AIE功能化介孔和层状材料的制备及其应用研究
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摘要
无机多孔材料具有规则有序的孔道结构、较大的比表面积,使其成为负载客体分子的良好载体。功能有机基团修饰的无机多孔材料融合了多孔结构和有机功能基团的双重优势,在催化、吸附、生物医学等方面均展现了优异的性能和良好的应用。具有聚集诱导发光(AIE)性质的有机分子作为一种新颖的荧光材料,自被报道以来便引起人们的广泛关注,并迅速应用于检测、细胞成像、有机光电二极管等领域。其中分子内旋转受限(RIR)是该类分子具有较强荧光的一个主要原因。因此,我们提出如果将该类分子固载到具有刚性骨架结构的无机材料中,分子的旋转将会受到抑制,产生较强的荧光。本论文的工作主要是以无机介孔材料和层状磷酸盐为研究基础,发展了通过后嫁接、共合成以及离子交换插层等方法制备AIE生色团功能化的无机有机杂化材料,并系统探索了该类材料在药物传输、化学检测、细胞成像等方面的应用。本论文的结果主要分为以下几个部分：
首次采用后嫁接的方式将AIE生色团四苯乙烯(TPE)修饰到介孔二氧化硅材料SBA-15上,并研究了其在药物传输和爆炸物检测等领域的应用。由于AIE分子连接到介孔材料后,其自身的旋转受到抑制,从而使复合材料发射出较强的蓝色荧光。材料对药物分子布洛芬具有较强的吸附能力,并且其荧光强度随着固载药物量的增加而增强,当药物释放达到平衡时,荧光强度又基本恢复到初始值。这种特性表明药物的释放过程有可能通过AIE功能化介孔材料的荧光强度变化监测,在生物医学领域展现出良好的应用价值。另外,该材料对爆炸物分子苦味酸(PA)具有较高灵敏的检测能力,随着AIE负载量的增加,其检测效果逐渐增强。当TPE的固载量为0.067mmol/g时,其在水溶液中的淬灭常数达到2.5×105M-1,远高于单纯TPE分子的淬灭常数。这是由于该材料对爆炸物分子存在富集作用,同时多孔结构有利于客体分子的传输,增强了检测效率。尤为重要的是,该材料可以多次循环使用,因此具有实际应用的意义。此外,我们将AIE分子修饰在介孔二氧化硅纳米粒子中,材料在2,4-二硝基甲苯(DNT)饱和蒸气中放置30秒时荧光强度淬灭了80%,表现出极灵敏的检测效率。材料对盐酸气体表现出较好的荧光淬灭效果,而在氨气中荧光可以完全恢复,并可以多次循环。实验结果表明这类AIE功能化介孔材料在化学传感等方面展现了较好的应用前景。
通过共合成的方式将含有四苯乙烯基元的有机磷酸通过P-O-Ca共价键杂化到羟基磷灰石(HAP)骨架中,得到具有较好生物相容性的椭球形空心纳米胶囊。与纯的介孔HAP相比,该材料具有较强的蓝色荧光,较高的药物固载量以及相对缓慢的释放速率。材料的荧光强度在吸附药物分子之后显著增强,而当药物释放达到平衡时其荧光强度又显著下降,这表明药物的释放过程可以通过荧光强度的变化来监测,展现出良好的生物应用前景。
采用离子交换插层法将AIE阳离子插入到纳米尺度的层状α-ZrP材料中,得到具有AIE发光性质的无机有机杂化材料。AIE阳离子插入后,α-ZrP层间距扩大为19.6A,并由于分子间静电相互作用限制了分子内转动,发射出较强的蓝色荧光。该复合材料不仅可以应用于细胞成像,而且对爆炸物分子苦味酸表现出相对较好的检测效果,淬灭常数为1.0×105M-1。
此外,我们通过共合成的方式制备了氨基修饰的介孔羟基磷灰石和羧基修饰的介孔磷酸钛材料。氨基修饰的介孔羟基磷灰石具有较高的比表面积以及较小的粒径尺寸,对布洛芬具有较高的药物固载量及相对缓慢的药物释放速率。羧基功能化的介孔磷酸钛材料对钯具有较好的配位能力,形成的钯粒子尺寸约为3nm,在Suzuki偶联反应中具有良好的催化活性。
Inorganic porous materials are excellent carriers for loading guest molecules due to their unique properties such as ordered pore structure and large surface area. Inorganic porous materials functionalized with organic groups combine the advantages of porous materials and organic functional groups, and have been widely used in catalysis, adsorption, biomedicine, and so on. Since the first material with intriguing aggregation induced emission (AIE) was discovered, many AIE molecules have been synthesized and widely used as efficient electroluminescent materials, sensitive chemosenors, bioprobes, and so on. Restriction of intramolecular rotation is the main cause for the AIE effect, therefore we proposed that after these molecules were introduced into mesoporous materials with rigid skeleton, their internal rotation would be largely restricted, leading to highly emission. In this thesis, based on inorganic mesoporous materials as well as layered phosphates, we developed AIE functionalized inorganic-organic hybrid materials through post grafting, co-condensation and ion exchange, and systematically explored their applications in drug delivery, chemical detection, cell imaging, etc. The main results of this thesis include the following sections:
