5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices

Watanabe, Motonori; Uemura, N.; Ida, Shintaro; Hagiwara, Hidehisa; Goto, Keisuké; Ishihara, Takeshi

doi:10.1016/j.tet.2016.05.069

Cited by 11 publications

(9 citation statements)

References 25 publications

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“…The Pt source was used as chloroplatinic acid solution of 8 wt % in water (Sigma-Aldrich). The preparation of the anatase phase thin-film has been described elsewhere . A thin film of 1 wt % Pt-co-loaded–TiO 2 was prepared to coat an FTO glass substrate, with the dimensions of the active area being controlled at 1.5 cm 2 .…”

Section: Methodsmentioning

confidence: 99%

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Visible Light-Driven Dye-Sensitized Photocatalytic Hydrogen Production by Porphyrin and its Cyclic Dimer and Trimer: Effect of Multi-Pyridyl-Anchoring Groups on Photocatalytic Activity and Stability

Watanabe

Sun

Ishihara

et al. 2018

ACS Appl. Energy Mater.

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The monomer, dimer, and trimer of 5,15-diphenyl-10,20di(pyridin-4-yl)porphyrin are used to investigate the multi-anchoring eff ect on TiO2 for visible light-driven photocatalytic hydrogen production in a water medium. Further, the porphyrin trimer is prepared and analyzed by nuclear magnetic resonance (NMR) spectroscopy, absorption spectroscopy, electrochemical voltammetry, fast atom bombardment (FAB) mass spectroscopy, and density functional theory (DFT) computation. The results of this study indicate that the peak intensities of the absorption spectra increase as the number of porphyrin units increases, while changes could be barely observed in the highest occupied molecular orbital (HOMO)−lowest unoccupied molecular orbital (LUMO) gaps. The porphyrin dimer in a 1 wt % Pt-loaded TiO2 powder photocatalyst system exhibited optimal hydrogen production performance in a stable state over a period of 80 h and at a superior rate of 1023 mol•g −1 •h −1. Further, the stability of the photocatalytic system was systematically investigated using films containing dyes on 1 wt % Pt-loaded TiO2/FTO. For a film containing the dimer, almost no change was observed in the hydrogen-bond coordination mode of the dimer and the photocurrent during the photocatalytic reaction. However, the photocurrents of the monomer and trimer were altered during visible light irradiation without altering the coordination mode, indicating that the arrangements and orientations of the porphyrins on TiO2 surfaces were altered. These results indicate that the presence of multiple anchoring groups enhance the stability of the photocatalytic system and the rate of hydrogen production.

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Section: Methodsmentioning

confidence: 99%

“…The preparation of the anatase phase thin-film has been described elsewhere. 83 A thin film of 1 wt % Pt-co-loaded−TiO 2 was prepared to coat an FTO glass substrate, with the dimensions of the active area being controlled at 1.5 cm 2 . The photocurrent was measured using a BAS ALS1200B instrument.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Visible Light-Driven Dye-Sensitized Photocatalytic Hydrogen Production by Porphyrin and its Cyclic Dimer and Trimer: Effect of Multi-Pyridyl-Anchoring Groups on Photocatalytic Activity and Stability

Watanabe

Sun

Ishihara

et al. 2018

ACS Appl. Energy Mater.

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“…For instance, a series of soluble 5,5' alkylated indigo derivatives were used for processing of optoelectronic devices. [ 4 ] Ngai et al attached long alkoxy chains to the aromatic ring of the indigo unit for applications in n‐type organic field‐effect transistors. [ 5 ] Alkyl‐ or alkoxyphenyl‐substituted indigo derivatives were synthesized from the corresponding isatins and used to grow chromophoric liquid crystals.…”

Section: Methodsmentioning

confidence: 99%

“…It is worthwhile mentioning that in some cases it was even observed that the solubility of some long alkyl‐substituted indigos further decreased with increasing the length of alkyl chains, which was explained by the hydrophobic effect of alkyl chains in 1,2‐dichlorobenzene. [ 4 ] The attachment of long alkyl chains to larger aromatic compounds may increase solubilities but on the other hand, the tendency to form larger crystalline domains or even single crystals is hampered, which reduces the possibility for certain organic electronics applications.…”

Section: Methodsmentioning

confidence: 99%

Triptycene End‐Capped Indigo Derivatives – Turning Insoluble Pigments to Soluble Dyes

et al. 2020

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The synthesis of a highly soluble triptycene end‐capped indigo and its bay annulated derivative is reported. Both compounds have been studied by absorption and emission spectroscopy cyclic voltammetry, as well as theoretical calculations and compared to the parent indigo and bay annulated indigo. Besides a large improvement of solubility in organic solvents by the factor of approx. 70(!) the compounds also show a pronounced tendency to form crystals. Both properties, making these compounds promising electron acceptors for organic electronics.

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“…This synthetic route was also found to be unsuccessful. Our next attempt was to prepare compound 4 and subsequent treatment with Mo(CO) 6 and organic peroxide to yield PNI via an oxidative coupling reaction . The synthetic method is described in Scheme c.…”

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Synthesis, Photophysical, Electrochemical, and Halochromic Properties of peri-Naphthoindigo

Das

Mahata

2018

Org. Lett.

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A facile synthesis of peri-naphthoindigo (PNI) was reported for the first time from simple precursor. Installation of a chromophore at the peri-position of naphthalene is very unique in terms of synthetic challenges and properties. PNI exists in monoenol form, undergoes halochromism in acidic medium, and displays a wide and strong absorption band (ε = 33390 Mcm) with maxima at 632 nm (chloroform). The dye undergoes oxidation and reduction at +0.30 and -0.58 V (vs Fc/Fc), respectively, in chloroform.

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5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices

Cited by 11 publications

References 25 publications

Visible Light-Driven Dye-Sensitized Photocatalytic Hydrogen Production by Porphyrin and its Cyclic Dimer and Trimer: Effect of Multi-Pyridyl-Anchoring Groups on Photocatalytic Activity and Stability

Visible Light-Driven Dye-Sensitized Photocatalytic Hydrogen Production by Porphyrin and its Cyclic Dimer and Trimer: Effect of Multi-Pyridyl-Anchoring Groups on Photocatalytic Activity and Stability

Triptycene End‐Capped Indigo Derivatives – Turning Insoluble Pigments to Soluble Dyes

Synthesis, Photophysical, Electrochemical, and Halochromic Properties of peri-Naphthoindigo

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