新型纤维素荧光材料的合成、结构与性能研究

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英文题名：Synthesis, Structure and Properties of Novel Cellulose-Based Fluorescent Materials 作者：张玲芝 论文级别：博士 学科专业名称：高分子化学与物理 中文关键词：功能材料 ; 荧光纤维素衍生物 ; 荧光性质 ; 猝灭 ; 传感检测 英文关键词：functional materials ; cellulose-based fluorescent materials ; fluorescent 英文关键词：properties ; quenching ; chemosensing detection 学位年度：2013 导师：周金平 学科代码：070305 学位授予单位：武汉大学 论文提交日期：2013-05-01

摘要

高分子荧光材料是一种新型功能材料,具有独特的光物理化学性质,在荧光探针、化学传感器、非线性光学装置、荧光成像、微电子等领域有广泛的应用前景。随着可持续发展的战略要求,以天然高分子为原料的荧光材料迅速崛起,并成为高分子科学的前沿领域之一。纤维素是地球上最丰富的可再生资源,它经化学改性后能以不同形式出现,提高了功能化的灵活性及其材料应用的广泛性。目前,荧光纤维素材料的研究正处于起步阶段,开发不同种类且具有特殊应用价值的纤维素荧光材料已引起了科技工作者的高度重视。本工作通过物理、化学改性方法合成基于纤维素的荧光材料,并对产物的结构、性质和应用进行深入研究。
     本论文的主要创新有以下几点：1)通过均相醚化、表面修饰、化学交联制备多种新型荧光纤维素材料,并对其结构与性能进行表征；2)通过疏水相互作用和主客体相互作用制备荧光纤维素纳米胶束和荧光增强的纤维素水凝胶,并表征其结构与性能；3)系统研究荧光纤维素材料的荧光性质,考察其在pH、温度、爆炸物分子和重金属离子等的传感检测和荧光增强作用。
     本论文的主要研究内容和结论包括以下几个部分。首先,在NaOH/尿素水体系均相合成羟乙基纤维素(HEC),进一步与N-3'-溴丙基咔唑在DMSO体系中合成咔唑基羟乙基纤维素(Cz-HEC)。通过红外、核磁共振、元素分析等对其结构进行表征,利用荧光光谱考察Cz-HEC在DMSO中的荧光性质。研究表明,咔唑基接至HEC后荧光寿命增加、荧光增强,但均出现浓度自猝灭现象。电子受体丙烯腈的加入对Cz-HEC有荧光猝灭作用,且随丙烯腈加入,猝灭符合Stern-Volmer方程,所得猝灭常数及荧光寿命变化表明是一个动态猝灭的过程。
     通过两步反应,首先咔唑与环氧氯丙烷反应合成9-(2,3-环氧丙基)-咔唑,再与甲基纤维素(MC)反应成功合成咔哗基取代的甲基纤维素(Cz-MC)。红外和核磁共振确定其结构,元素分析和紫外光谱确定咔唑基的取代度。通过动态光散射研究不同温度下Cz-MC稀溶液的聚集行为。研究表明,Cz-MC在较低温度下单链和聚集体共存；随着温度升高单链逐渐消失,形成大的聚集体且聚集体的流体力学半径减小；且随着咔唑基取代度增加聚集行为更明显,聚集体的流体力学半径亦更小。Cz-MC具有浓度自猝灭的荧光性质。Cz-MC荧光性质对温度的依赖关系表明,Cz-MC的热聚集行为改变了咔唑基团的微环境,在发生荧光自猝灭的浓度前后,溶液的荧光强度发生温度响应性改变。
     以HEC为原料,在DMSO体系以二月桂酸二丁基锡作催化剂,与异硫氰酸荧光素反应合成了荧光素标记的羟乙基纤维素(FITC-HEC)。通过红外和核磁共振确定其结构。利用荧光光谱研究其溶液、固体和膜的荧光性质,发现FITC在固态时基团之间互相影响形成激基缔合物,导致荧光增强且发生红移。此外,还探讨了pH和温度对FITC-HEC水溶液荧光性质的影响。研究表明,pH升高,FITC电离形式不同,溶液的荧光强度先增加后降低；温度升高,溶液发生荧光猝灭现象。由此说明FITC-HEC可作为pH和温度的传感器。
     通过对纤维素进行季铵化和不同疏水长链的烷基化制备两亲性纤维素衍生物(HMQC)。 HMQC能在水中自组装形成纳米胶束,FTIR、NMR、元素分析、ζ电位、DLS和TEM研究了HMQC和胶束的结构和形貌。将该胶束用于疏水荧光染料BTPETD的包覆制备了一种基于荧光纤维素胶束的化学传感体系。该体系具有优异的荧光性质,可用于爆炸物分子的痕量检测。研究表明,2,4-二硝基苯酚(DNP)和2,4,6-三硝基苯酚(PA)会导致较高的荧光猝灭,DNP对荧光的猝灭具有良好的Stern-Volmer线性关系,而PA在浓度大于6μM时显示超线性的关系,但都能实现对DNP和PA的定量检测,检测限分别达到200nM和50nM,可作为水环境下稳定、高灵敏的化学传感材料。
     将纤维素纳米晶须反应上环氧基团,然后开环引入伯胺基,伯胺基再与溴芘进行反应合成了表面芘标记的荧光纤维素纳米晶须(Py-CNC)。固体核磁确定其结构。荧光测试表明芘标记到CNC上对其荧光有显著增强。Py-CNC水分散液对不同金属离子具有不同的荧光响应,其中Fe3+的荧光猝灭效果最好,Fe3+与Py-CNC上N、O的配位作用是导致荧光猝灭的原因。Py-CNC对Fe3+有较高灵敏度和选择性,检测限达1μM,可用于环境体系中Fe3+的传感检测。
     以环氧氯丙烷为交联剂,在NaOH/尿素水体系中合成β-环糊精/纤维素水凝胶。以β-环糊精疏水空腔的包合作用研究了水凝胶对5-FU和BSA的释放行为,显示β-环糊精对5-FU的包合抑制了其释放。同时还研究水凝胶对苯胺蓝的吸附行为。结果表明,由于β-环糊精与苯胺蓝的1：1包合作用,使得水凝胶对苯胺蓝的吸附量随环糊精的含量增加而增加,且该水凝胶吸附苯胺蓝后荧光增强。
     本论文为基于纤维素的新型荧光材料的制备提供新的途径和方法。同时,还研究了荧光纤维素材料对pH、温度、重金属离子、爆炸物分子等的传感检测以及荧光增强。这些成果将为新型纤维素功能材料的制备与应用提供科学依据,具有重要的学术价值和应用前景。
Fluorescence polymer, as a new functional material, has its unique photophysical and photochemical properties. It has many potential applications such as fluorescent probes, chemical sensors, nonlinear optical devices, fluorescence imaging, microelectronics, and so on. Nowadays, with the strategic requirements of sustainable development, research and development of fluorescent materials based on the natural polymers has been one of the superior areas of polymer science. As the most abundant renewable resources on the earth, cellulose could be chemically or physically modified into many forms, such as films, fibers and hydrogels. Thus the functionalization and the extension of cellulose applications could be improved. So far, cellulose-based fluorescent materials are in their infancy, and how to develop novel fluorescent materials and convert cellulose into high value-added products have attracted a worldwide attention. In this thesis, we tried to prepare novel cellulose-based fluorescent materials via physical and chemical methods, and the structure, properties and their potential applications were investigated.
