Issue 7, 2005

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

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Feb 2005
Accepted
11 May 2005
First published
10 Jun 2005

New J. Chem., 2005,29, 972-976

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

D. P. Lydon, L. Porrès, A. Beeby, T. B. Marder and P. J. Low, New J. Chem., 2005, 29, 972 DOI: 10.1039/B502950C

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