4-[(4-ethynyl-benzylidene)]-2,6-diphenyl-4H-pyran | 1450722-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-[(4-ethynyl-benzylidene)]-2,6-diphenyl-4H-pyran
• 英文别名: 4-(4-ethynyl-benzylidene)-2,6-diphenyl-4H-pyran；4-(4-ethynylbenzylidene)-2,6-diphenyl-4H-pyran
• CAS: 1450722-32-3
• 化学式: C₂₆H₁₈O
• 分子量: 346.428
• InChiKey: WZAYLINHIMSKJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-[(4-ethynyl-benzylidene)]-2,6-diphenyl-4H-pyran 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium acetate 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.0h， 生成 4-[[4-[4-[4-[(2,6-Diphenylpyran-4-ylidene)methyl]phenyl]buta-1,3-diynyl]phenyl]methylidene]-2,6-diphenylpyran
  参考文献：
  名称：

  Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties

  摘要：

  This paper presents the synthesis of a series of push-pull and quadrupolar pi-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I-2 to give, after reduction by Na2S2O3, bismethylenepyran compounds via successive steps.The electrochemical redox properties of methylenepyrans 5-9 and extended bismethylenepyrans 10, 14, and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bistability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of mu beta were obtained. A positive dimer effect was also observed for bispyran derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.066
• 作为产物：
  描述：

  [4-(2,6-diphenyl-pyran-4-ylidenemethyl)-phenylethynyl]-trimethyl-silane 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以94%的产率得到4-[(4-ethynyl-benzylidene)]-2,6-diphenyl-4H-pyran
  参考文献：
  名称：

  Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties

  摘要：

  This paper presents the synthesis of a series of push-pull and quadrupolar pi-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I-2 to give, after reduction by Na2S2O3, bismethylenepyran compounds via successive steps.The electrochemical redox properties of methylenepyrans 5-9 and extended bismethylenepyrans 10, 14, and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bistability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of mu beta were obtained. A positive dimer effect was also observed for bispyran derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.066

文献信息

• New 8-substituted BODIPY-based chromophores: synthesis, optical and electrochemical properties
  作者：Nikolay Vologdin、Sylvain Achelle、Sébastien Gauthier、Bertrand Caro、Françoise Robin-le Guen

  DOI：10.1515/hc-2016-0151

  日期：2016.12.1

  BODIPY-based chromophores, in which an electron withdrawing difluoro-boraindacene fragment is connected via position 8 to different donor fragments, were synthesized. Their electrochemical and photophysical properties were studied. All compounds exhibit a quasi-reversible oxidation corresponding to the formation of a BODIPY π-radical cation at around 0.8 V vs. FeCp2+/FeCp2 that is slightly sensitive to the nature

  摘要 合成了基于 BODIPY 的发色团，其中吸电子二氟硼并五苯片段通过位置 8 连接到不同的供体片段。研究了它们的电化学和光物理性质。所有化合物都表现出准可逆氧化，对应于在 0.8 V 左右形成 BODIPY π-自由基阳离子，而 FeCp2+/FeCp2 对给电子基团的性质略敏感。在-1.6 V vs. FeCp2 +/FeCp2 附近观察到可逆还原，对应于 BODIPY π-自由基阴离子的形成。γ-亚甲基吡喃取代的 BODIPY 的循环伏安分析表明形成了具有高双稳定性的氧化还原双稳态体系。在二氯甲烷溶液中，发色团在 502 nm 附近表现出强烈的吸收带，并在 516-528 nm 范围内发射。在氨基和γ-亚甲基吡喃取代基的情况下观察到显着的发射猝灭。