Synthesis of Hydroxyalkyl‐Substituted, Push–Pull Chromophores based on Diphenylacetylenes and 1,4‐Bis(phenylethynyl)benzenes

Abstract

Six new push–pull chromophores based on phenylacetylenes were prepared: two 1,2‐diphenylacetylenes and four 1,4‐bis(phenylethynyl)benzenes. The donor amino groups have hydroxyethyl substituents, and the acceptor groups are cyano or nitro. More soluble versions were made by including two methoxy groups on the central phenyl ring.

Keywords:

• iodination
• 2‐methyl‐3‐butyn‐2‐ol
• palladium
• phenylacetylenes
• sonogashira

Acknowledgments

The generous financial support by the Army Research Laboratory is gratefully acknowledged. Thanks go to Geoffrey A. Lindsay (NAWCWD) for advice and encouragement throughout the course of this work, Robert D. Chapman (NAWCWD) for CAS/Beilstein database searches for 4‐bromoiodobenzene in the chemical literature, and Brian Zentner (NAWCWD) for supplying the iodine.