基于吲哚啉给体的染料敏化剂的构建及光伏性能研究
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摘要
相比于传统硅电池,染料敏化太阳能电池(DSSCs)由于具有制作工艺简单、生产成本低廉及环境友好等特点而引起全球的广泛关注。其中,有机小分子染料作为重要的光捕获材料,因具有便于结构修饰、摩尔消光系数高及其较低的合成成本等优势而引起研究者广泛的兴趣。通过合理的分子结构设计提高染料敏化太阳能电池的光电转换效率及稳定性是本论文研究的重点。本文设计合成了基于芴为桥连、四个苯胺衍生物为电子给体；以咔唑吲哚啉为电子给体、氰基乙酸及绕丹宁酸为电子受体；吲哚啉为电子给体,不同噻吩衍生物为共轭桥连等多个系列基于电子给体-共轭桥连-电子受体(D-π-A)构型的染料敏化剂,分别对染料结构中的供电子体、吸电子单元及共轭桥连进行优化。在此基础上,进一步设计了以苯甲酰亚胺及苯并三氮唑单元为辅助吸电子基的D-A-π-A构型染料,研究不同辅助吸电子基团对染料性能的影响。
本论文的主要内容和研究成果包括以下几个方面：
前言简要介绍了染料敏化太阳能电池的研究背景、工作原理,综述了DSSCs中染料敏化剂近年来的研究进展,并提出本论文的研究思路。
鉴于芴单元优异的共平面性,设计合成了以不同苯胺衍生物为供电子体、芴联噻吩为共轭桥连、氰基乙酸结构为电子受体的染料敏化剂S1-S4,对该系列染料进行了光物理和电化学性能测试、运用高斯软件对分子的电子云分布进行了理论计算、并将其作为敏化剂组装DSSCs器件,对其进行光伏性能测试。测试结果表明,染料第一氧化电位可以通过改变电子给体进行修饰。相对于N,N-二甲基苯胺及三苯胺,吲哚啉衍生物表现出更强的给电子能力,其对应的化合物S2、S3具有更好的光伏性能。在π-桥连芴结构中引入的两个辛基碳链能够有效地抑制染料在二氧化钛膜上的聚集,从而更好地抑制电子回传。此外,密度泛函理论(DFT)计算结果表明,具有刚性结构芴的引入使染料呈现一种扭曲结构,从而使该系列染料在最高占据分子轨道(HOMO)及最低未占分子轨道(LUMO)能态时电子云在芴单元上的分布都很小,从理论角度上对染料引入芴桥连后不太理想的吸收性质给予了合理的解释。随着电子给体的不同,该系列染料表现出3.04～4.26%的光电转换效率。其中,采用甲基吲哚啉为给体的染料S3的开路电压为(V_(oc))727mV,光电转换效率(ff)为4.26%,达到同等条件下N719效率的82%。
设计合成以咔唑取代的吲哚啉为供电子体、绕丹宁酸结构为电子受体的D-π-A染料C-RA,实现了染料的全吸收。在此基础上,设计合成氰基乙酸为吸电子基团的染料C-CA,系统地研究不同吸附基团对吲哚啉染料光伏性能的影响。与C-CA相比,C-RA虽具有更宽的光谱响应,但其光伏效率(0.57%～0.90%)仅为同等条件下C-CA(8.49%)的10%。含有不同吸附基团的染料间巨大的单色光电转换效率(IPCE)差异主要源于二者不同的激发电子注入效率。激发态电子寿命测试及DFT计算结果均表明,C-RA敏化的DSSCs中光生电子与氧化态染料间存在着严重的电荷复合(Charge recombination),不利于电子的有效注入,并导致其极低的短路光电流密度。此外,加强光诱导瞬态测试(SLIT)及电化学阻抗(EIS)测试结果表明,C-RA敏化的DSSC中TiO_2表面较低的电荷密度及较快的电荷复合速率导致其较低的开路电压。该项工作对设计有效的染料敏化剂,尤其是采用绕丹宁酸结构为吸附基团的D-π-A型染料具有一定的指导意义。
考虑到3,4-乙烯二氧噻吩(EDOT)单元易于与相邻芳环形成共平面结构,有利于优化分子的共轭性能,设计合成了以EDOT为共轭桥连的两个D-π-A染料LS-4及LS-5,研究染料光物理、电化学性质对光伏性能的影响。实验结果表明,EDOT的引入不仅拓宽了染料的光谱响应,同时有益于增加染料的吸光系数,提高了染料的短路光电流密度J_(sc)。相比而言,EDOT的引入对提升染料开路电压的作用不很明显(<20mV)。相对于三苯胺染料LS-5,LS-4具有更负的HOMO能级,且其吸收峰值更向长波长偏移,表明吲哚啉单元更强的给电子能力。在模拟标准光源照射下,经LS-4与2mM鹅去氧胆酸(CDCA)共吸附的DSSCs具有6.05%的光电转换效率,其中短路光电流密度J_(sc)=13.23mAcm~(-2),V_(oc)=642mV,ff=0.711。该工作同时表明,150mV的染料再生驱动力对该类吲哚啉有机染料而言是可行的,从优化染料再生过程的角度上有效地避免了能量损失。
