单线态氧与不饱和化合物的反应及其过氧化产物的化学发光研究
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摘要
单线态氧是一种重要的活性氧分子，其分子轨道具有与基态氧分子不同的电子排布，是氧的一种激发态分子的存在形式。由于其活性很高，极易与不饱和化合物发生反应，在物理、化学、环境以及生物医学许多领域都显现出重要的作用，因而近年来引起了研究者的广泛关注。光敏化方法因其简单可控而常用来产生单线态氧。光敏剂接受光辐照将能量传递给基态氧分子从而形成单线态氧分子。本论文旨在研究光敏化产生的单线态氧与不饱和化合物的反应及其后续的化学发光现象。以直链的十八碳不饱和脂肪酸，环状的氯酚类物质以及合成麝香为研究对象，通过实验条件的选择与控制来提高单线态氧对底物的的转化效率，得到最佳的敏化光转化条件。将纳米量子点引入敏化光转化体系，对量子点引发的化学发光机理进行深入研究探讨，探索构建新型光敏剂。利用量子化学手段研究单线态氧与氯酚类物质的具体反应路径，推测预氧化转化的中间物质及产物的结构，并对单线态氧与氯酚类物质反应速率的差异性进行理论解释。最后，将所建立的敏化光降解方法应用于实际样品中合成麝香的去除。这种基于单线态氧与不饱和化合物的预氧化作用机理及其后续的化学发光反应研究，不仅可提高对此类反应的认识水平，同时，本项目提出的原理有望在方法学上具有比较普遍的意义。具体内容分述如下：
1.综述了单线态氧的性质，产生方法，检测手段，在化学发光分析方法中的应用以及用量子化学计算研究其反应机理的研究现状。
2.表面活性剂对NaClO/H2O2化学发光体系影响的研究。单线态氧的寿命与溶剂的极性相关，在极性溶剂中寿命较短，因此不利于检测生物体系及生理环境中的单线态氧。而表面活性剂可以提供一种简单的模型来模拟生物膜。本章以一个经典的产生单线态氧的化学发光体系NaClO/H2O2为单线态氧源，将表面活性剂引入该体系，目的研究单线态氧在异相胶束微观体系中的活性及行为。研究表明，表面活性剂参与的NaClO/H2O2体系化学发光强度明显增强。考察不同表面活性剂对化学发光强度的影响，发现表面活性剂所形成的胶束的“笼效应”有效抑制了单线态氧的溶剂淬灭，增加了其稳定性，增强化学发光强度。由不同的醇溶剂对化学发光强度的增敏作用证实表面活性剂的疏水区域对化学发光强度有影响。结合单线态氧猝灭剂NaN3，化学捕获剂1,3-环己二烯-1,4-二乙酸钠以及化学发光光谱实验，进一步研究该体系的发光机理，化学发光光谱显示发射峰位于435-475nm波长范围内，推测单线态氧的双聚体(1O*2)2为体系可能的发光物质。同时发现N-溴代丁二酰亚胺(NBS)/H2O2体系也有类似的发光光谱，表明NBS/H2O2体系与NaClO/H2O2体系具有相似的化学发光机理，为研究NBS/过氧化物的发光机理研究起到辅助作用。
3.不饱和脂肪酸敏化光转化/化学发光规律研究。不饱和脂肪酸是动植物膜系统的重要组分之一，其过氧化反应是许多病理生物学过程中的基本组成部分，受到许多科学工作者的广泛重视。本章以油酸，亚油酸以及α-亚麻酸三种典型的十八碳不饱和脂肪酸为例，研究三种不饱和脂肪酸的敏化光转化/化学发光现象。对光敏剂，介质条件，光照时间等影响化学发光反应的多种因素进行考察。结果表明，不饱和脂肪酸的敏化光转化速率与其所含不饱和双键数目有关，其光转化速率顺序为：α-亚麻酸>亚油酸>油酸。并借助化学探针捕获，紫外可见吸收光谱，化学发光光谱等方法进一步对化学发光机理进行研究。推测激发态的孟加拉玫瑰红RB*为化学发光体系的发光物质，荧光染料RB与化学发光体系之间存在能量转移。计算光敏化过程中所产生的单线态氧的形成速率vf为1.74×10-6M-1s-1。
4. CdTe量子点引发的2,4-二氯苯酚的光转化及其化学发光反应。量子点由于其独特的光电性质而引起研究者的极大兴趣，作为光敏剂在光动力疗法以及太阳能电池领域应用广泛。本章将量子点作为光敏剂应用于有机污染物的光转化过程，研究CdTe QDs引发的2,4-二氯苯酚的光转化及其化学发光反应。水相合成了不同粒径的巯基乙酸包覆的CdTe QDs，并通过分子光谱，X-射线衍射以及透射电镜对其结构进行表征。在CdTe QDs存在下，2,4-二氯苯酚光转化生成一种发光前驱体，由NBS引发，可以产生化学发光现象。化学发光光谱显示单线态氧的双聚体(1O*2)*2以及激发态的(CdTe QDs)是最可能的发光体。通过D2O介质的溶剂效应对化学发光强度的增强以及化学捕获剂紫外光谱的变化确证光转化过程中的单线态氧的产生。建立测定2,4-二氯苯酚的化学发光分析方法。化学发光强度与2,4-二氯苯酚在0.36-36μmol L-1范围内呈线性关系，检测限为0.13μmol L-1。
5.氯酚类物质的过氧化反应的理论研究。本章运用密度泛函理论，对单线态氧与六种氯酚类物质(包括2-氯苯酚、3-氯苯酚、4-氯苯酚、2,4-二氯苯酚、2,4,6-三氯苯酚以及五氯苯酚)在液相中的反应机理进行探讨。对十二条反应路径的反应物，过渡态，产物以及可能的中间产物进行几何构型优化，研究反应的热力学以及动力学性质。结果表明，1,3-加成生成烯丙基氢过氧化物及1,4-加成生成酮类氢过氧化物在热力学上是最可能自发的反应路径。此外，根据反应动力学的研究，前者的反应能垒高于后者，因此，推测单线态氧进攻氯酚类化合物最佳的反应路径为1,4-加成路径，产物为酮类氢过氧化物。通过自由能能垒的比较，前线轨道理论及电离能分析进一步研究单线态氧与氯酚类物质的反应速率差异性，从多方面验证氯原子取代数目与光降解速率相关，氯酚类物质的光降解速率随着氯原子取代基的增加而越低。
