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Efficient Synthesis of 9,10-Bis(phenylethynyl)anthracene Derivatives by Integration of Sonogashira Coupling and Double-Elimination Reactions

Authors :
Ryo Tanaka
Daiki Mamiya
Akihiro Orita
Tetsuo Iwanaga
Shinji Toyota
Rie Yoshida
Junzo Otera
Source :
Synthesis. 45:1060-1068
Publication Year :
2013
Publisher :
Georg Thieme Verlag KG, 2013.

Abstract

9,10-Bis(phenylethynyl)anthracene (BPEA) derivatives were synthesized from 10-bromo-9-anthracenecarbaldehyde by stepwise Sonogashira coupling with phenylethynes and the one-shot double-elimination reaction with benzyl phenyl sulfones. Those two reactions could be integrated in a one-pot process to give unsymmetrically substituted BPEA derivatives in good yields by simple operations. This integrated process was applied to the synthesis of an extended BPEA derivative having an extra phenylethynyl group. The photophysical properties of the BPEA derivatives were investigated by UV/Vis and fluorescence spectroscopy.

Details

ISSN :
1437210X and 00397881
Volume :
45
Database :
OpenAIRE
Journal :
Synthesis
Accession number :
edsair.doi...........dcb47ea258633a7d544e95c5c216de36
Full Text :
https://doi.org/10.1055/s-0032-1316867