The effect of different alkyl chains on the photovoltaic performance of D–π–A porphyrin-sensitized solar cells

Chen, Jiangzhao; Ko, Song-Guk; Liu, Linfeng; Sheng, Yusong; Han, Hongwei; Li, Xiong

doi:10.1039/c4nj02263g

Cited by 23 publications

(15 citation statements)

References 59 publications

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“…Despite the substantially lower surface concentration, these molecules however, advantageously increase the PCE of the DSSC by 1.5% compared to that with the same dye but not terminated with alkyl chains (Scheme ) . A similar trend was reported elsewhere (Table ) …”

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

confidence: 83%

“…This favorable effect is caused by suppressing reduction of a charge mediating species by electrons from the CB of the MO. The lower PCE of DSSCs with porphyrins bearing long alkyl chain was most likely because the 3‐ up to 5‐carbon atom difference in the terminating alkyl chain of the 20‐ meso substituent did not affect much surface coverage of the TiO 2 with the dye . If an auxiliary donor is introduced in the 20‐ meso position, then a conjugated link is required for efficient electron transfer from the auxiliary donor to the porphyrin macrocycle.…”

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

confidence: 99%

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

confidence: 83%

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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“…p -Iodoanisole ( 10 ) was prepared according to the literature procedure. 54 A mixture of 4-iodophenol ( 9 ) (264 mg, 1.2 mmol), methyl iodide (170 mg, 1.2 mmol), and K 2 CO 3 (828 g, 6.0 mmol) in 10 mL of acetone was stirred at 60 °C for 24 h. After cooling to room temperature, the mixture was poured into 100 mL of water and extracted with diethyl ether (3 × 40 mL). The combined organic phase was evaporated under vacuum to remove the solvent.…”

Section: Methodsmentioning

confidence: 99%

An Efficient Synthesis of Deoxyrhapontigenin-3-O-β-d-glucuronide, a Brain-Targeted Derivative of Dietary Resveratrol, and Its Precursor 4′-O-Me-Resveratrol

et al. 2019

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Bioactive dietary polyphenols have health benefits against a variety of disorders, but some benefits of polyphenols may be not directly related to them but rather to their metabolites. Recently, we have identified the brain-available phenol glucuronide metabolite deoxyrhapontigenin-3- O -β- d -glucuronide ( 5 ) in perfused rat brains following subacute treatment with the stilbene resveratrol ( 1 ). However, the role of such a metabolite in the neuroprotective activity of resveratrol ( 1 ) is not understood, in part due to the noncommercial availability of 5 for performing biological evaluation in animal models of Alzheimer’s disease or other neurological disorders. Here, we describe a concise chemical synthesis of deoxyrhapontigenin-3- O -β- d -glucuronide ( 5 ) and its precursor 4- O -Me-resveratrol ( 2 ), accomplished in four and six steps with 74 and 21% overall yields, respectively, starting from commercially available 3,5-dihydroxybenzaldehyde. Pivotal reactions employed in the synthesis include the palladium-catalyzed C–C coupling between 3,5-di- tert -butyldiphenylsilyloxystyrene and p -iodoanisole in the presence of tributylamine and the acid-catalyzed glucuronidation between the trichloroacetimidate-activated glucuronic acid and 4- O -Me-resveratrol.

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“…A ready available di‐tolylamine 9 was coupled with iodobenzene 10 using a modified Ullmann protocol . The substituted triphenylamine derivative 11 obtained in this way was subjected to an aromatic iodination procedure to afford 12 in good yield (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Novel Turtle‐Shape Dendrimers Based on a Pyrene Core

et al. 2019

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The design and synthesis of X-shaped molecules bases on a central pyrene is reported. A Sonogashira cross-coupling reaction was applied to successfully bond the pyrene core through acetylene linkages to electroactive dendrons moieties such as triphenylamine or carbazole. Dendrons were function-alized with bulky alkyl groups to disrupt π-π stacking interactions and consequently affording soluble dendrimers. These novel π-conjugated turtle-shape dendrimers are organic materials with great potential applications in optoelectronic devices.

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The effect of different alkyl chains on the photovoltaic performance of D–π–A porphyrin-sensitized solar cells

Abstract: Compared to the DSSCs based on WH-C1 and YD20 with short alkyl chains, the device sensitized by WH-C2 with the hexyloxy group shows a significantly enhanced Voc, Jsc and power conversion efficiency (η).

Cited by 23 publications

References 59 publications

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

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

An Efficient Synthesis of Deoxyrhapontigenin-3-O-β-d-glucuronide, a Brain-Targeted Derivative of Dietary Resveratrol, and Its Precursor 4′-O-Me-Resveratrol

Novel Turtle‐Shape Dendrimers Based on a Pyrene Core

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