6872-04-4Relevant articles and documents
A tunable synthesis of indigoids: Targeting indirubin through temperature
Cheek, Joshua T.,Horner, John S.,Kaller, Kaylie S.,Kinsey, Ally L.,Shriver, James A.,Sterrenberg, Summer R.,Van Vors, Madison K.,Wang, Katelyn R.
, p. 5407 - 5414 (2022/03/01)
The spontaneous conversion of 3-indoxyl to indigo is a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids. This journal is
Total Synthesis of the Chlorinated Indigo-N-Glycosides Akashin A, B and C
Pfretzschner, Alexander T.,Unverzagt, Carlo
supporting information, p. 206 - 229 (2021/03/22)
A total synthesis of the indigo-derived natural products akashin A-C was developed. The key step was the N-glycosylation of soluble N-benzylated-indigos with a suitably protected viosaminyl trichloroacetimidate. This donor was obtained from D-galactose. U
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.
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
Total synthesis of cladoniamide G
Loosley, Benjamin C.,Andersen, Raymond J.,Dake, Gregory R.
, p. 1152 - 1154 (2013/04/10)
The total synthesis of cladoniamide G, a cytotoxic compound against MCF-7 breast cancer cells (10 μg/mL), was accomplished. Key steps in the sequence include oxidative dimerization of 3-acetoxy-5-chloroindole and a tandem process incorporating three steps
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.