     The novel creations of this work are as follows.(1) Novel cellulose-based fluorescent materials were prepared by homogeneously etherification, surface modification, and chemical crosslinking, and their structure and properties were investigated.(2) Cellulose-based fluorescent micelles and enhanced fluorescent cellulose-based hydrogels were obtained by hydrophobic interactions and host-guest complexion, respectively.(3) The fluorescence properties of the cellulose-based fluorescent materials were investigated, and their applications in chemosensors for pH, temperature, metal ions and explosives were studied.
     The main content and conclusions in this thesis are divided into the following part. Firstly, carbazole-substituted hydroxyethylcelluloses (Cz-HECs) were homogeneously synthesized by reacting HEC with N-3'-bromopropyl carbazole in DMSO. The structure was characterized with element analysis, FTIR and NMR. Fluorescent properties of Cz-HECs in DMSO were syudied by a spectrofluorimeter. The results showed that the fluorescence lifetime increased with increasing DS of carbazole, and the fluorescent intensity of Cz-HECs was enhanced than that of Br-Cz. All samples exhibited concentration self-quenching properties. The addition of acrylonitrile, as an electron-accepter, quenched the emission spectra of Cz-HECs, and the fluorescence quenching was found to be a dynamic quenching by analyzing with the Stern-Volmer equation and fluorescent lifetime.
     Carbazole-substituted methylcelluloses (Cz-MCs) were synthesized through a two-step reaction by firstly introducing epoxy group to carbazole, and then reacting with MC. The structure was characterized by FTIR, NMR, elemental analysis and UV-vis spectroscopy. Aggregation behavior of Cz-MCs in dilute aqueous solution was investigated by a thermotropic study performed with dynamic laser light scattering. Fluorescent properties of Cz-MCs were measured by a spectrofluorimeter and results showed that Cz-MCs displayed concentration self-quenching properties of fluorescence spectra both in H2O and DMSO. The temperature effect on the fluorescent emission in dilute aqueous solution was explored. The results showed that the DS of carbazole and thermal aggregation of Cz-MC contributed to the formation of network structure between the molecules, consequently leading to the enhancement or quenching in fluorescence intensity.
     Fluorescein-labeled hydroxyethylcellulose (FITC-HEC) was synthesized by reacting HEC with fluorescein isothiocyanate in DMSO, and dibutyltin dilaurate was used as a catalyst. The structure was characterized by FTIR and NMR. Fluorescent properties of FITC-HEC in solution, solid state and film were investigated, and the fluorescence emission in solid state appeared an enhanced and red shift fluorescence compared to that in solution because of the formation of excimers in solid state. The effect of pH and temperature on the fluorescence intensity of FITC-HEC solution was explored. The results indicated that increasing pH could cause an increasing and then decreasing fluorescent intensity by different forms of FITC. Increasing temperature would cause a fluorescent quenching. This novel fluorescent material could be used as chemosensors for pH and temperature.