6.水溶液中合成麝香的敏化光降解应用研究。本章利用敏化光降解手段对环境中的持久污染物合成麝香的降解进行探索。以四种应用广泛的合成麝香为研究对象，包括两种多环麝香(佳乐麝香和吐纳麝香)，两种硝基麝香(二甲苯麝香以及麝香酮)，选择光降解条件为：室温25oC，pH9.0，1.0mg L-1的RB为光敏剂，光照60min后，其光降解百分比分别为84.6%，86.1%，77.7%和49.2%。动力学研究表明，此过程为准一级反应动力学。此外，分别对四种合成麝香在纯水体系及天然水环境中的敏化光降解行为进行探索，发现四种合成麝香在天然水环境中的降解百分比高于纯水体系。结果表明，敏化光降解方法运用于天然水环境中合成麝香的去除具有可行性。
Singlet oxygen is a unique reactive oxygen species and its chemical reactivity derives from its characteristicelectronically-excited state. The involvement of singlet oxygen in many important atmospheric, physical,chemical, biological, and therapeutic processes has attracted intense research interest in recent years.Photosensitized generation of singlet oxygen is a simple, controllable method, requiring only oxygen, light of anappropriate wavelength, and a photosensitizer capable of absorbing and using light energy to excite oxygen to itssinglet state.
In this work, the interaction of singlet oxygen with the unsaturated organic compounds and the subsequentchemiluminescence (CL) reactions were studied. The transformation conditions of various unsaturated substrates,including unsaturated fatty acids, chlorophenols and synthetic musks were optimized to enhance thephototransformtion efficiency of substrates. Quantum dots were used as the photosensitizer in thephototransfomation process, the mechanism of quantum dot-induced phototransformation and its subsequent CLreaction were studied in detail. Furthermore, the primary and final products in the transformation reactionsbetween singlet oxygen and six chorophenols were studied by quantum theory calculation. Based on thesefindings, the relationship between photodegradation rates and the number of chlorine substitutions was illustratedtheoretically. Finally, the dye-sensitized photodegradation method was preliminarily studied for the removal ofsynthetic musks in real samples. This study is not confined to prompt the understanding of these reactions, moreimportantly, the principle proposed in this study is expected to have a general significance. The contents weresummarized as follows:
1. The basic properties, the production and the determination methods of singlet oxygen are reviewed.Applications of singlet oxygen in CL system and quantum theory calculations on the reaction mechanism ofsinglet oxygen with unsaturated organic compounds are addressed.
