2-[2-(4-methoxyphenyl)ethenyl]-3-(2-phenylethenyl)furan

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[2-(4-methoxyphenyl)ethenyl]-3-(2-phenylethenyl)furan
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: WGAYMFLVACHONU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-formyl-3-styrylfuran 、 4-甲氧基苄基三苯基膦溴化盐 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 2-[2-(4-methoxyphenyl)ethenyl]-3-(2-phenylethenyl)furan
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and photophysics of new functionalized 2,3-distyrylfurans: Substituent and solvent effects on their photobehavior

  摘要：

  Two new groups of p-chloro-, p-methoxy- and p-nitro-substituted derivatives of the trans,trans-isomers of 2.3-distyrylfuran have been synthesized by a sequence of reactions according to known methods. These new conjugated heterocyclic compounds along with the parent one and its methyl-derivative have been characterized spectrally, photophysically and photochemically. These compounds, except for the nitro-derivatives, display high fluorescence quantum yields in the non-polar n-hexane (Phi(F) = 0.76-0.98). In ethanol of high polarity, the lifetime of their singlet excited state increases from 1.31-2.59 ns to 2.01-4.77 ns, significantly enhancing the quantum yield of their photochemical reaction from 0.02-0.24 to 0.25-0.46, and diminishing their fluorescence efficiency (Phi(F) = 0.26-0.64). Deviating from the other compounds studied, the quantum yields for both the fluorescence and the photolysis of the nitro-derivatives are rather low (Phi(F) < 10(-4), Phi = 0.025-0.042 in ethanol), probably due to an efficient intersystem crossing leading to a non-reactive triplet state. Accordingly, their singlet-state lifetime is also relatively short (tau(F) < 0.3 ns). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.02.013

文献信息

• Synthesis, spectroscopic characterization and photophysics of new functionalized 2,3-distyrylfurans: Substituent and solvent effects on their photobehavior
  作者：Irena Škorić、Ilijana Kikaš、Margit Kovács、Marija Šindler-Kulyk、Ottó Horváth

  DOI：10.1016/j.jphotochem.2010.02.013

  日期：2010.4

  Two new groups of p-chloro-, p-methoxy- and p-nitro-substituted derivatives of the trans,trans-isomers of 2.3-distyrylfuran have been synthesized by a sequence of reactions according to known methods. These new conjugated heterocyclic compounds along with the parent one and its methyl-derivative have been characterized spectrally, photophysically and photochemically. These compounds, except for the nitro-derivatives, display high fluorescence quantum yields in the non-polar n-hexane (Phi(F) = 0.76-0.98). In ethanol of high polarity, the lifetime of their singlet excited state increases from 1.31-2.59 ns to 2.01-4.77 ns, significantly enhancing the quantum yield of their photochemical reaction from 0.02-0.24 to 0.25-0.46, and diminishing their fluorescence efficiency (Phi(F) = 0.26-0.64). Deviating from the other compounds studied, the quantum yields for both the fluorescence and the photolysis of the nitro-derivatives are rather low (Phi(F) < 10(-4), Phi = 0.025-0.042 in ethanol), probably due to an efficient intersystem crossing leading to a non-reactive triplet state. Accordingly, their singlet-state lifetime is also relatively short (tau(F) < 0.3 ns). (C) 2010 Elsevier B.V. All rights reserved.