16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione | 1027311-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione
• 英文别名: 30,34-Bis(2-ethylhexoxy)nonacyclo[18.10.2.22,5.03,16.04,13.06,11.017,31.022,27.028,32]tetratriaconta-1(30),2(34),3(16),4(13),5(33),6,8,10,14,17(31),18,20(32),22,24,26,28-hexadecaene-12,21-dione；30,34-bis(2-ethylhexoxy)nonacyclo[18.10.2.22,5.03,16.04,13.06,11.017,31.022,27.028,32]tetratriaconta-1(30),2(34),3(16),4(13),5(33),6,8,10,14,17(31),18,20(32),22,24,26,28-hexadecaene-12,21-dione
• CAS: 1027311-37-0
• 化学式: C₅₀H₄₈O₄
• 分子量: 712.929
• InChiKey: ZQVHBGMPLUOFAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  54
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴代异辛烷 、 16,17-二羟基蒽酮紫 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione
  参考文献：
  名称：

  Effect of substituents on the aggregate structure and photovoltaic property of violanthrone derivatives

  摘要：

  In this paper, three violanthrone derivatives with different substituents, 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (3), 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst] pentaphene-5,10-dione (4), 16,17-bis(hexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (5), are synthesized. It is found that the substituent has a great effect on the aggregate structures of violanthrone derivatives: the shorter the side chain is, the stronger the intermolecular pi-pi actions in the solid state is. Because all compounds are p-type semiconductive materials with the relatively low-lying highest occupied molecular orbital (HOMO) energy levels (similar to-5.1 eV) and low band gaps (similar to 1.8 eV), their photovoltaic properties are evaluated when the blends of violanthrone derivatives and [6,6]-phenyl-C-61-butyric acid methyl ester (PCBM) (1:1, w/w) are used as the active layers of organic solar cells. Among three violanthrone derivatives, compound 5 exhibits the best photovoltaic performance with the power conversion efficiency (PCE) of 0.54% since the aggregate structure of compound 5 is in favor of charge transport. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.05.003

文献信息

• Effect of substituents on the aggregate structure and photovoltaic property of violanthrone derivatives
  作者：Minmin Shi、Feng Hao、Lijian Zuo、Yi Chen、Yaxiong Nan、Hongzheng Chen

  DOI：10.1016/j.dyepig.2012.05.003

  日期：2012.11

  In this paper, three violanthrone derivatives with different substituents, 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (3), 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst] pentaphene-5,10-dione (4), 16,17-bis(hexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (5), are synthesized. It is found that the substituent has a great effect on the aggregate structures of violanthrone derivatives: the shorter the side chain is, the stronger the intermolecular pi-pi actions in the solid state is. Because all compounds are p-type semiconductive materials with the relatively low-lying highest occupied molecular orbital (HOMO) energy levels (similar to-5.1 eV) and low band gaps (similar to 1.8 eV), their photovoltaic properties are evaluated when the blends of violanthrone derivatives and [6,6]-phenyl-C-61-butyric acid methyl ester (PCBM) (1:1, w/w) are used as the active layers of organic solar cells. Among three violanthrone derivatives, compound 5 exhibits the best photovoltaic performance with the power conversion efficiency (PCE) of 0.54% since the aggregate structure of compound 5 is in favor of charge transport. (C) 2012 Elsevier Ltd. All rights reserved.