A simple “palladium-free” synthesis of phenyleneethynylene-based molecular materials revisited?

New Journal of Chemistry Pub Date: 2005-06-10 DOI: 10.1039/B502950C

Abstract

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.

Graphical abstract: A simple “palladium-free” synthesis of phenyleneethynylene-based molecular materials revisited
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