新型微孔聚合物材料的制备及应用
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摘要
孔材料在分离、多相催化和气体储存等多个领域具有很好的应用前景。在过去几十年中，科学家们研究了一系列孔材料，除传统的沸石和活性炭以外，还包括金属有机网络（MOFs），多孔有机笼子（Porous Organic Cages）和微孔有机聚合物（MOPs）等孔材料。其中，MOPs具有高比表面积、低骨架密度、高化学稳定性等独特的性质，还能在孔结构中引入功能性的化学官能团，近年来引起高度关注。开发具有更高比表面积、孔尺寸可控和功能性可调的MOPs是当前研究的热点。目前面临的主要问题是，合成共轭微孔聚合物（CMPs）和其它一些MOPs需要使用过渡金属催化剂或贵金属催化剂，成本高昂，只能用于实验室规模的生产。此外，合成MOPs的单体一般需含卤素、乙炔基或立体结构（如螺环），也难以合成。因此，发展低成本、可大规模生产MOPs是一个巨大的挑战。
本博士论文的主要工作是探寻新方法，用于设计合成低成本、功能化的MOPs。新方法获得的MOPs通过氮气吸附-解吸附等温线，固体核磁技术进行表征。根据这些MOPs的特性，将其分别作为气体吸附材料、多相催化剂和有毒金属离子吸附剂，开展了不同领域的应用性研究。论文主要包括以下内容：
第一章对微孔材料的研究背景，MOPs的特点以及其在气体吸附、多相催化、分离提纯和光电等领域的应用情况进行了综述。
在二至四章中对MOPs孔径调控、合成方法进行了研究。
第二章描述了精确调控超交联聚合物（HCPs）孔尺寸和孔分布的方法，最终获得含有均匀微孔结构的HCPs。随着DVB含量从0%增加至10%，HCPs的微孔孔尺寸变小，孔分布范围变窄，微孔孔体积与总孔体积的比例从6.82%增加到61.90%。当DVB含量高于7%时，HCPs变为纯微孔聚合物。实验数据显示，更小的微孔孔尺寸和更高的微孔孔体积有助于提高H2，CO2的气体吸附量。此外，还对对二乙烯基苯（DVB）调控孔结构的机理进行了探讨。
第三章和第四章提出了两种合成低成本、功能化MOPs的新方法。第三章提出了一种新的合成策略，即使用外交联剂编织刚性芳环结构单元获得编织微孔聚合物网络（KAPs）。通过廉价的外交联剂与普通低官能度的芳香化合物发生傅-克反应，简单一步法高效地合成了高比表面积的微孔聚合物。第四章的新方法基于Scholl反应，是以Lewis酸为催化剂的两个芳香化合物的偶联反应。这种廉价的方法能引入多样的官能团或功能性结构，适用于芳环、稠环或杂环化合物，最重要的是可以合成低成本的共轭的微孔聚合物。因此，这种方法可以灵活地实现MOPs的多功能化应用，例如，作为气体吸附材料，光电材料和半导体材料。
最后在五至八章对MOPs在气体储存、催化和水处理等方面的应用进行了探讨。
第五章研制了一种新型微孔聚合物纳米颗粒。首先通过乳液聚合法制备氯甲基苯乙烯-二乙烯基苯（VBC-DVB）前体纳米颗粒，再将前体纳米颗粒傅-克超交联，最终获得微孔聚合物纳米颗粒（MPNs）。调节前体制备过程中乳化剂用量可以调控纳米颗粒尺寸，其范围为36-131nm。MPNs的BET比表面积最高为1500m2/g，储氢量为1.59wt%。与先前报道的多分散微米尺寸的类似物相比，MPNs具有更高的微孔孔体积（0.56cm3/g），更高的氢气吸附量（1.59wt.%），更高的氢气吸附热和更快的吸附速率。
第六章和第七章主要探索了MOPs在多相催化领域的应用。通过KAPs和Scholl偶联方法分别合成了含有三苯基膦官能团的两种微孔聚合物。这两种材料与PdCl2配位后，用于催化水相中芳氯的Suzuki-Miyaura偶联反应。这两种多相催化剂对于不同的芳氯、芳硼酸底物都具有很高的催化活性。而且，这两项工作说明了含有三苯基磷配体的微孔聚合物骨架能有效地分散Pd来提高催化活性，在相似的条件下催化活性高于均相催化剂。
在最后一章中，探索了MOPs在水处理领域的应用。通过磺酸基改性合成了磺化超交联微孔聚合物，作为有毒金属离子的高容量吸附剂。表征结果表明改性树脂保留了它们的有机微孔结构和球形形态，成功引入磺酸基作为亲水基团和活性点。吸附实验表明磺化超交联微孔聚合物对金属离子具有很好的吸附能力，这是由于微孔孔结构和吸附活性点的协同效应。吸附动力学数据符合准二级动力学模型，在不同温度获得的吸附等温线符合Langmuir模型。另外，热力学参数，如，吸附过程的吉布斯自由能变(△G0)，焓变(△H0)，熵变(△S0)被计算得出，结果表明吸附过程是自发的吸热过程。而且，这些改性树脂能循环使用，吸附量仅少量下降，因此具有潜在的工业应用前景。
The porous materials have diverse potential applications in separation, heterogeneouscatalysis and gas storage. During the last few decades, the surge to develop such usefulmaterials has led the scientists to produce a number of novel porous materials such asmetal organic frameworks (MOFs), porous organic cages and microporous organicpolymers (MOPs), in addition to traditional porous materials such as zeolites and activatedcarbon etc. Among these porous materials, MOPs have some unique properties such aslarge surface area, low skeletal density and high chemical stability. Very recently, aparticular advantage of MOPs has attracted enormous scientific attention due to theirpotential to introduce a range of useful chemical functionalities within the porousframework. In these years, many approaches reported have aimed to develop newmicroporous organic materials with higher surface areas, controlled pore sizes andfunctions. However, the transition metal catalysts or noble metal catalysts used forsynthesis of CMPs, PAFs and some other MOPs are expensive and only lab-scale. It isoften also complicated to synthesize the monomers which must bear halogen, ethynyl orstereocontrolled structures such as spirocyclic monomers used in MOPs. Hence, thesustainable mass production of MOPs is an unanswered challenge.
