Dicyano-functionalized chlorophyll derivatives with ambipolar characteristic for organic photovoltaics

Wang, Yuwei; Sasaki, Shin‐ichi; Zhuang, Taojun; Tamiaki, Hitoshi; Zhang, Jianping; Ikeuchi, Toshitaka; Hong, Ziruo; Kido, Junji

doi:10.1016/j.orgel.2013.04.034

Cited by 22 publications

(30 citation statements)

References 43 publications

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“…[4][5][6][7][8] Chlorophylls (Chls), which are the most abundant natural pigments, play key roles in early photophysical and -chemical events in naturalp hotosynthesis. [9] In the last decade, we have carried out as eries of investigationst oe xplore the possibility of employing Chls and their derivatives in emerging photovoltaic techniques, such as biomimetic systems, [10][11][12][13] DSSCs, [14][15][16][17][18][19][20][21][22][23][24][25][26][27] organic solar cells (OSCs), [28][29][30][31] and perovskite solar cells (PSCs). [32] These investigations are purely based on the fact that Chls are the only naturallyo ccurringo rganic semiconductors that possess the merits of large-scale resources,p ollution free, and optoelectrical variability.…”

Section: Introductionmentioning

confidence: 99%

Chlorophyll‐Based Organic–Inorganic Heterojunction Solar Cells

Zhao

et al. 2017

Chemistry A European J

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Solid-state chlorophyll solar cells (CSCs) employing a carboxylated chlorophyll derivative, methyl trans-3 -carboxypyropheophorbide a, as a light-harvesting dye sensitizer chlorophyll (DSC) deposited on mesoporous TiO , on which four zinc hydroxylated chlorophyll derivatives were spin-coated for hole transporter chlorophylls (HTCs), are described. Key parameters, including the effective carrier mobility of the HTC films, as determined by the space charge-limited current method, and the frontier molecular orbitals of these DSCs and HTCs, as estimated from cyclic voltammetry and electronic absorption spectra, suggest that both charge separation and carrier transport are favorable. The power conversion efficiencies (PCEs) of the present CSCs with fluorine-doped tin oxide (FTO)/TiO /DSC/HTCs/Ag were determined to follow the order of HTC-1>HTC-2>HTC-3>HTC-4, which coincided perfectly with the order of their hole mobilities. The maximum PCE achieved was 0.86 % with HTC-1. The photovoltaic devices studied herein with two types of chlorophyll derivatives as dye sensitizers and hole transporters provide a unique solution for the utilization of solar energy with a view to truly realizing "green energy".

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Section: Introductionmentioning

confidence: 99%

Chlorophyll‐Based Organic–Inorganic Heterojunction Solar Cells

Zhao

et al. 2017

Chemistry A European J

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“…As a consequence, dicyano‐substituted chlorins have attracted considerable attentions, since the strong electron‐withdrawing nature of this functionality allows the enrichment of porphyrins with a multitude of chemical groups. Cyanochlorins are typically prepared by the Beckmann rearrangement of formylchlorins, which allows the installation of a cyano group directly conjugated to the chlorin core; the Knoevenagel reaction of carbonylchlorins to produce dicyanomethylene chlorins; and the Wittig reaction of formylchlorins, which affords cis / trans mixtures of cyanomethylene chlorins …”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Long‐wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner–Wadsworth–Emmons Reaction

Wang

Liu

et al. 2020

Bulletin Korean Chem Soc

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In this article, we report the stereoselective Horner-Wadsworth-Emmons reaction of reactive carbonyl-substituted chlorophyll a derivatives with diethyl cyanomethylphosphonate. We found that the formyl or keto group at the chlorin periphery can react stereoselectively with phosphonate carbanions to produce a series of cyanomethylenesubstituted chlorins with predominantly E geometry. Considering that no consistent records are available in the literature on the results of the allomerization of methyl pyropheophorbide a, we propose a reliable process for the transformation of this chlorophyll derivative. Our methodology represents a simple and efficient way for the preparation of novel, differently functionalized long-wavelength absorbing chlorins, those can be applied for photodynamic therapy, solar cells, and other relevant purposes.

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“…[7] In the past decade, the advantages of Chls, such as their infinite resources and excellent semiconductor properties, have stimulated as eries of investigations to employ Chls in emerging photovoltaic technologies, that is, dye-sensitized solar cells and organic solar cells. [8][9][10][11][12][13][14][15] Despite these attempts, the fabrication of Chl-based solar cells with high efficiencies and al ow cost remains challenging.…”

Section: Introductionmentioning

confidence: 99%

Dopant‐Free Zinc Chlorophyll Aggregates as an Efficient Biocompatible Hole Transporter for Perovskite Solar Cells

Sasaki

et al. 2016

ChemSusChem

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Chlorophylls (Chls) are abundant, naturally occurring pigments that play key roles in light-harvesting and electron/energy transfer in natural photosynthetic apparatus. To demonstrate the idea that Chls are suitable hole transporters, we employed two Chl derivatives, Chl-1 and Chl-2, which self-assembled readily into π-stacking aggregates through a simple spincasting process, in perovskite solar cells (PSCs). The Chl aggregate films exhibit an ultra-smooth film surface, high hole mobility, appropriate energy levels, and efficient hole injection efficiencies that are all key characteristics for efficient hole transporters in PSCs. CH NH PbI Cl -based PSCs with these Chls as hole transporters were fabricated and compared with P3HT as a standard hole transporter. PSCs based on Chl-1 and Chl-2 without the use of typical additives, such as 4-tert-butylpyridine and lithium bis(trifluoromethanesulfinyl)imide, gave power conversion efficiencies of 11.44 and 8.06 %, respectively. This research provides a unique way to incorporate low-cost and environmentally friendly natural photosynthetic materials in the development of highly efficient photovoltaic devices.

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Dicyano-functionalized chlorophyll derivatives with ambipolar characteristic for organic photovoltaics

Cited by 22 publications

References 43 publications

Chlorophyll‐Based Organic–Inorganic Heterojunction Solar Cells

Chlorophyll‐Based Organic–Inorganic Heterojunction Solar Cells

Efficient Synthesis of Long‐wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner–Wadsworth–Emmons Reaction

Dopant‐Free Zinc Chlorophyll Aggregates as an Efficient Biocompatible Hole Transporter for Perovskite Solar Cells

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