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Kupper F.C.,Scottish Association for Marine Science | Feiters M.C.,Radboud University Nijmegen | Olofsson B.,University of Stockholm | Kaiho T.,Kanto Natural Gas Development Co. | And 7 more authors.
Angewandte Chemie - International Edition | Year: 2011

Iodine was discovered as a novel element in 1811 during the Napoleonic Wars. To celebrate the bicentennial anniversary of this event we reflect on the history and highlight the many facets of iodine research that have evolved since its discovery. Iodine has an impact on many aspects of life on Earth as well as on human civilization. It is accumulated in high concentrations by marine algae, which are the origin of strong iodine fluxes into the coastal atmosphere which influence climatic processes, and dissolved iodine is considered a biophilic element in marine sediments. Iodine is central to thyroid function in vertebrates, with paramount implications for human health. Iodine can exist in a wide range of oxidation states and it features a diverse supramolecular chemistry. Iodine is amenable to several analytical techniques, and iodine compounds have found widespread use in organic synthesis. Elemental iodine is produced on an industrial scale and has found a wide range of applications in innovative materials, including semiconductors-in particular, in solar cells. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Fuse S.,Tokyo Institute of Technology | Asai Y.,Tokyo Institute of Technology | Sugiyama S.,Tokyo Institute of Technology | Matsumura K.,Tokyo Institute of Technology | And 6 more authors.
Tetrahedron | Year: 2014

We have developed a one-pot, four-component Suzuki-Miyaura coupling for the synthesis of thiophene-based donor-π-bridge-acceptor (D-π-A) dyes for dye-sensitized solar cells. Two D-π-A dyes, 19 and 20, retaining 3,4-ethylenedioxythiophene (EDOT) beside a cyanoacrylic acid moiety, and one D-π-A dye 21 without EDOT (reference compound) were rapidly synthesized in accordance with the developed procedure. The measurement of the absorption spectra and the electrochemical properties of synthesized dyes, and the photovoltaic properties of solar cells that were prepared using the synthesized dyes 19-21, revealed that the dyes retaining only one EDOT beside a cyanoacrylic acid moiety would exert a high Jsc. © 2014 Elsevier Ltd. Source


Irie S.,Tokyo Institute of Technology | Fuse S.,Tokyo Institute of Technology | Maitani M.M.,Tokyo Institute of Technology | Wada Y.,Tokyo Institute of Technology | And 6 more authors.
Chemistry - A European Journal | Year: 2016

Twenty-four D-A'-π-A dyes were rapidly synthesized through a one-pot three-component Suzuki-Miyaura coupling reaction, which was assisted by microwave irradiation. We measured the absorption spectra, electrochemical properties, and solar-cell performance of all the synthesized dyes. The D5 πA4 dye contained our originally designed rigid and nonplanar donor and exerted the highest efficiency at 5.4 %. The short-circuit current (Jsc) was the most important parameter for the conversion efficiency (η) in the case of the organic D-A'-π-A dyes. Optimal ranges for the D-A'-π-A dyes were observed for high values of Jsc/λmax at λ=560-620 nm, an optical-absorption edge of λ=690-790 nm, and EHOMO and ELUMO values of <1.14 and -0.56 to -0.76 V, respectively. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Matsumura K.,Tokyo Institute of Technology | Yoshizaki S.,Tokyo Institute of Technology | Maitani M.M.,Tokyo Institute of Technology | Wada Y.,Tokyo Institute of Technology | And 6 more authors.
Chemistry - A European Journal | Year: 2015

This one-pot, four-component coupling approach (Suzuki-Miyaura coupling/C-H direct arylation/Knoevenagel condensation) was developed for the rapid synthesis of thiophene-based organic dyes for dye-sensitized solar cells (DSSCs). Seven thiophene-based, organic dyes of various donor structures with/without the use of a 3,4-ethylenedioxythiophene (EDOT) moiety were successfully synthesized in good yields based on a readily available thiophene boronic acid pinacol ester scaffold (one-pot, 3-step, 35-61 %). Evaluation of the photovoltaic properties of the solar cells that were prepared using the synthesized dyes revealed that the introduction of an EDOT structure beside a cyanoacrylic acid moiety improved the short-circuit current (Jsc) while decreasing the fill factor (FF). The donor structure significantly influenced the open-circuit voltage (Voc), the FF, and the power conversion efficiency (PCE). The use of a n-hexyloxyphenyl amine donor, and our originally developed, rigid, and nonplanar donor, both promoted good cell performance (η=5.2-5.6 %). © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Fuse S.,Tokyo Institute of Technology | Sugiyama S.,Tokyo Institute of Technology | Maitani M.M.,Tokyo Institute of Technology | Wada Y.,Tokyo Institute of Technology | And 5 more authors.
Chemistry - A European Journal | Year: 2014

The creation of organic dyes with excellent high power conversion efficiency (PCE) is important for the further improvement of dye-sensitized solar cells. We wish to describe the rapid synthesis of a 112-membered donor-π-acceptor dye library by a one-pot procedure, evaluation of PCEs, and elucidation of structure-property relationships. No obvious correlations between ε, and the η were observed, whereas the HOMO and LUMO levels of the dyes were critical for η. The dyes with a more positive EHOMO, and with an ELUMO<-0.80 V, exerted higher PCEs. The proper driving forces were crucial for a high Jsc, and it was the most important parameter for a high η. The above criteria of EHOMO and E LUMO should be useful for creating high PCE dyes; nevertheless, that was not sufficient for identifying the best combination of donor, π, and acceptor blocks. Combinatorial synthesis and evaluation was important for identifying the best dye. Combinatorial chemistry: A 112-membered donor-π-acceptor dye library was rapidly constructed by a one-pot, three-component coupling procedure (see scheme, SM=Suzuki-Miyaura). The evaluation of absorption spectroscopic and electrochemical measurements of all synthesized dyes, and cell performances of the selected 54 dyes were performed. The dyes with a more positive EHOMO, and with an E LUMO<-0.80 V, exerted higher power conversion efficiencies. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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