Accordingly, the main task of this PhD thesis is to explore some new versatilemethods to design and synthesize cost-effective and functional MOPs. Characterization ofthese MOPs was realized by nitrogen adsorption/desorption isotherms, solid-state NMRtechniques. Application of these MOPs as gas adsorption materials, heterogeneouscatalysts and toxic metal ion adsorbent were also exploited.
Chapter I introduce the research background on microporous materials, andhighlighted the history of MOPs and their application in gas adsorption, heterogenouscatalysts, separation and purification and photoelectric filed.
Chapter II describe the method to produce hypercrosslinked polymers (HCPs) with afair control over the pore size and the pore size distribution, and to generate polymer withuniform microporous structure eventually. The mechanism of DVB content controlling thepore structure is proposed. With the DVB content varying from0to10%, the pore size ofHCPs decreases, the pore size distribution become narrower and the micropore volumecontent increases from6.82to61.90%. When the DVB content is higher than7%, theHCPs changes to pure microporous organic polymer. The experimental data indicate that the smaller micropore size and higher microporous volume favor the H2and CO2gasadsorption.
Chapter III and Chapter IV propose two kind of new method to synthesizecost-effective and functional MOPs. One method,‘knitting’ rigid building blocks with anexternal crosslinker, use a simple one-step Friedel-Crafts reaction of a low-cost crosslinkerwith ordinary, low functionality aromatic compounds to produce cost-effectivemicroporous polymers with very high surface areas and the only byproduct was methanol.The other method is based on Scholl reaction, a coupling reaction between two arenecompounds with the aid of a Lewis acid. This low-cost method can introduce a very broadvariety of functional groups or functional structures. This method suits for aryl ring, fusering or heterocyclic ring compound, hence, using this method can functionalize MOPs inextensive field, such as gas adsorption, photoelectricity and semiconductor
Chapter V describe the synthesis of uniform “Davankov-type” microporous polymernanoparticles via emulsion polymerization method and followed by a Friedel-Crafts-typehypercrosslinking. The particles size (39-131nm) are tunable via adjusting emulsifier dose.Friedel-Crafts-type hypercrosslinking reaction of the precursor yields monodispersenanoporous polymer nanoparticles (MPNs) with extremely high surface areas up to ca.1500m2/g (BET surface area). Moreover, MPNs present more micropore volume (0.56cm3/g), higher hydrogen adsorption capacity (1.59wt.%), higher hydrogen adsorptionisosteric heats and faster adsorption rate compared to polydisperse micro-size analogpreviously reported.