为了提高吲哚啉类染料的稳定性并优化染料的光伏性能,进一步引入辅助吸电子基,发展D-A-π-A型敏化染料。考虑到苯甲酰亚胺及苯并三氮唑具有较好的吸电子能力,且其结构中的N上可以方便地引入烷基链从而有效地改善染料的溶解性、抑制注入电子与电解质中氧化还原对间的电荷复合过程,将苯甲酰亚胺及苯并三氮唑单元作为辅助吸电子基,设计合成D-A-π-A型染料LS-2及WS-5。利用二者相似的分子结构,系统研究了辅助吸电子基团对染料的吸收、电化学及光伏性质的影响。实验结果及DFT理论模拟证明,具有相似苯并五元环结构的苯甲酰亚胺及苯并三氮唑单元的引入对染料的光物理、电化学性质及电子云分布有截然不同的影响：i)苯并三氮唑的引入使WS-5的HOMO能级有效地离域于整个分子骨架,而含两个羰基的苯甲酰亚胺单元的引入使LS-2呈现出很大的扭曲构型,其HOMO(?)级主要位于电子给体一端；ii)LS-2的基态优化构型结果表明,“D-A”及“A-π”平面间均呈现出较大的二面角,进一步证明苯甲酰亚胺的引入破坏了分子的离域,不利于分子内电荷迁移(ICT)过程；ⅲ) EIS测试结果表明,相比于LS-1,WS-5及LS-2的电子寿命分别提高了18.6及5.0倍。由于两个分子中均含有较长的烷基链,它们均表现出较高的开路电压(>750mV)。其中,WS-5表现出更高的短路光电流密度,光电转换效率达到8.38%,相比之下,扭曲构型的LS-2的光伏性能仅为同等条件下WS-5的60%。该工作表明在对D-A-π-A构型的染料进行结构修饰时,需谨慎选择辅助吸电子基团。
为了对吲哚啉染料LS-1的光伏性能进行优化,实现对太阳光更有效的吸收利用,分别将EDOT、双键、己基噻吩引入到LS-1中,设计合成染料LS-3、LS-6及LS-7,研究不同共轭基团对染料性能的影响。实验结果表明EDOT、双键及烷基链的引入能不同程度地实现对染料光吸收性能的优化,相比于双键及烷基链,EDOT单元的引入更有利于优化染料的光物理及电化学性质。I-V及EIS测试结果表明,噻吩基团上烷基链的引入可以实现对染料在二氧化钛表面的吸附形态及TiO_2/染料/电解液界面的优化过程,并获得较高的开路电压。在优化条件下,以己基噻吩为共轭桥连的LS-7表现出5.45%的光电转换效率,其中JSC=11.61mA cm-2,VOC=744mV,ff=0.63。
As a potential alternative to conventional inorganic photovoltaic devices, dye-sensitized solar cells (DSSCs) have attracted increasing attention in the past decades due to their high performance/price ratio and environmentally friendly nature. As a light-absorbing media in DSSCs, organic sensitizers are considered as promising candidates because of their facile structural modifications, low cost, and relatively high absorption coefficient with respect to ruthenium complexes. Extensive efforts have been focused on improving the overall efficiency and stablility of the sensitizers through rationalizing molecular structures. In this dissertation, we strived to optimize the donor moiety, conjugated bridge and acceptor/anchoring group of sensitizers with the configuration of D-π-A. Besides, we incorporated phthalimide and benzotriazole as auxiliary electron electron-withdrawing units in indoline based D-A-π-A sensitizers to systematically study their effect on the photophysical and electrochemical as well as photovoltaic properties in DSSCs.
