azaperylene | 24408-62-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: azaperylene
• 英文别名: 3-azapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6(20),7,9,11,13,15(19),16-decaene
• CAS: 24408-62-6
• 化学式: C₁₉H₁₁N
• 分子量: 253.303
• InChiKey: HDMSISRTSCLVOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  azaperylene 在 碘苯二乙酸 、 palladium diacetate 作用下， 以 正丁醇 为溶剂， 反应 25.0h， 以70%的产率得到12-hydroxy-1-azaperylene
  参考文献：
  名称：

  Strongly Emitting Fluorophores Based on 1-Azaperylene Scaffold

  摘要：

  A novel blue-emitting polycyclic aromatic system was synthesized via anion-radical coupling. Its efficient direct hydroxylation led to a phenol possessing an intramolecular hydrogen-bond system. Since the energy gap difference between the enol and keto forms of this molecule is very small, characteristic of ESIPT chromophores, bathochromically shifted fluorescence was not observed.

  DOI：

  10.1021/jo902443s
• 作为产物：
  描述：

  1-(naphthalen-1-yl)isoquinoline 在 氢化钾 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以30%的产率得到azaperylene
  参考文献：
  名称：

  Strongly Emitting Fluorophores Based on 1-Azaperylene Scaffold

  摘要：

  A novel blue-emitting polycyclic aromatic system was synthesized via anion-radical coupling. Its efficient direct hydroxylation led to a phenol possessing an intramolecular hydrogen-bond system. Since the energy gap difference between the enol and keto forms of this molecule is very small, characteristic of ESIPT chromophores, bathochromically shifted fluorescence was not observed.

  DOI：

  10.1021/jo902443s

文献信息

• Synthesis and Electrochemical and Photophysical Properties of Azaterrylene Derivatives
  作者：Akitsu Hirono、Hayato Sakai、Taku Hasobe

  DOI：10.1002/asia.201801410

  日期：2019.5.15

  (MATerry), 1,6‐diazaterrylene (DiATerry) and pristine terrylene (Terry), were synthesized by changing the number of nitrogen atoms at the bay region (1 and 6 positions of the Terry core). The electrochemical measurements suggested that the first one‐electron reduction and oxidation potentials became positively shifted with increasing numbers of nitrogen atoms. This agreed with the energies of the corresponding

  通过改变海湾区域（Terry核的1和6位）上的氮原子数，合成了一系列三萘嵌苯衍生物，例如单氮杂三甲苯（MATerry），1,6-二氮杂戊二烯（DiATerry）和原始三甲苯（Terry）。 ）。电化学测量表明，随着氮原子数量的增加，第一个电子还原和氧化电势正移。这与通过DFT方法估算的相应最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）状态的能量一致。相反，HOMO-LUMO间隙大致保持恒定。这种趋势与通过吸收光谱和荧光光谱观察到的光谱行为非常相似。DiATerry的溶剂极性相关光谱趋势表明了分子内电荷转移（ICT）特性。对各种溶剂中激发态动力学的评估表明，通过ICT激发态相对于基态的电子构型变化。Lippert-MAtaga图支持了这一点。最后，还观察到了可逆的质子化和去质子化过程。
• Aggregate organic light emitting diode devices with improved operational stability
  申请人：Jarikov V. Viktor

  公开号：US20050106415A1

  公开（公告）日：2005-05-19

  An organic light emitting device includes a substrate, an anode and a cathode disposed over the substrate, and a luminescent layer disposed between the anode and the cathode wherein the luminescent layer includes a host and at least one dopant. The host of the luminescent layer is selected to include a solid organic material comprising a mixture of at least two components, one of which contains at least one perylene carbocyclic ring structure or at least one mono-aza-perylene or poly-aza-perylene ring structure and is capable of forming both monomer state and an aggregate state.

  有机发光器件包括基板、位于基板上的阳极和阴极以及位于阳极和阴极之间的发光层，其中发光层包括宿主和至少一种掺杂剂。发光层的宿主被选择为包含至少两种组分的固态有机材料的混合物，其中一种组分包含至少一个苝環烷环结构或至少一个单氮杂苝環或多氮杂苝環环结构，并能够形成单体态和聚集态。
• [EN] CHIRAL METAL COMPLEXES AS EMITTERS FOR ORGANIC POLARIZED ELECTROLUMINESCENT DEVICES<br/>[FR] COMPLEXES MÉTALLIQUES CHIRAUX COMME ÉMETTEURS DANS DE DISPOSITIFS ÉLECTROLUMINESCENTS POLARISÉE ORGANIQUE
  申请人：UNIV ARIZONA STATE

  公开号：WO2015131158A1

  公开（公告）日：2015-09-03

  Chiral metal complexes having one of general formulae (1)-(4).

  具有以下一般式之一的手性金属配合物（1）-（4）。
• Exploring Cyclometalated Ir Complexes as Donor Materials for Organic Solar Cells
  作者：Tyler B. Fleetham、Zixing Wang、Jian Li

  DOI：10.1021/ic3023453

  日期：2013.7.1

  The performance of small molecular organic photovoltaic materials is typically limited by their low exciton diffusion lengths' ? solubility, and Poor energy level alignment with fullerenes so that the design and synthesis of new materials remain a top priority. To overcome these limitations, we explored the use of an iridium complex as a donor material with the potential for compatibility with solution processing, long exciton diffusion length and easy molecular modification for tunable optical or electrical properties. A bilayer device with a cyclometalated iridium complex and C-60 resulted in a power conversion efficiency as high as 2.8%. Furthermore, a V-OC of 1 V was achieved in the bilayer device despite an estimated exciton energy of only 1.55 eV, and the device showed minimal temperature and light intensity dependence.
• Organometallic Materials for Optical Emission, Optical Absorption, and Devices Including Organometallic Materials
  申请人：Jabbour Ghassan E.

  公开号：US20080269491A1

  公开（公告）日：2008-10-30

  A near infrared phosphorescent organometallic complex includes a cyclometalating ligand and a transition metal. The cyclometalating ligand includes a fused aromatic ring structure with carbon atoms, and a heteronuclear aromatic ring with a nitrogen atom. The transition metal is bonded to the nitrogen atom in the heteronuclear aromatic ring and one of the carbon atoms in the fused aromatic ring structure. The heteronuclear ring can be part of the fused aromatic ring. The organometallic complex is capable of phosphorescent emission with maximum emission intensity occurring at a wavelength in a range from about 650 nm to about 2000 nm.