有序介孔金属有机膦酸盐和磺酸盐材料的合成与应用
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摘要
随着当今现代化社会的高速发展,环境污染和能源危机已经成为全人类面临的两大最严重的问题。为了解决这两个问题,开发可持续的绿色能源受到越来越多的关注。其中,研发多功能的先进能源材料处于核心位置,因为这种材料能减少有害物质的排放,有利于清洁生产,而且能提供稳定的能源供给。在众多先进能源材料之中,具有介孔结构的有机-无机杂化材料由于其环境友好性以及多功能性成为世界科研工作者的研究热点。杂化介孔材料中的有机和无机组分不是简单的物理混合,而是在分子尺度上的融合,其优点在于其骨架中均匀分布着有机官能团,可以对其密度、化学性能、稳定性等进行调控。由于同时结合了无机、有机组分的不同性质,杂化介孔材料在吸附与分离、催化、离子交换、光电转化等方面表现出许多潜在的应用价值。
有序介孔有机硅杂化材料(PMOs)无疑是研究最早且研究最多的杂化介孔材料,这种材料的合成通常都是采用有机硅烷作为前驱体,其主要缺点是反应原料不易得,有机硅烷种类有限而且价格昂贵等。于是对于杂化介孔材料的研究逐渐向非硅基材料发展,其中最重要的代表是介孔金属有机膦酸盐材料。合成膦酸盐所需有机前驱体主要为有机多聚膦酸及其相应的盐和酯类化合物,这些有机分子种类繁多,并且来源丰富。一些合成中常用的有机膦酸螯合分子,例如羟基亚乙基二膦酸(HEDP),氨基三亚甲基膦酸(ATMP),乙二胺四亚甲基膦酸(EDTMP)和二乙烯三胺五甲叉膦酸(DTPMP)是常用自来水管道清洁剂的主要成分,价格十分低廉。
但是目前针对介孔金属有机膦酸盐的研究仍然存在许多问题。在不使用表面活性剂制得的无序介孔或介孔-大孔膦酸盐中,比表面积和孔容普遍较低,孔径分布不均匀,孔壁结晶度不高且热稳定性低,虽然可以利用多种有机膦酸分子进行合成,但是其应用性能仍然受到很大限制;对于使用表面活性剂诱导合成的有序介孔膦酸盐材料,目前国内外报道中都只限于膦酸铝,并且所用膦酸为简单的烷基桥连二磷酸,官能团少,功能性弱;对于有序介孔磺酸盐的报道几乎没有。所以本文旨在合成和应用具有高比表面积和孔容,规则有序介孔孔道,高热稳定性和丰富表面官能团的金属膦酸盐和磺酸盐材料。具体内容分为如下四点：
1.介孔结构调控。通过结合高压反应釜水热方法和溶剂挥发诱导自组装方法制备出具有有序六方介孔结构的有机膦酸钛材料。有机基团均匀地掺杂进入了杂化骨架中,其热稳定可以达到450℃。该材料对重金属离子有很高的吸附容量和一定的选择吸附性；光催化活性高于商品化的二氧化钛光催化剂,并且在重金属离子存在下进一步增强。本文首次报道了具有立方相有序介孔结构的金属有机膦酸钛材料,在合成中使用了阳离子表面活性剂十六烷基三甲基溴化铵作为模板,所得到的立方相介孔膦酸盐材料同样在吸附和光催化等方面表现出多功能性。具有不同介孔结构的有机膦酸钛材料可以在保持其它合成条件不变的情况下,通过简单地改变反应物和表面活性剂的加入量而得到,这将对设计合成其它杂化介孔材料具有重要的指导意义;
2.后修饰。HEDP螫合分子中特殊的碳羟基基团使得金属膦酸盐很容易与CISO3H发生硫酸酯化作用,从而实现介孔膦酸盐材料的进一步功能化。硫酸酯化后的材料不但具有较高的离子交换容量,可以作为一种有效的离子交换剂；而且是一种强酸性催化剂,可以用于某些在室温或低温条件下进行的反应,如常见的酯化反应等。另外,这种有机-无机杂化膦酸盐可以很容易地塑造成不同的块体形状,对于用作一些纳米器件或今后可能的工业应用有很大意义。鉴于某些金属膦酸盐材料骨架中含有丰富的类乙二胺基团,Cu2+离子首先与乙二胺基团配位,服从单层吸附的规律,经过焙烧后Cu2+离子转化为相应的CuO纳米粒子,高度分散在膦酸盐载体表面。通过这种先吸附再焙烧的方法制备的负载有高分散CuO纳米粒子的催化剂被用作CO催化氧化反应,相对于使用传统浸渍方法制备的无机载体负载的CuO催化剂,膦酸盐催化活性明显提高；
3.提高孔壁结晶度。通过微波辅助结晶的方法合成了一系列具有微孔-介孔分级孔结构的金属膦酸盐材料,这是非硅基介孔有机-无机介孔膦酸盐中首例具有结晶孔墙的材料。材料中的介孔是以非离子嵌段共聚物F127为模板形成的,而微孔是由金属膦酸盐晶粒相互堆积而成。有机膦酸基团均匀地分布在杂化介孔材料的骨架中,热稳定性可以达到约450℃。这类合成的膦酸盐材料可以被用作开管毛细管电泳技术中的固定相,分离多种芳香酸、酸性植物激素、碱性化合物和中性稠环芳烃,分离效率高并且分析时间短；
4.介孔有机磺酸盐。在嵌段共聚物表面活性剂诱导自组装的条件下,通过一种简单的水热合成方法,制备出具有六方有序介孔结构的金属有机磺酸盐材料。酞菁铜结构均匀的分布在有机-无机杂化骨架中。酞菁铜染料分子被无机二氧化钛组分有效地分离开来,避免了染料分子之间的自淬灭现象。所合成的材料是一种含有双金属的大共轭结构,这一结构对于光电转化应用有很大价值。这种杂化介孔材料可以被用作有效的电极材料,在模拟太阳光照射下表现出较高的光电转化效率。使用冠醚辅助合成孔壁结晶的六方介孔磺酸盐,萘二磺酸等多种有机二磺酸配体可以用作螯合分子,这是目前少数有报道的表面活性剂诱导形成的介孔金属-有机骨架材料之一。其热稳定高,对不同客体分子的吸附也表现出较高稳定性。
