Synthesis of diarylenynes by olefination of 1-arylpropyne with arylaldehyde and their optical properties

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• 作者：Kenta Shinohara^a ; Takanori Nishida^a ; Ryosuke Wada^a ; Lifen Peng^b ; Yuju Minoda^a ; Akihiro Orita^a ; ^{orita@dac.ous.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Junzo Otera^a
• 关键词：1-(Diphenylphosphoryl)propyne ; Sonogashira coupling ; 1.4-Diarylbut-1-en-3-ynes ; Photoluminescence ; Solvatofluorochromism
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：21 July 2016
• 年：2016
• 卷：72
• 期：29
• 页码：4427-4434
• 全文大小：1456 K

文摘

A new synthetic protocol of 1-arylpropyne was developed by taking advantage of 1-(diphenylphosphoryl)propyne as propyne equivalent in Sonogashira coupling: consecutive subjection of phosphorylpropyne to t-BuOK and to aryl halides in the presence of Pd and Cu catalysts afforded the corresponding 1-arylpropynes. The following olefination of the 1-arylpropyne with aldehyde provided the corresponding diarylenyne. When the enynes thus obtained were irradiated with UV light, they showed strong emission in organic solvents and in the solid states. In solution, Ph₂N-substituted enynes exhibited remarkable solvatofluorochromism, and Lippert–Mataga plot analysis demonstrated that they undergo the larger polarization in the excited states than in the ground states.