CN110437466A - 一种主客体络合的超分子聚合物网状凝胶及其应用 - Google Patents

一种主客体络合的超分子聚合物网状凝胶及其应用 Download PDF

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CN110437466A
CN110437466A CN201910872822.1A CN201910872822A CN110437466A CN 110437466 A CN110437466 A CN 110437466A CN 201910872822 A CN201910872822 A CN 201910872822A CN 110437466 A CN110437466 A CN 110437466A
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魏太保
安军年
张芹棚
樊彦青
马小强
曲文娟
姚虹
张有明
林奇
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Abstract

本发明设计合成了一种主客体络合的超分子聚合物网状凝胶，是以巯基乙酰腙功能化双柱[5]芳烃为主体化合物，4‑氨基吡啶修饰的三足化合物为客体化合物，加热溶解在DMSO/H2O的混合溶剂中，通过主客体相互作用络合成超分子聚合物凝胶；超分子聚合物凝胶经冷冻干燥得到干凝胶。该干凝胶对有机染料具有很好的吸附去除效果，尤其对于结晶紫、罗丹明B具有很高的去除率：对结晶紫的去除率达96.3%，对罗丹明B的去除率达95.4%，因此可用于去除水溶液中的有机染料。

Description

一种主客体络合的超分子聚合物网状凝胶及其应用
技术领域
本发明涉及一种主客体络合的超分子聚合物网状凝胶，尤其涉及一种以巯基乙酰腙功能化双柱[5]芳烃为主体化合物，4-氨基吡啶修饰的三足化合物为客体化合物，通过主客体相互作用络合的超分子聚合物网状凝胶，主要用于有机染料的去除，属于超分子材料领域和有机污染物去除领域。
背景技术
超分子聚合物是超分子化学与高分子化学的交叉方向。与传统聚合物相比，超分子聚合物是单体间通过非共价弱相互作用结合形成的。由于非共价相互作用的动态和可逆性质，超分子聚合物显示出许多独特的性质，如外部刺激反应，可逆剪切敏感性和卓越的自我修复能力。因为这些特性，超分子聚合物在许多领域显示出潜在的应用，例如化学传感，催化剂，分离材料，药物递送和污染物去除。
染料是应用较为广泛的一种材料之一，多种制造业都需要借助于染料对产品进行染色处理。当它们直接排放到含水环境中时，高毒性染料将极大地威胁环境和人类健康。为了保护水质，从污染水中有效去除染料至关重要。虽然有许多方法包括化学或物理方法已被报道并应用于检测或去除这些污染物。然而，它仍然面临许多局限性，例如缺乏选择性，低污染吸收和昂贵的再生过程等。因此，提供选择性吸附染料的先进吸附剂具有很好的应用前景。
发明内容
本发明的目的是提供了一种主客体络合的超分子聚合物网状凝胶及其制备方法；
本发明的另一个目的是对上述超分子聚合物网状凝胶对于染料分子的去除效果进行研究。
一、超分子聚合物网状凝胶
本发明主客体络合的超分子聚合物网状凝胶，是以巯基乙酰腙功能化双柱[5]芳烃（标记为DP5）为主体化合物，4-氨基吡啶修饰的三足化合物（标记为SZ）为客体化合物，加热溶解在DMSO/H2O的混合溶剂中，通过主客体相互作用络合成超分子聚合物凝胶（标记为DP5G）；超分子聚合物凝胶经冷冻干燥得到干凝胶。
其中，主体化合物巯基乙酰腙功能化双柱[5]芳烃（DP5）的结构式如下：
客体化合物4-氨基吡啶修饰的三足化合物（SZ）的结构式如下：
DMSO/H2O的混合溶剂中，DMSO与H2O的体积比为5:1~2:1；主体化合物巯基乙酰腙功能化双柱[5]芳烃与客体化合物4-氨基吡啶修饰的三足化合物的摩尔比为1:1~1:1.2，且主客体的含量为0.12~0.14 g/mL。
图1为DP5与SZ的部分核磁滴定图。其中（a）DP5；（b）在（a）的基础上加入1.0倍当量的SZ；（c）SZ。结果表明，巯基乙酰腙功能化双柱[5]芳烃DP5上的苯环、桥连亚甲基及甲氧基上的Ha，Hb，Hc质子峰均向低场移动；而4-氨基吡啶修饰的三足化合物SZ上的H1，H2质子峰均向高场移动，这说明4-氨基吡啶修饰的三足化合物SZ上的吡啶基进入到巯基乙酰腙功能化双柱[5]芳烃DP5的空腔中形成了主客体复合物从而构建了超分子聚合物DP5G。
图2为DP5、SZ和DP5G的扫描电镜图。其中（a）DP5；（b）SZ；（c）DP5G。从图2中可看出，主体化合物DP5呈现纳米簇状结构，客体化合物SZ呈现块状结构；而它们两者组装后，电镜图（c）呈现网状结构，这说明客体化合物SZ上的吡啶穿入巯基乙酰腙功能化双柱[5]芳烃（DP5）的空腔中，从而形成了超分子聚合物DP5G。
二、超分子聚合物网状凝胶的染料去除性能
将0.002g干凝胶加入到5 mL2.5×10-5 mol/L的结晶紫、罗丹明 B、甲基蓝和甲基橙的水溶液中，并进行常温搅拌，每隔1 h对其进行吸光度测试，直至吸光度保持不变，并通过标准曲线，确定吸附后各种染料的残余浓度，通过计算，得到其吸附曲线图。
图3为加入DP5G后各种染料随时间的紫外-可见光谱。由图3可以看出，在加入DP5G后，结晶紫（a）与罗丹明 B（b）溶液的吸光度，随着时间的变化下降非常明显；而甲基蓝（c）与甲基橙（d）溶液的吸光度的变化明显比上述两种染料的变化小。
图4为超分子聚合物干凝胶DP5G对各种染料的吸附曲线图。从图4可知，30 min后结晶紫（a）与罗丹明 B（b）的去除率已达50%以上，而甲基蓝（c）与甲基橙（d）的去除效果只有30%。吸附达到平衡以后，结晶紫与罗丹明 B的去除率达95% 以上，而甲基蓝去除率不足75%、甲基橙的去除率只有35%。因此，超分子聚合物网状凝胶DP5G能够实现对阳离子染料的高效去除。
图5为超分子聚合物干凝胶DP5G与结晶紫的核磁滴定图。其中a是DP5G，b~d是含有不同当量的结晶紫；e是结晶紫。从图5中可以看出，超分子聚合物干凝胶DP5G与结晶紫上的质子峰均有移动，说明它们之间发生了作用，进行了高效的吸附。罗丹明 B与结晶紫为同一类染料，结构相似，其吸附机理相同。
附图说明
图1为DP5与SZ的部分核磁滴定图。
图2为DP5、SZ和DP5G的扫描电镜图。
图3为加入DP5G后各种染料随时间的紫外-可见光谱。
图4为DP5G对各种染料的吸附曲线图。
图5为DP5G与结晶紫的部分核磁滴定图。
具体实施方式
下面通过具体实施例对本发明超分子聚合物网状凝胶的制备和应用做进一步说明。
1、主体化合物的DP5的合成
（1）单边四个碳的巯基乙酰肼柱[5]芳烃SP5J的合成：见文献J. Liu, Y. Q. Fan, S.S. Song, G. F. Gong, J. Wang, X. W. Guan, H. Yao, Y. M. Zhang, T. B. Wei, andQ. Lin. ACS Sustainable Chem. Eng., 2019, 7(14): 11999-12007。SP5J的结构式如下：
（2）DP5的合成：在30mL无水乙醇中加入0.4934g（0.55mmol）SP5J，3滴冰醋酸和0.0336g（0.25mmol）对苯二甲醛，在80~85℃下搅拌回流12小时后静置并冷却至室温，此时有大量浅黄色固体析出，抽滤，用冷的无水乙醇淋洗后得到浅黄色粉末状固体0.3850g，产率为82%，熔点为130℃~133℃。
2、SZ的合成：参见文献方法：X. Z. Luo, X. J. Jia, J. H. Deng, J. L.Zhong, H. J. Liu, K. J. Wang and D. C. Zhong, J. Am. Chem. Soc., 2013, 135(32): 11684-11687。
3、超分子聚合物凝胶（DP5G）的制备：在80 μL DMSO和20μL H2O的混合体系中，加入主体化合物DP5（0.01g，5.3×10-6mol），客体化合物SZ（0.0023g，5.3×10-6mol），加热使其完全溶解，再冷却至室温，得到稳定的超分子聚合物凝胶DP5G。将上述凝胶加热溶解形成溶胶，置于玻璃板上进行冷冻干燥12h得到干凝胶。
4、超分子聚合物凝胶（DP5G）的对阳染料结晶紫和罗丹明 B的高效去除
将0.002g干凝胶加入到5 mL2.5×10-5 mol/L的结晶紫、罗丹明 B、甲基蓝和甲基橙的水溶液中，并进行常温搅拌，每隔1 h对其进行吸光度测试，直至吸光度保持不变。测得干凝胶DP5G对结晶紫的去除率达96.3%，对罗丹明 B的去除率达95.4%。

