6-(1-pyrenyl)-2-oxo-4-piperidin-1-yl-2H-pyran-3-carbonitrile | 1122565-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 6-(1-pyrenyl)-2-oxo-4-piperidin-1-yl-2H-pyran-3-carbonitrile
• 英文别名: 4-(piperidin-1-yl)-2-oxo-6-(pyren-1-yl)-2H-pyran-3-carbonitrile；2-oxo-4-(piperidin-1-yl)-6-(pyren-1-yl)-2H-pyran-3-carbonitrile；2-Oxo-4-piperidin-1-yl-6-pyren-1-ylpyran-3-carbonitrile
• CAS: 1122565-64-3
• 化学式: C₂₇H₂₀N₂O₂
• 分子量: 404.468
• InChiKey: YNSUXTAMAFYKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(1-pyrenyl)-2-oxo-4-piperidin-1-yl-2H-pyran-3-carbonitrile 在 NaH 作用下， 以 四氢呋喃 为溶剂， 生成 3-piperidin-1-yl-1-pyren-1-yl-9H-fluorene-4-carbonitrile
  参考文献：
  名称：

  NOVEL DONOR-ACCEPTOR FLUORENE SCAFFOLDS: A PROCESS AND USES THEREOF

  摘要：

  本发明涉及新型供体-受体芴化合物，可用于制造电致发光器件，并提供了制备这些新化合物的方法。更具体地说，本发明涉及胺供体和腈/酯受体芴，芴酮的π-共轭系统及相关化合物，制备这些化合物的方法包括将芴氧化为相应的芴酮，并将它们用于制备有机电子器件，例如有机发光二极管（OLEDs），光伏/太阳能电池，场效应晶体管和其他有用的电致发光器件。这些化合物是通过在有机溶剂中在碱的存在下，用含有亚甲基羰基基团的环状酮与2H-吡喃-2-酮在孤立或刚性构象下反应而制备的。本发明还涉及一种新的概念和方法，以克服9-未取代芴基有机发光二极管中的“绿色发射缺陷”问题，该问题是由于芴转化为主要在绿黄色区域发射的芴酮而引起的。在本发明中，我们将供体-受体取代基放置在这样的位置，使得供体-受体芴酮的发射在蓝色区域（而不是绿黄色区域）显示，从而提高了蓝色纯度并克服了绿色发射缺陷问题。

  公开号：

  US20110210315A1
• 作为产物：
  描述：

  1-乙酰基芘 在 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 6-(1-pyrenyl)-2-oxo-4-piperidin-1-yl-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  Non-aggregating solvatochromic bipolar benzo[f]quinolines and benzo[a]acridines for organic electronics

  摘要：

  在温和的条件下，通过 C-C 键的形成，设计并制备了一系列新型发光且热稳定的非聚集苯并喹啉类和吖啶类化合物。对这些双极性 N-杂环化合物进行的光物理和电化学分析表明，由于分子内电荷转移特性，这些化合物具有强烈的溶解变色特性，以 9b 为例，在使用不同极性的钝化溶剂时，其聚光范围从蓝色（480 纳米）到绿色（501 纳米）到黄色（562 纳米）到橙色（589 纳米）。成功制备了器件配置为 ITO/PEDOT:PSS (40 nm)/NPB (20 nm)/(N-heterocyclic compound) (50 nm)/BCP (7 nm)/LiF (0.7 nm)/Al (200 nm) 的有机发光器件。通过控制调节苯并[f]喹啉和苯并[a]吖啶中的供体-受体和芳香π-共轭，这些化合物的光电性质发生了改变，表现出低开启电压，电致发光范围从蓝色（6c：λEL 455 nm）到绿色（8a：λEL 496 nm）到黄色（11：λEL 545 nm）再到红色（9b：λEL 630 nm）。

