Organic Dyes Containing a Coplanar Indacenodithiophene Bridge for High-Performance Dye-Sensitized Solar Cells

Chen, Jia Hung; Tsai, Chih‐Hung; Wang, Shao-An; Lin, Ya-Yan; Huang, Tsung‐Wei; Chiu, Stephan; Wu, Chung‐Chih; Wong, Ken‐Tsung

doi:10.1021/jo201730a

Cited by 84 publications

(32 citation statements)

References 61 publications

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“…In this regard, Wong et al have attached bisphenylamino units directly to the cyanoacrylic acid capped indacenodithiophene for a series of D‐A dyes. On the other hand, perylene derivatives have been widely employed as a fluorescent lipid probe in cell membrane cytochemistry, a blue dopant material in organic light‐emitting diodes, and a significant class of high‐quality pigments for the coloration of automotive paint, synthetic fibers, and engineering resins .…”

Section: Introductionmentioning

confidence: 99%

N‐Annulated Perylene as a Coplanar π‐Linker Alternative to Benzene as a Low Energy‐Gap, Metal‐Free Dye in Sensitized Solar Cells

Yao

Yan

Zhang

et al. 2014

Advanced Energy Materials

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Perylenes are well‐known pigments with excellent chemical, thermal, and photochemical stabilities and have been used in various optical and electronic fields. Although for sensitized mesoscopic solar cells there is rapid progress of metal‐free thiophene dyes, which now reach over 11.5% power conversion efficiency (PCE) at air mass 1.5 global (AM1.5G) conditions, the so far reported highest PCE of a perylene dye is only 6.8%. Here, a new metal‐free organic donor‐acceptor (D‐A) dye (C261) featuring a bisarylamino functionalized N‐annulated perylene electron‐releasing segment and a cyanoacrylic acid electron‐withdrawing unit is synthesized. Combining a mesoporous titania film grafted by this structurally simple perylene dye with a non‐corrosive cobalt redox shuttle, an 8.8% PCE is achieved at an irradiance of the AM1.5G sunlight. By selecting the model dye G221 as a reference, theoretical calculations, steady‐state and time‐resolved spectroscopies, and electrical measurements are used to compare the energy‐levels, light absorptions, and mutichannel charge transfer dynamics that contribute to the photovoltaic behavior.

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Section: Introductionmentioning

confidence: 99%

N‐Annulated Perylene as a Coplanar π‐Linker Alternative to Benzene as a Low Energy‐Gap, Metal‐Free Dye in Sensitized Solar Cells

Yao

Yan

Zhang

et al. 2014

Advanced Energy Materials

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“…Nevertheless, many organic sensitizers have still presented a low conversion efficiency and low stability. A successful molecular engineering for the high efficiency was achieved by incorporating planar units, such as cyclopentadithiophene, [13][14][15] dithienosilole, [16,17] carbon-bridged phenylenevinylene, [18] indacenodithiophene, [19] cyclopenta [1,2- [2',1':4,5]thieno [2,3-d]thiophene, [20] and indeno [1,2-b]thiophene bridging group, [21] into the p-linker unit. [7][8][9] Several strategies have been considered for addressing both these issues such as the use of b-cyclodextrin-encapsulated molecules, [10] the structural modification of the sensitizers, [11] and the use of additives.…”

Section: Introductionmentioning

confidence: 99%

“…In addition to the electron donor and acceptor units in a push-pull dye, the p-conjugated linker is of importance in improving the cell performance. A successful molecular engineering for the high efficiency was achieved by incorporating planar units, such as cyclopentadithiophene, [13][14][15] dithienosilole, [16,17] carbon-bridged phenylenevinylene, [18] indacenodithiophene, [19] cyclopenta[1,2b:4,5-b']dithiophene [2',1':4,5]thieno [2,3-d]thiophene, [20] and indeno [1,2-b]thiophene bridging group, [21] into the p-linker unit. In addition, the co-adsorption of dyes with additives, such as decylphosophonic acid, [22] dineohexyl bis(3,3-dimethylbutyl)phosphinic acid, [23] chenodeoxycholic acid (CDCA), [24] and 4-[bis (9,9-dimethyl-9H-fluoren-2-yl)amino]benzoic acid (HC-A), [25][26][27] is proven to be effective in dissociating p-p stacking or dye aggregation.…”