The main contents of the manuscript are summarized as follows:
In introduction, the research background and basic working principle of DSSCs were introduced. The recent progress of typical dye sensitizers was reviewed, and the research strategy of the dissertation was presented.
A novel series of organic dyes containing a fluorene unit as the conjunction bridge (S1-S4) have been designed and synthesized for a potential application in DSSCs. Their absorption spectra, electrochemical and photovoltaic properties have been investigated in detail. The tuning of the HOMO and LUMO energy levels can be conveniently realized by alternating the donor moiety. As demonstrated, the indoline unit can exhibit a stronger electron donating ability, realizing a broader absorption when coated onto TiO2. The incorporation of octyl-substituted fluorene is highly beneficial to prevent close π-π aggregation, thus favorably suppressing charge recombination and intermolecular interaction. In both HOMO and LUMO orbitals, the electron density located at the conjunction bridge (fluorene unit) is quite low, suggesting that the incorporated fluorene unit plays quite small role in the electron delocalization between the donor and acceptor units due to the twist conformation. The overall conversion efficiencies of DSSCs based on these dyes are in the range of3.04to4.26%and highly dependent upon their donor moieties. Among these dyes, S3,which utilizes a methyl-substituted indoline moiety as an electron donor, has shown a maximum short current destiny (JSc), with a relatively high open circuit voltage (Foc) of727mV.
For developing panchromatic dyes, we develop sensitizer C-RA, and focus on the effect of rhodanine acceptor on photovoltaic performances in D-π-A indoline dye. Upon changing from cyanoacrylic acid (C-CA) to rhodanine-3-acetic acid (C-RA) as acceptor and anchoring group, C-RA shows broader absorption band, which can overlap with the solar spectrum more preferably. However, the power conversion efficiency of DSSCs based on C-RA (0.57%～0.90%) is one order of magnitude with respect to C-RA (8.49%). We find that the distinct difference of IPCE values between C-CA and C-RA is predominately attributed to the different excited electron injection yield (Φinj). Both the excited electron lifetime and DFT calculation indicate that the serious charge recombination between the photo-induced electron and the oxidized dye state in C-RA results in a low electron injection efficiency, leading to a low Jsc. Moreover, with respect to C-CA, the systematic SLIT and EIS studies demonstrate that C-RA holds the relatively low injection charge density in the TiO2electrode and fast charge recombination rate, leading to a low Voc. Our studies are highly helpful to the design of novel metal-free D-π-A organic sensitizers, especially for those using rhodanine-3-acetic acid as acceptor.
Two novel D-π-A organic dyes LS-4and LS-5, containing3,4-ethylenedioxythiophene (EDOT) in the conjugated bridge, are developed for nanocrystalline TiO2-based DSSCs. Systematic investigation is carried out on focus of the joint photophysical and electrochemical analysis on photovoltaic properties. Incorporating EDOT as conjugated bridge brings several characteristics:(i) distinctly increasing the light-harvesting ability such as broadening absorption range and increasing molar extinction coefficients;(ii) improving electron injection with the predominant enhancement of short-circuit photocurrent;(iii) exhibiting little effect on the open circuit voltage. LS-4shows a more negative oxidation potential and a bathochromic shift in absorption spectra with respect to LS-5, indicative of the more powerful electron-donating capability of indoline unit than that of triphenylamine. With coadsorption of2mM chenodeoxycholic acid (CDCA), the LS-4based DSSC exhibits a promising conversion efficiency of6.05%, with a,Jsc of13.23mA cm-2, Voc of642mV, and fill factor (ff) of0.711under AM1.5illumination (100mW cm-2). Moreover, in the system of LS-4, DSSCs is workable with the driving force of150mV for dye regeneration process, paving a road towards minimizing energy losses in dye regeneration process.