Environmental pollution and energy crisis have become two of the most serious problems with the rapid development of the modern society. In response to those petroleum crisis and environmental problems, the principles of green energy and sustainable living movements gain popularity. Development of multifunctional and advanced energy materials is essential for alternative and renewable sources, reducing emission of harmful substances, clean production, as well as attaining stable energy provision. Chemically designed mesoporous organic-inorganic hybrid solids are considered to be promising candidates for environmentally friendly materials with multifunctionality, which have attracted much attention because of the combination of superior properties due to the organic and the inorganic components.They are not just physical mixtures of organic and inorganic moieties, but considered as nanocomposites with organic and inorganic components that are intimately mixed on a molecular level. The incorporation of mesoporosity with extra large surface area, pore size and pore volume could contribute to the enhanced performances in gas storage, catalyst supporting and macromolecule adsorption.
Periodic mesoporous organosilicas (PMOs), which contain organic groups in siloxane bridges of the silica framework, were the most widely investigated. However, besides the limited choices and the high cost of the organosiloxane, the functions of silica are limited to physical properties concerned with catalytic supports and adsorbents. Thus, the preparation of porous hybrid materials was further extended to non-silica-based organic-inorganic hybrid mesoporous materials, in which the metal phosphonate mesoporous materials are one of the important families. Organophosphorus acids and their derivatives (salts, esters) are quite complementary of organosilicon coupling molecules for the preparation of mesoporous hybrid organic-inorganic materials by sol-gel processing or surface modification, because of their low cost and great variety. Noticeably, some polyphosphonic acids are of very wide sources and low cost, which·have already been used as the main components in industrial detergents, such as1-hydroxy ethylidene-1,1-diphosphonic acid (HEDP), amino tri(methylene phosphonic acid)(ATMP), ethylenediamine tetra(methylene phosphonic acid)(EDTMP) and diethylenetriamine penta(methylene phosphonic acid)(DTPMP).
However, the reported mesoporous metal phosphonate materials still suffer from poorly structured mesopores with low surface area and pore volume, low crystallinity and stability, etc. There are some examples of ordered mesoporous aluminum phosphonates, which were prepared only by alkyl bridged diphosphonates. The ordered mesoporous metal sulfonates were scarcely reported. Therefore, it is important and challenge for the synthesis and application of ordered metal phosphonates and sulfonates with various organic functional groups and metal centers. The following results and conclusions have been obtained in this dissertation:
1. Mesostructure adjustment. Hexagonal mesoporous titanium phosphonate materials were synthesized by an autoclaving process combined with the evaporation-induced self-assembly (EISA) strategy, with the assistance of surfactant Brij56(C16EO10). EDTMP was used as the coupling molecule. The organophosphonate groups were homogeneously incorporated in the network of the mesoporous solids. The obtained materials were thermally stable up to450℃. The hybrid materials could be used as not only efficient adsorbents for heavy metal ions in the water but also as outstanding photocatalysts. By changing the molar ratios of adding raw materials, namely, Ti/P molar ratio and CTAB/Ti molar ratio, cubic mesoporous titanium phosphonates could also be synthesized, which exhibited multifunctionality in photocatalysis and adsorption;
2. Post-treatments. Ordered mesoporous titanium phosphonates were prepared using HEDP as the anchoring molecule. The alkyl hydroxyl groups of HEDP made it possible for the further functionalization by ClSO3H treatment. The modified materials acted not only an ion exchanger with large ion exchange capacity but also a strong acid catalyst possible for some room-temperature reactions. Moreover, the organic-inorganic hybrids were proved to be molded and incised into various shapes facilely, making them practical materials for industrial scale manufacture. The homogeneous integrity of organic groups inside the hybrid framework also allowed Cu2+ions extensively coordinated with these organic ligands. And further calcination of the Cu2+ion-dispersed matrix resulted in the highly dispersed CuO active components on the pore surface of mesoporous titanium phosphonates, making them promising catalysts for low-temperature CO oxidation;
3. Crystalline mesopore walls. Ordered hexagonal mesoporous metal (Ti, Zr, V, Al) phosphonate materials with microporous crystalline walls were synthesized through a microwave assisted procedure by using triblock copolymer F127as the template. Corresponding metal chlorides and EDTMP were chosen as the inorganic precursors and the coupling molecule, respectively. The metal phosphonate materials could be thermally stable up to around450℃with the pore structure and hybrid framework well preserved. For the first time, the mesoporous hybrid materials were employed as the stationary phase in open tubular capillary electrochromatography (OTCEC) technique for the separation of various substances including acidic, basic and neutral compounds, showing good selectivity and reproducibility;
