2,3-bis(dibromomethyl)anthraquinone | 63859-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3-bis(dibromomethyl)anthraquinone
• 英文别名: 2.3-Bis(dibrommethyl)-9.10-anthrachinon；2,3-bis(dibromomethyl)anthracene-9,10-dione
• CAS: 63859-33-6
• 化学式: C₁₆H₈Br₄O₂
• 分子量: 551.854
• InChiKey: BDHAMRXASFYEKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(dibromomethyl)anthraquinone 在 异丙基氯化镁 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.33h， 生成
  参考文献：
  名称：

  Compression of a Flapping Mechanophore Accompanied by Thermal Void Collapse in a Crystalline Phase

  摘要：

  Mechanical control of the molecular energy landscape is an important issue in modern materials science. Mechanophores play a unique role in that the mechanical responses are induced against the activation barrier for intramolecular transformation with the aid of external forces. Here we report an unprecedented activation process of a flexible flapping mechanophore. Namely, thermal void collapse in a crystalline phase triggers mechanophore compression in a definite proportion. Unfavored conformational planarization of the flapping mechanophore is compulsorily induced by packing force, leading to a total energy gain in crystal packing. Fluorescence chromism indicates extended pi conjugation resulting from the mechanophore compression, giving rise to an energy transfer from the unpressed to compressed conformers.

  DOI：

  10.1021/jacs.8b03833
• 作为产物：
  描述：

  2,3-二甲基蒽醌 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 72.0h， 以65%的产率得到2,3-bis(dibromomethyl)anthraquinone
  参考文献：
  名称：

  Compression of a Flapping Mechanophore Accompanied by Thermal Void Collapse in a Crystalline Phase

  摘要：

  Mechanical control of the molecular energy landscape is an important issue in modern materials science. Mechanophores play a unique role in that the mechanical responses are induced against the activation barrier for intramolecular transformation with the aid of external forces. Here we report an unprecedented activation process of a flexible flapping mechanophore. Namely, thermal void collapse in a crystalline phase triggers mechanophore compression in a definite proportion. Unfavored conformational planarization of the flapping mechanophore is compulsorily induced by packing force, leading to a total energy gain in crystal packing. Fluorescence chromism indicates extended pi conjugation resulting from the mechanophore compression, giving rise to an energy transfer from the unpressed to compressed conformers.

  DOI：

  10.1021/jacs.8b03833

文献信息

• Compression of a Flapping Mechanophore Accompanied by Thermal Void Collapse in a Crystalline Phase
  作者：Takuya Yamakado、Kazuya Otsubo、Atsuhiro Osuka、Shohei Saito

  DOI：10.1021/jacs.8b03833

  日期：2018.5.23

  Mechanical control of the molecular energy landscape is an important issue in modern materials science. Mechanophores play a unique role in that the mechanical responses are induced against the activation barrier for intramolecular transformation with the aid of external forces. Here we report an unprecedented activation process of a flexible flapping mechanophore. Namely, thermal void collapse in a crystalline phase triggers mechanophore compression in a definite proportion. Unfavored conformational planarization of the flapping mechanophore is compulsorily induced by packing force, leading to a total energy gain in crystal packing. Fluorescence chromism indicates extended pi conjugation resulting from the mechanophore compression, giving rise to an energy transfer from the unpressed to compressed conformers.