二苯并[a,d]环庚烯-5,10,11-三酮 | 108653-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 中文名称: 二苯并[a,d]环庚烯-5,10,11-三酮
• 英文名称: 5H-dibenzo[a,d][7]annulene-5,10,11-trione
• 英文别名: dibenzo[a,d]cycloheptene-5,10,11-trione；Dibenzo[a,d]cyclohepten-5,10,11-trion；Tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-2,9,10-trione；tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-2,9,10-trione
• CAS: 108653-03-8
• 化学式: C₁₅H₈O₃
• 分子量: 236.227
• InChiKey: QAOPSDIVXJUFBO-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  439.2±15.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二苯并[a,d]环庚烯-5,10,11-三酮 在 氢氧化钾 、 十氢化-2-萘酚 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 9-Oxo-1,4-diphenyl-9H-tribenzo[a,c,e]cycloheptene-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Ried,W.; Ehret,J., Angewandte Chemie, 1968, vol. 80, p. 365 - 366

  摘要：

  DOI：
• 作为产物：
  描述：

  5-二苯并环庚烯酮 在 selenium(IV) oxide 作用下， 以 氯苯 为溶剂， 反应 24.0h， 生成 二苯并[a,d]环庚烯-5,10,11-三酮
  参考文献：
  名称：

  氮杂烯二苯并亚砜。

  摘要：

  通过使二苯并亚甲基三酮与一系列取代的二氨基-和四氨基-芳烃缩合获得一系列的二苯并亚砜基-稠合的N-杂蒽。缺电子的三酮在室温下反应，并以良好至极佳的产率提供含吡嗪或双吡嗪的缩合产物。靶都根据单晶结构显示负曲率。

  DOI：

  10.1021/acs.joc.9b02756

文献信息

• Spirally Configured<i>cis</i>‐Stilbene/fluorene (STIF), 10,11‐Benzo‐, and Imidazole‐fused STIF Hybrids as Electron‐Transporting Materials for Organic Light‐Emitting Diode Applications
  作者：Chien‐Tien Chen、Po‐Hsun Fang、Jia‐Hong Jou、Wei‐Hua Chen

  DOI：10.1002/asia.202300482

  日期：2023.7.17

  A new class ofcis‐stilbene/fluorene (STIF) and 10,11‐benzo‐ and imidazole‐fused dibenzosuberane/fluorene (Bz‐STIF and Imd‐STIF) spiro hybrid systems with paired cyanophenyl, pyridyl, and/or pyrimidyl units was synthesized as electron transporting materials (ETMs) for blue fluorescent OLEDs (FOLEDs) and phosphorescent organic light emitting diodes (PhOLEDs). Their photophysical (UV‐Vis absorption and emission), electrochemical (E_ox/E_red), morphological (glassy transition temperature, T_g), and thermal stability (decomposition temperature, T_d) properties are systematical compared. Their correlations regarding the effects of the fused unit/substituent(s) in the STIF core on the morphological/thermal stability, HOMO/LUMO energy level, π‐electron distribution profiles by DFT calculations, and electron mobility are established. Blue FOLEDs are fabricated by using them and TmPyPB (a control) as ETMs. The effects of their LUMO energy levels and electron mobilities on the device turn‐on voltage, performance efficiencies including external quantum efficiency/current efficiency (EQE/CE), power efficiency (PE), and device lifetime at 5% luminescence decay (T₉₅) are correlated. Among them, three best ETMs and TmPyPB (a control) are selected for further green and blue PhOLED fabrications. The effects of their LUMO energy levels and electron mobilities on the device turn‐on voltage and performance efficiencies are confirmed, allowing for potential commercial applications.

  摘要 合成了一类新的顺式链烯/芴（STIF）和 10,11-苯并和咪唑融合二苯并呋喃/芴（Bz-STIF 和 Imd-STIF）螺杂体系，这些体系具有成对的氰基、吡啶基和/或嘧啶基单元，可用作蓝色荧光有机发光二极管（FOLED）和磷光有机发光二极管（PhOLED）的电子传输材料（ETM）。对它们的光物理（紫外可见吸收和发射）、电化学（Eox/Ered）、形态（玻璃态转变温度，Tg）和热稳定性（分解温度，Td）特性进行了系统比较。通过 DFT 计算，建立了 STIF 内核中熔融单元/取代基对形貌/热稳定性、HOMO/LUMO 能级、π 电子分布图和电子迁移率影响的相关性。利用它们和 TmPyPB（对照）作为 ETM 制作了蓝色 FOLED。研究了它们的 LUMO 能级和电子迁移率对器件开启电压、性能效率（包括外部量子效率/电流效率 (EQE/CE)）、功率效率 (PE) 和 5% 发光衰减 (T95) 时器件寿命的影响。其中，三种最佳 ETM 和 TmPyPB（对照）被选中用于进一步制造绿色和蓝色 PhOLED。它们的 LUMO 能级和电子迁移率对器件开启电压和性能效率的影响得到了证实，从而实现了潜在的商业应用。
• Aromatic Saddles Containing Two Heptagons
  作者：Kwan Yin Cheung、Xiaomin Xu、Qian Miao

  DOI：10.1021/jacs.5b00403

  日期：2015.3.25

  Soluble derivatives of C70H26 (1a,b) and C70H30 (2a,b), two new saddle-shaped polycyclic arenes containing two heptagons, were successfully synthesized from saddle-shaped diketones.(3a,b), whose Carbonyl groups are the key in the reactions to extend the polycyclic pi-framework. As found from the crystal structures, the polycyclic backbone of 1b has a deep saddle shape, while that of 2b is even more distorted because of the existence of two [4]-helicene moieties. Oh the basis of crystal structures, local aromaticity and nonplanarity of individual rings in the saddle-shaped pi-backbone were analyzed; and were found to follow Clar's rule in general: It was found that 1b and 3b behaved as p-type semiconductors in solution-processed thin film transistors while the amorphous films of 2b appeared insulating.
• Rigaudy; Nedelec, Bulletin de la Societe Chimique de France, 1959, p. 638,642
  作者：Rigaudy、Nedelec

  DOI：——

  日期：——
• Azaacenodibenzosuberones
  作者：Victor Brosius、Matthias Müller、Jan Borstelmann、Frank Rominger、Jan Freudenberg、Uwe H. F. Bunz

  DOI：10.1021/acs.joc.9b02756

  日期：2020.1.3

  N-heteroacenes was obtained by the condensation of dibenzosuberonetriketone with a series of substituted diamino- and tetramino-arenes. The electron-deficient triketone reacts at room temperature and furnishes the pyrazine or bis-pyrazine-containing condensation products in good to excellent yield. The targets all display negative curvature according to single crystal structures.

  通过使二苯并亚甲基三酮与一系列取代的二氨基-和四氨基-芳烃缩合获得一系列的二苯并亚砜基-稠合的N-杂蒽。缺电子的三酮在室温下反应，并以良好至极佳的产率提供含吡嗪或双吡嗪的缩合产物。靶都根据单晶结构显示负曲率。
• Ried,W.; Ehret,J., Angewandte Chemie, 1968, vol. 80, p. 365 - 366
  作者：Ried,W.、Ehret,J.

  DOI：——

  日期：——