Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes

Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes

A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of β-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescen...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 51; no. 6; pp. 917 - 920
Main Authors: Fang, Jing-Kun, An, De-Lie, Wakamatsu, Kan, Ishikawa, Takeharu, Iwanaga, Tetsuo, Toyota, Shinji, Matsuo, Daisuke, Orita, Akihiro, Otera, Junzo
Format: Journal Article
Language:English
Published: Elsevier Ltd 10-02-2010
Online Access:Get full text
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Summary:A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of β-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescence. The emission underwent a large bathochromic shift in polar solvent because of stabilization of their charge-separated excited states. Analyses of fluorescence life times of aminoacetylenes revealed that radiationless process was suppressed in the polar solvent CH 2Cl 2, resulting in high quantum yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.12.023