染料敏化太阳能电池中含二氢喹啉、希夫碱、硝基结构三种染料和硫、碘双组份电解质的研究
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摘要
光敏染料作为染料敏化太阳能电池的主要部分之一,起到吸收光子并将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中的氧化还原电对还原再生。光敏染料对电池的光电转换效率起到决定性的作用,同时也是敏化太阳能电池中成本最高的部分之一。为了降低染料的成本、简化合成工艺,本文设计合成了3个以二氢喹啉为供电子基团、异佛尔酮结构为π-桥基、以氰基丙烯酸基为吸电子基团的D-π-A型纯有机光敏染料,并用1H-NMR、MS等对这些染料进行了结构表征。通过研究发现在二氢喹啉结构中的氮原子上引入较长的烷基链,可以在一定程度上防止染料分子在Ti02表面的堆积。对三个染料的理论计算表明,染料处于基态时,吸电子部分有少量电子云分布,可能与Ti02导带发生电子的复合作用,从而降低电池的电压。在以后的设计中,应该减少基态下吸电子和桥基部分电子云分布。
近红外光敏染料由于其HOMO(Highest Occupied Molecular Orbital,最高占有轨道)和LUMO(Lowest Unoccupied Molecular Orbital,最低空余轨道)相距较近,难以满足和宽禁带半导体的能级匹配,是染料敏化太阳能电池研究中的难点。为了使太阳能电池对近红外范围内的光更加有效的利用,本文设计合成了2个含有希夫碱结构的纯有机光敏染料,并用1H-NMR、MS等对这些染料进行了结构表征。对含希夫碱结构的光敏染料研究表明,过强的吸电子基团容易使染料的LUMO能级过正,从而使电子不能有效的注入到Ti02半导体的导带,导致电池不能工作。对吸电子部分进行了改进,我们发现以羟基作为吸附基团虽然减弱了吸电子部分的吸电性,但是染料吸附到Ti02表面时,紫外-可见吸收光谱的截止吸收大大增加。从而导致染料LUMO能级向正向移动。产生这种现象的原因可能是由于羟基的结构较短,与TiO2结合后,Ti02能起到一定的吸电子作用。这种现象的发现,为以后用于染料敏化太阳能电池的光敏染料的设计开辟了新的思路。
硝基是一种良好的发色基团且易于引入有机化合物。本文合成了2个含有硝基和侧链吸附基团的D-π-A型纯有机光敏染料,并用1H-NMR、MS等对这些染料进行了结构表征。首次将含有硝基的纯有机D-π-A型光敏染料应用于染料敏化太阳能电池,通过研究发现,虽然染料的HOMO、LUMO能级很好的满足了氧化态染料被碘电解质还原和染料向Ti02导带注入电子的能级要求,但是在实际测试过程中发现电池的效率不高。对于产生这种现象的原因,我们进行了深入的研究,发现是硝基结构不能有效的将电子注入到Ti02半导体的导带。通过对封装好的染料敏化太阳能电池施加反向偏压发现,电池的颜色由原来的红色转变成后来的浅黄色,而电池的效率有了大幅度的提高。对电池进行优化后由染料JYl封装的染料敏化太阳能电池的总光电转换效率提高了五倍。通过对染料紫外可见光谱、傅里叶变换红外光谱、单色光转换效率光谱等的研究,并参考相关文献,对产生颜色变化的机理作出了合理的推断。当受到外加电场作用下,染料的-N02得到电子转化成-N022-基团,然后与Ti02表面发生键合。这种键合使电子能够有效的注入到Ti02导带,从而使电池效率大幅提高。
电解质是染料敏化太阳电池的重要组成部分。目前最常用高效电解质中的电对为I-/I3-,但是由于其中I3-和多碘离子的存在,使得电解质在可见光有一定的吸收,损失了部分太阳光能量,并且基于碘本身化学性质,其氧化还原电势与染料HOMO能级之间也有一定的差距,造成能量损失。因此,我们设计、合成并配制了硫、碘双组份电解质。这种电解质是一种无色透明的电解质。通过对电解质的研究发现,双组份电解质无论从短路电流、开路电压还是总的光电转换效率来说,都优于碘基电解质。使得电池的短路电流得以提高的原因主要是电解质的无色透明性质使染料吸收了更多的光。通过实验表明,双组份电解质的电势比I-／I3-电对的电势更正,而且双组份电解质能在一定程度上抑制Ti02半导体表面和电解质之间的复合。另外,相比碘基电解质,双组份电解质使得Ti02的导带负向移动。以上三点是由双组份电解质封装的电池获得较高开路电压的原因。通过电对再生性计算和测试表明,双组份电解质中的电对可以良好的再生,说明由双组份电解质封装的电池可以持续、稳定的工作。通过对实验结果的总结和分析,我们对双组份电解质的工作原理做出了合理的推断。
As one of main components of dye-sensitized solar cells (DSCs), dye sensitizer takes the function of injecting the photo-excited electrons into conduction band of semiconductor. The oxidized dye is then regenerated by the redox couple in electrolyte. Dye sensitizer is the key factor of DSCs'light-to-electricity efficiency, and also one of the components with highest price. To cut the cost and simplify the synthesis procedures, we designed and synthetized three D-π-A (donor-π conjuction-acceptor) metal-free organic dyes, which was based on dihydroquinoline donor, isophorone conjunction and cyanoacrylic acid acceptor. The structures of the dyes have been characterized by mass spectra (MS) and proton nuclear magnetic resonance ('H-NMR) technology. The results showed that the introduction of alkyl chains prevent the congregation of dyes on TiO2surface. Seen from calculation, there is some distribution of electric cloud in acceptor at ground state. This probably increases the possibility of electron recombination between dyes and TiO2conduction band, and causes the decrease of open circuit voltages of DSCs. The distribution of electons in electron-withdrawing and conjuction parts should be reduced in future dyes design.
The HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) of near infrared (near-IR) photosensitizer is very close, which makes the energy levels of dye are difficult to fit the high-gap semicondutioner. This makes the design of near-IR photoshensitizer a challenging field in DSCs. In order to utilize the light in near-IR region more efficiently, two metal-free dyes with Schiff base structure were designed and synthesized. The structures of the dyes have been characterized by MS and1H-NMR spectra. Results showed that the LUMO (Lowest Unoccupied Molecular Orbital) level of dye T1was too positive, causing that the excited electrons cannot efficiently inject to the conduction band of TiO2. This made the DSCs sensitized by dye T1did not work. To lower the LUMO, the carboxyl group of T1was changed to hydroxyl group. However, the cut-off absorption of UV-Vis (ultraviolet-visible) spectrum was red shifted a lot, when the dye sensitized to the surface of TiO2. This caused great decrease of LUMO level. The reason might structure of hydroxyl group is too short. When connected to the TiO2surface, TiO2helped acceptor to withdraw electrons. The discovery of this phenomenon broadened the design mentality of photosensitizer for DSCs.
Nitro group is a good electron-withdraw chromophore, which can be easily introduced into the organic compouds. In this paper, pure organic D-π-A photosensitizers with nitro groups were firstly applied in DSCs. Two pure organic D-π-A dyes with nitro group as acceptor were designed and synthesized. The structures of the dyes have been characterized by MS and1H-NMR spectra. Results showed the HOMO and LUMO levels are fit the dye regeneration and electron injection. However, the efficiencies of DSCs sensitized by this kind of dye are not very high. The reason was found to be the nitro group cannot efficiently inject the electrons to the conduction band of TiO2. When a reverse bias was added to the DSCs, the color was changed from red to light yellow, and the efficiencies raised a lot. Efficiencies of DSCs sensitized by JY1had five-fold increase, when a reverse voltage was added to the devices. A reasonable mechanism was concluded according to the UV-Vis, Near-IR, IPCE (Incident Photon-to-Current Conversion Efficiency) spectra and related references. When a bias was added to the device,-NO2received electrons and changed to-NO22-; and then bonding to the HO2surface. The bonding makes the injection more efficient, and makes the device a higher light-to-electricity efficiency.