Claims (6)

1.一种主客体络合的超分子聚合物网状凝胶，是以巯基乙酰腙功能化双柱[5]芳烃为主体化合物，4-氨基吡啶修饰的三足化合物为客体化合物，加热溶解在DMSO/H2O的混合溶剂中，通过主客体相互作用络合成超分子聚合物凝胶；超分子聚合物凝胶经冷冻干燥得到干凝胶；
主体化合物巯基乙酰腙功能化双柱[5]芳烃的结构式如下：
客体化合物4-氨基吡啶修饰的三足化合物的结构式如下：
。
2.如权利要求1所述主客体络合的超分子聚合物网状凝胶，其特征在于：主体化合物巯基乙酰腙功能化双柱[5]芳烃与客体化合物4-氨基吡啶修饰的三足化合物的摩尔比为1:1~1:1.2。
3.如权利要求1所述主客体络合的超分子聚合物网状凝胶，其特征在于：DMSO/H2O的混合溶剂中，DMSO与H2O的体积比为5:1~2:1。
4.如权利要求1所述主客体络合的超分子聚合物网状凝胶，其特征在于：DMSO/H2O的混合溶剂中，主客体的含量为0.12~0.14 g/mL。
5.如权利要求1所述主客体络合的超分子聚合物网状凝胶用于去除水溶液中的有机染料。
6.如权利要求4所述主客体络合的超分子聚合物网状凝胶用于去除水溶液中的有机染料，其特征在于：有机染料为结晶紫、罗丹明 B。
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