芳胺类光敏染料用于染料敏化太阳能电池的研究
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摘要
光敏染料在染料敏化太阳能电池中起到吸收太阳光并将激发态电子注入到纳米半导体导带中的作用。同时产生的氧化态染料又能快速被电解质(I_3~-/I~-)还原再生。它是DSC获得高光电转换效率的决定因素之一。为了降低染料敏化太阳能电池的成本,纯有机光敏染料作为贵金属配合物光敏剂的替代品在近几年里有了长足的发展。
基于有机光敏染料的应用前景,本论文共设计合成了29个芳胺类纯有机光敏染料,其中包括14个三苯胺染料和15个杂葸(吩噻嗪和吩噁嗪)染料。并利用质谱、核磁共振氢谱对这些化合物进行结构表征。研究了光敏染料的光物理、电化学等性质,并将其应用于染料敏化太阳能电池,系统地考察了光敏染料结构与电池性能之间的关系。同时,本论文还对模型有机光敏染料进行了分子内能量转移和电子转移的实验和理论方面的研究。
光敏染料的结构与其光物理、电化学性质具有密切关系。对于三苯胺D-π-A型光敏染料,通过在苯乙烯桥基中引入不同的取代基可以微调染料的吸收光谱,吸电子基的引入能够使得染料的吸收光谱发生红移。采用并噻吩乙烯作为桥基也能使得染料的吸收光谱发生红移。类似结构的吩噁嗪染料比吩噻嗪染料具有更好的紫外可见吸收光谱。对于所有的D-π-A染料,采用(联)绕丹宁乙酸基替代氰基丙烯酸基作为电子受体使得染料的紫外可见吸收光谱发生明显的红移现象。所设计的光敏染料的LUMO和HOMO能级同时满足了染料激发态电子向TiO_2导带注入和染料还原再生的电位要求。噻吩基或(并)噻吩乙烯基作为桥基会导致染料HOMO能级的升高,使得染料与电解质中I_3~-/I~-电对的电位差降低,导致染料被还原的驱动力减小。与氰基丙烯酸基相比,(联)绕丹宁乙酸基团作为电子受体更能降低染料的LUMO能级,从而使得激发态染料分子的电子注入驱动力变弱。
研究发现进行二氧化钛膜敏化时所用的溶剂会对最终的电池性能产生较大的影响。主要表现在不同的溶剂会使得染料在二氧化钛上有不同的吸收光谱,不同的吸附量和不同的键合方式。实验证明本论文染料采用二氯甲烷作为染浴溶剂能够得到更好的光电转换效率。由于光物理和电化学性质的不同,光敏染料的结构变化对电池的性能也会产生重要影响。对本论文所合成的三苯胺D-π-A染料来说,苯乙烯桥基上取代基的引入导致染料光电转换效率的降低,特别是吸电子基的引入阻碍了激发态电子的注入过程。对于吩噻嗪染料来说,吩噻嗪基上不同的饱和碳链长度对电池性能影响较大,主要是因为碳链长度会影响染料在二氧化钛上的排列方式。基于优化的染料结构和测试条件,染料TH208和TH302分别得到了6.4%和6.3%的光电转换效率。
对于不同电子给体对电池性能影响的研究表明,在没有聚集抑制剂(如:鹅去氧胆酸)的存在下,具有非平面电子给体结构的染料可以有效防止染料在二氧化钛表面的聚集并获得高的光电转换效率。
通过对模型光敏染料的系统研究发现染料分子内能量转移和电子转移过程对电池性能有提高的作用。基于此理论设计的吩噁嗪染料TH305得到了7.7%的光电转换效率,相似条件下参比染料N719得到了8.0%的光电转换效率。
Photosensitizer is the one of the most important parts for dye sensitized solar cells(DSC) getting higher efficiency,which harvestes the sunlight to form excited state and achieves the process of electrons injection into the conduction band of the oxide.Then,the dye is regenerated by the electrolyte,such as an ionic liquid containing most frequently the iodide/triiodide couple as a redox system.To decrease the cost of DSC,the organic photosensitizers as the alternate to noble metal complex sensitizers have developed rapidly in recent years.
In this thesis,twenty-nine novel aromatic organic dyes containing fourteen triphenylamine dyes and fifiteen heteroanthracene(phenothizaine and phenoxazine) derivatives have been engineered and synthesized as sensitizers for the application in DSC.The structures of the dyes have been characterized by mass spectra(MS) and proton nuclear magnetic resonance (~1H NMR) technology.The photophysical and electrochemical properties of the dyes were studied.DSCs based on these dyes were constructed and detailed relationship between dye structures and solar cell performances has been investigated.At the same time,the model compounds were introduced to study the intromolecular energy transfer(E_nT) and charge transfer(ICT) processes.
The significant differences in the photophysical and electrochemical properties of the sensitizers can be influenced by small structure changes.For triphenylamine dyes,the introduction of electron-withdrawing units can achieve bathochromic shift of absorption spectra.Also,the absorption band of dye can be red-shifted and broadened by the introduction of largeπ-conjugation spacer.For heteroanthracene,with the similar structure,phenoxazine dyes show more perfect absorption spectra than phenothizaine dyes.HOMO and LUMO level of the dyes match well with that of I_3~-/I~- and TiO_2 conduction band,respectively.Introduction of largeπ-conjugation spacer moieties(such as,thienyl and DTT unit) will shift HOMO level of dye negatively,and results in a reduced gap between that and redox potential of I_3~-/I~-.This might reduce the efficiency of regeneration of the oxidized dye by I~-.Compared to cyanoacrylic acid group,the(co) rhodanine acetic can also shift LUMO of dye positively and reduce the force of electron injection into conduction band of TiO_2.
The different dye-baths for semiconductor sensitization have a crucial effect on the performance of the DSC due to the different absorption spectra,different absorbed amount and different binding modes of anchored dyes on TiO_2 surface in various solvents.The result suggestes that CH_2Cl_2 as dye-bath solvent can obtain the prominent solar-to-electricity conversion efficiency of DSC based on our dyes.Also,due to the differences of photophysical and electrochemical properties,different dyes show different photovoltaic properties.For triphenylamine dyes,the electron-withdrawing groups on phenylene units asπ-spacers show the negative effect on the performance of DSC.For heteroanthracen dyes,the different substituted alkyl length in electron-donating groups has significant effect on DSC performance.Based on the optimized dye structure and measurement method,TH208 and TH302 dyes achieve the solar-to-electricity conversion efficiency 6.4%and 6.3%.
The study of the effect of different electron donating groups on DSC performance demonstrates that organic sensitizer with non-planar electron donating group could be further designed to complete the monomolecular adsorption and obtain the prominent efficiency without H-aggregation depressor(for example,CDCA).
Intramolecular energy transfer and charge transfer processes show positive effect on the performance of DSC.Based on the theory,the phenoxazine dye TH305 shows prominent efficiency,7.7%.Under similar test conditions,the reference dye N719 shows 8.0% efficiency.
基于有机光敏染料的应用前景,本论文共设计合成了29个芳胺类纯有机光敏染料,其中包括14个三苯胺染料和15个杂葸(吩噻嗪和吩噁嗪)染料。并利用质谱、核磁共振氢谱对这些化合物进行结构表征。研究了光敏染料的光物理、电化学等性质,并将其应用于染料敏化太阳能电池,系统地考察了光敏染料结构与电池性能之间的关系。同时,本论文还对模型有机光敏染料进行了分子内能量转移和电子转移的实验和理论方面的研究。
光敏染料的结构与其光物理、电化学性质具有密切关系。对于三苯胺D-π-A型光敏染料,通过在苯乙烯桥基中引入不同的取代基可以微调染料的吸收光谱,吸电子基的引入能够使得染料的吸收光谱发生红移。采用并噻吩乙烯作为桥基也能使得染料的吸收光谱发生红移。类似结构的吩噁嗪染料比吩噻嗪染料具有更好的紫外可见吸收光谱。对于所有的D-π-A染料,采用(联)绕丹宁乙酸基替代氰基丙烯酸基作为电子受体使得染料的紫外可见吸收光谱发生明显的红移现象。所设计的光敏染料的LUMO和HOMO能级同时满足了染料激发态电子向TiO_2导带注入和染料还原再生的电位要求。噻吩基或(并)噻吩乙烯基作为桥基会导致染料HOMO能级的升高,使得染料与电解质中I_3~-/I~-电对的电位差降低,导致染料被还原的驱动力减小。与氰基丙烯酸基相比,(联)绕丹宁乙酸基团作为电子受体更能降低染料的LUMO能级,从而使得激发态染料分子的电子注入驱动力变弱。
研究发现进行二氧化钛膜敏化时所用的溶剂会对最终的电池性能产生较大的影响。主要表现在不同的溶剂会使得染料在二氧化钛上有不同的吸收光谱,不同的吸附量和不同的键合方式。实验证明本论文染料采用二氯甲烷作为染浴溶剂能够得到更好的光电转换效率。由于光物理和电化学性质的不同,光敏染料的结构变化对电池的性能也会产生重要影响。对本论文所合成的三苯胺D-π-A染料来说,苯乙烯桥基上取代基的引入导致染料光电转换效率的降低,特别是吸电子基的引入阻碍了激发态电子的注入过程。对于吩噻嗪染料来说,吩噻嗪基上不同的饱和碳链长度对电池性能影响较大,主要是因为碳链长度会影响染料在二氧化钛上的排列方式。基于优化的染料结构和测试条件,染料TH208和TH302分别得到了6.4%和6.3%的光电转换效率。
对于不同电子给体对电池性能影响的研究表明,在没有聚集抑制剂(如:鹅去氧胆酸)的存在下,具有非平面电子给体结构的染料可以有效防止染料在二氧化钛表面的聚集并获得高的光电转换效率。
通过对模型光敏染料的系统研究发现染料分子内能量转移和电子转移过程对电池性能有提高的作用。基于此理论设计的吩噁嗪染料TH305得到了7.7%的光电转换效率,相似条件下参比染料N719得到了8.0%的光电转换效率。