  DOI：

  10.1039/c2jm31052j

文献信息

• Donor−Acceptor 9-Uncapped Fluorenes and Fluorenones as Stable Blue Light Emitters^,
  作者：Atul Goel、Sumit Chaurasia、Manish Dixit、Vijay Kumar、Sattey Prakash、Bijayalaxmi Jena、Jai K. Verma、Mayank Jain、R. S. Anand、S. Sundar Manoharan

  DOI：10.1021/ol9000679

  日期：2009.3.19

  The "green emission defect" (GED) produced by fluorenones has significantly retarded the commercial scope of fluorene-based B-OLEDs. In this paper, for the first time, it is demonstrated that the "green light" emitting fluorenones 7 can be converted to "blue light" emitting fluorenones 10 by appropriate positioning of donor-acceptor and chromophoric groups onto the fluorene/fluorenone backbone. Additionally, we report an elegant highly rapid synthetic route for donor-acceptor fluorenes and fluorenones at room temperature with excellent yields.
• Synthesis, Electrochemical and Optical Properties of Stable Yellow Fluorescent Fluoranthenes
  作者：Atul Goel、Vijay Kumar、Sumit Chaurasia、Madhu Rawat、Ramesh Prasad、R. S. Anand

  DOI：10.1021/jo100420x

  日期：2010.6.4

  A novel series of thermally stable yellow light emitting fluoranthenes with an amine donor and a nitrite acceptor was prepared from a ketene-S,S-acetal under mild conditions without using an organometal catalyst. The organic light emitting device of yellow fluoranthene 10b exhibited substantially low turn-on voltage (2.6 V) and maximum brightness of 470 Cd/m(2) with luminance efficiency of 2.0 Cd/A without using any dopant.
• Thermally Stable Nonaggregating Pyrenylarenes for Blue Organic Light-Emitting DevicesCDRI communication No. 8097.
  作者：Atul Goel、Vijay Kumar、Pankaj Nag、Vikas Bajpai、Brijesh Kumar、Charan Singh、Sattey Prakash、R. S. Anand

  DOI：10.1021/jo2011768

  日期：2011.9.16

  A new series of thermally stable blue light-emitting nonplanar pyrenylarenes having an amine donor and a nitrile acceptor group was prepared from a ketene-S,S-acetal under conventional heating and/or microwave irradiation. The photophysical, electrochemical, and optical behavior of donor acceptor pyrenylarenes are demonstrated. The performance of blue light-emitting pyrenylarenes was investigated by fabricating a multilayer device with the device configuration of ITO/PEDOT:PSS (40 nm)/NPB (30 nm)/pyrenylarene (55 nm)/BCP (8 nm)/LiF (0.6 nm)/Al (200 nm), which exhibited low turn-on voltage (5 V) with luminance efficiency of 0.8 Cd/A with nonaggregation behavior in both solution and solid state.
• US8946682B2
  申请人：——

  公开号：US8946682B2

  公开（公告）日：2015-02-03
• [EN] SUBSTITUTED NAPHTHO[2,1-b][1,10]PHENANTHROLINE BASED FLUORESCENT DYES AND APPLICATION THEREOF<br/>[FR] COLORANTS FLUORESCENTS À BASE DE NAPHTHO[2,1-B][1,10]PHÉNANTHROLINE SUBSTITUÉ ET APPLICATION ASSOCIÉE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016005992A1

  公开（公告）日：2016-01-14

  The present invention relates to novel dihydronaphtho[2,l-b][l,10]phenanthrolines and naphtho[2,l-b][l,10]phenanthrolines of the general formula I which can be used potentially as fluorescent probes in chemical and biological sciences such as cell imaging applications, diagnostics, fluorescent tags, ion sensor, pharmaceuticals and other useful applications, and a process of preparing said novel compounds and quantification of reactive oxygen species. The compounds are prepared by reacting lactones in isolated or rigid conformations with methylene carbonyl moiety in the presence of a base in an organic solvent.