phenyl[2]benzopyrano[6′,5′,4′:10,5,6]anthra[2,1,9-def]imidazo[4,5-h]isoquinoline-1,3,8,10(9H,11H)-tetrone | 1402921-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: phenyl[2]benzopyrano[6′,5′,4′:10,5,6]anthra[2,1,9-def]imidazo[4,5-h]isoquinoline-1,3,8,10(9H,11H)-tetrone
• 英文别名: 23-Phenyl-18-tridecan-7-yl-7-oxa-18,22,24-triazaoctacyclo[14.9.2.22,5.03,12.04,9.013,26.020,27.021,25]nonacosa-1(25),2(29),3(12),4(9),5(28),10,13(26),14,16(27),20,23-undecaene-6,8,17,19-tetrone；23-phenyl-18-tridecan-7-yl-7-oxa-18,22,24-triazaoctacyclo[14.9.2.22,5.03,12.04,9.013,26.020,27.021,25]nonacosa-1(25),2(29),3(12),4(9),5(28),10,13(26),14,16(27),20,23-undecaene-6,8,17,19-tetrone
• CAS: 1402921-10-1
• 化学式: C₄₄H₃₉N₃O₅
• 分子量: 689.811
• InChiKey: UKNJHCFAPAIWNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl[2]benzopyrano[6′,5′,4′:10,5,6]anthra[2,1,9-def]imidazo[4,5-h]isoquinoline-1,3,8,10(9H,11H)-tetrone 在 3-甲基吡啶 、 溴 、 铜 作用下， 以 氯仿 为溶剂， 反应 26.5h， 生成 5-bromo-21-phenyl-16-tridecan-7-yl-16,20,22-triazaheptacyclo[12.9.2.12,6.011,24.018,25.019,23.010,26]hexacosa-1(23),2,4,6,8,10(26),11(24),12,14(25),18,20-undecaene-15,17-dione
  参考文献：
  名称：

  Controlling UV/vis Absorption and Stokes Shifts in Highly Fluorescent Chromophores by Molecular Dynamics in Targeted Construction of Dyads

  摘要：

  Perylenedicarboximides were interlinked in their free pen-position to form dyads where the UV/vis absorptivity was amplified by exciton effects and the strong fluorescence bathochromically shifted by molecular dynamics. Applications of this type of dye with such increased Stokes shifts were discussed.

  DOI：

  10.1021/jo301417p
• 作为产物：
  描述：

  2,9-二(1-己基庚基)-蒽并[2,1,9-def:6,5,10-d'e'f']二异喹啉-1,3,8,10(2H,9H)-四酮 在 sodium amide 作用下， 以 叔丁醇 为溶剂， 反应 7.0h， 生成 phenyl[2]benzopyrano[6′,5′,4′:10,5,6]anthra[2,1,9-def]imidazo[4,5-h]isoquinoline-1,3,8,10(9H,11H)-tetrone
  参考文献：
  名称：

  一步级联合成邻-湾-咪唑并延伸苝双羧酰亚胺（OBISIM）及其作为广谱荧光染料的应用

  摘要：

  描述了在氨基钠和苯甲腈的级联反应中通过缩合咪唑一步合成具有侧向延伸的苝染料，其中多次延伸可以通过反应条件控制。这些延伸导致吸收和荧光发生红移，同时保持高荧光量子产率。稠合的咪唑单元在减色可见光区域产生额外的吸收带，从而产生宽带吸收体。芳香系统的多重扩展使得光谱的近红外光谱方法成为可能。具有苝双甲酰亚胺的二元组的能量转移（荧光共振能量转移，FRET）非常有效，并且无论间隔基的长度和方向如何，都可以实现接近一致的量子产率。讨论了作为宽带吸收荧光染料的应用，例如在太阳能收集器中的应用。

  DOI：

  10.1021/acs.joc.3c01694

文献信息

• Controlling UV/vis Absorption and Stokes Shifts in Highly Fluorescent Chromophores by Molecular Dynamics in Targeted Construction of Dyads
  作者：Heinz Langhals、Alexander Hofer

  DOI：10.1021/jo301417p

  日期：2012.11.2

  Perylenedicarboximides were interlinked in their free pen-position to form dyads where the UV/vis absorptivity was amplified by exciton effects and the strong fluorescence bathochromically shifted by molecular dynamics. Applications of this type of dye with such increased Stokes shifts were discussed.
• One-Step Cascade Synthesis of <i>ortho</i>–<i>bay</i>-Imidazolo-Extended Perylene Biscarboximides (OBISIM) and Their Application as Broad-Spectrum Fluorescent Dyes
  作者：Heinz Langhals、Simon Kinzel、Andreas Obermeier

  DOI：10.1021/acs.joc.3c01694

  日期：2024.2.16

  A one-step synthesis of perylene dyes with lateral extension by condensed imidazoles in a cascade reaction of sodium amide and benzonitrile is described in which multiple extensions can be controlled by the reaction conditions. The extensions lead to bathochromic shifts in absorption and fluorescence while maintaining high fluorescence quantum yields. The condensed imidazole units cause additional

  描述了在氨基钠和苯甲腈的级联反应中通过缩合咪唑一步合成具有侧向延伸的苝染料，其中多次延伸可以通过反应条件控制。这些延伸导致吸收和荧光发生红移，同时保持高荧光量子产率。稠合的咪唑单元在减色可见光区域产生额外的吸收带，从而产生宽带吸收体。芳香系统的多重扩展使得光谱的近红外光谱方法成为可能。具有苝双甲酰亚胺的二元组的能量转移（荧光共振能量转移，FRET）非常有效，并且无论间隔基的长度和方向如何，都可以实现接近一致的量子产率。讨论了作为宽带吸收荧光染料的应用，例如在太阳能收集器中的应用。