     Amphiphilic cationic cellulose derivatives with different long alkyl chains as hydrophobic segments (HMQC) were synthesized. They can self-assemble into cationic micelles in distilled water. Structure and properties of HMQC and micelles were characterized by element analysis, FT-IR,1H NMR, ξ-potential measurements, DLS, TEM, and fluorescence spectroscopy. The hydrophobic cores of micelles were used to load hydrophobic dye, BTPETD, to obtain fluorescent micelles which exhibiting stable photoluminescence. Fluorescence quenching was used to detect explosives, and found that the fluorescent intensity had highly sensitive respond to2,4-dinitrophenol (DNP) and picric acid (PA). It has a good linear relationship to DNP detection, while having a superlinear for c>6μM to PA, and both of them can be quantitatively detected. The limit of detection could reach to200and50nM, respectively. This novel fluorescent cellulose micelle is potential to prepare feasible, sensitive and stable sensor systems for detecting explosives in aqueous solutions.
     Cellulose nanocrystals were converted into pyrene labeling nanoparticles (Py-CNC) by a three-step procedure. The fluorescence emission of pyrene was enhanced after the modification to CNC. Py-CNC was evaluated for its sensing ability towards metal ions and exhibited high selectivity towards Fe3+among other screened metal ions with good discrimination between Fe2+and Fe+. The excellent selectivity for Fe+over a wide linear concentration range was observed through changes in the emission spectra. Spectroscopic analyses proved that the coordination interaction between Fe3+and Py-CNC led to the recognition process. This sensing nanomaterial can be employed as a chemosensor for Fe3+and promoted for many applications in chemical, environmental, and biological systems.
     β-cyclodextrin ((3-CD)/cellulose hydrogels were prepared in NaOH/urea aqueous solutions by crosslinking with epichlorohydrin. The structure and morphology of the hydrogels were characterized with FTIR, XRD, and SEM. The swelling test,5-fluorouracil (5-FU) and BSA, and aniline blue (AnB) were used to investigate the swelling capability, drug release behavior, and the fluorescent property of hydrogels. The results indicated that the swelling degree and water uptake of the hydrogels decreased with an increase of the β-CD content. The in vitro release showed an inclusion complex was formed for5-FU with β-CD to inhibit the controlled release. P-CD/cellulose hydrogels adsorbed aniline blue lead to a fluorescence enhancement attributing to the1:1host-guest complex between (3-CD and AnB.
     The thesis provided a new pathway for the synthesis of novel cellulose-based fluorescent materials. Meanwhile, this work has explored the potential applications in chemosensors for pH, temperature, metal ions, explosives, and so on. This thesis provided important information and scientific evidence for the preparation and utilization of cellulose-based fluorescent materials. Therefore, there are great scientific significance and prospects of applications.

引文

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