Push–pull type porphyrin based sensitizers: The effect of donor structure on the light-harvesting ability and photovoltaic performance

Qi, Qingbiao; Li, Renzhi; Luo, Jie; Zheng, Bin; Huang, Kuo‐Wei; Wang, Peng; Wu, Jishan

doi:10.1016/j.dyepig.2015.06.019

Cited by 27 publications

(20 citation statements)

References 43 publications

(11 reference statements)

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“…RuCp* (dppe)Cl [32] and Intermediates 2 b, 3 b and 4 b were prepared by similar reported literature. [23,24] Synthesis of intermediates 3 b and 4 b [24] Prepare for 3 b: 1-bromonaphthalene (3 a) (310 mg, 1.50 mmol), bis (4-methoxyphenyl)amine (344 mg, 1.50 mmol), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (23 mg, 0.025 mmol), t Bu 3 P (6 μL, 3.40 mmol) and potassium tert-butoxide (KO t Bu) (1.74 g, 0.015 mmol) were placed in a 50 mL round bottom flask that was outfitted with a condenser and stir bar. The reaction apparatus was evacuated and backfilled with dry argon.…”

Section: Methodsmentioning

confidence: 99%

“…Brominated intermediate 2 b was prepared via classical Ullman reaction [23] using 3-bromoaniline and p-iodoanisole as starting materials. 3 b and 4 b were obtained by Pd-catalyzed BuchwaldÀ Hartwig CÀ N coupling reactions [24] and converted into 3 c and 4 c by bromination in the next step. Monobromotriarylamines 2 b and 3 c-4 c and trimethylsilylacetylene underwent Pd-catalyzed Sonogashira coupling reactions [25] to obtain trimethylsilyl-protected compounds 2 c and 3 d-4 d with 40%-79% yields, respectively.…”

Section: Synthesis Characterization and Crystallographic Analysismentioning

confidence: 99%

“…51, 121.10, 124.50, 125.37, 126.37, 126.42, 128.84, 130.71, 132.85, 137.84, 142.04, 153.82. Synthesis of brominated intermediates b [23] and 3 c-4 c [24] b: KOH (2.8 g, 50 mmol) and CuI (0.1 g, 0.5 mmol) were added to a stirred toluene solution of p-iodoanisole (2.93 g, 12.5 mmol), 3-bromoaniline 2 a (0.86 g, 5.0 mmol) and 1,10-phenanthroline (90 mg, 0.5 mmol) under an argon atmosphere, the mixture was stirred at 125°C for 12 h. Chromatography on silica gel (CH 2 Cl 2 / petroleum ether(v/v) = 1 : 1) gave 2 b of a black solid. Yield: 0.80 g, 41%.…”

Section: Bmentioning

confidence: 99%

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Rutheniumethynyl‐Triarylamine Organic−Inorganic Mixed‐Valence Systems: Regulating Ru‐N Electronic Coupling by Different Aryl Bridge Cores

Zhang

Wang

et al. 2020

Chemistry An Asian Journal

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Four rutheniumethynyl-triarylamine complexes 1-4 with different aryl bridge cores were prepared. The solid structures of complexes 2-4 were fully confirmed by X-ray single-crystal diffraction analysis. Two consecutive one-electron oxidation processes of complexes 1-4 were attributed to the ruthenium and nitrogen centers, as revealed by cyclic voltammetry and square-wave voltammogram. Results also showed decreasing potential difference ΔE of complexes 1, 3, and 4, with the largest value for 2. Upon chemical oxidation of complexes 1-4 by 1.0 eq oxidation reagents FcPF 6 or AgSbF 6 , the mixed-valence complexes, except for 2 + , show characteristic broad NIR absorptions in the UV-vis-NIR spec-troscopic experiments. NIR multiple absorptions were assigned to NAr 2 !RuCp*(dppe) intervalence charge transfer (IVCT) and metal-to-ligand charge transfer transitions by TDDFT calculations. Coupling parameter (H ab) from Hush theory revealed that increasing electronic communication in 1 + , 3 + , and 4 +. Electron density distribution of the HOMO for neutral molecules (1, 3, and 4) and spin density distribution of the corresponding single-oxidized states (1 + , 3 + , and 4 +) increases progressively on the bridge as the size of the aromatic system increases, proving incremental contributions from bridge cores during oxidation.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Characterization and Crystallographic Analysismentioning

confidence: 99%

Section: Bmentioning

confidence: 99%

See 1 more Smart Citation

Rutheniumethynyl‐Triarylamine Organic−Inorganic Mixed‐Valence Systems: Regulating Ru‐N Electronic Coupling by Different Aryl Bridge Cores

