- Nucleophilic Replacement in Decafluoroanthracene
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Decafluoroanthracene undergoes replacement of the 2-fluorine when treated with sodium methoxide or with dimethylamine, and this is not in accord with the amplified I?-repulsion theory which requires attack at the 9-position; there is now no theory which rationalizes the position of nucleophilic replacement in all polyfluoro-aromatic compounds.
- Burdon, James,Childs, Ann C.,Parsons, Ian W.,Tatlow, John Colin
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- 9,10-Dichlorooctafluoroanthracene as a building block for n-type organic semiconductors
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(Chemical Equation Presented) 9,10-Dichlorooctafluoroanthracene (1) was synthesized from commercially available tetrafluorophthalic acid by an optimized solution-phase route. To establish 1 as a synthon for n-type organic semiconductors, the compound was reacted with phenylboronic acid under modified Suzuki-Miyaura coupling conditions to generate octafluoro-9,10- diphenylanthracene (7) in high yield. Cyclic voltammetry and X-ray crystallography indicate that 7 has a stabilized LUMO energy level and exhibits extended π stacking, which should lead to efficient electron transport in solid-state devices. 1,2,3,4,5,6,7,8-Octafluoroanthracene (2) was also synthesized as a potential n-type building block, but suitable C-C coupling conditions for this compound were not found, and 2 could not be converted into 9,10-dibromooctafluoroanthracene or octafluoro-9,10-diiodoanthracene.
- Tannaci, John F.,Noji, Masahiro,McBee, Jennifer,Tilley, T. Don
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p. 5567 - 5573
(2008/02/09)
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