2. The influence of surfactant micelles on hydrogen peroxide and sodium hypochlorite CL system wasinvestigated. The micellar media based on anionic, cationic and non-ionic surfactants were employed as thesimple models to mimic more complex biological environments. The formation of surfactants cage canimprove the CL quantum yield of singlet oxygen by protecting singlet oxygen from solvent quenching. Theresults showed that the CL emission is related to the hydrophobic group of surfactant medium, which isfurther confirmed by the enhancing effect of the alcohol solvent on the CL intensity. The involvement ofsinglet oxygen was characterized by the quenching effect of a specific singlet oxygen scavenger sodiumazide and chemical trapping of singlet oxygen with the sodium1,3-cyclohexadiene-1,4-diethanoate.Moreover, the CL spectrum of the sodium hypochlorite/hydrogen peroxide system was measured. The lightemission is observed in a wavelength range from435to475nm, which may attributes to the singlet oxygendimol species (1O2)*2.
3. A dye-sensitized phototransformation method was developed for the evaluation of oxidation damage tounsaturated fatty acids induced by singlet oxygen. The singlet oxygen was generated in thephotosensitization process. Results showed that the order of phototransformation rate of three unsaturatedfatty acids is α-Linolenic acid>Linoleic acid>Oleic acid. The participation of singlet oxygen during thephototransformation process was confirmed by the changes in the UV spectra of a chemical trap CHDDE.The CL spectrum indicates that the excited state of rose bengal was responsible for the light emission.Kinetic studies showed the formation rate of singlet oxygen (vf) is1.74×10-6M-1s-1in the photosensitizedprocess.
4. We have studied the CdTe quantum dot-induced phototransformation of2,4-dichlorophenol (2,4-DCP) andits subsequent CL reaction. Quantum dots (QDs) of different sizes and capped with thioglycolic acid were prepared and characterized by molecular spectroscopy, X-ray diffraction and transmission electronmicroscopy. In the presence of QDs,2,4-DCP is photochemically transformed into a long-living1ightemitting precursor which can react with N-bromosuccinimide (NBS) to produce CL. The CL spectra indicatethat the singlet oxygen dimol species and the excited state of QDs were responsible for the light emission.The formation of singlet oxygen during the phototransformation process was confirmed by the enhancementeffect of deuterium oxide on the CL reaction and the changes in the UV spectra of a chemical trap. The CLintensity is linearly related to the concentration of2,4-DCP in the range from0.36to36μmol L-1, and thedetection limit (at3σ) is0.13μmol L-1.
5. With the intention of finding certain predictors to be used for the determination of the most probable reactionpath and estimating the dye-sensitized photodegradation rates of chlorophenols, the reactions of1O2with sixchorophenols (CPs), including2-chlorophenol (2-CP),3-chlorophenol (3-CP),4-chlorophenol (4-CP),2,4-dichlorophenol (2,4-DCP),2,4,6-trichlorophenol (2,4,6-TCP) and pentachlorophenol (PCP), wereinvestigated in aqueous solution by using the density functional theory. Results suggested that1,3-addition toa double bond connected to a hydrogen-carrying group, resulting in the formation of allylic hydroperoxides,and1,4-addition to chlorophenols to form of hydroperoxide ketones are thermodynamically more likely totake place. Furthermore, the reaction barrier of the former one is higher than that of later one, which tends toconclude that1,4-addition to chlorophenols to form of hydroperoxide ketones is the most likely route inaqueous solution. The computational results are in agreement with previous experimental results. Also it wasobserved that with the increase of chlorine substitutions, the reactions become less exergonic and kineticallyless favorable due to the increase in reaction barriers. The relationship between photodegradation rates andthe number of chlorine substitutions was illustrated theoretically by using the energies of frontier molecularorbitals and the ionization potentials, which are further confirmed that monochlorophenols are more readilyreact with singlet oxygen.
