Panchromatic dyes having diketopyrrolopyrrole and ethylenedioxythiophene applied to dye-sensitized solar cells

Imae, Ichiro; Itô, Yôhei; Matsuura, Shinya; Harima, Yutaka

doi:10.1016/j.orgel.2016.07.022

Cited by 8 publications

(3 citation statements)

References 55 publications

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“…Even if the progress achieved in the design of push-pull dyes is remarkable, there are still incentives for developing new materials with more extended absorptions, thus providing panchromatic dyes. [17][18][19] These structures are notably extensively studied in solar cells. In this specific research field, low bandgap materials are actively researched as these compounds can also be easily oxidized and transfer an electron from the electrondonating material towards the electron-accepting one upon sunlight irradiation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

et al. 2021

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A series of chromophores was designed and synthesized using 2-(3-cyano-4,5,5-trimethylfuran-2 (5H) -ylidene) malononitrile (TCF) as the electron acceptor and differing from each other by the use of thirteen different electron donors. The different dyes were characterized for their optical and electrochemical properties and theoretical calculations were also carried out to support the experimental results. By changing the electron donor in the thirteen dyes, chromophores absorbing between 430 nm and 700 nm could be synthesized. Solvatochromism of the different dyes was analyzed in 23 solvents of different polarity and a positive solvatochromism was determined for all chromophores using the semi-empirical solvent polarity scales based on the Kamlet-Taft parameters (π *) or the Catalan parameters (SdP and SPP).

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Section: Introductionmentioning

confidence: 99%

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

et al. 2021

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“…The excited state would ideally have a long lifetime to effectively drive subsequent processes such as energy/electron transfer that initiate chemistry or photocurrent. Although there have been various approaches to attaining molecular panchromatic absorbers, − no clear design criteria have emerged to attain superchromophores that simultaneously afford panchromatic absorption and favorable excited-state properties.…”

Section: Introductionmentioning

confidence: 99%

Origin of Panchromaticity in Multichromophore–Tetrapyrrole Arrays

et al. 2018

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Panchromatic absorbers that have robust photophysical properties enable new designs for molecular-based light-harvesting systems. Herein, we report experimental and theoretical studies of the spectral, redox, and excited-state properties of a series of perylene-monoimide-ethyne-porphyrin arrays wherein the number of perylene-monoimide units is stepped from one to four. In the arrays, a profound shift of absorption intensity from the strong violet-blue (B and B) bands of typical porphyrins into the green, red, and near-infrared (Q and Q) regions stems from mixing of chromophore and tetrapyrrole molecular orbitals (MOs), which gives multiplets of MOs having electron density spread over the entire array. This reduces the extensive mixing between porphyrin excited-state configurations and the transition-dipole addition and subtraction that normally leads to intense B and weak Q bands. Reduced configurational mixing derives from moderate effects of the ethyne and perylene on the MO energies and a more substantial effect of electron-density delocalization to reduce the configuration-interaction energy. Quantitative oscillator-strength analysis shows that porphyrin intensity is also shifted into the perylene-like green-region absorption and that the ethyne linkers lend absorption intensity. The reduced porphyrin configurational mixing also endows the S state with bacteriochlorin-like properties, including a 1-5 ns lifetime.

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“…Bis(dibenzylideneacetone)palladium [Pd(dba) 2 ], tris(o-methoxyphenyl)phosphine [P(o-MeOPh) 3 ], cesium carbonate (Cs 2 CO 3 ), and pivalic acid (PivOH) were purchased from Aldrich, Wako, and Nacalai Tesque, and used without purification. D-A polymers were synthesized according to our previous reports 20,21) by direct C-H arylation polycondensation using oligothiophenes 17,20) and bis(bromothienyl)diketopyrrolopyrrole 22) as monomers (Fig. 2).…”

Section: Materials and Instrumentationmentioning

confidence: 99%

Fine-tuning of electronic properties in donor–acceptor conjugated polymers based on oligothiophenes

Imae

Sagawa

Harima

2017

Jpn. J. Appl. Phys.

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A novel series of donor-acceptor conjugated polymers having oligothiophenes with well-defined structures were synthesized and their optical, electrochemical, and photovoltaic properties were investigated. It was found that the absorption bands of polymers were red-shifted with increasing number of ethylenedioxy groups added to each oligothiophene unit and that their band edges reached over 1000 nm. The systematical fine-tuning of the electronic properties was achieved using the chemical structures of oligothiophene units. Photovoltaic cells based on polymer/(6,6)-phenyl C 61 butyric acid methyl ester (PC 61 BM) exhibited power conversion efficiencies in the range from 0.004 to 1.10%, reflecting the electronic properties of the polymers.

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Panchromatic dyes having diketopyrrolopyrrole and ethylenedioxythiophene applied to dye-sensitized solar cells

Cited by 8 publications

References 55 publications

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

Origin of Panchromaticity in Multichromophore–Tetrapyrrole Arrays

Fine-tuning of electronic properties in donor–acceptor conjugated polymers based on oligothiophenes

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