Two organic D-A-π-A sensitizers LS-2and WS-5containing N-octyl substituted phthalimide and benzotriazole as auxiliary electron withdrawing units with similar dimension and structure architecture were systematically studied on focus of photophysical, electrochemical as well as photovoltaic properties in nanocrystalline TiO2-based dye-sensitized solar cells. Interestingly, with similar five-member benzo-heterocycles, the two auxiliary acceptors of phthalimide and benzotriazole play exact different roles in absorption and intramolecular charge transfer:(ⅰ) in contrast with WS-5delocalized throughout the entire chromophore, the HOMO orbital of LS-2is mainly located at the donor part due to the twist conformation with the existence of two carbonyl groups in phthalimide;(ⅱ) the dihedral angles of "D-A" plane and "A-π" plane in LS-2further suggest that the incorporation of phthalimide moiety results in curvature of electron delocalization over the whole molecule;(ⅲ) in contrast with the beneficial charge transfer of benzotriazole in WS-5, the phthalimide unit in LS-2plays an opposite negative contribution to the charge transfer, that is, blocking ICT from donor to accepter to some extent; and (ⅳ) in electrochemical impedance spectroscopy, the incorporated benzotriazole unit enhances electron lifetime by18.6-fold, the phthalimide only increases electron lifetime by5.0-fold. Without coadsorption of CDCA, the DSSCs based on WS-5exhibited a promising maximum conversion efficiency of8.38%with significant enhancement in all photovoltaic parameters (Jsc=15.79mA cm-2, Voc=791mV,ff=0.67). In contrast, with the very similar D-A-π-A feature changing the additional acceptor from benzotriazole to phthalimide unit, the photovoltatic efficiency based on LS-2was only5.11%, with less efficient photovoltaic parameters (Jsc=10.06mA cm-2, Voc=748mV,ff=0.68). Therefore, our results demonstrate that it is essential to choose proper subsidiary withdrawing unit in D-A-π-A sensitizer configuration for DSSCs.
To optimize the photovoltaic performance of LS-1, the π-bridges of EDOT, methylene methine chain and hexyl-thiophene was introduced into indoline based sensitizer to develop dyes LS-3, LS-6and LS-7, and systematically studied the effect of different conjugated bridges on the photophysical, electrochemical as well as photovoltaic properties in DSSCs. The absorption spectra of three dyes show significant red-shift with respect to LS-1. Among them, EDOT in LS-3shows a priority in optimizing the photophysical and electrochemical properties of indoline based sensitizers. I-V and EIS results indicate that the introduction of alkyl chains on thiophene unit is effective in TiO2/dye/electrolyte interface modification, and realizing the enhancement of Voc. Under optimized condition, LS-7based DSSC exhibits a conversion efficiency of5.45%, with the parameters Jsc=11.61mA cm-2, Voc=744mV,ff=0.63.
本论文的主要内容和研究成果包括以下几个方面：
前言简要介绍了染料敏化太阳能电池的研究背景、工作原理,综述了DSSCs中染料敏化剂近年来的研究进展,并提出本论文的研究思路。
