203579-53-7Relevant academic research and scientific papers
Efficient, multigram-scale synthesis of three 2,5-dihalobenzoquiones
Lopez-Alvarado, Pilar,Avendano, Carmen,Menendez, J. Carlos
, p. 3233 - 3239 (2002)
2,5-Dibromo-, 2,5-dichloro- and 2,5-diiodobenzoquinone were conveniently prepared from 1,4-dimethoxybenzene in 87%, 97% and 84% overall yields. None of the two steps of the synthesis required purification.
Versatile strategy to access fully functionalized benzodifurans: Redox-active chromophores for the construction of extended φ-conjugated materials
Yi, Chenyi,Blum, Carmen,Lehmann, Mario,Keller, Stephan,Liu, Shi-Xia,Frei, Gabriela,Neels, Antonia,Hauser, Juerg,Schuerch, Stefan,Decurtins, Silvio
experimental part, p. 3350 - 3357 (2010/07/02)
An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b′]difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended φ-conjugated BDF derivatives, e.g., with pyridine termini (4-6) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.
Multistep Reversible Redox Systems, LXIII. 2,5-Disubstituted N,N'-Dicyanoquinone Diimines (DCNQIs) - Syntheses, and Redox Properties
Huenig, Siegfried,Bau, Robert,Kemmer, Martina,Meixner, Hubert,Metzenthin, Tobias,et al.
, p. 335 - 348 (2007/10/03)
Quinones 1a-q and DCNQIs 2a-g have been synthesized in order to investigate substituent effects.It was necessary to employ novel synthetic routes for the introduction of iodine into 1f (7), the trifluoromethyl group into 1g-i, deuterium into 1m-p, and esp
