Efficient near infrared D–π–A sensitizers with lateral anchoring group for dye-sensitized solar cells

Hao, Yan; Yang, Xichuan; Cong, Jiayan; Tian, Haining; Hagfeldt, Anders; Sun, Licheng

doi:10.1039/b908396k

Cited by 114 publications

(95 citation statements)

References 14 publications

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“…[16] The withdrawing ability of indan-1,3-dione can be further enhanced by replacing one or both carbonyl groups by dicyanovinyl or sulfoxide moieties to afford 3-(dicyanomethylene)indan-1-one, 1,3-bis(dicyanomethylene)indan, and 3-dicyanomethylene-2,3-dihydrobenzo [b]thiophene 1,1-dioxide. [17] In addition to significant NLO activity, [18] push-pull molecules bearing these acceptor moieties have also found numerous applications in DSSCs, [19] bulk heterojunction solar cells (BHJSCs), [20] organic photovoltaic cells (OPVCs), [21] OLEDs, [22] as vesicle-, gel-, and glass-forming molecules, [23] or chromoionophores for anion sensing and recognition. [24] A joint feature of all of the aforementioned, mostly linear D-π-A systems is their terminal indan-1,3-dione acceptor.…”

Section: Introductionmentioning

confidence: 99%

T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

et al. 2015

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Sixteen model (donor-π-) 2 acceptor-π-donor [(D-π-) 2 A-π-D] molecules with an extraordinary T-shaped arrangement were designed and synthesized. Indan-1,3-dione was employed as a central acceptor with electron donors linked at the C-2, C-4, and C-7 positions. These push-pull molecules represent a first systematic modification of an indan-1,3-dione-fused benzene ring. The structures and properties of all target molecules were investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry, electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. A thorough evaluation of all of the gathered data has been performed,

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Section: Introductionmentioning

confidence: 99%

T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

et al. 2015

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“…This modification afforded near-IR organic dyes. [12] However, this series of dyes did not absorb the in 400-550 nm part of the sunlight spectrum and also showed lower photovoltage.…”

Section: Ling LImentioning

confidence: 98%

“…[14] Motivated by this natural tandem system, we report a tandem DSC [15] in which the front sub-cell employs a ZrO 2 -doped nanostructured TiO 2 semiconductor to improve the photovoltage and an organic dye (TH305 [16] ) to harvest sunlight in the 400-750 nm region, giving an efficiency of 9.05 % with a high photovoltage (794 mV), while the back sub-cell employs a normal TiO 2 electrode sensitized with a different organic dye (HY103 [12] ) to capture sunlight in the 500-800 nm region, achieving an additional efficiency of 2.45 %. The overall energy conversion efficiency of this tandem DSC is 11.5 %.…”

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confidence: 99%

A Double‐Band Tandem Organic Dye‐sensitized Solar Cell with an Efficiency of 11.5 %

Hao

Yang

et al. 2011

ChemSusChem

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In the two decades that have passed since O'Regan and Grät-zel first reported mesoporous nanostructured dye-sensitized solar cells (DSCs) in 1991, great progress has been made. [1] Recently, particular attention has been given to the development of organic dyes and tuning their lowest unoccupied and highest occupied molecular orbital (LUMO and HOMO) levels to match the conduction band (CB) of nanostructured semiconductors and redox potential of the electrolyte, respectively, to increase the total solar energy conversion efficiency. [2][3][4] However, the absorption spectra of most organic dyes reported thus far mainly cover the visiblelight region. [5,6] This has motivated research towards the development of new types of organic dyes [7][8][9][10] with absorption spectra extended to the near-IR and IR region. By adjusting the donor, linker, and acceptor units, our group obtained an organic "black dye" that absorbs panchromatic light up to 920 nm.[11] However, the efficiency of the dye was unsatisfactory owing to a lower photovoltage, caused by a large dark current. Recently, we also developed another series of donor-acceptor organic dyes with lateral carboxylic acid anchoring groups instead of cyanoacetic acid units. This modification afforded near-IR organic dyes.[12] However, this series of dyes did not absorb the in 400-550 nm part of the sunlight spectrum and also showed lower photovoltage.We turn to nature for inspiration on how to overcome these problems and achieve broader dye absorption spectra and lower photovoltages.[13] Two types of chlorophylls are used in natural photosynthesis: P680 to drive the high-voltage water oxidation reaction in Photosystem II; and P700 to drive the relatively low-voltage NADP + reduction in Photosystem I. [14] Motivated by this natural tandem system, we report a tandem DSC [15] in which the front sub-cell employs a ZrO 2 -doped nanostructured TiO 2 semiconductor to improve the photovoltage and an organic dye (TH305 [16] ) to harvest sunlight in the 400-750 nm region, giving an efficiency of 9.05 % with a high photovoltage (794 mV), while the back sub-cell employs a normal TiO 2 electrode sensitized with a different organic dye (HY103 [12] ) to capture sunlight in the 500-800 nm region, achieving an additional efficiency of 2.45 %. The overall energy conversion efficiency of this tandem DSC is 11.5 %.The two sub-cells are separated by a double-sided fluordoped tin oxide (FTO) conducting glass. Figure 1 shows pictures of the actual cell setup and a schematic of its construction. Shifting the CB band of TiO 2 towards more negative values is an effective way to improve the open-circuit photovoltage (V oc ) and increase the DSC's efficiency. There are two methods to make the CB more negative: adding an organic base to the electrolyte, and doping the TiO 2 with semiconductor materials with a more-negative CB energy level (E CB ). In our system, we added 4-tert-butylpyridine (TBP) to the electrolyte and also adopted the doping method by using ZrO 2 , which has a wider band gap (ca....

