胍、胍盐离子液体的合成及其在催化和阴离子交换膜中的应用
摘要
离子液体（IL）是一种绿色环保的有机液态物质，从Hurley等人的首次发现到Robert Ostyoung等人将其用于电化学和光化学领域，人们对离子液体的研究逐渐深入。离子液体具有较低的蒸汽压、较宽的电化学稳定电位窗口、良好的热力学和化学稳定性以及可调的物理化学性能等优点。随着离子液体的发展，现在人们也把一些含有离子基团的高分子聚合物称为聚离子液体（PIL），并且对其在催化、纳米科学、电化学组件、气体储存和分离等领域的应用做了深入的研究。
近年来，离子液体、聚离子液体及其相关技术得到了迅速发展，人们对其在催化和电化学组件等领域中的应用研究也越来越深入。其中，胍、胍盐离子液体由于其自身结构的特点，表现出了优异和独特的物理化学性质。例如：五烷基胍具有很强的碱性，可以和多种过渡金属配位。因此，我们主要研究了胍、胍盐离子液体在催化和阴离子交换膜中的应用。希望通过简单的合成方法制备具有催化活性高、绿色环保的催化剂配体及具有优异性能的阴离子交换膜材料，总结规律，探索原理。具体内容如下：
首先评述了离子液体的发展和研究概况；然后介绍了离子液体在有机催化领域中的应用；最后着重介绍了聚离子液体的合成及其在催化、纳米技术、气体储存和分离以及电化学组件领域中的应用。
我们合成了一系列芳烃胍化合物，作为配体用于钯催化的Suzuki偶联反应。研究了不同结构配体的催化活性、催化剂用量、反应时间、溶剂和碱等因素对反应的影响，找到了该催化体系最优化的反应条件，研究了该催化体系对Suzuki偶联反应底物的普适性。实验结果表明，所合成的芳烃胍是Suzuki偶联反应良好的配体，并且随着配体供电子效应和位阻效应的增强，配体的催化活性逐渐增强。该催化体系的反应条件温和，催化产率高，适用于多种官能团的反应底物，为无膦催化体系的研究提供了新的方法。除此之外，该反应体系的催化剂用量少，可以在空气和水相中进行，有利于Suzuki偶联反应在大规模工业生产中的应用。
通过简单的合成方法，制备了三溴代的胍盐单体，通过Suzuki偶联反应成功的制备了含有胍盐离子基团的交联网络聚合物。研究了引入胍盐离子基团对微孔聚合物材料的孔结构、气体储存和分离性能的影响。实验结果表明，胍盐离子基团的引入可以有效的提高聚合物材料的二氧化碳吸附和二氧化碳/氮气的选择性。我们还通过离子交换的方法将过渡金属钯固载到了微孔聚合物上，制备了非均相钯催化剂，研究了其对Suzuki偶联反应的催化活性和催化剂的回收情况。实验结果表明，该催化剂对于碘代芳烃、溴代芳烃及活化氯代芳烃的Suzuki偶联反应具有很好的催化活性，催化产率在95%以上。催化剂循环使用5次后催化剂的催化活性未见明显下降。
以廉价的4-4′-联苯二酚和二氯二苯砜反应制备的工程塑料聚芳醚砜作为聚合物骨架，通过传统的氯甲基化反应，定量的将胍盐离子基团引入到聚合物中，成功的制备了一系列胍盐聚芳醚砜阴离子交换膜材料。对所得聚合物薄膜的热稳定性、机械性能、吸水率、尺寸变化、离子传导率和碱稳定性做了详细的研究和分析。实验结果表明，胍盐离子基团的结构对膜的性能有很大的影响。烷烃胍盐型聚芳醚砜阴离子交换膜具有较高的导电率，并且随着烷基链的增长，导电率和碱稳定性都有所下降；芳烃胍盐型的膜具有较好的碱稳定性和机械性能，在室温条件下的导电率保持在10-2以上。以上实验结果在一定程度上表明了胍盐型聚芳醚砜阴离子交换膜在碱性燃料电池的应用中具有很大的潜能。
进一步完善了之前的工作，制备了一系列不同胍盐含量的直链型聚芳醚砜阴离子交换膜。然后通过控制五甲基胍与氯甲基化聚芳醚砜的投料比，精确的保留了一定量的苄基氯用于四甲基胍的化学交联，制备了交联型胍盐聚芳醚砜阴离子交换膜。对比了两种类型膜的机械性能、吸水率、尺寸变化、离子导电率和甲醇透过率。实验结果表明，通过该方法得到的交联型胍盐聚芳醚砜阴离子交换膜，即使在高的IEC值条件下，依然可以保持合适的吸水率与尺寸变化，同时离子导电率也得到一定的提高，接近于商业化的质子交换膜Nafion，而甲醇透过率远远低于Nafion。因此，我们开发了一条制备交联型胍盐聚芳醚砜阴离子交换膜的新方法。
Ionic liquids (ILs) are generally defined as organic/inorganic salts with a meltingpoint lower than100oC. The advantages of ILs include good thermal and chemicalstability, negligible vapour pressure, high ionic conductivity, designedphysico-chemical properties, etc. Interestingly, functionalizationed polymers with ILsgroups, which were also named in the scientific literature as poly(ionic liquid)s (PILs),have been pursued as a way of developing a new class of polyelectrolytes.
In recent years, ILs, PILs and their related technologies been have found manyapplications in catalytic and electrochemical devices. Guanidine and guanidine saltionic liquid exhibit excellent physical and chemical properties, due to thecharacteristics of their structures. Our main work focused on the application ofguanidine and guanidine salt ionic liquids in catalytic and conductive polymermembranes.
