2-piperidin-1-yl-4-pyren-1-yl-9H-fluorene-1-carbonitrile | 1122565-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-piperidin-1-yl-4-pyren-1-yl-9H-fluorene-1-carbonitrile
• 英文别名: 4-pyrenyl-2-piperidin-1-yl-9H-fluorene-1-carbonitrile；2-(piperidin-1-yl)-4-(pyren-1-yl)-9H-fluorene-1-carbonitrile
• CAS: 1122565-67-6
• 化学式: C₃₅H₂₆N₂
• 分子量: 474.605
• InChiKey: ZMKJQRVJRCEMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-piperidin-1-yl-4-pyren-1-yl-9H-fluorene-1-carbonitrile 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 9-oxo-2-piperidin-1-yl-4-pyren-1-yl-9H-fluorene-1-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：

  6-(1-pyrenyl)-2-oxo-4-piperidin-1-yl-2H-pyran-3-carbonitrile 、 2-茚酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.08h， 以90%的产率得到2-piperidin-1-yl-4-pyren-1-yl-9H-fluorene-1-carbonitrile
  参考文献：
  名称：

  Donor−Acceptor 9-Uncapped Fluorenes and Fluorenones as Stable Blue Light Emitters^,

  摘要：

  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.

  DOI：

  10.1021/ol9000679

文献信息

• NOVEL DONOR-ACCEPTOR FLUORENE SCAFFOLDS: A PROCESS AND USES THEREOF
  申请人：GOEL Atul

  公开号：US20110210315A1

  公开（公告）日：2011-09-01

  The present invention relates to novel donor-acceptor fluorene compounds, which can be used as for the fabrication of electroluminescent devices, and a process of preparing said novel compounds. More particularly, the present invention relates to amine donor and nitrile/ester acceptor fluorenes, fluorenones their π-conjugated systems and related compounds, processes for preparing the said compounds including oxidation of fluorenes to corresponding fluorenones and their use in preparing organic electronic devices such as organic light emitting diodes (OLEDs), photovoltaic/solar cell, Field effect transistors and other useful electroluminescent devices. The compounds are prepared by reacting 2H-pyran-2-ones in isolated or rigid conformations with cyclic ketones containing methylene carbonyl moiety in the presence of a base in an organic solvent. The present invention also relates to a new concept and approach to overcome the problem of ‘Green emission defect’ in 9-unsubstituted fluorene-based organic light emitting diodes which occurs due to the conversion of fluorenes to fluorenones that show emission mainly in green-yellow region. In the present invention we have placed donor-acceptor substituents in such a way that donor-acceptor fluorenones show emission in the blue region (instead of green-yellow region) thus improving the blue colour purity and overcoming the problem of green emission defect.

  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。
• Donor-acceptor fluorene scaffolds: a process and uses thereof
  申请人：Goel Atul

  公开号：US08946682B2

  公开（公告）日：2015-02-03

  The present invention relates to novel donor-acceptor fluorene compounds, which can be used as for the fabrication of electroluminescent devices, and a process of preparing said novel compounds. More particularly, the present invention relates to amine donor and nitrile/ester acceptor fluorenes, fluorenones their π-conjugated systems and related compounds, processes for preparing the said compounds including oxidation of fluorenes to corresponding fluorenones and their use in preparing organic electronic devices such as organic light emitting diodes (OLEDs), photovoltaic/solar cell, Field effect transistors and other useful electroluminescent devices. The compounds are prepared by reacting 2H-pyran-2-ones in isolated or rigid conformations with cyclic ketones containing methylene carbonyl moiety in the presence of a base in an organic solvent. The present invention also relates to a new concept and approach to overcome the problem of ‘Green emission defect’ in 9-unsubstituted fluorene-based organic light emitting diodes which occurs due to the conversion of fluorenes to fluorenones that show emission mainly in green-yellow region. In the present invention we have placed donor-acceptor substituents in such a way that donor-acceptor fluorenones show emission in the blue region (instead of green-yellow region) thus improving the blue color purity and overcoming the problem of green emission defect.

  本发明涉及一种新型给体-受体芴化合物，可用于制造电致发光器件，并提供了制备所述新型化合物的方法。更具体地，本发明涉及胺给体和腈/酯受体芴烯、芴酮的π-共轭系统及相关化合物，制备所述化合物的方法包括将芴烯氧化为相应的芴酮，并将其用于制备有机电子器件，例如有机发光二极管（OLED）、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。所述化合物通过在有机溶剂中，在存在碱的情况下，将2H-吡喃-2-酮与含有亚甲基羰基的环状酮反应而制备得到。本发明还涉及一种新的概念和方法，以克服基于9-未取代芴的有机发光二极管中的“绿色发射缺陷”问题，该问题是由于将芴烯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，我们将给体-受体取代基放置在一定的位置，使得给体-受体芴酮在蓝色区域发射（而不是绿黄色区域），从而提高蓝色纯度并克服绿色发射缺陷问题。
• US8946682B2
  申请人：——

  公开号：US8946682B2

  公开（公告）日：2015-02-03
• [EN] NOVEL DONOR-ACCEPTOR FLUORENE SCAFFOLDS : A PROCESS AND USES THEREOF<br/>[FR] NOUVEAUX ÉCHAFAUDAGES DE FLUORÈNE DONNEUR-ACCEPTEUR : UN PROCÉDÉ ET SES UTILISATIONS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2009122445A2

  公开（公告）日：2009-10-08

  The present invention relates to novel donor-acceptor fluorene compounds, which can be used as for the fabrication of electroluminescent devices, and a process of preparing said novel compounds. More particularly, the present invention relates to amine donor and nitrile/ester acceptor fluorenes, fluorenones their π-conjugated systems and related compounds, processes for preparing the said compounds including oxidation of fluorenes to corresponding fluorenones and their use in preparing organic electronic devices such as organic light emitting diodes (OLEDs), photovoltaic/solar cell, Field effect transistors and.other useful electroluminescent devices. The compounds are prepared by reacting 2H-pyran- 2-ones in isolated or rigid conformations with cyclic ketones containing methylene carbonyl moiety in the presence of a base in- an organic solvent.The present invention also relates to a new concept and approach to overcome the problem of 'Green emission defect' in 9- unsubstituted fluorene-based organic light emitting diodes which occurrs due to the conversion of fluorenes to fluorenones that show emission mainly in green-yellow region. In the present invention we have placed donor-acceptor substituents in such a way that donor- acceptor fluorenones show emission in the blue region (instead of green-yellow region) thus improving the blue colour purity and overcoming the problem of green emission defect.
• 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.