In Chapter VI and VII, the two methods in Chapter III and Chapter IV are used tosynthesize two kind of MOPs with triphenylphosphine functional group respectively.These two kind functionalized MOPs coordinated with PdCl2are excellent heterogeneouscatalyst of Suzuki-Miyaura coupling reactions of aryl chlorides in aqueous media. Forvarious aryl halide and arylboronic acid, the heterogeneous catalysts all exhibit high yields.Moreover, these work demonstrate that the microporous polymer backbone knitting withphosphine ligand can efficiently disperse Pd to promote the catalytic activity, which ismuch higher than that of homogeneous catalysts under the similar conditions.
In the last Chapter, sulfonic acid-modified microporous hypercrosslinked polymerssynthesized by sulfonation of microporous hypercrosslinked polymers have beeninvestigated as a high-capacity adsorbent for toxic metal ions. The results show that themodified resins retained their original microporous structure and spherical morphology,and possess sulfonic acid groups as hydrophilic groups and active sites. Sulfonic acids-modified materials have been found to attain very good adsorption capacity formetal ions, which is due to the synergic effect of microporous structure and active sites.The kinetic data obtained from of adsorption experiments supports a pseudo-second ordermodel and adsorption isotherms obtained at different temperatures are all fitted with theLangmuir isotherms. In addition, the thermodynamic parameters, i.e. Gibbs free energychange (△G0), enthalpy change (△H0), entropy change (△S0) of the adsorption processwere calculated, and the results confirmed the adsorption to be spontaneous andendothermic. Moreover, these modified resins can be recycled several times with minimalloss of adsorption capacity and thus may have potential industrial applications.
本博士论文的主要工作是探寻新方法，用于设计合成低成本、功能化的MOPs。新方法获得的MOPs通过氮气吸附-解吸附等温线，固体核磁技术进行表征。根据这些MOPs的特性，将其分别作为气体吸附材料、多相催化剂和有毒金属离子吸附剂，开展了不同领域的应用性研究。论文主要包括以下内容：
第一章对微孔材料的研究背景，MOPs的特点以及其在气体吸附、多相催化、分离提纯和光电等领域的应用情况进行了综述。
在二至四章中对MOPs孔径调控、合成方法进行了研究。
第二章描述了精确调控超交联聚合物（HCPs）孔尺寸和孔分布的方法，最终获得含有均匀微孔结构的HCPs。随着DVB含量从0%增加至10%，HCPs的微孔孔尺寸变小，孔分布范围变窄，微孔孔体积与总孔体积的比例从6.82%增加到61.90%。当DVB含量高于7%时，HCPs变为纯微孔聚合物。实验数据显示，更小的微孔孔尺寸和更高的微孔孔体积有助于提高H2，CO2的气体吸附量。此外，还对对二乙烯基苯（DVB）调控孔结构的机理进行了探讨。
第三章和第四章提出了两种合成低成本、功能化MOPs的新方法。第三章提出了一种新的合成策略，即使用外交联剂编织刚性芳环结构单元获得编织微孔聚合物网络（KAPs）。通过廉价的外交联剂与普通低官能度的芳香化合物发生傅-克反应，简单一步法高效地合成了高比表面积的微孔聚合物。第四章的新方法基于Scholl反应，是以Lewis酸为催化剂的两个芳香化合物的偶联反应。这种廉价的方法能引入多样的官能团或功能性结构，适用于芳环、稠环或杂环化合物，最重要的是可以合成低成本的共轭的微孔聚合物。因此，这种方法可以灵活地实现MOPs的多功能化应用，例如，作为气体吸附材料，光电材料和半导体材料。
最后在五至八章对MOPs在气体储存、催化和水处理等方面的应用进行了探讨。
第五章研制了一种新型微孔聚合物纳米颗粒。首先通过乳液聚合法制备氯甲基苯乙烯-二乙烯基苯（VBC-DVB）前体纳米颗粒，再将前体纳米颗粒傅-克超交联，最终获得微孔聚合物纳米颗粒（MPNs）。调节前体制备过程中乳化剂用量可以调控纳米颗粒尺寸，其范围为36-131nm。MPNs的BET比表面积最高为1500m2/g，储氢量为1.59wt%。与先前报道的多分散微米尺寸的类似物相比，MPNs具有更高的微孔孔体积（0.56cm3/g），更高的氢气吸附量（1.59wt.%），更高的氢气吸附热和更快的吸附速率。
第六章和第七章主要探索了MOPs在多相催化领域的应用。通过KAPs和Scholl偶联方法分别合成了含有三苯基膦官能团的两种微孔聚合物。这两种材料与PdCl2配位后，用于催化水相中芳氯的Suzuki-Miyaura偶联反应。这两种多相催化剂对于不同的芳氯、芳硼酸底物都具有很高的催化活性。而且，这两项工作说明了含有三苯基磷配体的微孔聚合物骨架能有效地分散Pd来提高催化活性，在相似的条件下催化活性高于均相催化剂。