The aim of the present thesis is the design and synthesis of catalyst andconductive polymer membrane with superior performance by simple processes.Furthermore, we not only developed simple and rapid synthetic routes andsummarized its mechanism, but also explored them application in the field ofcatalytic, gas capture, gas separation and anion exchange membrane. The specificcontents are as follows:
1. The development, synthesis and application of ILs and PILs were reviewed.
2. Four kinds of alyl-guanidine (AG) were synthesized and used for thepalladium-catalyzed Suzuki cross-coupling reaction to test the catalytic activity. The influence of the solvent and base were also researched to obtain the optimal reactionconditions. AG4with steric bulk shows the best performance for palladium-catalyzedSuzuki cross-coupling reaction, and this catalytic system could tolerate a broad rangeof functional groups under mild reaction conditions. Results from these studiesindicated that AG acted as a ligand to stabilize the Pd species in Suzukicross-coupling reaction, and gave high yields of coupling products. Moreover, thesereactions can be performed in air condition without any special experimentalprecautions, rendering this method highly attractive for large-scale synthesis.
3. Quaternary guanidine group functionalized networks were designed andsynthesized by Pd-catalyzed Suzuki cross-coupling reaction. The porosity of thesepolymers were determined by nitrogen adsorption-desorption isotherms, whichindicated that PON-G-2was microporous with1028m2g-1BET surface area and1.9nm pore size. Moreover, Gas (CO2and N2) adsorption isotherms show their CO2storage was79mg g-1and98mg g-1respectively. Pd nanoparticles supported on thePON-G-2was also prepared by ionic exchange, which exhibits high catalytic activityfor Suzuki cross-coupling reaction between aryl bromide and phenylboronic acid(Yield>95%). Last but not the least, there was no apparent activity decrease after thecatalyst was recycled five times.
4. Poly(arylene ether sulfone)s were functionalized with quaternaryguanidinium groups in order to investigate their properties as novel polymerichydroxide exchange membrane materials. The polymers were synthesized viachloromethylation of poly(arylene ether sulfone)s, followed by reactions withpentaalkyllguanidine. PSFG1OH-1.0displayed a high ionic conductivity andPSFG5OH-1.0showed an outstanding alkaline stability in1M NaOH at60oC.