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“…[14] Compared to conventional D-p-A dyes (that use cyanoacrylic acid as acceptor and anchoring group), the anchoring group in these dyes was separated from the acceptor units. This change allowed tuning of the highest occupied-lowest unoccupied molecular orbital (HOMO-LUMO) levels (absorption spectra) in an easier way, through modifying the structure of the acceptor units.…”

mentioning

confidence: 99%

Molecular Design to Improve the Performance of Donor–π Acceptor Near‐IR Organic Dye‐Sensitized Solar Cells

Hao¹,

Yang²,

Zhou³

et al. 2011

ChemSusChem

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Since Grätzel and O'Brian first reported dye-sensitized solar cells (DSCs) in 1991, much effort has been devoted towards improving their energy conversion efficiency. [1][2][3] Recently, the design and synthesis of infrared/near-infrared (IR/near-IR)-dyes has become an important topic in the area of solar cells since it has been recognized that the solar spectrum has a large photon flux in the region of 500-1000 nm. Improving the absorption of solar light in this region is one of the main directions in aiming for DSC efficiencies beyond 15 %. Near-IR sensitizers are also of interest because of their potential applications in transparent solar cells for windows and tandem cells.When used in DSCs, near-IR dyes reported in the literature, such as squaraines, [4][5][6] zinc phthalocyanines [7][8][9][10] and perylene dyes, [11][12][13] normally show low incident-photon-to-current conversion efficiency (IPCE) values and poor stability compared to donorp spacer-acceptor (D-p-A) organic dyes. Recently, Ko [5] and Marder [6] independently reported several panchromatic squaraine sensitizers, which yielded relatively high power conversion efficiencies (PCEs) (6.29 % and 6.74 %) under AM 1.5 G irradiation. However, both displayed low IPCE values (< 70 %) from in the wavelength range 400-770 nm. Also, although a promising PCE of 4.6 % was achieved in a DSC based on a structurally related zinc phthalocyanine by Taya and co-workers, [9] the highest IPCE value was only 80 % at 680 nm.Recently, novel D-p-A organic dyes with two features were reported: new chromophores for sensitization in the near-IR region and new design of the anchoring group. [14] Compared to conventional D-p-A dyes (that use cyanoacrylic acid as acceptor and anchoring group), the anchoring group in these dyes was separated from the acceptor units. This change allowed tuning of the highest occupied-lowest unoccupied molecular orbital (HOMO-LUMO) levels (absorption spectra) in an easier way, through modifying the structure of the acceptor units. By adopting this strategy, we succeeded for the first time in extending the absorption spectra of D-p-A sensitizers for DSCs to the near-IR region. In particular, the dye HY103 gave a maximum IPCE of 86 % at 660 nm and an overall solarenergy-to-electricity conversion efficiency (h) of 3.7 %. The low open-circuit voltage (464 mV) limited its photovoltaic performance.To improve this system, we report a novel D-p-A organic dye with a lateral anchoring group: HY113. In HY113, a flexible, long carbon chain replaces the methyl group of the donor part of HY103. The aim of the present work is to make use of this carbon chain to prevent the formation of molecular aggregates on the semiconductor nanoparticles, thereby blocking charge recombination at relatively high open-circuit voltages and short-circuit photocurrent densities. HY113 performed impressively, with a maximum IPCE of 93 % at 660 nm and an overall solar-energy-to-electricity conversion efficiency of 5.1 %; the highest IPCE value in the near-IR region and the highest ...

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Efficient near infrared D–π–A sensitizers with lateral anchoring group for dye-sensitized solar cells

Abstract: A new strategy in which the anchoring group is separated from the acceptor groups of the dyes was developed; among these dyes, the HY103 dye gives a maximum IPCE value of 86% at 660 nm and an eta value of 3.7% in the NIR region reported in DSCs.

Cited by 114 publications

References 14 publications

T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

A Double‐Band Tandem Organic Dye‐sensitized Solar Cell with an Efficiency of 11.5 %

Molecular Design to Improve the Performance of Donor–π Acceptor Near‐IR Organic Dye‐Sensitized Solar Cells

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Efficient near infrared D–π–A sensitizers with lateral anchoring group for dye-sensitized solar cells

Abstract: A new strategy in which the anchoring group is separated from the acceptor groups of the dyes was developed; among these dyes, the HY103 dye gives a maximum IPCE value of 86% at 660 nm and an eta value of 3.7% in the NIR region reported in DSCs.

Cited by 114 publications

References 14 publications

T‐Shaped (Donor–π–)2Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

T‐Shaped (Donor–π–)2Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

A Double‐Band Tandem Organic Dye‐sensitized Solar Cell with an Efficiency of 11.5 %

Molecular Design to Improve the Performance of Donor–π Acceptor Near‐IR Organic Dye‐Sensitized Solar Cells

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T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione

T‐Shaped (Donor–π–)₂Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione