4,5-二硝基-9-氧代-9H-芴-2,7-二羧胺 | 213598-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 4,5-二硝基-9-氧代-9H-芴-2,7-二羧胺
• 英文名称: 4,5-dinitrofluoren-9-one-2,7-dicarboxamide
• 英文别名: 4,5-Dinitro-9-oxo-9H-fluorene-2,7-dicarboxamide；4,5-dinitro-9-oxofluorene-2,7-dicarboxamide
• CAS: 213598-63-1
• 化学式: C₁₅H₈N₄O₇
• 分子量: 356.251
• InChiKey: SEBZOHHXJWZGJS-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)
• 沸点：
  591.8±50.0 °C(Predicted)
• 密度：
  1.730±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  195
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,5-二硝基-9-氧代-9H-芴-2,7-二羧胺 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以48%的产率得到2,7-dicyano-4,5-dinitrofluorenone
  参考文献：
  名称：

  硝基芳族化合物作为场效应晶体管的n型有机半导体。

  摘要：

  硝基（NO 2）是最常见的吸电子基团之一，但很少用于有机半导体（OSC）的设计中。在本文中，我们报告了由NO 2和CN基官能化的简单芴酮衍生物的n型半导体行为。尽管在薄膜场效应晶体管中测得的电子迁移率适中（10 -6 –10 -4 cm 2 V -1 s -1），但硝基芴酮OSC具有出色的空气稳定性和出色的能量级可调性，可通过替换模式的轻松修改。我们研究了取代基对电化学性能，分子和晶体结构以及硝基芴酮的电荷传输性能的影响，以振兴有机电子中被低估的NO 2功能化潜力。

  DOI：

  10.1039/d0cc01236j
• 作为产物：
  描述：

  4,5-二硝基芴-9-酮-2,7-二羧酸 在 氯化亚砜 、 氨 作用下， 生成 4,5-二硝基-9-氧代-9H-芴-2,7-二羧胺
  参考文献：
  名称：

  Electron Acceptors of the Fluorene Series. 7.¹ 2,7-Dicyano-4,5-dinitro-9-X-fluorenes:  Synthesis, Cyclic Voltammetry, Charge Transfer Complexation with N-Propylcarbazole in Solution, and X-ray Crystal Structures of Two Tetrathiafulvalene Complexes

  摘要：

  The synthesis and physical properties of a series of novel fluorene pi-electron accepters (7-9) are described. Cyclic voltammograms of 7 and 8 exhibit three separate reversible (or quasi-reversible) one-electron redox waves, characteristic of strong electron accepters. Spectroelectrochemical experiments show the appearance in the long-wavelength visible region of absorption bands at appropriate potentials which were attributed to the transformations A --> A(.-) and A(.-) --> A(2-). Charge-transfer complexation with N-propylcarbazole in dioxane shows the formation of 1:1 complexes with parameters characteristic for other fluorene accepters. The single-crystal X-ray structures of 1:1 charge-transfer complexes of tetrathiafulvalene with the electron acceptor 8 and with the strongest fluorene acceptor 1f both show ..A...D...A...D.. stacking in the crystal.

  DOI：

  10.1021/jo9803481

文献信息

• Nitroaromatics as n-type organic semiconductors for field effect transistors
  作者：Muhammad Rizwan Niazi、Ehsan Hamzehpoor、Pegah Ghamari、Igor F. Perepichka、Dmitrii F. Perepichka

  DOI：10.1039/d0cc01236j

  日期：——

  design of organic semiconductors (OSCs). Herein, we report the n-type semiconducting behavior of simple fluorenone derivatives functionalized with NO2 and CN groups. While the electron mobilities measured in the thin film field-effect transistors are modest (10−6–10−4 cm2 V−1 s−1), the nitrofluorenone OSCs offer excellent air-stability and remarkable tunability of energy levels via facile modification

  硝基（NO 2）是最常见的吸电子基团之一，但很少用于有机半导体（OSC）的设计中。在本文中，我们报告了由NO 2和CN基官能化的简单芴酮衍生物的n型半导体行为。尽管在薄膜场效应晶体管中测得的电子迁移率适中（10 -6 –10 -4 cm 2 V -1 s -1），但硝基芴酮OSC具有出色的空气稳定性和出色的能量级可调性，可通过替换模式的轻松修改。我们研究了取代基对电化学性能，分子和晶体结构以及硝基芴酮的电荷传输性能的影响，以振兴有机电子中被低估的NO 2功能化潜力。
• Electron Acceptors of the Fluorene Series. 7.¹ 2,7-Dicyano-4,5-dinitro-9-X-fluorenes:  Synthesis, Cyclic Voltammetry, Charge Transfer Complexation with <i>N</i>-Propylcarbazole in Solution, and X-ray Crystal Structures of Two Tetrathiafulvalene Complexes
  作者：Igor F. Perepichka、Lyudmila G. Kuz'mina、Dmitrii F. Perepichka、Martin R. Bryce、Leonid M. Goldenberg、Anatolii F. Popov、Judith A. K. Howard

  DOI：10.1021/jo9803481

  日期：1998.9.1

  The synthesis and physical properties of a series of novel fluorene pi-electron accepters (7-9) are described. Cyclic voltammograms of 7 and 8 exhibit three separate reversible (or quasi-reversible) one-electron redox waves, characteristic of strong electron accepters. Spectroelectrochemical experiments show the appearance in the long-wavelength visible region of absorption bands at appropriate potentials which were attributed to the transformations A --> A(.-) and A(.-) --> A(2-). Charge-transfer complexation with N-propylcarbazole in dioxane shows the formation of 1:1 complexes with parameters characteristic for other fluorene accepters. The single-crystal X-ray structures of 1:1 charge-transfer complexes of tetrathiafulvalene with the electron acceptor 8 and with the strongest fluorene acceptor 1f both show ..A...D...A...D.. stacking in the crystal.