鉴于芴单元优异的共平面性,设计合成了以不同苯胺衍生物为供电子体、芴联噻吩为共轭桥连、氰基乙酸结构为电子受体的染料敏化剂S1-S4,对该系列染料进行了光物理和电化学性能测试、运用高斯软件对分子的电子云分布进行了理论计算、并将其作为敏化剂组装DSSCs器件,对其进行光伏性能测试。测试结果表明,染料第一氧化电位可以通过改变电子给体进行修饰。相对于N,N-二甲基苯胺及三苯胺,吲哚啉衍生物表现出更强的给电子能力,其对应的化合物S2、S3具有更好的光伏性能。在π-桥连芴结构中引入的两个辛基碳链能够有效地抑制染料在二氧化钛膜上的聚集,从而更好地抑制电子回传。此外,密度泛函理论(DFT)计算结果表明,具有刚性结构芴的引入使染料呈现一种扭曲结构,从而使该系列染料在最高占据分子轨道(HOMO)及最低未占分子轨道(LUMO)能态时电子云在芴单元上的分布都很小,从理论角度上对染料引入芴桥连后不太理想的吸收性质给予了合理的解释。随着电子给体的不同,该系列染料表现出3.04～4.26%的光电转换效率。其中,采用甲基吲哚啉为给体的染料S3的开路电压为(V_(oc))727mV,光电转换效率(ff)为4.26%,达到同等条件下N719效率的82%。
设计合成以咔唑取代的吲哚啉为供电子体、绕丹宁酸结构为电子受体的D-π-A染料C-RA,实现了染料的全吸收。在此基础上,设计合成氰基乙酸为吸电子基团的染料C-CA,系统地研究不同吸附基团对吲哚啉染料光伏性能的影响。与C-CA相比,C-RA虽具有更宽的光谱响应,但其光伏效率(0.57%～0.90%)仅为同等条件下C-CA(8.49%)的10%。含有不同吸附基团的染料间巨大的单色光电转换效率(IPCE)差异主要源于二者不同的激发电子注入效率。激发态电子寿命测试及DFT计算结果均表明,C-RA敏化的DSSCs中光生电子与氧化态染料间存在着严重的电荷复合(Charge recombination),不利于电子的有效注入,并导致其极低的短路光电流密度。此外,加强光诱导瞬态测试(SLIT)及电化学阻抗(EIS)测试结果表明,C-RA敏化的DSSC中TiO_2表面较低的电荷密度及较快的电荷复合速率导致其较低的开路电压。该项工作对设计有效的染料敏化剂,尤其是采用绕丹宁酸结构为吸附基团的D-π-A型染料具有一定的指导意义。
考虑到3,4-乙烯二氧噻吩(EDOT)单元易于与相邻芳环形成共平面结构,有利于优化分子的共轭性能,设计合成了以EDOT为共轭桥连的两个D-π-A染料LS-4及LS-5,研究染料光物理、电化学性质对光伏性能的影响。实验结果表明,EDOT的引入不仅拓宽了染料的光谱响应,同时有益于增加染料的吸光系数,提高了染料的短路光电流密度J_(sc)。相比而言,EDOT的引入对提升染料开路电压的作用不很明显(<20mV)。相对于三苯胺染料LS-5,LS-4具有更负的HOMO能级,且其吸收峰值更向长波长偏移,表明吲哚啉单元更强的给电子能力。在模拟标准光源照射下,经LS-4与2mM鹅去氧胆酸(CDCA)共吸附的DSSCs具有6.05%的光电转换效率,其中短路光电流密度J_(sc)=13.23mAcm~(-2),V_(oc)=642mV,ff=0.711。该工作同时表明,150mV的染料再生驱动力对该类吲哚啉有机染料而言是可行的,从优化染料再生过程的角度上有效地避免了能量损失。
为了提高吲哚啉类染料的稳定性并优化染料的光伏性能,进一步引入辅助吸电子基,发展D-A-π-A型敏化染料。考虑到苯甲酰亚胺及苯并三氮唑具有较好的吸电子能力,且其结构中的N上可以方便地引入烷基链从而有效地改善染料的溶解性、抑制注入电子与电解质中氧化还原对间的电荷复合过程,将苯甲酰亚胺及苯并三氮唑单元作为辅助吸电子基,设计合成D-A-π-A型染料LS-2及WS-5。利用二者相似的分子结构,系统研究了辅助吸电子基团对染料的吸收、电化学及光伏性质的影响。实验结果及DFT理论模拟证明,具有相似苯并五元环结构的苯甲酰亚胺及苯并三氮唑单元的引入对染料的光物理、电化学性质及电子云分布有截然不同的影响：i)苯并三氮唑的引入使WS-5的HOMO能级有效地离域于整个分子骨架,而含两个羰基的苯甲酰亚胺单元的引入使LS-2呈现出很大的扭曲构型,其HOMO(?)级主要位于电子给体一端；ii)LS-2的基态优化构型结果表明,“D-A”及“A-π”平面间均呈现出较大的二面角,进一步证明苯甲酰亚胺的引入破坏了分子的离域,不利于分子内电荷迁移(ICT)过程；ⅲ) EIS测试结果表明,相比于LS-1,WS-5及LS-2的电子寿命分别提高了18.6及5.0倍。由于两个分子中均含有较长的烷基链,它们均表现出较高的开路电压(>750mV)。其中,WS-5表现出更高的短路光电流密度,光电转换效率达到8.38%,相比之下,扭曲构型的LS-2的光伏性能仅为同等条件下WS-5的60%。该工作表明在对D-A-π-A构型的染料进行结构修饰时,需谨慎选择辅助吸电子基团。
为了对吲哚啉染料LS-1的光伏性能进行优化,实现对太阳光更有效的吸收利用,分别将EDOT、双键、己基噻吩引入到LS-1中,设计合成染料LS-3、LS-6及LS-7,研究不同共轭基团对染料性能的影响。实验结果表明EDOT、双键及烷基链的引入能不同程度地实现对染料光吸收性能的优化,相比于双键及烷基链,EDOT单元的引入更有利于优化染料的光物理及电化学性质。I-V及EIS测试结果表明,噻吩基团上烷基链的引入可以实现对染料在二氧化钛表面的吸附形态及TiO_2/染料/电解液界面的优化过程,并获得较高的开路电压。在优化条件下,以己基噻吩为共轭桥连的LS-7表现出5.45%的光电转换效率,其中JSC=11.61mA cm-2,VOC=744mV,ff=0.63。
As a potential alternative to conventional inorganic photovoltaic devices, dye-sensitized solar cells (DSSCs) have attracted increasing attention in the past decades due to their high performance/price ratio and environmentally friendly nature. As a light-absorbing media in DSSCs, organic sensitizers are considered as promising candidates because of their facile structural modifications, low cost, and relatively high absorption coefficient with respect to ruthenium complexes. Extensive efforts have been focused on improving the overall efficiency and stablility of the sensitizers through rationalizing molecular structures. In this dissertation, we strived to optimize the donor moiety, conjugated bridge and acceptor/anchoring group of sensitizers with the configuration of D-π-A. Besides, we incorporated phthalimide and benzotriazole as auxiliary electron electron-withdrawing units in indoline based D-A-π-A sensitizers to systematically study their effect on the photophysical and electrochemical as well as photovoltaic properties in DSSCs.
