A novel ruthenium sensitizer with a hydrophobic 2-thiophen-2-yl-vinyl-conjugated bipyridyl ligand for effective dye sensitized TiO2 solar cells

Jiang, Ke‐Jian; Masaki, N; Xia, Jiangbin; Noda, Shuji; Yanagida, Shozo

doi:10.1039/b602989b

Cited by 176 publications

(78 citation statements)

References 17 publications

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“…[28] The ruthenium dye, cisRu(dhtbpy)(dcbpy)(NCS) 2 [dhtbpy¼4,4 0 -di(hexyl thienylvinyl)-2,2 0 -bipyridyl; dcbpy¼4,4 0 -dicarboxylic acid-2,2 0 -bipyridyl] (HRS-1), was reported previously. [29] Scheme 1 presents the chemical structures of the two dye molecules. Both of them contain one or two carboxylic acid groups for interlocking to the nc-TiO 2 surface through chemically bonding.…”

Section: Resultsmentioning

confidence: 99%

Photovoltaics Based on Hybridization of Effective Dye‐Sensitized Titanium Oxide and Hole‐Conductive Polymer P3HT

Jiang

Manseki

et al. 2009

Adv Funct Materials

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122

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Here, the fabrication of quasi‐solid‐state TiO2/dye/poly(3‐hexylthiophene) (P3HT) solar cells is reported, in which the dyes with oleophilic thienyl groups were employed and ionic liquid (IL), 1‐ethyl‐3‐methylimidazolium (EMIm) containing lithium bis(trifluromethanesulfone)amide (Li‐TFSI) and 4‐tert‐butylpyridine (t‐BP) are assembled with dyed TiO2 surfaces. One of the devices gave a high conversion efficiency of up to 2.70% under 1 sun illumination. The excellent performance is ascribed to successful molecular self‐organization at interface of the dye molecules and P3HT, and to the efficient charge separation and diffusion acquired by introduction of the IL coupled with Li‐TFSI and t‐BP.

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Section: Resultsmentioning

confidence: 99%

Photovoltaics Based on Hybridization of Effective Dye‐Sensitized Titanium Oxide and Hole‐Conductive Polymer P3HT

Jiang

Manseki

et al. 2009

Adv Funct Materials

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122

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“…The electronic absorption spectra of the dye molecules measured in dimethylformamide (DMF) (Fig. 3a) ported previously, [8] it is close to that of HRS-1 (cis-di(thiocyanato)-4,4′-di(hexylthienylvinyl)-2,2′-bipyridine-4,4′-dicarboxylate-2,2′-bipyridine ruthenium(II)), [9] which uses thienylvinyl-conjugated bipyridine as an ancillary ligand. The electronic absorption spectra (in transmission mode) of SJW-E1, CYC-B3, and N3 assembled on the TiO 2 thin films ( Fig.…”

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confidence: 89%

A New Route to Enhance the Light‐Harvesting Capability of Ruthenium Complexes for Dye‐Sensitized Solar Cells

Chen

et al. 2007

Advanced Materials

178

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Dye-sensitized solar cells (DSCs) have been explored for more than a decade for realistic photovoltaic applications owing to their high conversion efficiency and low cost.[1] Molecular engineering of the sensitizers to achieve high photovoltaic performance and long-term device stability is one of the critical strategies. Since the first high-efficiency ruthenium-based sensitizer, cis-di(thiocyanato)-bis-(2,2′-bipyridyl)-4,4′-dicarboxylate ruthenium(II) (N3), reported by Grätzel and coworkers in 1993, [2] various structural modifications have been performed to improve the molar extinction coefficient of the sensitizers. It was found that elongating the conjugation length of the anchoring or ancillary ligand is the best route, [3][4][5] although it may come up against the problem of solubility, which is not only a critical point for dye preparation, purification, and identification but also one of the crucial factors for the photovoltaic performance of DSCs.[6] Nevertheless, it is essential to enhance the light-harvesting capacity and at the same time maintain the desirable solubility of dyes to be used in DSCs. Here we report the synthesis and performance of a new well-designed ruthenium complex, SJW-E1 (cis-di(thiocyanato)-4,4′-di(octylethylenedioxythienyl)-2,2′-bipyridine-4,4′-dicarboxylate-2,2′-bipyridine ruthenium(II)), which showed high light-harvesting capacity and good solubility in organic solvents. Another new ruthenium complex, denoted CYC-B3 (cis-di(thiocyanato)-4,4′-di(octylthienyl)-2,2′-bipyridine-4,4′-dicarboxylate-2,2′-bipyridine ruthenium(II)), was also prepared not only to explore the effect of thiophene moieties but also for comparison with SJW-E1 to investigate the impact of the ethylenedioxy groups on the physicochemical properties and performance of the dye molecules.The structures of SJW-E1 and CYC-B3, which incorporate a-octyl-ethylene-dioxythiophene (O-EDOT) and octyl-thiophene-substituted bipyridine, respectively, as an ancillary ligand, are shown in Figure 1. The synthetic details and structure characterizations are provided in the Supporting Information. The frontier orbitals of SJW-E1 and CYC-B3 obtained with a semiempirical [7] calculation method (ZINDO/1) were illustrated in Figure 2. The results showed that both the highest-occupied molecular orbitals (HOMOs) and lowest-unoccupied molecular orbitals (LUMOs) of SJW-E1 and CYC-B3 have similar localizations: The HOMOs and LUMOs are contributed from the metal center with the NCS ligands and the anchoring ligand (4,4′-dicarboxylate-2,2′-bipyridine), respectively. In other words, the two dyes have a similar metal-to-ligand charge transfer (MLCT) excitation. In addition, the same anchoring group in the two dyes provides a comparable interfacial electron transfer process. Therefore the efficiency of the dyes will depend primarily on the absorption coefficients of their MLCT bands. The electronic absorption spectra of the dye molecules measured in dimethylformamide (DMF) (Fig. 3a) display that the lower energy MLCT band for SJW-E1 is centered...

