Synthesis 2015; 47(24): 3997-4007
DOI: 10.1055/s-0035-1560474
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis and Electronic Spectra of Unsymmetrical 5,12-Diethynyltetracene Derivatives

Tetsuo Iwanaga*, Yuta Yamamoto, Keita Nishioka, Shinji Toyota*
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Publication History

Received: 02 July 2015

Accepted after revision: 17 August 2015

Publication Date:
16 September 2015 (eFirst)

Abstract

Unsymmetrical 5,12-diethynyltetracene derivatives were synthesized from tetracenequinone by the addition of two types of ethynyllithium reagents, followed by reductive aromatization with SnCl. These three-step reactions could be integrated into a one-pot process to give unsymmetrically substituted 5,12-diethynyltetracene derivatives in moderate yields. Some unsymmetrical 5,12-bis(phenylethynyl)tetracene derivatives were synthesized from 5-ethynyl-12-phenylethynyltetracene and iodobenzenes by Sonogashira coupling. This integrated process was applied to the synthesis of a π-extended tetracene dimer. The photophysical properties of these compounds were examined by UV/Vis and fluorescence spectroscopy.

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