5-(diphenylamino)acenaphthylene-1,2-dione | 820212-06-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(diphenylamino)acenaphthylene-1,2-dione
• 英文别名: 5-(Diphenylamino)acenaphthylene-1,2-dione；5-(N-phenylanilino)acenaphthylene-1,2-dione
• CAS: 820212-06-4
• 化学式: C₂₄H₁₅NO₂
• 分子量: 349.389
• InChiKey: UPGJVBZBSZYHLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(diphenylamino)acenaphthylene-1,2-dione 、 2,3-diaminomaleonitrile 以 正丁醇 为溶剂， 反应 4.0h， 以88.5%的产率得到3-(diphenylamino)acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile
  参考文献：
  名称：

  A new class of organic dyes based on acenaphthopyrazine for dye-sensitized solar cells

  摘要：

  A new class of organic dyes based on acenaphthopyrazine derivatives, containing pyrazine group as the electron acceptor and o-dicarboxyl acids as the anchoring groups were designed and synthesized for application in dye-sensitized solar cells (DSCs). These dyes have short synthesis routes and are easily adsorbed on the surface of TiO2. Under illumination of simulated AM1.5 solar light (100 mW cm(-2)), a total solar energy conversion efficiency (eta) of 4.04% was obtained for the 3-(diphenylamino)acenaphtho[1,2-b] pyrazine-8,9-dicarboxylic acid (AP-1) in the preliminary tests, in comparison with the conventional N719 dye (eta=7.05%) under the same conditions. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.05.017
• 作为产物：
  描述：

  5-溴萘乙基-1,2-二酮 、 二苯胺 在 potassium tert-butylate 、 palladium diacetate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 以26.4%的产率得到5-(diphenylamino)acenaphthylene-1,2-dione
  参考文献：
  名称：

  A new class of organic dyes based on acenaphthopyrazine for dye-sensitized solar cells

  摘要：

  A new class of organic dyes based on acenaphthopyrazine derivatives, containing pyrazine group as the electron acceptor and o-dicarboxyl acids as the anchoring groups were designed and synthesized for application in dye-sensitized solar cells (DSCs). These dyes have short synthesis routes and are easily adsorbed on the surface of TiO2. Under illumination of simulated AM1.5 solar light (100 mW cm(-2)), a total solar energy conversion efficiency (eta) of 4.04% was obtained for the 3-(diphenylamino)acenaphtho[1,2-b] pyrazine-8,9-dicarboxylic acid (AP-1) in the preliminary tests, in comparison with the conventional N719 dye (eta=7.05%) under the same conditions. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.05.017

文献信息

• 一种苊并荧蒽衍生物及其制备方法和应用
  申请人：上海大学

  公开号：CN117510346A

  公开（公告）日：2024-02-06

  本发明属于光电技术领域，具体涉及一种苊并荧蒽衍生物及其制备方法和应用，该衍生物的通式如式(Ⅰ)所示：#imgabs0#式(Ⅰ)中，X1～X14包括至少一个电子给体基团和至少一个电子受体基团。与现有技术相比，本发明解决现有技术中有机TADF材料存在的发光效率和稳定性不足的问题。本发明提供一类新型的基于苊并荧蒽结构的衍生物，这类材料具有稠环π共轭母核结构，使其具有较高的化学键键能，因此可以实现良好的光化学与光物理稳定性，并且其刚性稠环结构与非键电子结构可以有效抑制分子内的振动，有助于抑制激发态的非辐射跃迁行为并获得高光致发光效率，在应用于电致发光器件中实现高电致发光效率。
• A new class of organic dyes based on acenaphthopyrazine for dye-sensitized solar cells
  作者：Zhixia Kong、Huizhi Zhou、Jingnan Cui、Tingli Ma、Xichuan Yang、Licheng Sun

  DOI：10.1016/j.jphotochem.2010.05.017

  日期：2010.6

  A new class of organic dyes based on acenaphthopyrazine derivatives, containing pyrazine group as the electron acceptor and o-dicarboxyl acids as the anchoring groups were designed and synthesized for application in dye-sensitized solar cells (DSCs). These dyes have short synthesis routes and are easily adsorbed on the surface of TiO2. Under illumination of simulated AM1.5 solar light (100 mW cm(-2)), a total solar energy conversion efficiency (eta) of 4.04% was obtained for the 3-(diphenylamino)acenaphtho[1,2-b] pyrazine-8,9-dicarboxylic acid (AP-1) in the preliminary tests, in comparison with the conventional N719 dye (eta=7.05%) under the same conditions. (C) 2010 Elsevier B.V. All rights reserved.