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“…45,46 It has been shown that Ru(II) polypyridyl complexes perform very efficiently in DSSCs. [47][48][49][50][51][52][53] The complexes used for DSSCs exhibit interesting photophysical properties, such as light absorption across the visible spectrum and long excited-state lifetimes. [54][55][56][57] These properties make this class of complexes highly interesting as potential PS in PDT.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of New Ru(II) Polypyridyl Photosensitizers for Photodynamic Therapy

et al. 2014

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Two Ru(II) polypyridyl complexes, Ru(DIP)2(bdt) (1) and [Ru(dqpCO2Me)(ptpy)](2+) (2) (DIP = 4,7-diphenyl-1,10-phenanthroline, bdt = 1,2-benzenedithiolate, dqpCO2Me = 4-methylcarboxy-2,6-di(quinolin-8-yl)pyridine), ptpy = 4'-phenyl-2,2':6',2 -terpyridine) have been investigated as photosensitizers (PSs) for photodynamic therapy (PDT). In our experimental settings, the phototoxicity and phototoxic index (PI) of 2 (IC50(light): 25.3 M, 420 nm, 6.95 J/cm(2); PI >4) and particularly of 1 (IC50(light): 0.62 M, 420 nm, 6.95 J/cm(2); PI: 80) are considerably superior compared to the two clinically approved PSs porfimer sodium and 5-aminolevulinic acid. Cellular uptake and distribution of these complexes was investigated by confocal microscopy (1) and by inductively coupled plasma mass spectrometry (1 and 2). Their phototoxicity was also determined against the Gram-(+) Staphylococcus aureus and Gram-(-) Escherichia coli for potential antimicrobial PDT (aPDT) applications. Both complexes showed significant aPDT activity (420 nm, 8 J/cm(2)) against Gram-(+) (S. aureus; >6 log10 CFU reduction) and, for 2, also against Gram-(-) E. coli (>4 log10 CFU reduction). Two Ru(II) polypyridyl complexes, Ru(DIP)2(bdt) (1) and [Ru(dqpCO2Me)(ptpy)] 2+ (2) (DIP = 4,7-diphenyl-1,10-phenanthroline; bdt = 1,2-benzenedithiolate; dqpCO2Me = 4-methylcarboxy-2,6-di(quinolin-8-yl)pyridine); ptpy = 4'-phenyl-2,2':6',2''-terpyridine) have been investigated as photosensitizers (PSs) for photodynamic therapy (PDT). In our experimental settings, the phototoxicity and photo-index (PI) of 2 (IC50(light): 25.3 μM, 420 nm, 6.95 J/cm 2 ; PI: >4) and particularly of 1 (IC50(light): 0.62 μM, 420 nm, 6.95 J/cm 2 ; PI: 80) are considerably superior compared to the two clinically approved PSs porfimer sodium and 5-aminolevulinic. Cellular uptake and distribution of these complexes was investigated by confocal microscopy (1) and by inductively coupled plasma-mass spectrometry (1 and 2). Their phototoxicity was also determined against the Gram-(+) S. aureus and Gram-(−) E. coli for potential antimicrobial PDT (aPDT) applications. Both complexes showed significant aPDT activity (420 nm, 8 J/cm 2 ) against Gram-(+) (S. aureus; >6 log10 CFU reduction) and, for 2, also against Gram-(−) E. coli (>4 log10 CFU reduction). 3Introduction.

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A novel ruthenium sensitizer with a hydrophobic 2-thiophen-2-yl-vinyl-conjugated bipyridyl ligand for effective dye sensitized TiO2 solar cells

Cited by 176 publications

References 17 publications

Photovoltaics Based on Hybridization of Effective Dye‐Sensitized Titanium Oxide and Hole‐Conductive Polymer P3HT

Photovoltaics Based on Hybridization of Effective Dye‐Sensitized Titanium Oxide and Hole‐Conductive Polymer P3HT

A New Route to Enhance the Light‐Harvesting Capability of Ruthenium Complexes for Dye‐Sensitized Solar Cells

Synthesis, Characterization, and Biological Evaluation of New Ru(II) Polypyridyl Photosensitizers for Photodynamic Therapy

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