We modified mesoporous SBA-15with AIE luminogen tetraphenylethene (TPE) for the first time through post grafting method and explored their applications in drug delivery and explosive detection. The internal rotation of AIE molecules was largely restricted by the rigid inorganic skeleton, leading to strong blue emission, so the composite materials exhibit typical AIE-like characteristics. The fluorescence intensity of the materials enhanced with the increasing amount of the drug adsorbed on the materials. When the drug release reached equilibrium, the fluorescence intensity can almost return to the initial value, showing great potential for biomedical application. In addition, such materials show high sensing performance to explosive molecules, e.g., picric acid (PA). When the amount of TPE modified on SBA-15reaches to0.067mmol/g, the quenching constant is about2.5×105M-1, much higher than that of TPE molecules. This is because PA molecules can quickly diffuse into the pores and be effectively adsorbed around fluorophores (TPE) via acid-base interaction, enhancing the fluorescence quenching efficiency. Furthermore, the materials are recyclable by washing with proper solvents, which is a key factor for future practical application. In addition, we fabricated AIE functionalized mesoporous silica nanoparticles, which are excellent solid-state sensors for2,4-dinitrotoluene (DNT) saturated vapors, with the fluorescence quenched by80%in30seconds, showing an extremely sensitive detection efficiency. The materials also have better detection ability for HC1gas with the fluorescence quenching, and can be recovered by NH3gas. Therefore, AIE luminogen-functionalized mesoporous materials promise to be excellent fluorescence probes for potential applications in biomedicine as well as chemical and explosive detections.
The organic phosphate based on AIE molecule was fabricated into bioactive hydroxyapatite (HAP) by a one-pot condensation process with P-O-Ca covalent bond to form hollow mesoporous nanocapsules of ellipsoidal morphology. The as-prepared AIE luminogen bridged mesostructured HAP exhibits strong blue luminescence and good biocompatibility, and shows a high ibuprofen (IBU) storage capacity and favorable drug release behavior compared to pure mesoporous HAP. More importantly, the fluorescence intensity changes with the amount of drug molecules adsorbed to the materials, suggesting that the drug release may be tracked and monitored by the change of luminescence intensity, showing potential for bioapplications.
AIE cation (TPEN) was successfully intercalated into layered nano a-ZrP by ion exchange to form organic-inorganic hybrid materials with the interlayer distance expanded to19.6A. The obtained materials emit strong blue fluorescence centered at474nm in aqueous media because internal rotation of AIE molecules was largely restricted caused by electrostatic interactions. This material can serve as an effective fluorescence visualizer for HeLa cells and sensitive fluorescent sensor for the detection of explosive PA in a water solution with the quenching constant of about1.0 ×105M-1.