6. The removal of synthetic musks in aqueous solution by means of a dye-sensitized photodegradation methodwas preliminarily studied. Two polycyclic musks (HHCB and AHTN) and two nitro musks (MX and MK)were selected as the model compounds due to their wide applications. Important factors that may affect thedegradation process were investigated and the result showed that the optimum performance can be achievedwith rose bengal as the sensitizer (1.0mg L-1) in aqueous solution at pH9.0. Room temperature (25oC) wasfound to be suitable for the degradation of the four musks. The degradation percentages obtained for HHCB,AHTN, MX and MK were84.6%,86.1%,77.7%and49.2%, respectively. The experiment data suggestedthat the kinetics of the dye-sensitized photodegradation followed pseudo first-order reaction. Furthermore,the photodegradation in natural water was simulated and the results were compared with the degradationpercentages in pure water. It was found that the degradation percentages obtained in pure water were lowerthan that in natural water, suggesting that the approach of the dye-sensitized photodegradation could beapplied for the removal of the synthetic musks from water resources.
1.综述了单线态氧的性质，产生方法，检测手段，在化学发光分析方法中的应用以及用量子化学计算研究其反应机理的研究现状。
2.表面活性剂对NaClO/H2O2化学发光体系影响的研究。单线态氧的寿命与溶剂的极性相关，在极性溶剂中寿命较短，因此不利于检测生物体系及生理环境中的单线态氧。而表面活性剂可以提供一种简单的模型来模拟生物膜。本章以一个经典的产生单线态氧的化学发光体系NaClO/H2O2为单线态氧源，将表面活性剂引入该体系，目的研究单线态氧在异相胶束微观体系中的活性及行为。研究表明，表面活性剂参与的NaClO/H2O2体系化学发光强度明显增强。考察不同表面活性剂对化学发光强度的影响，发现表面活性剂所形成的胶束的“笼效应”有效抑制了单线态氧的溶剂淬灭，增加了其稳定性，增强化学发光强度。由不同的醇溶剂对化学发光强度的增敏作用证实表面活性剂的疏水区域对化学发光强度有影响。结合单线态氧猝灭剂NaN3，化学捕获剂1,3-环己二烯-1,4-二乙酸钠以及化学发光光谱实验，进一步研究该体系的发光机理，化学发光光谱显示发射峰位于435-475nm波长范围内，推测单线态氧的双聚体(1O*2)2为体系可能的发光物质。同时发现N-溴代丁二酰亚胺(NBS)/H2O2体系也有类似的发光光谱，表明NBS/H2O2体系与NaClO/H2O2体系具有相似的化学发光机理，为研究NBS/过氧化物的发光机理研究起到辅助作用。
3.不饱和脂肪酸敏化光转化/化学发光规律研究。不饱和脂肪酸是动植物膜系统的重要组分之一，其过氧化反应是许多病理生物学过程中的基本组成部分，受到许多科学工作者的广泛重视。本章以油酸，亚油酸以及α-亚麻酸三种典型的十八碳不饱和脂肪酸为例，研究三种不饱和脂肪酸的敏化光转化/化学发光现象。对光敏剂，介质条件，光照时间等影响化学发光反应的多种因素进行考察。结果表明，不饱和脂肪酸的敏化光转化速率与其所含不饱和双键数目有关，其光转化速率顺序为：α-亚麻酸>亚油酸>油酸。并借助化学探针捕获，紫外可见吸收光谱，化学发光光谱等方法进一步对化学发光机理进行研究。推测激发态的孟加拉玫瑰红RB*为化学发光体系的发光物质，荧光染料RB与化学发光体系之间存在能量转移。计算光敏化过程中所产生的单线态氧的形成速率vf为1.74×10-6M-1s-1。
4. CdTe量子点引发的2,4-二氯苯酚的光转化及其化学发光反应。量子点由于其独特的光电性质而引起研究者的极大兴趣，作为光敏剂在光动力疗法以及太阳能电池领域应用广泛。本章将量子点作为光敏剂应用于有机污染物的光转化过程，研究CdTe QDs引发的2,4-二氯苯酚的光转化及其化学发光反应。水相合成了不同粒径的巯基乙酸包覆的CdTe QDs，并通过分子光谱，X-射线衍射以及透射电镜对其结构进行表征。在CdTe QDs存在下，2,4-二氯苯酚光转化生成一种发光前驱体，由NBS引发，可以产生化学发光现象。化学发光光谱显示单线态氧的双聚体(1O*2)*2以及激发态的(CdTe QDs)是最可能的发光体。通过D2O介质的溶剂效应对化学发光强度的增强以及化学捕获剂紫外光谱的变化确证光转化过程中的单线态氧的产生。建立测定2,4-二氯苯酚的化学发光分析方法。化学发光强度与2,4-二氯苯酚在0.36-36μmol L-1范围内呈线性关系，检测限为0.13μmol L-1。
5.氯酚类物质的过氧化反应的理论研究。本章运用密度泛函理论，对单线态氧与六种氯酚类物质(包括2-氯苯酚、3-氯苯酚、4-氯苯酚、2,4-二氯苯酚、2,4,6-三氯苯酚以及五氯苯酚)在液相中的反应机理进行探讨。对十二条反应路径的反应物，过渡态，产物以及可能的中间产物进行几何构型优化，研究反应的热力学以及动力学性质。结果表明，1,3-加成生成烯丙基氢过氧化物及1,4-加成生成酮类氢过氧化物在热力学上是最可能自发的反应路径。此外，根据反应动力学的研究，前者的反应能垒高于后者，因此，推测单线态氧进攻氯酚类化合物最佳的反应路径为1,4-加成路径，产物为酮类氢过氧化物。通过自由能能垒的比较，前线轨道理论及电离能分析进一步研究单线态氧与氯酚类物质的反应速率差异性，从多方面验证氯原子取代数目与光降解速率相关，氯酚类物质的光降解速率随着氯原子取代基的增加而越低。
6.水溶液中合成麝香的敏化光降解应用研究。本章利用敏化光降解手段对环境中的持久污染物合成麝香的降解进行探索。以四种应用广泛的合成麝香为研究对象，包括两种多环麝香(佳乐麝香和吐纳麝香)，两种硝基麝香(二甲苯麝香以及麝香酮)，选择光降解条件为：室温25oC，pH9.0，1.0mg L-1的RB为光敏剂，光照60min后，其光降解百分比分别为84.6%，86.1%，77.7%和49.2%。动力学研究表明，此过程为准一级反应动力学。此外，分别对四种合成麝香在纯水体系及天然水环境中的敏化光降解行为进行探索，发现四种合成麝香在天然水环境中的降解百分比高于纯水体系。结果表明，敏化光降解方法运用于天然水环境中合成麝香的去除具有可行性。