4. Mesoporous sulfonates. Ordered hexagonal mesoporous titanium tetrasulfonate materials were synthesized through a hydrothermal process with the assistance of surfactant F127, by using the copper(II) phthalocyanine-tetrasulfonic acid tetrasodium salt (CuPcS4) as coupling molecules. A novel model of isolated dye centers surrounded by semiconductor oligomers was set, which could effectively suppress the aggregation of dye molecules. The synthesized materials exhibited a photoelectric conversion efficiency of0.53%. Ordered mesoporous metal-organic frameworks were prepared by a bottom-up strategy through the simple self-assembly of metal sulfonate ligands, metal ions and block coplymer template F127, with the aid of crown ether to control the coordination rate between metal ions and sulfonate ligands. The synthesized materials have high stability upon thermal treatment to300℃and guest molecule adsorption.
有序介孔有机硅杂化材料(PMOs)无疑是研究最早且研究最多的杂化介孔材料,这种材料的合成通常都是采用有机硅烷作为前驱体,其主要缺点是反应原料不易得,有机硅烷种类有限而且价格昂贵等。于是对于杂化介孔材料的研究逐渐向非硅基材料发展,其中最重要的代表是介孔金属有机膦酸盐材料。合成膦酸盐所需有机前驱体主要为有机多聚膦酸及其相应的盐和酯类化合物,这些有机分子种类繁多,并且来源丰富。一些合成中常用的有机膦酸螯合分子,例如羟基亚乙基二膦酸(HEDP),氨基三亚甲基膦酸(ATMP),乙二胺四亚甲基膦酸(EDTMP)和二乙烯三胺五甲叉膦酸(DTPMP)是常用自来水管道清洁剂的主要成分,价格十分低廉。
但是目前针对介孔金属有机膦酸盐的研究仍然存在许多问题。在不使用表面活性剂制得的无序介孔或介孔-大孔膦酸盐中,比表面积和孔容普遍较低,孔径分布不均匀,孔壁结晶度不高且热稳定性低,虽然可以利用多种有机膦酸分子进行合成,但是其应用性能仍然受到很大限制;对于使用表面活性剂诱导合成的有序介孔膦酸盐材料,目前国内外报道中都只限于膦酸铝,并且所用膦酸为简单的烷基桥连二磷酸,官能团少,功能性弱;对于有序介孔磺酸盐的报道几乎没有。所以本文旨在合成和应用具有高比表面积和孔容,规则有序介孔孔道,高热稳定性和丰富表面官能团的金属膦酸盐和磺酸盐材料。具体内容分为如下四点：
1.介孔结构调控。通过结合高压反应釜水热方法和溶剂挥发诱导自组装方法制备出具有有序六方介孔结构的有机膦酸钛材料。有机基团均匀地掺杂进入了杂化骨架中,其热稳定可以达到450℃。该材料对重金属离子有很高的吸附容量和一定的选择吸附性；光催化活性高于商品化的二氧化钛光催化剂,并且在重金属离子存在下进一步增强。本文首次报道了具有立方相有序介孔结构的金属有机膦酸钛材料,在合成中使用了阳离子表面活性剂十六烷基三甲基溴化铵作为模板,所得到的立方相介孔膦酸盐材料同样在吸附和光催化等方面表现出多功能性。具有不同介孔结构的有机膦酸钛材料可以在保持其它合成条件不变的情况下,通过简单地改变反应物和表面活性剂的加入量而得到,这将对设计合成其它杂化介孔材料具有重要的指导意义;
2.后修饰。HEDP螫合分子中特殊的碳羟基基团使得金属膦酸盐很容易与CISO3H发生硫酸酯化作用,从而实现介孔膦酸盐材料的进一步功能化。硫酸酯化后的材料不但具有较高的离子交换容量,可以作为一种有效的离子交换剂；而且是一种强酸性催化剂,可以用于某些在室温或低温条件下进行的反应,如常见的酯化反应等。另外,这种有机-无机杂化膦酸盐可以很容易地塑造成不同的块体形状,对于用作一些纳米器件或今后可能的工业应用有很大意义。鉴于某些金属膦酸盐材料骨架中含有丰富的类乙二胺基团,Cu2+离子首先与乙二胺基团配位,服从单层吸附的规律,经过焙烧后Cu2+离子转化为相应的CuO纳米粒子,高度分散在膦酸盐载体表面。通过这种先吸附再焙烧的方法制备的负载有高分散CuO纳米粒子的催化剂被用作CO催化氧化反应,相对于使用传统浸渍方法制备的无机载体负载的CuO催化剂,膦酸盐催化活性明显提高；
3.提高孔壁结晶度。通过微波辅助结晶的方法合成了一系列具有微孔-介孔分级孔结构的金属膦酸盐材料,这是非硅基介孔有机-无机介孔膦酸盐中首例具有结晶孔墙的材料。材料中的介孔是以非离子嵌段共聚物F127为模板形成的,而微孔是由金属膦酸盐晶粒相互堆积而成。有机膦酸基团均匀地分布在杂化介孔材料的骨架中,热稳定性可以达到约450℃。这类合成的膦酸盐材料可以被用作开管毛细管电泳技术中的固定相,分离多种芳香酸、酸性植物激素、碱性化合物和中性稠环芳烃,分离效率高并且分析时间短；
4.介孔有机磺酸盐。在嵌段共聚物表面活性剂诱导自组装的条件下,通过一种简单的水热合成方法,制备出具有六方有序介孔结构的金属有机磺酸盐材料。酞菁铜结构均匀的分布在有机-无机杂化骨架中。酞菁铜染料分子被无机二氧化钛组分有效地分离开来,避免了染料分子之间的自淬灭现象。所合成的材料是一种含有双金属的大共轭结构,这一结构对于光电转化应用有很大价值。这种杂化介孔材料可以被用作有效的电极材料,在模拟太阳光照射下表现出较高的光电转化效率。使用冠醚辅助合成孔壁结晶的六方介孔磺酸盐,萘二磺酸等多种有机二磺酸配体可以用作螯合分子,这是目前少数有报道的表面活性剂诱导形成的介孔金属-有机骨架材料之一。其热稳定高,对不同客体分子的吸附也表现出较高稳定性。
Environmental pollution and energy crisis have become two of the most serious problems with the rapid development of the modern society. In response to those petroleum crisis and environmental problems, the principles of green energy and sustainable living movements gain popularity. Development of multifunctional and advanced energy materials is essential for alternative and renewable sources, reducing emission of harmful substances, clean production, as well as attaining stable energy provision. Chemically designed mesoporous organic-inorganic hybrid solids are considered to be promising candidates for environmentally friendly materials with multifunctionality, which have attracted much attention because of the combination of superior properties due to the organic and the inorganic components.They are not just physical mixtures of organic and inorganic moieties, but considered as nanocomposites with organic and inorganic components that are intimately mixed on a molecular level. The incorporation of mesoporosity with extra large surface area, pore size and pore volume could contribute to the enhanced performances in gas storage, catalyst supporting and macromolecule adsorption.