In addition, we prepared amino-modified mesoporous HAP and carboxyl-modified mesoporous titanium phosphate materials by co-concentration. Compared to pure mesoporous HAP, the amino-modified mesoporous HAP with larger surface area and smaller particles sizes, shows higher drug loading and relatively slower release rate. Carboxyl group functionalized mesoporous titanium phosphate shows better coordination for palladium, with the formation of the palladium particle size of about3nm, exhibiting better catalytic activity in the Suzuki coupling reaction.
首次采用后嫁接的方式将AIE生色团四苯乙烯(TPE)修饰到介孔二氧化硅材料SBA-15上,并研究了其在药物传输和爆炸物检测等领域的应用。由于AIE分子连接到介孔材料后,其自身的旋转受到抑制,从而使复合材料发射出较强的蓝色荧光。材料对药物分子布洛芬具有较强的吸附能力,并且其荧光强度随着固载药物量的增加而增强,当药物释放达到平衡时,荧光强度又基本恢复到初始值。这种特性表明药物的释放过程有可能通过AIE功能化介孔材料的荧光强度变化监测,在生物医学领域展现出良好的应用价值。另外,该材料对爆炸物分子苦味酸(PA)具有较高灵敏的检测能力,随着AIE负载量的增加,其检测效果逐渐增强。当TPE的固载量为0.067mmol/g时,其在水溶液中的淬灭常数达到2.5×105M-1,远高于单纯TPE分子的淬灭常数。这是由于该材料对爆炸物分子存在富集作用,同时多孔结构有利于客体分子的传输,增强了检测效率。尤为重要的是,该材料可以多次循环使用,因此具有实际应用的意义。此外,我们将AIE分子修饰在介孔二氧化硅纳米粒子中,材料在2,4-二硝基甲苯(DNT)饱和蒸气中放置30秒时荧光强度淬灭了80%,表现出极灵敏的检测效率。材料对盐酸气体表现出较好的荧光淬灭效果,而在氨气中荧光可以完全恢复,并可以多次循环。实验结果表明这类AIE功能化介孔材料在化学传感等方面展现了较好的应用前景。
通过共合成的方式将含有四苯乙烯基元的有机磷酸通过P-O-Ca共价键杂化到羟基磷灰石(HAP)骨架中,得到具有较好生物相容性的椭球形空心纳米胶囊。与纯的介孔HAP相比,该材料具有较强的蓝色荧光,较高的药物固载量以及相对缓慢的释放速率。材料的荧光强度在吸附药物分子之后显著增强,而当药物释放达到平衡时其荧光强度又显著下降,这表明药物的释放过程可以通过荧光强度的变化来监测,展现出良好的生物应用前景。
采用离子交换插层法将AIE阳离子插入到纳米尺度的层状α-ZrP材料中,得到具有AIE发光性质的无机有机杂化材料。AIE阳离子插入后,α-ZrP层间距扩大为19.6A,并由于分子间静电相互作用限制了分子内转动,发射出较强的蓝色荧光。该复合材料不仅可以应用于细胞成像,而且对爆炸物分子苦味酸表现出相对较好的检测效果,淬灭常数为1.0×105M-1。
此外,我们通过共合成的方式制备了氨基修饰的介孔羟基磷灰石和羧基修饰的介孔磷酸钛材料。氨基修饰的介孔羟基磷灰石具有较高的比表面积以及较小的粒径尺寸,对布洛芬具有较高的药物固载量及相对缓慢的药物释放速率。羧基功能化的介孔磷酸钛材料对钯具有较好的配位能力,形成的钯粒子尺寸约为3nm,在Suzuki偶联反应中具有良好的催化活性。
Inorganic porous materials are excellent carriers for loading guest molecules due to their unique properties such as ordered pore structure and large surface area. Inorganic porous materials functionalized with organic groups combine the advantages of porous materials and organic functional groups, and have been widely used in catalysis, adsorption, biomedicine, and so on. Since the first material with intriguing aggregation induced emission (AIE) was discovered, many AIE molecules have been synthesized and widely used as efficient electroluminescent materials, sensitive chemosenors, bioprobes, and so on. Restriction of intramolecular rotation is the main cause for the AIE effect, therefore we proposed that after these molecules were introduced into mesoporous materials with rigid skeleton, their internal rotation would be largely restricted, leading to highly emission. In this thesis, based on inorganic mesoporous materials as well as layered phosphates, we developed AIE functionalized inorganic-organic hybrid materials through post grafting, co-condensation and ion exchange, and systematically explored their applications in drug delivery, chemical detection, cell imaging, etc. The main results of this thesis include the following sections:
