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Synthesis 2008(4): 605-609  
DOI: 10.1055/s-2008-1032156
PAPER
© Georg Thieme Verlag Stuttgart · New York

Sonogashira Coupling Applied in the Synthesis of 1,2,4-Oxadiazole-Based Nonsymmetrical Liquid Crystals

Hugo Gallardo*a, Rodrigo Cristianoa, André A. Vieiraa, Ricardo A.W. Neves Filhob, Rajendra M. Srivastava*b
a Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil
Fax: +55(48)37216850 ; e-Mail: hugo@qmc.ufsc.br ;
b Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE 50740-540, Brazil
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Publication History

Received 9 October 2007
Publication Date:
31 January 2008 (online)

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Abstract

A series of highly π-conjugated nonsymmetrical liquid crystals, based on the core 3,5-(disubstituted)-1,2,4-oxadiazole with a shape similar to a hockey stick, were successfully synthesized by convergent Sonogashira coupling reaction between the building blocks of aryl iodides and the corresponding terminal arylacetylenes, using 3-[4-(decyloxy)phenyl]-5-(haloaryl)-1,2,4-oxadiazoles or decyl 4-iodobenzoate (10) and terminal arylacetylenes. This versatile synthetic route yielded luminescent mesogens with smectic and nematic phases, typical of calamitic compounds.

Key words

Sonogashira coupling - liquid crystals - 1,2,4-oxadi­azoles - acetylenes