5A series of linear quaternary guanidine group functionalized poly(aryleneether sulfone)s anion exchange membrane were prepared. By controlling the feedingratio of pentamethylguanidine vs benzyl chloride groups, we can precisely preserve a certain number of benzyl chloride, which are easy to have chemical cross-linkingwith tetramethylguanidine. The resulting cross-linking anion exchange membranesenhanced the ion conductivity as holding appropriate water uptake rate and swellingrate under high IECs.
近年来，离子液体、聚离子液体及其相关技术得到了迅速发展，人们对其在催化和电化学组件等领域中的应用研究也越来越深入。其中，胍、胍盐离子液体由于其自身结构的特点，表现出了优异和独特的物理化学性质。例如：五烷基胍具有很强的碱性，可以和多种过渡金属配位。因此，我们主要研究了胍、胍盐离子液体在催化和阴离子交换膜中的应用。希望通过简单的合成方法制备具有催化活性高、绿色环保的催化剂配体及具有优异性能的阴离子交换膜材料，总结规律，探索原理。具体内容如下：
首先评述了离子液体的发展和研究概况；然后介绍了离子液体在有机催化领域中的应用；最后着重介绍了聚离子液体的合成及其在催化、纳米技术、气体储存和分离以及电化学组件领域中的应用。
我们合成了一系列芳烃胍化合物，作为配体用于钯催化的Suzuki偶联反应。研究了不同结构配体的催化活性、催化剂用量、反应时间、溶剂和碱等因素对反应的影响，找到了该催化体系最优化的反应条件，研究了该催化体系对Suzuki偶联反应底物的普适性。实验结果表明，所合成的芳烃胍是Suzuki偶联反应良好的配体，并且随着配体供电子效应和位阻效应的增强，配体的催化活性逐渐增强。该催化体系的反应条件温和，催化产率高，适用于多种官能团的反应底物，为无膦催化体系的研究提供了新的方法。除此之外，该反应体系的催化剂用量少，可以在空气和水相中进行，有利于Suzuki偶联反应在大规模工业生产中的应用。
通过简单的合成方法，制备了三溴代的胍盐单体，通过Suzuki偶联反应成功的制备了含有胍盐离子基团的交联网络聚合物。研究了引入胍盐离子基团对微孔聚合物材料的孔结构、气体储存和分离性能的影响。实验结果表明，胍盐离子基团的引入可以有效的提高聚合物材料的二氧化碳吸附和二氧化碳/氮气的选择性。我们还通过离子交换的方法将过渡金属钯固载到了微孔聚合物上，制备了非均相钯催化剂，研究了其对Suzuki偶联反应的催化活性和催化剂的回收情况。实验结果表明，该催化剂对于碘代芳烃、溴代芳烃及活化氯代芳烃的Suzuki偶联反应具有很好的催化活性，催化产率在95%以上。催化剂循环使用5次后催化剂的催化活性未见明显下降。
以廉价的4-4′-联苯二酚和二氯二苯砜反应制备的工程塑料聚芳醚砜作为聚合物骨架，通过传统的氯甲基化反应，定量的将胍盐离子基团引入到聚合物中，成功的制备了一系列胍盐聚芳醚砜阴离子交换膜材料。对所得聚合物薄膜的热稳定性、机械性能、吸水率、尺寸变化、离子传导率和碱稳定性做了详细的研究和分析。实验结果表明，胍盐离子基团的结构对膜的性能有很大的影响。烷烃胍盐型聚芳醚砜阴离子交换膜具有较高的导电率，并且随着烷基链的增长，导电率和碱稳定性都有所下降；芳烃胍盐型的膜具有较好的碱稳定性和机械性能，在室温条件下的导电率保持在10-2以上。以上实验结果在一定程度上表明了胍盐型聚芳醚砜阴离子交换膜在碱性燃料电池的应用中具有很大的潜能。
进一步完善了之前的工作，制备了一系列不同胍盐含量的直链型聚芳醚砜阴离子交换膜。然后通过控制五甲基胍与氯甲基化聚芳醚砜的投料比，精确的保留了一定量的苄基氯用于四甲基胍的化学交联，制备了交联型胍盐聚芳醚砜阴离子交换膜。对比了两种类型膜的机械性能、吸水率、尺寸变化、离子导电率和甲醇透过率。实验结果表明，通过该方法得到的交联型胍盐聚芳醚砜阴离子交换膜，即使在高的IEC值条件下，依然可以保持合适的吸水率与尺寸变化，同时离子导电率也得到一定的提高，接近于商业化的质子交换膜Nafion，而甲醇透过率远远低于Nafion。因此，我们开发了一条制备交联型胍盐聚芳醚砜阴离子交换膜的新方法。
Ionic liquids (ILs) are generally defined as organic/inorganic salts with a meltingpoint lower than100oC. The advantages of ILs include good thermal and chemicalstability, negligible vapour pressure, high ionic conductivity, designedphysico-chemical properties, etc. Interestingly, functionalizationed polymers with ILsgroups, which were also named in the scientific literature as poly(ionic liquid)s (PILs),have been pursued as a way of developing a new class of polyelectrolytes.
