84-40-2Relevant academic research and scientific papers
High-Performance Ambipolar Polymers Based on Electron-Withdrawing Group Substituted Bay-Annulated Indigo
Yang, Jie,Jiang, Yaqian,Tu, Zeyi,Zhao, Zhiyuan,Chen, Jinyang,Yi, Zhengran,Li, Yifan,Wang, Shuai,Yi, Yuanping,Guo, Yunlong,Liu, Yunqi
, (2019/01/05)
For donor–acceptor conjugated polymers, it is an effective strategy to improve their electron mobilities by introducing electron-withdrawing groups (EWGs, such as F, Cl, or CF3) into the polymer backbone. However, the introduction of different EWGs always requires a different synthetic approach, leading to additional arduous work. Here, an effective two-step method is developed to obtain EWG substituted bay-annulated indigo (BAI) units. This method is effective to introduce various EWGs (F, Cl, or CF3) into BAI at different substituted positions. Based on this method, EWG substituted BAI acceptors, including 2FBAI, 2ClBAI, and 2CF3BAI, are reported for the first time. Furthermore, four polymers of PBAI-V, P2FBAI-V, P2ClBAI-V, and P4OBAI-V are developed. All the polymers show ambipolar transport properties. Particularly, P2ClBAI-V exhibits remarkable hole and electron mobilities of 4.04 and 1.46 cm2 V?1 s?1, respectively. These mobilities are among the highest values for BAI-based polymers.
An iodine effect in ambipolar organic field-effect transistors based on indigo derivatives
Pitayatanakul, Oratai,Iijima, Kodai,Ashizawa, Minoru,Kawamoto, Tadashi,Matsumoto, Hidetoshi,Mori, Takehiko
, p. 8612 - 8617 (2015/08/24)
5,5′-Diiodoindigo (4) exhibits excellent ambipolar transistor properties with hole/electron mobilities of μh/μe = 0.42/0.85 cm2 V-1 s-1. The halogen substituted indigos show decreasing tilt angles from F to I in the crystals. In addition, the iodine-iodine interaction provides extraordinarily large interchain interaction. However, the X-ray diffraction suggests that the indigo molecules are arranged approximately perpendicular to the substrate in the thin films, probably due to the extra iodine-iodine interaction. The remarkable performance is ascribed to this characteristic supramolecular interaction.
Peroxygenase and oxidase activities of dehaloperoxidase-hemoglobin from Amphitrite ornata
Barrios, David A.,D'Antonio, Jennifer,McCombs, Nikolette L.,Zhao, Jing,Franzen, Stefan,Schmidt, Andreas C.,Sombers, Leslie A.,Ghiladi, Reza A.
supporting information, p. 7914 - 7925 (2014/06/23)
The marine globin dehaloperoxidase-hemoglobin (DHP) from Amphitrite ornata was found to catalyze the H2O2-dependent oxidation of monohaloindoles, a previously unknown class of substrate for DHP. Using 5-Br-indole as a representative substrate, the major monooxygenated products were found to be 5-Br-2-oxindole and 5-Br-3-oxindolenine. Isotope labeling studies confirmed that the oxygen atom incorporated was derived exclusively from H2O2, indicative of a previously unreported peroxygenase activity for DHP. Peroxygenase activity could be initiated from either the ferric or oxyferrous states with equivalent substrate conversion and product distribution. It was found that 5-Br-3-oxindole, a precursor of the product 5-Br-3-oxindolenine, readily reduced the ferric enzyme to the oxyferrous state, demonstrating an unusual product-driven reduction of the enzyme. As such, DHP returns to the globin-active oxyferrous form after peroxygenase activity ceases. Reactivity with 5-Br-3-oxindole in the absence of H2O2 also yielded 5,5′-Br2-indigo above the expected reaction stoichiometry under aerobic conditions, and O2-concentration studies demonstrated dioxygen consumption. Nonenzymatic and anaerobic controls both confirmed the requirements for DHP and molecular oxygen in the catalytic generation of 5,5′-Br2-indigo, and together suggest a newly identified oxidase activity for DHP.
High performance ambipolar organic field-effect transistors based on indigo derivatives
Pitayatanakul, Oratai,Higashino, Toshiki,Kadoya, Tomofumi,Tanaka, Masaki,Kojima, Hirotaka,Ashizawa, Minoru,Kawamoto, Tadashi,Matsumoto, Hidetoshi,Ishikawa, Ken,Mori, Takehiko
, p. 9311 - 9317 (2015/01/09)
A bio-inspired organic semiconductor 5,5′-diphenylindigo shows excellent and well-balanced ambipolar transistor properties; its hole and electron mobilities are 0.56 and 0.95 cm2 V-1 s-1, respectively. The enhanced performance is attributed to the extended π-π overlap of the phenyl groups as well as the characteristic packing pattern that is a hybrid of the herringbone and brickwork structures. The ambipolar transistor characteristics are analyzed considering its operating regions, where a large unipolar saturated region appears due to the difference of the electron and hole threshold voltages.
Design of indigo derivatives as environment-friendly organic semiconductors for sustainable organic electronics
Klimovich,Leshanskaya,Troyanov,Anokhin,Novikov,Piryazev,Ivanov,Dremova,Troshin
, p. 7621 - 7631 (2014/12/10)
We report the synthesis and systematic investigation of nine different indigo derivatives as promising materials for sustainable organic electronics. It has been shown that chemical design allows one to tune optoelectronic properties of indigoids as well
Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
Rioz-Martinez, Ana,Kopacz, Malgorzata,De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Gotor, Vicente,Fraaije, Marco W.
experimental part, p. 1337 - 1341 (2011/04/23)
A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.
