14825-85-5Relevant academic research and scientific papers
A simple "palladium-free" synthesis of phenyleneethynylene-based molecular materials revisited
Lydon, Donocadh P.,Porres, Laurent,Beeby, Andrew,Marder, Todd B.,Low, Paul J.
, p. 972 - 976 (2007/10/03)
Nucleophilic attack of acetylide anions at the two carbonyl moieties of para-quinones readily affords the corresponding diols. Subsequent reduction with stannous chloride affords a number of useful compounds, including 1,4-bis[(trimethylsilyl)ethynyl]benzene, 1,4-bis[(trimethylsilyl)ethynyl] naphthalene and 9,10-bis[(trimethylsilyl)ethynyl]anthracene. Sequential attack by different acetylide anions followed by reduction provides a useful route to differentially substituted compounds including 1-[(4-nonyloxyphenyl)ethynyl]-4- (phenylethynyl)benzene, a new luminescent liquid-crystalline material. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
Synthesis and Evaluation of Fluorescent Materials for Colour Control of Peroxyoxalate Chemiluminescence. I. The Phenylethynylation of Anthraquinone
Hanhela, Peter J.,Paul, D. Brenton
, p. 1669 - 1686 (2007/10/02)
The synthesis of 9,10-bis(phenylethynyl)anthracene has been examined in detail prior to the synthesis of a series of phenylethynyl substituted aromatic compounds which are of interest as fluorescent materials for peroxyoxalate chemiluminescence.Reductions of the 9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol precursor by stannous chloride and by sodium hypophosphite-potassium iodide both gave a series of byproducts, in addition to 9,10-bis(phenylethynyl)anthracene.The formation of these compounds is interpreted in terms of a free-radical process.The interaction of 10-hydroxy-10-(phenylethynyl)anthrone with both the reducing systems has been rationalized and the reaction with concentrated sulfuric acid reinterpreted.
