5-cyanoacenaphthenequinone | 109179-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-cyanoacenaphthenequinone
• 英文别名: 5-Cyan-acenaphthenchinon-1,2；1,2-dioxo-acenaphthene-5-carbonitrile；5-Cyan-acenaphthenchinon；Acenaphthenchinon-carbonsaeure-(5)-nitril；1,2-Dioxo-acenaphthen-5-carbonitril；1,2-Dioxo-1,2-dihydroacenaphthylene-5-carbonitrile；1,2-dioxoacenaphthylene-5-carbonitrile
• CAS: 109179-38-6
• 化学式: C₁₃H₅NO₂
• 分子量: 207.188
• InChiKey: TVURWCUBAHSGLW-UHFFFAOYSA-N

物化性质

• 熔点：
  258-260 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  463.0±24.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 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：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-cyanoacenaphthenequinone 在 potassium hydroxide 作用下， 以 乙醇 、 硝基苯 为溶剂， 生成 6-Octyl-5,7-dioxo-3,9-dithiophen-2-yl-6-azapentacyclo[9.7.1.02,10.04,8.015,19]nonadeca-1(18),2(10),3,8,11(19),12,14,16-octaene-14-carbonitrile
  参考文献：
  名称：

  A Non-Fullerene Small Molecule as Efficient Electron Acceptor in Organic Bulk Heterojunction Solar Cells

  摘要：

  A novel n-type small molecule FFI-1 was synthesized as the electron acceptor to replace PCBM in solution-processed organic BHJ solar cells. Its LUMO level (around -3.5 eV) both matches the work function of the cathode and increases VOC of the devices, making it a promising acceptor candidate. With P3HT: FFI-1 (1: 2 w/w) as active layer and LiF/Al as the cathode, the best power conversion effi ciency (PCE) reaches 1.86%.

  DOI：

  10.1002/adma.201103927
• 作为产物：
  描述：

  5-溴苊 在 chromium(VI) oxide 、 乙酸酐 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 5-cyanoacenaphthenequinone
  参考文献：
  名称：

  A Non-Fullerene Small Molecule as Efficient Electron Acceptor in Organic Bulk Heterojunction Solar Cells

  摘要：

  A novel n-type small molecule FFI-1 was synthesized as the electron acceptor to replace PCBM in solution-processed organic BHJ solar cells. Its LUMO level (around -3.5 eV) both matches the work function of the cathode and increases VOC of the devices, making it a promising acceptor candidate. With P3HT: FFI-1 (1: 2 w/w) as active layer and LiF/Al as the cathode, the best power conversion effi ciency (PCE) reaches 1.86%.

  DOI：

  10.1002/adma.201103927

文献信息

• A Convenient One-Pot Synthesis of Acenaphthenequinones from 1-Acenaphthenones by NBS–DMSO Oxidation
  作者：Jiro Tatsugi、Shigeo Okumura、Yasuji Izawa

  DOI：10.1246/bcsj.59.3311

  日期：1986.10

  Acenaphthenequinone was obtained in 95% yield when the reaction of 1-acenaphthenone with N-bromosuccinimide was carried out in dimethyl sulfoxide at room temperature. Under similar conditions, several acenaphthenequinones were prepared from the corresponding 1-acenaphthenones in good yields.

  室温下，在二甲亚砜中使 1-苊酮与 N-溴代丁二酰亚胺反应，可获得 95% 的苊醌。在类似条件下，从相应的 1-苊酮制备出了几种苊醌，收率都很高。
• [EN] VISIBLY TRANSPARENT, NEAR-INFRARED-ABSORBING AND ULTRAVIOLET-ABSORBING PHOTOVOLTAIC DEVICES<br/>[FR] DISPOSITIFS PHOTOVOLTAÏQUES VISIBLEMENT TRANSPARENTS, ABSORBANT LE PROCHE INFRAROUGE ET ABSORBANT LES ULTRAVIOLETS
  申请人：UBIQUITOUS ENERGY INC

  公开号：WO2018232358A1

  公开（公告）日：2018-12-20

  Visibly transparent photovoltaic devices are disclosed, such as those are transparent to visible light but absorb near-infrared light and/or ultraviolet light. The photovoltaic devices make use of transparent electrodes and near-infrared or ultraviolet absorbing visibly transparent photoactive compounds, optical materials, and/or buffer materials.

  可见透明光伏器件公开，例如那些对可见光透明但吸收近红外光和/或紫外光的器件。这些光伏器件利用透明电极和近红外或紫外吸收的可见透明光活性化合物、光学材料和/或缓冲材料。
• Polycyclic Imide Derivatives: Synthesis and Effective Tuning of Lowest Unoccupied Molecular Orbital Levels through Molecular Engineering
  作者：Lin Ding、Han-Ze Ying、Yan Zhou、Ting Lei、Jian Pei

  DOI：10.1021/ol1024103

  日期：2010.12.3

  A series of fluoranthene-fused imide derivatives were facilely developed through a Diels−Alder reaction followed by decarbonylation. The investigation of their photophysical and electrochemical properties demonstrated that their LUMO levels were effectively tuned from −3.2 to −3.8 eV through the introduction of a fused imide unit, which provides a platform to design new air-stable and solution-processable

  通过Diels-Alder反应，然后进行脱羰作用，可以轻松地开发出一系列荧蒽融合的酰亚胺衍生物。对它们的光物理和电化学性质的研究表明，通过引入熔融酰亚胺单元，可将其LUMO能级有效地从-3.2调节至-3.8 eV，这为设计新的对空气稳定且可溶液处理的n型材料提供了平台。
• 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR20170065974A

  公开（公告）日：2017-06-14

  본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.

  本规范提供了异构化合物及其所含的有机发光器件。
• Karrer; Rebmann; Zeller, Helvetica Chimica Acta, 1920, vol. 3, p. 266
  作者：Karrer、Rebmann、Zeller

  DOI：——

  日期：——