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Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes |
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| Authors: | Jing-Kun Fang De-Lie An Kan Wakamatsu Tetsuo Iwanaga Daisuke Matsuo Junzo Otera |
| Institution: | a Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China b Department of Chemistry, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan c Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan |
| Abstract: | 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 CH2Cl2, resulting in high quantum yields. |
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