Photosensitizer is the one of the most important parts for dye sensitized solar cells(DSC) getting higher efficiency,which harvestes the sunlight to form excited state and achieves the process of electrons injection into the conduction band of the oxide.Then,the dye is regenerated by the electrolyte,such as an ionic liquid containing most frequently the iodide/triiodide couple as a redox system.To decrease the cost of DSC,the organic photosensitizers as the alternate to noble metal complex sensitizers have developed rapidly in recent years.
In this thesis,twenty-nine novel aromatic organic dyes containing fourteen triphenylamine dyes and fifiteen heteroanthracene(phenothizaine and phenoxazine) derivatives have been engineered and synthesized as sensitizers for the application in DSC.The structures of the dyes have been characterized by mass spectra(MS) and proton nuclear magnetic resonance (~1H NMR) technology.The photophysical and electrochemical properties of the dyes were studied.DSCs based on these dyes were constructed and detailed relationship between dye structures and solar cell performances has been investigated.At the same time,the model compounds were introduced to study the intromolecular energy transfer(E_nT) and charge transfer(ICT) processes.
The significant differences in the photophysical and electrochemical properties of the sensitizers can be influenced by small structure changes.For triphenylamine dyes,the introduction of electron-withdrawing units can achieve bathochromic shift of absorption spectra.Also,the absorption band of dye can be red-shifted and broadened by the introduction of largeπ-conjugation spacer.For heteroanthracene,with the similar structure,phenoxazine dyes show more perfect absorption spectra than phenothizaine dyes.HOMO and LUMO level of the dyes match well with that of I_3~-/I~- and TiO_2 conduction band,respectively.Introduction of largeπ-conjugation spacer moieties(such as,thienyl and DTT unit) will shift HOMO level of dye negatively,and results in a reduced gap between that and redox potential of I_3~-/I~-.This might reduce the efficiency of regeneration of the oxidized dye by I~-.Compared to cyanoacrylic acid group,the(co) rhodanine acetic can also shift LUMO of dye positively and reduce the force of electron injection into conduction band of TiO_2.
The different dye-baths for semiconductor sensitization have a crucial effect on the performance of the DSC due to the different absorption spectra,different absorbed amount and different binding modes of anchored dyes on TiO_2 surface in various solvents.The result suggestes that CH_2Cl_2 as dye-bath solvent can obtain the prominent solar-to-electricity conversion efficiency of DSC based on our dyes.Also,due to the differences of photophysical and electrochemical properties,different dyes show different photovoltaic properties.For triphenylamine dyes,the electron-withdrawing groups on phenylene units asπ-spacers show the negative effect on the performance of DSC.For heteroanthracen dyes,the different substituted alkyl length in electron-donating groups has significant effect on DSC performance.Based on the optimized dye structure and measurement method,TH208 and TH302 dyes achieve the solar-to-electricity conversion efficiency 6.4%and 6.3%.
The study of the effect of different electron donating groups on DSC performance demonstrates that organic sensitizer with non-planar electron donating group could be further designed to complete the monomolecular adsorption and obtain the prominent efficiency without H-aggregation depressor(for example,CDCA).
Intramolecular energy transfer and charge transfer processes show positive effect on the performance of DSC.Based on the theory,the phenoxazine dye TH305 shows prominent efficiency,7.7%.Under similar test conditions,the reference dye N719 shows 8.0% efficiency.
引文
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