2-[6-[4-(4-methylphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indol-7-yl]-1,3-dioxobenzo[de]isoquinolin-2-yl]acetic acid | 1293967-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-[6-[4-(4-methylphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indol-7-yl]-1,3-dioxobenzo[de]isoquinolin-2-yl]acetic acid
• CAS: 1293967-26-6
• 化学式: C₃₂H₂₆N₂O₄
• 分子量: 502.569
• InChiKey: JWUOXYUWJQUFRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-(1,3-dioxo-6-(4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)-1H-benzo[de]isoquinolin-2(3H)-yl)acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以0.15 g的产率得到2-[6-[4-(4-methylphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]indol-7-yl]-1,3-dioxobenzo[de]isoquinolin-2-yl]acetic acid
  参考文献：
  名称：

  Novel dyes based on naphthalimide moiety as electron acceptor for efficient dye-sensitized solar cells

  摘要：

  Four novel naphthalimide-based dyes (D-1, D-2, D-3 and D-4) were synthesized and utilized as sensitizers in dye-sensitized solar cells (DSCs), in which the triphenylamine (TPA) or indoline groups, naphthalimide unit and carboxylic group were functionalized as electron donor, acceptor and anchoring group, respectively. The naphthalimide unit was employed as the pi-conjugation ring and electron acceptor for effectively realizing intramolecular charge separation in the oxidized states. In the series of dyes, the LUMO orbital is delocalized mainly on naphthalimide moieties, especially on the carbonyl group. Consequently, the LUMO electrons are isolated from the carboxyl anchoring group (-CH2CO2H) due to the presence of the methylene group, which could suppress the electron injection efficiency from the excited dyes to the TiO2 conduction band, thus leading to the inferior efficiencies of 1.10, 1.18, 2.27 and 2.70%, respectively, even though they exhibit broad spectral response and high extinction coefficients. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.01.010