Synthesis, optical properties, crystal structures and phase behaviour of symmetric, conjugated ethynylarene-based rigid rods with terminal carboxylate groups

Tolulope M. Fasina, Jonathan C. Collings, Jacqueline M. Burke, Andrei S. Batsanov, Richard M. Ward, David Albesa-Jové, Laurent Porrès, Andrew Beeby, J. A K Howard, Andrew J. Scott, William Clegg, Stephen W. Watt, Christopher Viney, Todd B. Marder

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Sonogashira cross-coupling reactions of 4-ethynylmethylbenzoate (1) with aryl halides gave 1,2-bis(4-carbomethoxyphenyl)ethyne (2), 1,4-bis(4- carbomethoxyphenylethynyl)benzene (3), 1,4-bis(4-carbomethoxyphenylethynyl) tetrafluorobenzene (4) and 9,10-bis(4-carbomethoxyphenylethynyl)anthracene (5), protected precursors to conjugated rigid rod bis(carboxylato) ligands. The compound 1,4-bis(4-carbomethoxyphenyl)butadiyne (6) was prepared by the oxidative homo-coupling of 1. The hydrolysis of 2 and 3 by NaOH in methanol gave the sodium salts of the respective carboxylate anions and subsequent treatment with HCl gave the corresponding free carboxylic acids. Compounds 2-6 were characterised by absorption, emission, IR, NMR and mass spectrometry and examined for liquid crystal phase behaviour by differential thermal analysis (DTA) and transmitted polarised light microscopy (TPLM). Compound 4 exhibited a nematic phase stable from 233.6 °C until decomposition at 320 °C. The single-crystal structures of 2, 5 and 6 were determined by X-ray diffraction at 110-160 K. © The Royal Society of Chemistry 2005.

Original languageEnglish
Pages (from-to)690-697
Number of pages8
JournalJournal of Materials Chemistry
Volume15
Issue number6
DOIs
Publication statusPublished - 14 Feb 2005

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