
4.如权利要求2所述功能化三柱[5]芳烃化合物的合成方法，其特征在于：对羟基苯甲醛功能化柱[5]芳烃的结构式为：
Figure 52327DEST_PATH_IMAGE006
。
5.如权利要求2所述功能化三柱[5]芳烃化合物的合成方法，其特征在于：催化剂冰醋酸的用量为两种功能化柱[5]芳烃总摩尔量的0.05~0.06倍。
6.如权利要求1所述功能化三柱[5]芳烃化合物用于吸附去除环境中的甲基紫精。
7.如权利要求1所述功能化三柱[5]芳烃化合物用于检测环境中甲基紫精的浓度。
8.如权利要求7所述功能化三柱[5]芳烃化合物用于检测环境中甲基紫精的浓度，其特征在于：在0.001 ~0.04mmol/L的浓度范围内，功能化三柱[5]芳烃化合物溶液的紫外吸光度与甲基紫精浓度呈如下线性关系：
y=0.00429+30.807x，R2=0.9998
x——BCK的浓度，单位：mmol/L
Y——TP2-I吸附BCK后的紫外吸光度。
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111517947A (zh) * 2020-03-18 2020-08-11 西北师范大学 一种基于功能化的双边柱[5]芳烃传感器分子及其合成和应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107827796A (zh) * 2017-11-06 2018-03-23 西北师范大学 一种超分子聚合物单体及金属配合物的制备和应用
CN109400501A (zh) * 2018-11-28 2019-03-01 中国科学院上海高等研究院 功能化柱芳烃衍生物及其制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107827796A (zh) * 2017-11-06 2018-03-23 西北师范大学 一种超分子聚合物单体及金属配合物的制备和应用
CN109400501A (zh) * 2018-11-28 2019-03-01 中国科学院上海高等研究院 功能化柱芳烃衍生物及其制备方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHUNJU LI 等: "Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 *
QI LIN 等: "Ultrasensitive Detection of Formaldehyde in Gas and Solutions by a Catalyst Preplaced Sensor Based on a Pillar[5]arene Derivative", 《ACS SUSTAINABLE CHEMISTRY & ENGINEERING》 *
TAI-BAO WEI 等: "A cyanide-triggered hydrogen-bond-breaking deprotonation mechanism: fluorescent detection of cyanide using a thioacetohydrazone-functionalized bispillar[5]arene", 《NEW J.CHEM.》 *
XIAODONG CHI 等: "Redox-Responsive Complexation between a Pillar[5]arene with Mono(ethylene oxide) Substituents and Paraquat", 《ORGANIC LETTERS》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111517947A (zh) * 2020-03-18 2020-08-11 西北师范大学 一种基于功能化的双边柱[5]芳烃传感器分子及其合成和应用

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