Section: Introductionmentioning

confidence: 99%

Organic Sensitizers Featuring a Planar Indeno[1,2‐b]‐thiophene for Efficient Dye‐Sensitized Solar Cells

lim

Song

et al. 2013

ChemSusChem

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An efficient organic sensitizer (JK-306) featuring a planar indeno[1,2-b]thiophene as the π-linker of a bridging unit for dye-sensitized solar cells (DSSCs) was synthesized. The sensitizer had a strong molar absorption coefficient and a red-shifted absorption band compared with JK-305, which resulted in a significant increase in the short-circuit photocurrent density. We incorporated a highly congested bulky amino group into the 2',4'-dihexyloxybiphenyl-4-yl moiety, an electron donor, to diminish the charge recombination and to prevent aggregation of the sensitizer. Under standard AM 1.5G solar conditions, JK-306-sensitized cells in the presence of co-adsorbents chenodeoxycholic acid (CDCA) and 4-[bis(9,9-dimethyl-9H-fluoren-2-yl)amino]benzoic acid (HC-A), which afforded an overall conversion efficiency of 8.37% and 8.52%, respectively. Upon changing the I(-) /I3 (-) electrolyte to the Co(II) /Co(III) redox couple, the cell gave rise to a significantly improved conversion efficiency of 10.02% with the multifunctional HC-A, which is one of the highest values reported for DSSCs with a cobalt-based electrolyte. Furthermore, the JK-306-based solar cell with a polymer gel electrolyte revealed a high conversion efficiency of 7.61%, which is one of the highest values for cells based on organic sensitizers.

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“…Due to the rigid structural feature and good π‐conjugation, the IDT unit has also been considered for use in DSSC dyes. With TPA or DPA as the electron donor, the IDT unit has been employed as a conjugated spacer to construct the organic sensitizer for DSSCs. The dyes show intense and broad absorption, and best efficiency of the cells reaches 6.70%.…”

Section: Introductionmentioning

confidence: 99%

Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

Fan

Zhao

Liu

et al. 2019

Int J of Quantum Chemistry

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Indacenodithiophene (IDT)‐based high‐efficiency photovoltaics have received increasing attention recently. This paper reports a density functional theory investigation of the electronic and optical properties of three IDT‐based organic dyes together with the dye/(TiO2)46 interface. In order to enhance the photoelectric properties of IDT dyes, this paper considers two methods for the structure modification of the experimentally reported dye DPInDT (J. Org. Chem. 2011, 76, 8977): the extension of the conjugation length by dithienothiophene as well as the heteroatom substitution of the bridging atoms by electron‐rich nitrogen atoms. Our calculations show that both methods obviously affect the distributions of the molecular orbitals and notably red shift the absorption peaks of around 20 nm, with the former method demonstrating enhanced light harvesting efficiency. The structure modifications proposed also enhance the emission spectrum properties for IDT‐based organic dyes. The calculated ultrafast injection time of electrons from the excited state of IDT dyes to the (TiO2)46 belongs to the femtosecond order of magnitude, and is ideal for efficient photoelectric conversion process in dye‐sensitized solar cells (DSSCs) applications. The IDT dyes designed in this paper have good electronic and spectroscopic properties. This study is expected to provide useful guidance for the development of novel IDT dyes for applications in DSSCs.

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Organic Dyes Containing a Coplanar Indacenodithiophene Bridge for High-Performance Dye-Sensitized Solar Cells

Cited by 84 publications

References 61 publications

N‐Annulated Perylene as a Coplanar π‐Linker Alternative to Benzene as a Low Energy‐Gap, Metal‐Free Dye in Sensitized Solar Cells

N‐Annulated Perylene as a Coplanar π‐Linker Alternative to Benzene as a Low Energy‐Gap, Metal‐Free Dye in Sensitized Solar Cells

Organic Sensitizers Featuring a Planar Indeno[1,2‐b]‐thiophene for Efficient Dye‐Sensitized Solar Cells

Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

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