Zhang

Wang

et al. 2020

Chemistry An Asian Journal

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“…Carbazole groups possess large similarity to the DPA, but with more rigid configuration (Zhao et al, 2016 ). Considering the “ring fusion” effect, one can expect a lower HOMO energy level of carbazole conjugated porphyrin compared to the DPA porphyrin (Qi et al, 2015 ). Xie et al demonstrated that an ethynylene bridge between carbazole and porphyrin causes a decrease in the energy gaps, resulting in a red shifting of the absorption band (Sun et al, 2014 ; Wang et al, 2014c ; Tang et al, 2015 ).…”

Section: The Development Of Porphyrins For Solar Cell Applicationmentioning

confidence: 99%

Push-Pull Zinc Porphyrins as Light-Harvesters for Efficient Dye-Sensitized Solar Cells

Liu

Wang

2018

Front. Chem.

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Dye-sensitized solar cell (DSSC) has been attractive to scientific community due to its eco-friendliness, ease of fabrication, and vivid colorful property etc. Among various kinds of sensitizers, such as metal-free organic molecules, metal-complex, natural dyes etc., porphyrin is one of the most promising sensitizers for DSSC. The first application of porphyrin for sensitization of nanocrystaline TiO2 can be traced back to 1993 by using [tetrakis(4-carboxyphenyl) porphyrinato] zinc(II) with an overall conversion efficiency of 2.6%. After 10 years efforts, Officer and Grätzel improved this value to 7.1%. Later in 2009, by constructing porphyrin sensitizer with an arylamine as donor and a benzoic acid as acceptor, Diau and Yeh demonstrated that this donor-acceptor framwork porphyrins could attain remarkable photovoltaic performance. Now the highest efficiencies of DSSC are dominated by donor-acceptor porphyrins, reaching remarkable values around 13.0% with cobalt-based electrolytes. This achievement is largely contributed by the structural development of donor and acceptor groups within push-pull framwork. In this review, we summarized and discussed the developement of donor-acceptor porphyrin sensitizers and their applications in DSSC. A dicussion of the correlation between molecular structure and the spectral and photovoltaic properties is the major target of this review. Deeply dicussion of the substitution group, especially on porphyrin's meso-position were presented. Furthermore, the limitations of DSSC for commercialization, such as the long-term stability, sophisticated synthesis procedures for high efficiency dye etc., have also been discussed.

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“…That is, this moiety influences the PCE of a DSSC only slightly unless its structure is complex. The PCE of DSSCs with porphyrin bearing different light harvesting moieties can vary in the absence of a bulky alkyl termination of this substituent . Fine‐tuning of polycyclic aromatic systems for light harvesting at the 20‐ meso substituent in combination with a co‐sensitizer can result in a highly performing DSSC because of red‐shifted absorbance spectra of porphyrins bearing these substituents …”

Section: Functional Design Of Porphyrins For Dye‐sensitized Solar Cellsmentioning

confidence: 99%

Evolution of Molecular Design of Porphyrin Chromophores for Photovoltaic Materials of Superior Light‐to‐Electricity Conversion Efficiency

2017

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Zinc porphyrins (ZnPs) attract high interest as efficient chromophores for dye-sensitized solar cells (DSSCs). Progress in the molecular design and solar cell materials led to a record of 13% power conversion efficiency of porphyrin-sensitized solar cells. Until recently, ZnPs were limitedly used in bulk-heterojunction solar cells (BHJ SC). However, application of porphyrin chromophores designed for DSSCs to BHJ SCs has rapidly increased the efficiency of the latter with both small-molecule and polymer ZnP donors. Herein, we briefly review the developmental history of molecular design of ZnPs for DSSCs, and illustrate the influence of this development on the design of small-molecule and polymer ZnP donors for BHJ SCs.

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Push–pull type porphyrin based sensitizers: The effect of donor structure on the light-harvesting ability and photovoltaic performance

Cited by 27 publications

References 43 publications

Rutheniumethynyl‐Triarylamine Organic−Inorganic Mixed‐Valence Systems: Regulating Ru‐N Electronic Coupling by Different Aryl Bridge Cores

Rutheniumethynyl‐Triarylamine Organic−Inorganic Mixed‐Valence Systems: Regulating Ru‐N Electronic Coupling by Different Aryl Bridge Cores

Push-Pull Zinc Porphyrins as Light-Harvesters for Efficient Dye-Sensitized Solar Cells

Evolution of Molecular Design of Porphyrin Chromophores for Photovoltaic Materials of Superior Light‐to‐Electricity Conversion Efficiency

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