Electrolyte is one of the most important components in DSCs. By now,I/I3-redox is the most efficient redox that ever found. However, the containing of I3-and polyiodide in this kind of electrolyte can absorb some of the visible light causing the energy loss. Moreover, the gap between potential of I-/I3-and HOMO level of efficient dyes (e.g. N719) is large. This also caused energy loss. Therefore, a new kind of sulfur, iodine hybrid electrolyte was designed, synthesized and prepared. Results showed the transparent and colorless hybrid electrolytes obtained higher short-circuit current, open-circuit voltage and efficiency than conventional I-/I3-based electrolyte. The increase of current was found to be the more light absorption of dye, which was ascribed to the colorless of hybrid electrolyte. The higher voltage was ascribed to the more positive redox potential, inhabitation of recombination between dyes/TiO2and the conduction band move of TiO2in different electrolytes. The regeneration experiments showed that DSCs with hybrid electrolytes can work continuously and stably. According to the experimental results, the mechanism of how hybrid electrolyte works was assumed.
近红外光敏染料由于其HOMO(Highest Occupied Molecular Orbital,最高占有轨道)和LUMO(Lowest Unoccupied Molecular Orbital,最低空余轨道)相距较近,难以满足和宽禁带半导体的能级匹配,是染料敏化太阳能电池研究中的难点。为了使太阳能电池对近红外范围内的光更加有效的利用,本文设计合成了2个含有希夫碱结构的纯有机光敏染料,并用1H-NMR、MS等对这些染料进行了结构表征。对含希夫碱结构的光敏染料研究表明,过强的吸电子基团容易使染料的LUMO能级过正,从而使电子不能有效的注入到Ti02半导体的导带,导致电池不能工作。对吸电子部分进行了改进,我们发现以羟基作为吸附基团虽然减弱了吸电子部分的吸电性,但是染料吸附到Ti02表面时,紫外-可见吸收光谱的截止吸收大大增加。从而导致染料LUMO能级向正向移动。产生这种现象的原因可能是由于羟基的结构较短,与TiO2结合后,Ti02能起到一定的吸电子作用。这种现象的发现,为以后用于染料敏化太阳能电池的光敏染料的设计开辟了新的思路。
硝基是一种良好的发色基团且易于引入有机化合物。本文合成了2个含有硝基和侧链吸附基团的D-π-A型纯有机光敏染料,并用1H-NMR、MS等对这些染料进行了结构表征。首次将含有硝基的纯有机D-π-A型光敏染料应用于染料敏化太阳能电池,通过研究发现,虽然染料的HOMO、LUMO能级很好的满足了氧化态染料被碘电解质还原和染料向Ti02导带注入电子的能级要求,但是在实际测试过程中发现电池的效率不高。对于产生这种现象的原因,我们进行了深入的研究,发现是硝基结构不能有效的将电子注入到Ti02半导体的导带。通过对封装好的染料敏化太阳能电池施加反向偏压发现,电池的颜色由原来的红色转变成后来的浅黄色,而电池的效率有了大幅度的提高。对电池进行优化后由染料JYl封装的染料敏化太阳能电池的总光电转换效率提高了五倍。通过对染料紫外可见光谱、傅里叶变换红外光谱、单色光转换效率光谱等的研究,并参考相关文献,对产生颜色变化的机理作出了合理的推断。当受到外加电场作用下,染料的-N02得到电子转化成-N022-基团,然后与Ti02表面发生键合。这种键合使电子能够有效的注入到Ti02导带,从而使电池效率大幅提高。
电解质是染料敏化太阳电池的重要组成部分。目前最常用高效电解质中的电对为I-/I3-,但是由于其中I3-和多碘离子的存在,使得电解质在可见光有一定的吸收,损失了部分太阳光能量,并且基于碘本身化学性质,其氧化还原电势与染料HOMO能级之间也有一定的差距,造成能量损失。因此,我们设计、合成并配制了硫、碘双组份电解质。这种电解质是一种无色透明的电解质。通过对电解质的研究发现,双组份电解质无论从短路电流、开路电压还是总的光电转换效率来说,都优于碘基电解质。使得电池的短路电流得以提高的原因主要是电解质的无色透明性质使染料吸收了更多的光。通过实验表明,双组份电解质的电势比I-／I3-电对的电势更正,而且双组份电解质能在一定程度上抑制Ti02半导体表面和电解质之间的复合。另外,相比碘基电解质,双组份电解质使得Ti02的导带负向移动。以上三点是由双组份电解质封装的电池获得较高开路电压的原因。通过电对再生性计算和测试表明,双组份电解质中的电对可以良好的再生,说明由双组份电解质封装的电池可以持续、稳定的工作。通过对实验结果的总结和分析,我们对双组份电解质的工作原理做出了合理的推断。
As one of main components of dye-sensitized solar cells (DSCs), dye sensitizer takes the function of injecting the photo-excited electrons into conduction band of semiconductor. The oxidized dye is then regenerated by the redox couple in electrolyte. Dye sensitizer is the key factor of DSCs'light-to-electricity efficiency, and also one of the components with highest price. To cut the cost and simplify the synthesis procedures, we designed and synthetized three D-π-A (donor-π conjuction-acceptor) metal-free organic dyes, which was based on dihydroquinoline donor, isophorone conjunction and cyanoacrylic acid acceptor. The structures of the dyes have been characterized by mass spectra (MS) and proton nuclear magnetic resonance ('H-NMR) technology. The results showed that the introduction of alkyl chains prevent the congregation of dyes on TiO2surface. Seen from calculation, there is some distribution of electric cloud in acceptor at ground state. This probably increases the possibility of electron recombination between dyes and TiO2conduction band, and causes the decrease of open circuit voltages of DSCs. The distribution of electons in electron-withdrawing and conjuction parts should be reduced in future dyes design.
The HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) of near infrared (near-IR) photosensitizer is very close, which makes the energy levels of dye are difficult to fit the high-gap semicondutioner. This makes the design of near-IR photoshensitizer a challenging field in DSCs. In order to utilize the light in near-IR region more efficiently, two metal-free dyes with Schiff base structure were designed and synthesized. The structures of the dyes have been characterized by MS and1H-NMR spectra. Results showed that the LUMO (Lowest Unoccupied Molecular Orbital) level of dye T1was too positive, causing that the excited electrons cannot efficiently inject to the conduction band of TiO2. This made the DSCs sensitized by dye T1did not work. To lower the LUMO, the carboxyl group of T1was changed to hydroxyl group. However, the cut-off absorption of UV-Vis (ultraviolet-visible) spectrum was red shifted a lot, when the dye sensitized to the surface of TiO2. This caused great decrease of LUMO level. The reason might structure of hydroxyl group is too short. When connected to the TiO2surface, TiO2helped acceptor to withdraw electrons. The discovery of this phenomenon broadened the design mentality of photosensitizer for DSCs.
Nitro group is a good electron-withdraw chromophore, which can be easily introduced into the organic compouds. In this paper, pure organic D-π-A photosensitizers with nitro groups were firstly applied in DSCs. Two pure organic D-π-A dyes with nitro group as acceptor were designed and synthesized. The structures of the dyes have been characterized by MS and1H-NMR spectra. Results showed the HOMO and LUMO levels are fit the dye regeneration and electron injection. However, the efficiencies of DSCs sensitized by this kind of dye are not very high. The reason was found to be the nitro group cannot efficiently inject the electrons to the conduction band of TiO2. When a reverse bias was added to the DSCs, the color was changed from red to light yellow, and the efficiencies raised a lot. Efficiencies of DSCs sensitized by JY1had five-fold increase, when a reverse voltage was added to the devices. A reasonable mechanism was concluded according to the UV-Vis, Near-IR, IPCE (Incident Photon-to-Current Conversion Efficiency) spectra and related references. When a bias was added to the device,-NO2received electrons and changed to-NO22-; and then bonding to the HO2surface. The bonding makes the injection more efficient, and makes the device a higher light-to-electricity efficiency.
Electrolyte is one of the most important components in DSCs. By now,I/I3-redox is the most efficient redox that ever found. However, the containing of I3-and polyiodide in this kind of electrolyte can absorb some of the visible light causing the energy loss. Moreover, the gap between potential of I-/I3-and HOMO level of efficient dyes (e.g. N719) is large. This also caused energy loss. Therefore, a new kind of sulfur, iodine hybrid electrolyte was designed, synthesized and prepared. Results showed the transparent and colorless hybrid electrolytes obtained higher short-circuit current, open-circuit voltage and efficiency than conventional I-/I3-based electrolyte. The increase of current was found to be the more light absorption of dye, which was ascribed to the colorless of hybrid electrolyte. The higher voltage was ascribed to the more positive redox potential, inhabitation of recombination between dyes/TiO2and the conduction band move of TiO2in different electrolytes. The regeneration experiments showed that DSCs with hybrid electrolytes can work continuously and stably. According to the experimental results, the mechanism of how hybrid electrolyte works was assumed.
引文
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