In recent years, ILs, PILs and their related technologies been have found manyapplications in catalytic and electrochemical devices. Guanidine and guanidine saltionic liquid exhibit excellent physical and chemical properties, due to thecharacteristics of their structures. Our main work focused on the application ofguanidine and guanidine salt ionic liquids in catalytic and conductive polymermembranes.
The aim of the present thesis is the design and synthesis of catalyst andconductive polymer membrane with superior performance by simple processes.Furthermore, we not only developed simple and rapid synthetic routes andsummarized its mechanism, but also explored them application in the field ofcatalytic, gas capture, gas separation and anion exchange membrane. The specificcontents are as follows:
1. The development, synthesis and application of ILs and PILs were reviewed.
2. Four kinds of alyl-guanidine (AG) were synthesized and used for thepalladium-catalyzed Suzuki cross-coupling reaction to test the catalytic activity. The influence of the solvent and base were also researched to obtain the optimal reactionconditions. AG4with steric bulk shows the best performance for palladium-catalyzedSuzuki cross-coupling reaction, and this catalytic system could tolerate a broad rangeof functional groups under mild reaction conditions. Results from these studiesindicated that AG acted as a ligand to stabilize the Pd species in Suzukicross-coupling reaction, and gave high yields of coupling products. Moreover, thesereactions can be performed in air condition without any special experimentalprecautions, rendering this method highly attractive for large-scale synthesis.
3. Quaternary guanidine group functionalized networks were designed andsynthesized by Pd-catalyzed Suzuki cross-coupling reaction. The porosity of thesepolymers were determined by nitrogen adsorption-desorption isotherms, whichindicated that PON-G-2was microporous with1028m2g-1BET surface area and1.9nm pore size. Moreover, Gas (CO2and N2) adsorption isotherms show their CO2storage was79mg g-1and98mg g-1respectively. Pd nanoparticles supported on thePON-G-2was also prepared by ionic exchange, which exhibits high catalytic activityfor Suzuki cross-coupling reaction between aryl bromide and phenylboronic acid(Yield>95%). Last but not the least, there was no apparent activity decrease after thecatalyst was recycled five times.
4. Poly(arylene ether sulfone)s were functionalized with quaternaryguanidinium groups in order to investigate their properties as novel polymerichydroxide exchange membrane materials. The polymers were synthesized viachloromethylation of poly(arylene ether sulfone)s, followed by reactions withpentaalkyllguanidine. PSFG1OH-1.0displayed a high ionic conductivity andPSFG5OH-1.0showed an outstanding alkaline stability in1M NaOH at60oC.
5A series of linear quaternary guanidine group functionalized poly(aryleneether sulfone)s anion exchange membrane were prepared. By controlling the feedingratio of pentamethylguanidine vs benzyl chloride groups, we can precisely preserve a certain number of benzyl chloride, which are easy to have chemical cross-linkingwith tetramethylguanidine. The resulting cross-linking anion exchange membranesenhanced the ion conductivity as holding appropriate water uptake rate and swellingrate under high IECs.
引文
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