Synthesis 2014; 46(12): 1667-1673
DOI: 10.1055/s-0033-1338608
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,9-Diethynylanthracene Derivatives

Shinji Toyota*, Takahiro Kawakami, Tetsuo Iwanaga
  • Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan   Fax: +81(86)2569457   Email: stoyo@chem.ous.ac.jp
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Publication History

Received: 29 January 2014

Accepted after revision: 24 February 2014

Publication Date:
28 March 2014 (eFirst)

Abstract

New fluorescent 2,9-diethynylanthracene derivatives ethynylated at unsymmetrical positions were synthesized. The addition of a (trialkylsilyl)ethynyllithium to 2-chloro-9-anthrone gave the corresponding 2-chloro-9-ethynylanthracene, and subsequent nickel-catalyzed coupling with a (trialkylsilyl)ethynyl Grignard reagent furnished the disilylated derivatives. These compounds were used for the synthesis of various 2,9-bis(phenylethynyl)anthracenes and dianthrylbutadiynes. UV–vis and fluorescence spectra were measured to evaluate the substituent effects on the absorption and emission bands.

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