The main contents of the manuscript are summarized as follows:
In introduction, the research background and basic working principle of DSSCs were introduced. The recent progress of typical dye sensitizers was reviewed, and the research strategy of the dissertation was presented.
A novel series of organic dyes containing a fluorene unit as the conjunction bridge (S1-S4) have been designed and synthesized for a potential application in DSSCs. Their absorption spectra, electrochemical and photovoltaic properties have been investigated in detail. The tuning of the HOMO and LUMO energy levels can be conveniently realized by alternating the donor moiety. As demonstrated, the indoline unit can exhibit a stronger electron donating ability, realizing a broader absorption when coated onto TiO2. The incorporation of octyl-substituted fluorene is highly beneficial to prevent close π-π aggregation, thus favorably suppressing charge recombination and intermolecular interaction. In both HOMO and LUMO orbitals, the electron density located at the conjunction bridge (fluorene unit) is quite low, suggesting that the incorporated fluorene unit plays quite small role in the electron delocalization between the donor and acceptor units due to the twist conformation. The overall conversion efficiencies of DSSCs based on these dyes are in the range of3.04to4.26%and highly dependent upon their donor moieties. Among these dyes, S3,which utilizes a methyl-substituted indoline moiety as an electron donor, has shown a maximum short current destiny (JSc), with a relatively high open circuit voltage (Foc) of727mV.
For developing panchromatic dyes, we develop sensitizer C-RA, and focus on the effect of rhodanine acceptor on photovoltaic performances in D-π-A indoline dye. Upon changing from cyanoacrylic acid (C-CA) to rhodanine-3-acetic acid (C-RA) as acceptor and anchoring group, C-RA shows broader absorption band, which can overlap with the solar spectrum more preferably. However, the power conversion efficiency of DSSCs based on C-RA (0.57%～0.90%) is one order of magnitude with respect to C-RA (8.49%). We find that the distinct difference of IPCE values between C-CA and C-RA is predominately attributed to the different excited electron injection yield (Φinj). Both the excited electron lifetime and DFT calculation indicate that the serious charge recombination between the photo-induced electron and the oxidized dye state in C-RA results in a low electron injection efficiency, leading to a low Jsc. Moreover, with respect to C-CA, the systematic SLIT and EIS studies demonstrate that C-RA holds the relatively low injection charge density in the TiO2electrode and fast charge recombination rate, leading to a low Voc. Our studies are highly helpful to the design of novel metal-free D-π-A organic sensitizers, especially for those using rhodanine-3-acetic acid as acceptor.