Singlet oxygen is a unique reactive oxygen species and its chemical reactivity derives from its characteristicelectronically-excited state. The involvement of singlet oxygen in many important atmospheric, physical,chemical, biological, and therapeutic processes has attracted intense research interest in recent years.Photosensitized generation of singlet oxygen is a simple, controllable method, requiring only oxygen, light of anappropriate wavelength, and a photosensitizer capable of absorbing and using light energy to excite oxygen to itssinglet state.
In this work, the interaction of singlet oxygen with the unsaturated organic compounds and the subsequentchemiluminescence (CL) reactions were studied. The transformation conditions of various unsaturated substrates,including unsaturated fatty acids, chlorophenols and synthetic musks were optimized to enhance thephototransformtion efficiency of substrates. Quantum dots were used as the photosensitizer in thephototransfomation process, the mechanism of quantum dot-induced phototransformation and its subsequent CLreaction were studied in detail. Furthermore, the primary and final products in the transformation reactionsbetween singlet oxygen and six chorophenols were studied by quantum theory calculation. Based on thesefindings, the relationship between photodegradation rates and the number of chlorine substitutions was illustratedtheoretically. Finally, the dye-sensitized photodegradation method was preliminarily studied for the removal ofsynthetic musks in real samples. This study is not confined to prompt the understanding of these reactions, moreimportantly, the principle proposed in this study is expected to have a general significance. The contents weresummarized as follows:
1. The basic properties, the production and the determination methods of singlet oxygen are reviewed.Applications of singlet oxygen in CL system and quantum theory calculations on the reaction mechanism ofsinglet oxygen with unsaturated organic compounds are addressed.
2. The influence of surfactant micelles on hydrogen peroxide and sodium hypochlorite CL system wasinvestigated. The micellar media based on anionic, cationic and non-ionic surfactants were employed as thesimple models to mimic more complex biological environments. The formation of surfactants cage canimprove the CL quantum yield of singlet oxygen by protecting singlet oxygen from solvent quenching. Theresults showed that the CL emission is related to the hydrophobic group of surfactant medium, which isfurther confirmed by the enhancing effect of the alcohol solvent on the CL intensity. The involvement ofsinglet oxygen was characterized by the quenching effect of a specific singlet oxygen scavenger sodiumazide and chemical trapping of singlet oxygen with the sodium1,3-cyclohexadiene-1,4-diethanoate.Moreover, the CL spectrum of the sodium hypochlorite/hydrogen peroxide system was measured. The lightemission is observed in a wavelength range from435to475nm, which may attributes to the singlet oxygendimol species (1O2)*2.
3. A dye-sensitized phototransformation method was developed for the evaluation of oxidation damage tounsaturated fatty acids induced by singlet oxygen. The singlet oxygen was generated in thephotosensitization process. Results showed that the order of phototransformation rate of three unsaturatedfatty acids is α-Linolenic acid>Linoleic acid>Oleic acid. The participation of singlet oxygen during thephototransformation process was confirmed by the changes in the UV spectra of a chemical trap CHDDE.The CL spectrum indicates that the excited state of rose bengal was responsible for the light emission.Kinetic studies showed the formation rate of singlet oxygen (vf) is1.74×10-6M-1s-1in the photosensitizedprocess.
4. We have studied the CdTe quantum dot-induced phototransformation of2,4-dichlorophenol (2,4-DCP) andits subsequent CL reaction. Quantum dots (QDs) of different sizes and capped with thioglycolic acid were prepared and characterized by molecular spectroscopy, X-ray diffraction and transmission electronmicroscopy. In the presence of QDs,2,4-DCP is photochemically transformed into a long-living1ightemitting precursor which can react with N-bromosuccinimide (NBS) to produce CL. The CL spectra indicatethat the singlet oxygen dimol species and the excited state of QDs were responsible for the light emission.The formation of singlet oxygen during the phototransformation process was confirmed by the enhancementeffect of deuterium oxide on the CL reaction and the changes in the UV spectra of a chemical trap. The CLintensity is linearly related to the concentration of2,4-DCP in the range from0.36to36μmol L-1, and thedetection limit (at3σ) is0.13μmol L-1.
5. With the intention of finding certain predictors to be used for the determination of the most probable reactionpath and estimating the dye-sensitized photodegradation rates of chlorophenols, the reactions of1O2with sixchorophenols (CPs), including2-chlorophenol (2-CP),3-chlorophenol (3-CP),4-chlorophenol (4-CP),2,4-dichlorophenol (2,4-DCP),2,4,6-trichlorophenol (2,4,6-TCP) and pentachlorophenol (PCP), wereinvestigated in aqueous solution by using the density functional theory. Results suggested that1,3-addition toa double bond connected to a hydrogen-carrying group, resulting in the formation of allylic hydroperoxides,and1,4-addition to chlorophenols to form of hydroperoxide ketones are thermodynamically more likely totake place. Furthermore, the reaction barrier of the former one is higher than that of later one, which tends toconclude that1,4-addition to chlorophenols to form of hydroperoxide ketones is the most likely route inaqueous solution. The computational results are in agreement with previous experimental results. Also it wasobserved that with the increase of chlorine substitutions, the reactions become less exergonic and kineticallyless favorable due to the increase in reaction barriers. The relationship between photodegradation rates andthe number of chlorine substitutions was illustrated theoretically by using the energies of frontier molecularorbitals and the ionization potentials, which are further confirmed that monochlorophenols are more readilyreact with singlet oxygen.
6. The removal of synthetic musks in aqueous solution by means of a dye-sensitized photodegradation methodwas preliminarily studied. Two polycyclic musks (HHCB and AHTN) and two nitro musks (MX and MK)were selected as the model compounds due to their wide applications. Important factors that may affect thedegradation process were investigated and the result showed that the optimum performance can be achievedwith rose bengal as the sensitizer (1.0mg L-1) in aqueous solution at pH9.0. Room temperature (25oC) wasfound to be suitable for the degradation of the four musks. The degradation percentages obtained for HHCB,AHTN, MX and MK were84.6%,86.1%,77.7%and49.2%, respectively. The experiment data suggestedthat the kinetics of the dye-sensitized photodegradation followed pseudo first-order reaction. Furthermore,the photodegradation in natural water was simulated and the results were compared with the degradationpercentages in pure water. It was found that the degradation percentages obtained in pure water were lowerthan that in natural water, suggesting that the approach of the dye-sensitized photodegradation could beapplied for the removal of the synthetic musks from water resources.
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