(N,N'-dicyclohexyl-1-dodecyloxy-7-dodecylthio)perylene-3,4:9,10-tetracarboxydiimide

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (N,N'-dicyclohexyl-1-dodecyloxy-7-dodecylthio)perylene-3,4:9,10-tetracarboxydiimide
• 英文别名: 7,18-Dicyclohexyl-11-dodecoxy-22-dodecylsulfanyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• 化学式: C₆₀H₇₈N₂O₅S
• 分子量: 939.356
• InChiKey: OCNJFTCSNXLIIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19
• 重原子数：
  68
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N'-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxylic dianhydride 在 十六烷基三甲基溴化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 邻二甲苯 为溶剂， 反应 29.25h， 生成 (N,N'-dicyclohexyl-1-dodecyloxy-7-dodecylthio)perylene-3,4:9,10-tetracarboxydiimide
  参考文献：
  名称：

  Di(alkoxy)- and Di(alkylthio)-Substituted Perylene-3,4;9,10-tetracarboxy Diimides with Tunable Electrochemical and Photophysical Properties

  摘要：

  Nucleophilic substitution of N,N'-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxydiimide (PTCDI) with an excess of corresponding alkanol in the presence of sodium hydride or anhydrous potassium carbonate at 85-100 degrees C provided both di(alkoxy)- and mono(alkoxy)-substituted PTCDI compounds, namely, N,N'-dicyclohexyl-1,7-di(alkoxy)perylene-3,4:9,10-tetracarboxydiimide (3) and N,N'-dicyclohexyl-1-bromo-7-alkoxyperylene-3,4:9,10-tetracarboxydiimide (2). Starting from mono(alkoxy)-substituted PTCDI, nucleophilic substitution with thiol, thiophenol, or alkylamine led to the formation of unsymmetrical 1,7-di(substituted) PTCDI compounds (7-10). For the purpose of comparative studies, symmetrical di(substituted) N,N'-dicyclohexyl-1,7-di(alkylthio)perylene-3,4:9,10-tetracarboxydiimide (4), N,N'-dicyclohexyl-1,7-di(thiophenyl)perylene-3,4:9,10-tetracarboxydiimide (5), and N,N'-dicyclohexyl-1,7-di(alkylamine)perylene-3,4:9,10-tetracarboxydiimide (6) have also been prepared by a similar nucleophilic substitution. These newly prepared PTCDI compounds have been characterized by a wide range of spectroscopic methods in addition to elemental analysis. Electronic absorption and fluorescence studies revealed that the absorption and emission bands as well as the fluorescence quantum yield can be tuned continuously over a large range by incorporating substituents with different electron-donating abilities.

  DOI：

  10.1021/jo062150j

文献信息

• Di(alkoxy)- and Di(alkylthio)-Substituted Perylene-3,4;9,10-tetracarboxy Diimides with Tunable Electrochemical and Photophysical Properties
  作者：Chuntao Zhao、Yuexing Zhang、Renjie Li、Xiyou Li、Jianzhuang Jiang

  DOI：10.1021/jo062150j

  日期：2007.3.1

  Nucleophilic substitution of N,N'-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxydiimide (PTCDI) with an excess of corresponding alkanol in the presence of sodium hydride or anhydrous potassium carbonate at 85-100 degrees C provided both di(alkoxy)- and mono(alkoxy)-substituted PTCDI compounds, namely, N,N'-dicyclohexyl-1,7-di(alkoxy)perylene-3,4:9,10-tetracarboxydiimide (3) and N,N'-dicyclohexyl-1-bromo-7-alkoxyperylene-3,4:9,10-tetracarboxydiimide (2). Starting from mono(alkoxy)-substituted PTCDI, nucleophilic substitution with thiol, thiophenol, or alkylamine led to the formation of unsymmetrical 1,7-di(substituted) PTCDI compounds (7-10). For the purpose of comparative studies, symmetrical di(substituted) N,N'-dicyclohexyl-1,7-di(alkylthio)perylene-3,4:9,10-tetracarboxydiimide (4), N,N'-dicyclohexyl-1,7-di(thiophenyl)perylene-3,4:9,10-tetracarboxydiimide (5), and N,N'-dicyclohexyl-1,7-di(alkylamine)perylene-3,4:9,10-tetracarboxydiimide (6) have also been prepared by a similar nucleophilic substitution. These newly prepared PTCDI compounds have been characterized by a wide range of spectroscopic methods in addition to elemental analysis. Electronic absorption and fluorescence studies revealed that the absorption and emission bands as well as the fluorescence quantum yield can be tuned continuously over a large range by incorporating substituents with different electron-donating abilities.