Two novel D-π-A organic dyes LS-4and LS-5, containing3,4-ethylenedioxythiophene (EDOT) in the conjugated bridge, are developed for nanocrystalline TiO2-based DSSCs. Systematic investigation is carried out on focus of the joint photophysical and electrochemical analysis on photovoltaic properties. Incorporating EDOT as conjugated bridge brings several characteristics:(i) distinctly increasing the light-harvesting ability such as broadening absorption range and increasing molar extinction coefficients;(ii) improving electron injection with the predominant enhancement of short-circuit photocurrent;(iii) exhibiting little effect on the open circuit voltage. LS-4shows a more negative oxidation potential and a bathochromic shift in absorption spectra with respect to LS-5, indicative of the more powerful electron-donating capability of indoline unit than that of triphenylamine. With coadsorption of2mM chenodeoxycholic acid (CDCA), the LS-4based DSSC exhibits a promising conversion efficiency of6.05%, with a,Jsc of13.23mA cm-2, Voc of642mV, and fill factor (ff) of0.711under AM1.5illumination (100mW cm-2). Moreover, in the system of LS-4, DSSCs is workable with the driving force of150mV for dye regeneration process, paving a road towards minimizing energy losses in dye regeneration process.
Two organic D-A-π-A sensitizers LS-2and WS-5containing N-octyl substituted phthalimide and benzotriazole as auxiliary electron withdrawing units with similar dimension and structure architecture were systematically studied on focus of photophysical, electrochemical as well as photovoltaic properties in nanocrystalline TiO2-based dye-sensitized solar cells. Interestingly, with similar five-member benzo-heterocycles, the two auxiliary acceptors of phthalimide and benzotriazole play exact different roles in absorption and intramolecular charge transfer:(ⅰ) in contrast with WS-5delocalized throughout the entire chromophore, the HOMO orbital of LS-2is mainly located at the donor part due to the twist conformation with the existence of two carbonyl groups in phthalimide;(ⅱ) the dihedral angles of "D-A" plane and "A-π" plane in LS-2further suggest that the incorporation of phthalimide moiety results in curvature of electron delocalization over the whole molecule;(ⅲ) in contrast with the beneficial charge transfer of benzotriazole in WS-5, the phthalimide unit in LS-2plays an opposite negative contribution to the charge transfer, that is, blocking ICT from donor to accepter to some extent; and (ⅳ) in electrochemical impedance spectroscopy, the incorporated benzotriazole unit enhances electron lifetime by18.6-fold, the phthalimide only increases electron lifetime by5.0-fold. Without coadsorption of CDCA, the DSSCs based on WS-5exhibited a promising maximum conversion efficiency of8.38%with significant enhancement in all photovoltaic parameters (Jsc=15.79mA cm-2, Voc=791mV,ff=0.67). In contrast, with the very similar D-A-π-A feature changing the additional acceptor from benzotriazole to phthalimide unit, the photovoltatic efficiency based on LS-2was only5.11%, with less efficient photovoltaic parameters (Jsc=10.06mA cm-2, Voc=748mV,ff=0.68). Therefore, our results demonstrate that it is essential to choose proper subsidiary withdrawing unit in D-A-π-A sensitizer configuration for DSSCs.
To optimize the photovoltaic performance of LS-1, the π-bridges of EDOT, methylene methine chain and hexyl-thiophene was introduced into indoline based sensitizer to develop dyes LS-3, LS-6and LS-7, and systematically studied the effect of different conjugated bridges on the photophysical, electrochemical as well as photovoltaic properties in DSSCs. The absorption spectra of three dyes show significant red-shift with respect to LS-1. Among them, EDOT in LS-3shows a priority in optimizing the photophysical and electrochemical properties of indoline based sensitizers. I-V and EIS results indicate that the introduction of alkyl chains on thiophene unit is effective in TiO2/dye/electrolyte interface modification, and realizing the enhancement of Voc. Under optimized condition, LS-7based DSSC exhibits a conversion efficiency of5.45%, with the parameters Jsc=11.61mA cm-2, Voc=744mV,ff=0.63.
引文
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