We modified mesoporous SBA-15with AIE luminogen tetraphenylethene (TPE) for the first time through post grafting method and explored their applications in drug delivery and explosive detection. The internal rotation of AIE molecules was largely restricted by the rigid inorganic skeleton, leading to strong blue emission, so the composite materials exhibit typical AIE-like characteristics. The fluorescence intensity of the materials enhanced with the increasing amount of the drug adsorbed on the materials. When the drug release reached equilibrium, the fluorescence intensity can almost return to the initial value, showing great potential for biomedical application. In addition, such materials show high sensing performance to explosive molecules, e.g., picric acid (PA). When the amount of TPE modified on SBA-15reaches to0.067mmol/g, the quenching constant is about2.5×105M-1, much higher than that of TPE molecules. This is because PA molecules can quickly diffuse into the pores and be effectively adsorbed around fluorophores (TPE) via acid-base interaction, enhancing the fluorescence quenching efficiency. Furthermore, the materials are recyclable by washing with proper solvents, which is a key factor for future practical application. In addition, we fabricated AIE functionalized mesoporous silica nanoparticles, which are excellent solid-state sensors for2,4-dinitrotoluene (DNT) saturated vapors, with the fluorescence quenched by80%in30seconds, showing an extremely sensitive detection efficiency. The materials also have better detection ability for HC1gas with the fluorescence quenching, and can be recovered by NH3gas. Therefore, AIE luminogen-functionalized mesoporous materials promise to be excellent fluorescence probes for potential applications in biomedicine as well as chemical and explosive detections.
The organic phosphate based on AIE molecule was fabricated into bioactive hydroxyapatite (HAP) by a one-pot condensation process with P-O-Ca covalent bond to form hollow mesoporous nanocapsules of ellipsoidal morphology. The as-prepared AIE luminogen bridged mesostructured HAP exhibits strong blue luminescence and good biocompatibility, and shows a high ibuprofen (IBU) storage capacity and favorable drug release behavior compared to pure mesoporous HAP. More importantly, the fluorescence intensity changes with the amount of drug molecules adsorbed to the materials, suggesting that the drug release may be tracked and monitored by the change of luminescence intensity, showing potential for bioapplications.
AIE cation (TPEN) was successfully intercalated into layered nano a-ZrP by ion exchange to form organic-inorganic hybrid materials with the interlayer distance expanded to19.6A. The obtained materials emit strong blue fluorescence centered at474nm in aqueous media because internal rotation of AIE molecules was largely restricted caused by electrostatic interactions. This material can serve as an effective fluorescence visualizer for HeLa cells and sensitive fluorescent sensor for the detection of explosive PA in a water solution with the quenching constant of about1.0 ×105M-1.
In addition, we prepared amino-modified mesoporous HAP and carboxyl-modified mesoporous titanium phosphate materials by co-concentration. Compared to pure mesoporous HAP, the amino-modified mesoporous HAP with larger surface area and smaller particles sizes, shows higher drug loading and relatively slower release rate. Carboxyl group functionalized mesoporous titanium phosphate shows better coordination for palladium, with the formation of the palladium particle size of about3nm, exhibiting better catalytic activity in the Suzuki coupling reaction.
引文
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