2,6-Bis[[4-(bromomethyl)phenyl]methyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone | 944247-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,6-Bis[[4-(bromomethyl)phenyl]methyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• 英文别名: 2,6-bis[[4-(bromomethyl)phenyl]methyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 944247-90-9
• 化学式: C₂₆H₁₈Br₂N₂O₄
• 分子量: 582.248
• InChiKey: NZHPPIHAFOFFIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-Bis[[4-(bromomethyl)phenyl]methyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone 、 4,4'-联吡啶 、 1,5-dinaphtho[38]crown-10 在 ammonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 240.0h， 以52%的产率得到
  参考文献：
  名称：

  Probing Donor−Acceptor Interactions and Co-Conformational Changes in Redox Active Desymmetrized [2]Catenanes

  摘要：

  We describe the synthesis and characterization of a series of desymmetrized donor-acceptor [2]catenanes where different donor and acceptor units are assembled within a confined catenated geometry. Remarkable translational selectivity is maintained in all cases, including two fully desymmetrized [2]catenanes where both donors and acceptors are different, as revealed by X-ray crystallography in the solid state, and by H-1 NMR spectroscopy and electrochemistry in solution. In all desymmetrized [2]catenanes the co-conformation is dominated by the strongest donor and acceptor pairs, whose charge-transfer interactions also determine the visible absorption properties. Voltammetric and spectroelectrochemical experiments show that the catenanes can be reversibly switched among as many as seven states, characterized by distinct electronic and optical properties, by electrochemical stimulation in a relatively narrow and easily accessible potential window. Moreover in some of these compounds the oxidation of the electron donor units or the reduction of the electron acceptor ones causes the circumrotation of one molecular ring with respect to the other. These features make these compounds appealing for the development of molecular electronic devices and mechanical machines.

  DOI：

  10.1021/ja909041g
• 作为产物：
  描述：

  均苯四甲酸二酐 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 2,6-Bis[[4-(bromomethyl)phenyl]methyl]pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
  参考文献：
  名称：

  具有非对称翻译选择性的[2]邻苯二酚的模板化合成。

  摘要：

  合成了不对称的[2]邻苯二酚，显示出优异的翻译选择性。模板化合成是通过在富含pi的冠醚和pi缺乏的均苯四甲酸（PmI）单元之间形成假轮烷，然后在冠醚周围进行大环化并生成双吡啶（BPy）单元而实现的。如各种光谱分析所表明的，冠醚优选在溶液和固态中都以所得的[2]邻苯二甲基环抱BPy单元。

  DOI：

  10.1021/ol070970s

文献信息

• Probing Donor−Acceptor Interactions and <i>Co</i>-Conformational Changes in Redox Active Desymmetrized [2]Catenanes
  作者：Dennis Cao、Matteo Amelia、Liana M. Klivansky、Gayane Koshkakaryan、Saeed I. Khan、Monica Semeraro、Serena Silvi、Margherita Venturi、Alberto Credi、Yi Liu

  DOI：10.1021/ja909041g

  日期：2010.1.27

  We describe the synthesis and characterization of a series of desymmetrized donor-acceptor [2]catenanes where different donor and acceptor units are assembled within a confined catenated geometry. Remarkable translational selectivity is maintained in all cases, including two fully desymmetrized [2]catenanes where both donors and acceptors are different, as revealed by X-ray crystallography in the solid state, and by H-1 NMR spectroscopy and electrochemistry in solution. In all desymmetrized [2]catenanes the co-conformation is dominated by the strongest donor and acceptor pairs, whose charge-transfer interactions also determine the visible absorption properties. Voltammetric and spectroelectrochemical experiments show that the catenanes can be reversibly switched among as many as seven states, characterized by distinct electronic and optical properties, by electrochemical stimulation in a relatively narrow and easily accessible potential window. Moreover in some of these compounds the oxidation of the electron donor units or the reduction of the electron acceptor ones causes the circumrotation of one molecular ring with respect to the other. These features make these compounds appealing for the development of molecular electronic devices and mechanical machines.
• Templated Synthesis of Desymmetrized [2]Catenanes with Excellent Translational Selectivity
  作者：Yi Liu、Liana M. Klivansky、Saeed I. Khan、Xiyun Zhang

  DOI：10.1021/ol070970s

  日期：2007.6.1

  Desymmetrized [2]catenanes were synthesized and shown to exhibit excellent translational selectivity. The templated synthesis takes effect from the formation of pseudorotaxanes between pi-rich crown ethers and a pi-deficient pyromellitic (PmI) unit, followed by macrocyclization around the crown ethers with the creation of a bipyridinium (BPy) unit. The crown ethers preferably encircle the BPy unit

  合成了不对称的[2]邻苯二酚，显示出优异的翻译选择性。模板化合成是通过在富含pi的冠醚和pi缺乏的均苯四甲酸（PmI）单元之间形成假轮烷，然后在冠醚周围进行大环化并生成双吡啶（BPy）单元而实现的。如各种光谱分析所表明的，冠醚优选在溶液和固态中都以所得的[2]邻苯二甲基环抱BPy单元。