Periodic mesoporous organosilicas (PMOs), which contain organic groups in siloxane bridges of the silica framework, were the most widely investigated. However, besides the limited choices and the high cost of the organosiloxane, the functions of silica are limited to physical properties concerned with catalytic supports and adsorbents. Thus, the preparation of porous hybrid materials was further extended to non-silica-based organic-inorganic hybrid mesoporous materials, in which the metal phosphonate mesoporous materials are one of the important families. Organophosphorus acids and their derivatives (salts, esters) are quite complementary of organosilicon coupling molecules for the preparation of mesoporous hybrid organic-inorganic materials by sol-gel processing or surface modification, because of their low cost and great variety. Noticeably, some polyphosphonic acids are of very wide sources and low cost, which·have already been used as the main components in industrial detergents, such as1-hydroxy ethylidene-1,1-diphosphonic acid (HEDP), amino tri(methylene phosphonic acid)(ATMP), ethylenediamine tetra(methylene phosphonic acid)(EDTMP) and diethylenetriamine penta(methylene phosphonic acid)(DTPMP).
However, the reported mesoporous metal phosphonate materials still suffer from poorly structured mesopores with low surface area and pore volume, low crystallinity and stability, etc. There are some examples of ordered mesoporous aluminum phosphonates, which were prepared only by alkyl bridged diphosphonates. The ordered mesoporous metal sulfonates were scarcely reported. Therefore, it is important and challenge for the synthesis and application of ordered metal phosphonates and sulfonates with various organic functional groups and metal centers. The following results and conclusions have been obtained in this dissertation:
1. Mesostructure adjustment. Hexagonal mesoporous titanium phosphonate materials were synthesized by an autoclaving process combined with the evaporation-induced self-assembly (EISA) strategy, with the assistance of surfactant Brij56(C16EO10). EDTMP was used as the coupling molecule. The organophosphonate groups were homogeneously incorporated in the network of the mesoporous solids. The obtained materials were thermally stable up to450℃. The hybrid materials could be used as not only efficient adsorbents for heavy metal ions in the water but also as outstanding photocatalysts. By changing the molar ratios of adding raw materials, namely, Ti/P molar ratio and CTAB/Ti molar ratio, cubic mesoporous titanium phosphonates could also be synthesized, which exhibited multifunctionality in photocatalysis and adsorption;
2. Post-treatments. Ordered mesoporous titanium phosphonates were prepared using HEDP as the anchoring molecule. The alkyl hydroxyl groups of HEDP made it possible for the further functionalization by ClSO3H treatment. The modified materials acted not only an ion exchanger with large ion exchange capacity but also a strong acid catalyst possible for some room-temperature reactions. Moreover, the organic-inorganic hybrids were proved to be molded and incised into various shapes facilely, making them practical materials for industrial scale manufacture. The homogeneous integrity of organic groups inside the hybrid framework also allowed Cu2+ions extensively coordinated with these organic ligands. And further calcination of the Cu2+ion-dispersed matrix resulted in the highly dispersed CuO active components on the pore surface of mesoporous titanium phosphonates, making them promising catalysts for low-temperature CO oxidation;
3. Crystalline mesopore walls. Ordered hexagonal mesoporous metal (Ti, Zr, V, Al) phosphonate materials with microporous crystalline walls were synthesized through a microwave assisted procedure by using triblock copolymer F127as the template. Corresponding metal chlorides and EDTMP were chosen as the inorganic precursors and the coupling molecule, respectively. The metal phosphonate materials could be thermally stable up to around450℃with the pore structure and hybrid framework well preserved. For the first time, the mesoporous hybrid materials were employed as the stationary phase in open tubular capillary electrochromatography (OTCEC) technique for the separation of various substances including acidic, basic and neutral compounds, showing good selectivity and reproducibility;
4. Mesoporous sulfonates. Ordered hexagonal mesoporous titanium tetrasulfonate materials were synthesized through a hydrothermal process with the assistance of surfactant F127, by using the copper(II) phthalocyanine-tetrasulfonic acid tetrasodium salt (CuPcS4) as coupling molecules. A novel model of isolated dye centers surrounded by semiconductor oligomers was set, which could effectively suppress the aggregation of dye molecules. The synthesized materials exhibited a photoelectric conversion efficiency of0.53%. Ordered mesoporous metal-organic frameworks were prepared by a bottom-up strategy through the simple self-assembly of metal sulfonate ligands, metal ions and block coplymer template F127, with the aid of crown ether to control the coordination rate between metal ions and sulfonate ligands. The synthesized materials have high stability upon thermal treatment to300℃and guest molecule adsorption.
引文
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