Triphenylamine- and benzothiadiazole-based dyes with multiple acceptors for application in dye-sensitized solar cells

Mikroyannidis, John A.; Suresh, P.; Roy, M.S.; Sharma, G. D.

doi:10.1016/j.jpowsour.2009.10.107

Cited by 21 publications

(4 citation statements)

References 48 publications

(58 reference statements)

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“…For this purpose, various low bandgap sensitizers for DSSCs have been prepared by implementing, e.g., the electrondeficient benzothiadiazole (BTDA) unit into the bridging framework of D-π-A molecules. [10][11][12][13][14][15][16] In search of new metal-free sensitizers for DSSCs, we present new D-A sensitizers 1 and 2 that are built up by a triarylaminebithiophene donor (D) and a BTDA-substituted cyanoacrylic…”

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confidence: 99%

Significant Improvement of Dye‐Sensitized Solar Cell Performance by Small Structural Modification in π‐Conjugated Donor–Acceptor Dyes

Haid

Marszałek

Mishra

et al. 2012

Adv Funct Materials

415

253

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Two donor-π-acceptor (D-π-A) dyes are synthesized for application in dyesensitized solar cells (DSSC). These D-π-A sensitizers use triphenylamine as donor, oligothiophene as both donor and π-bridge, and benzothiadiazole (BTDA)/cyanoacrylic acid as acceptor that can be anchored to the TiO 2 surface. Tuning of the optical and electrochemical properties is observed by the insertion of a phenyl ring between the BTDA and cyanoacrylic acid acceptor units. Density functional theory (DFT) calculations of these sensitizers provide further insight into the molecular geometry and the impact of the additional phenyl group on the photophysical and photovoltaic performance. These dyes are investigated as sensitizers in liquid-electrolyte-based dye-sensitized solar cells. The insertion of an additional phenyl ring shows significant influence on the solar cells' performance leading to an over 6.5 times higher efficiency (η = 8.21%) in DSSCs compared to the sensitizer without phenyl unit (η = 1.24%). Photophysical investigations reveal that the insertion of the phenyl ring blocks the back electron transfer of the charge separated state, thus slowing down recombination processes by over 5 times, while maintaining efficient electron injection from the excited dye into the TiO 2 -photoanode. DOI IntroductionDye-sensitized solar cells (DSSCs) are one of the most promising environmentally friendly photovoltaic devices because of their low material costs, flexiblity, and easy manufacturing processes. [ [17] gave intermediates 11 and 12 in yields of 86% and 92%, respectively. Final Knoevenagel condensation of 11 and 12 with cyanoacetic acid in the presence of ammonium acid as acceptor and anchoring group (A). Dye 1 contains the BTDA unit directly adjacent to the anchoring group, whereas dye 2 contains "only" an additional phenyl ring between both acceptor units. We investigate the influence of the structural modification of the sensitizer on optical, redox, and solar cell performance. This subtle structural change in the sensitizer induced a significant influence on the DSSCs performance. Results and Discussion SynthesisD-A dyes 1 and 2 were synthesized as shown in Scheme 1. phenyl]aniline 3 was coupled Scheme 1. Synthesis of dyes 1 and 2. a) Pd 2 (dba) 3 ·CHCl 3 , HP t Bu 3 BF 4 , 2 m aq. K 3 PO 4 (4 eq.), THF, room temperature (r.t.). b) (i) n -BuLi, THF, -78 °C (ii) Bu 3 SnCl. c) K 2 CO 3 , 1,4-dioxane/water, reflux, 1 h. 350 to 800 nm (Figure 1a). All data are summarized in Table 1. The bands at 395 nm (dye 1) and 392 nm (dye 2) correspond to the π-π * transition of the conjugated system. The longest wavelength absorption of dye 2 (λ max = 515 nm) is assigned to a charge transfer (CT) transition and is significantly blue-shifted compared to the CT-band of dye 1 (λ max = 570 nm). Furthermore, the intensity and molar extinction coefficient for the CT transition of dye 2 (ε = 29,400 L mol) is increased by a factor of 1.6 compared to dye 1 (ε = 18,900 L mol). The emission maxima of dyes 1 and 2 can be found at 681 and 665 nm, respect...

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confidence: 99%

Significant Improvement of Dye‐Sensitized Solar Cell Performance by Small Structural Modification in π‐Conjugated Donor–Acceptor Dyes

Haid

Marszałek

Mishra

et al. 2012

Adv Funct Materials

415

253

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“…In a report, the Ag metal:BCP hybrid complex formed upon Ag evaporation, possess favorable states (LUMO level of the complex) inside the bandgap of BCP, leading to efficientelectron extraction in such cells 25 . In the past benzothiadiazole (BTD) based polymers and small molecules have been widely employed in opto-electrical devices, such as organic light emitting diodes (OLEDs) due to its fluorescent properties 26,27 , while the development of D-A structures in combination with triphenylamine (TPA) moieties have been extensively employed as dye/active materials in dye sensitized solar cells (DSSC) 28,29 /OSCs 30,31 . BTD-TPA2 is a small organic molecule, having an electron-poor benzothiadiazole core with two electron-rich triphenylamine arms, and has been explored as red-light-emitting material in OLED application 32,33 .…”

Section: Introductionmentioning

confidence: 99%

Benzothiadiazole–triphenylamine as an efficient exciton blocking layer in small molecule based organic solar cells

Calió

Patil

Benduhn

et al. 2018

Sustainable Energy Fuels

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“…Ternary semiconductor, ZTO, has high electron mobility, high electrical conductivity, and has attractive optical properties making it suitable for application in dye-sensitized solar cells [6], Li-ion batteries, amongst others [7][8][9]. Compared to the photoelectrodes fabricated with ZnO and SnO 2 particles in dyesensitized solar cell configuration, ZTO photoelectrodes are reported to be more stable and improve the solar cell performance [10,11]. ZTO has also been demonstrated to be an interesting material for gas sensing applications [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Phase transformation behavior of zinc metastannates obtained by aqueous precipitation at different temperatures

Al-Hinai

Dutta

2014

J Mater Sci

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Phase transformation studies in ZnO-SnO 2 system from zinc metastannate (ZnSnO 3 ) to zinc orthostannate (Zn 2 SnO 4 ) with annealing temperature are reported. Non-centrosymmetric oxides show unique symmetry dependent and spontaneous polarization properties, which are technologically important. ZnSnO 3 particles were synthesized by a simple aqueous synthesis at low temperatures designed with the assistance of potential-pH diagrams. ZnSnO 3 particles synthesized at 4°C are more porous losing the ilmenite structure upon annealing at 200°C, while the other samples prepared at higher temperatures (25-65°C) becomes amorphous at 300°C. The phase transformation into the inverse spinel orthostannate phase occurs around 750°C in all the samples.

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Triphenylamine- and benzothiadiazole-based dyes with multiple acceptors for application in dye-sensitized solar cells

Cited by 21 publications

References 48 publications

Significant Improvement of Dye‐Sensitized Solar Cell Performance by Small Structural Modification in π‐Conjugated Donor–Acceptor Dyes

Significant Improvement of Dye‐Sensitized Solar Cell Performance by Small Structural Modification in π‐Conjugated Donor–Acceptor Dyes

Benzothiadiazole–triphenylamine as an efficient exciton blocking layer in small molecule based organic solar cells

Phase transformation behavior of zinc metastannates obtained by aqueous precipitation at different temperatures

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