在最后一章中，探索了MOPs在水处理领域的应用。通过磺酸基改性合成了磺化超交联微孔聚合物，作为有毒金属离子的高容量吸附剂。表征结果表明改性树脂保留了它们的有机微孔结构和球形形态，成功引入磺酸基作为亲水基团和活性点。吸附实验表明磺化超交联微孔聚合物对金属离子具有很好的吸附能力，这是由于微孔孔结构和吸附活性点的协同效应。吸附动力学数据符合准二级动力学模型，在不同温度获得的吸附等温线符合Langmuir模型。另外，热力学参数，如，吸附过程的吉布斯自由能变(△G0)，焓变(△H0)，熵变(△S0)被计算得出，结果表明吸附过程是自发的吸热过程。而且，这些改性树脂能循环使用，吸附量仅少量下降，因此具有潜在的工业应用前景。
The porous materials have diverse potential applications in separation, heterogeneouscatalysis and gas storage. During the last few decades, the surge to develop such usefulmaterials has led the scientists to produce a number of novel porous materials such asmetal organic frameworks (MOFs), porous organic cages and microporous organicpolymers (MOPs), in addition to traditional porous materials such as zeolites and activatedcarbon etc. Among these porous materials, MOPs have some unique properties such aslarge surface area, low skeletal density and high chemical stability. Very recently, aparticular advantage of MOPs has attracted enormous scientific attention due to theirpotential to introduce a range of useful chemical functionalities within the porousframework. In these years, many approaches reported have aimed to develop newmicroporous organic materials with higher surface areas, controlled pore sizes andfunctions. However, the transition metal catalysts or noble metal catalysts used forsynthesis of CMPs, PAFs and some other MOPs are expensive and only lab-scale. It isoften also complicated to synthesize the monomers which must bear halogen, ethynyl orstereocontrolled structures such as spirocyclic monomers used in MOPs. Hence, thesustainable mass production of MOPs is an unanswered challenge.
Accordingly, the main task of this PhD thesis is to explore some new versatilemethods to design and synthesize cost-effective and functional MOPs. Characterization ofthese MOPs was realized by nitrogen adsorption/desorption isotherms, solid-state NMRtechniques. Application of these MOPs as gas adsorption materials, heterogeneouscatalysts and toxic metal ion adsorbent were also exploited.
Chapter I introduce the research background on microporous materials, andhighlighted the history of MOPs and their application in gas adsorption, heterogenouscatalysts, separation and purification and photoelectric filed.
Chapter II describe the method to produce hypercrosslinked polymers (HCPs) with afair control over the pore size and the pore size distribution, and to generate polymer withuniform microporous structure eventually. The mechanism of DVB content controlling thepore structure is proposed. With the DVB content varying from0to10%, the pore size ofHCPs decreases, the pore size distribution become narrower and the micropore volumecontent increases from6.82to61.90%. When the DVB content is higher than7%, theHCPs changes to pure microporous organic polymer. The experimental data indicate that the smaller micropore size and higher microporous volume favor the H2and CO2gasadsorption.
Chapter III and Chapter IV propose two kind of new method to synthesizecost-effective and functional MOPs. One method,‘knitting’ rigid building blocks with anexternal crosslinker, use a simple one-step Friedel-Crafts reaction of a low-cost crosslinkerwith ordinary, low functionality aromatic compounds to produce cost-effectivemicroporous polymers with very high surface areas and the only byproduct was methanol.The other method is based on Scholl reaction, a coupling reaction between two arenecompounds with the aid of a Lewis acid. This low-cost method can introduce a very broadvariety of functional groups or functional structures. This method suits for aryl ring, fusering or heterocyclic ring compound, hence, using this method can functionalize MOPs inextensive field, such as gas adsorption, photoelectricity and semiconductor
Chapter V describe the synthesis of uniform “Davankov-type” microporous polymernanoparticles via emulsion polymerization method and followed by a Friedel-Crafts-typehypercrosslinking. The particles size (39-131nm) are tunable via adjusting emulsifier dose.Friedel-Crafts-type hypercrosslinking reaction of the precursor yields monodispersenanoporous polymer nanoparticles (MPNs) with extremely high surface areas up to ca.1500m2/g (BET surface area). Moreover, MPNs present more micropore volume (0.56cm3/g), higher hydrogen adsorption capacity (1.59wt.%), higher hydrogen adsorptionisosteric heats and faster adsorption rate compared to polydisperse micro-size analogpreviously reported.
In Chapter VI and VII, the two methods in Chapter III and Chapter IV are used tosynthesize two kind of MOPs with triphenylphosphine functional group respectively.These two kind functionalized MOPs coordinated with PdCl2are excellent heterogeneouscatalyst of Suzuki-Miyaura coupling reactions of aryl chlorides in aqueous media. Forvarious aryl halide and arylboronic acid, the heterogeneous catalysts all exhibit high yields.Moreover, these work demonstrate that the microporous polymer backbone knitting withphosphine ligand can efficiently disperse Pd to promote the catalytic activity, which ismuch higher than that of homogeneous catalysts under the similar conditions.
In the last Chapter, sulfonic acid-modified microporous hypercrosslinked polymerssynthesized by sulfonation of microporous hypercrosslinked polymers have beeninvestigated as a high-capacity adsorbent for toxic metal ions. The results show that themodified resins retained their original microporous structure and spherical morphology,and possess sulfonic acid groups as hydrophilic groups and active sites. Sulfonic acids-modified materials have been found to attain very good adsorption capacity formetal ions, which is due to the synergic effect of microporous structure and active sites.The kinetic data obtained from of adsorption experiments supports a pseudo-second ordermodel and adsorption isotherms obtained at different temperatures are all fitted with theLangmuir isotherms. In addition, the thermodynamic parameters, i.e. Gibbs free energychange (△G0), enthalpy change (△H0), entropy change (△S0) of the adsorption processwere calculated, and the results confirmed the adsorption to be spontaneous andendothermic. Moreover, these modified resins can be recycled several times with minimalloss of adsorption capacity and thus may have potential industrial applications.
引文
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[1] McKeown, N. B. and Budd, P. M., Polymers of Intrinsic Microporosity (PIMs):Organic Materials for Membrane Separations, Heterogeneous Catalysis andHydrogen Storage, Chem. Soc. Rev.,2006,35675-683.
[2] Li, B., Su, F., Luo, H.-K., et al., Hypercrosslinked Microporous Polymer Networksfor Effective Removal of Toxic Metal Ions from Water, Microporous MesoporousMater.,2011,138(1-3):207-214.
[3] Du, X., Sun, Y., Tan, B., et al., Troger's Base-Functionalised Organic NanoporousPolymer for Heterogeneous Catalysis, Chem. Commun.,2010,46(6):970-972.
[4] Dang, D., Wu, P., He, C., et al., Homochiral Metal Organic Frameworks forHeterogeneous Asymmetric Catalysis, J. Am. Chem. Soc.,2010,132(41):14321-14323.
[5] Furukawa, H. and Yaghi, O. M., Storage of Hydrogen, Methane, and CarbonDioxide in Highly Porous Covalent Organic Frameworks for Clean EnergyApplications, J. Am. Chem. Soc.,2009,131(25):8875-8883.
[6] McKeown, N. B., Gahnem, B., Msayib, K. J., et al., Towards Polymer-BasedHydrogen Storage Materials: Engineering Ultramicroporous Cavities withinPolymers of Intrinsic Microporosity, Angew. Chem., Int. Ed.,2006,118(11):1836-1839.
[7] Wood, C. D., Tan, B., Trewin, A., et al., Microporous Organic Polymers forMethane Storage, Adv. Mater.,2008,20(10):1916-1921.
[8] Li, B., Huang, X., Liang, L., et al., Synthesis of Uniform Microporous PolymerNanoparticles and Their Applications for Hydrogen Storage, J. Mater. Chem.,2010,20(35):7444-7450.
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[1] McKeown, N. B. and Budd, P. M., Polymers of Intrinsic Microporosity (PIMs):Organic Materials for Membrane Separations, Heterogeneous Catalysis andHydrogen Storage, Chem. Soc. Rev.,2006,35(8):675-683.
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[3] Du, X., Sun, Y., Tan, B., et al., Troger's Base-Functionalised Organic NanoporousPolymer for Heterogeneous Catalysis, Chem. Commun.,2010,46(6):970-972.
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[1] McKeown, N. B. and Budd, P. M., Polymers of Intrinsic Microporosity (PIMs):Organic Materials for Membrane Separations, Heterogeneous Catalysis andHydrogen Storage, Chem. Soc. Rev.,2006,35675-683.
[2] Li, B., Su, F., Luo, H.-K., et al., Hypercrosslinked Microporous Polymer Networksfor Effective Removal of Toxic Metal Ions from Water, Microporous MesoporousMater.,2011,138(1-3):207-214.
[3] Du, X., Sun, Y., Tan, B., et al., Troger's Base-Functionalised Organic NanoporousPolymer for Heterogeneous Catalysis, Chem. Commun.,2010,46(6):970-972.
[4] Dang, D., Wu, P., He, C., et al., Homochiral Metal Organic Frameworks forHeterogeneous Asymmetric Catalysis, J. Am. Chem. Soc.,2010,132(41):14321-14323.
[5] Furukawa, H. and Yaghi, O. M., Storage of Hydrogen, Methane, and CarbonDioxide in Highly Porous Covalent Organic Frameworks for Clean EnergyApplications, J. Am. Chem. Soc.,2009,131(25):8875-8883.
[6] McKeown, N. B., Gahnem, B., Msayib, K. J., et al., Towards Polymer-BasedHydrogen Storage Materials: Engineering Ultramicroporous Cavities withinPolymers of Intrinsic Microporosity, Angew. Chem., Int. Ed.,2006,118(11):1836-1839.
[7] Wood, C. D., Tan, B., Trewin, A., et al., Microporous Organic Polymers forMethane Storage, Adv. Mater.,2008,20(10):1916-1921.
[8] Li, B., Huang, X., Liang, L., et al., Synthesis of Uniform Microporous PolymerNanoparticles and Their Applications for Hydrogen Storage, J. Mater. Chem.,2010,20(35):7444-7450.
[9] Holst, J. R. and Cooper, A. I., Ultrahigh Surface Area in Porous Solids, Adv. Mater.,2010,22(45):5212-5216.
[10] Ferey, G., Mellot-Draznieks, C., Serre, C., et al., A Chromium Terephthalate-BasedSolid with Unusually Large Pore Volumes and Surface Area, Science,2005,309(5743):2040-2042.
[11] Cote, A. P., Benin, A. I., Ockwig, N. W., et al., Porous, Crystalline, CovalentOrganic Frameworks, Science,2005,310(5751):1166-1170.
[12] El-Kaderi, H. M., Hunt, J. R., Mendoza-Cortes, J. L., et al., Designed Synthesis of3d Covalent Organic Frameworks, Science,2007,316(5822):268-272.
[13] Tozawa, T., Jones, J. T. A., Swamy, S. I., et al., Porous Organic Cages, Nat. Mater.,2009,8(12):973-978.
[14] Jiang, J.-X. and Cooper, A., in Functional Metal-Organic Frameworks: GasStorage, Separation and Catalysis, ed. M. Schr der, Springer Berlin/Heidelberg,2010, pp.1-33.
[15] Du, X., Sun, Y., Tan, B., et al., Troger's Base-Functionalised Organic NanoporousPolymer for Heterogeneous Catalysis, Chem. Commun.,2010,46(6):970-972.
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