4-formyl-15-(2-phenylethane-1,2-dione)[2.2]paracyclophane | 1571074-38-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-formyl-15-(2-phenylethane-1,2-dione)[2.2]paracyclophane
• CAS: 1571074-38-8
• 化学式: C₂₅H₂₀O₃
• 分子量: 368.432
• InChiKey: RQECQHCMVFPMGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-formyl-15-(2-phenylethane-1,2-dione)[2.2]paracyclophane 在 ammonium acetate 、 溶剂黄146 、 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 苯 为溶剂， 反应 15.5h， 生成 4',5,5',7-Tetraphenylspiro[6,8-diazapentacyclo[10.8.2.03,18.04,8.010,15]docosa-1,3(18),4,6,10(15),11,13,19-octaene-9,2'-imidazole]
  参考文献：
  名称：

  Enhancing the Versatility and Functionality of Fast Photochromic Bridged Imidazole Dimers by Flipping Imidazole Rings

  摘要：

  The widely tunable optical properties and the visible sensitivity have been required for fast photochromic molecules whose coloration decoloration cycle completes in mu s to ms time scale not only for practical applications such as full-color holographic displays but also for fundamental researches in biochemistry. However, the so far developed [2.2]paracyclophane-bridged imidazole dimers, which are one of the best candidates for fast photochromic molecules, have their weaknesses for these requirements. Herein, we overcome the issues with sustaining fast photochromism and high durability by flipping the two imidazole rings (the head-to-tail and tail-to-tail forms). The alteration in the relative configuration of the imidazole rings suppresses the broad absorption band resulting from the radical-radical interaction. The substitution to the 2-position of the imidazole ring of the tail-to-tail form gives the drastic changes in the steady-state and the transient absorption spectra. The pyrene-substituted tail-to-tail form demonstrates that the transient absorption spectrum is featured by the inherent spectrum of the imidazolyl radical. This molecular framework is easy to functionalize fast photochromic molecules such as sensitizations to the red light, chirality, and biological tagging, and therefore it is versatile for various fast photochromic applications.

  DOI：

  10.1021/ja501028v
• 作为产物：
  描述：

  4-formyl-15-phenylethynyl[2.2]paracyclophane 在 palladium diacetate 、 copper(ll) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 35.0h， 以46%的产率得到4-formyl-15-(2-phenylethane-1,2-dione)[2.2]paracyclophane
  参考文献：
  名称：

  Enhancing the Versatility and Functionality of Fast Photochromic Bridged Imidazole Dimers by Flipping Imidazole Rings

  摘要：

  The widely tunable optical properties and the visible sensitivity have been required for fast photochromic molecules whose coloration decoloration cycle completes in mu s to ms time scale not only for practical applications such as full-color holographic displays but also for fundamental researches in biochemistry. However, the so far developed [2.2]paracyclophane-bridged imidazole dimers, which are one of the best candidates for fast photochromic molecules, have their weaknesses for these requirements. Herein, we overcome the issues with sustaining fast photochromism and high durability by flipping the two imidazole rings (the head-to-tail and tail-to-tail forms). The alteration in the relative configuration of the imidazole rings suppresses the broad absorption band resulting from the radical-radical interaction. The substitution to the 2-position of the imidazole ring of the tail-to-tail form gives the drastic changes in the steady-state and the transient absorption spectra. The pyrene-substituted tail-to-tail form demonstrates that the transient absorption spectrum is featured by the inherent spectrum of the imidazolyl radical. This molecular framework is easy to functionalize fast photochromic molecules such as sensitizations to the red light, chirality, and biological tagging, and therefore it is versatile for various fast photochromic applications.

  DOI：

  10.1021/ja501028v