(N,N'-dicyclohexyl-1-bromo-7-dodecyloxy)perylene-3,4:9,10-tetracarboxydiimide | 935660-63-2

• 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-bromo-7-dodecyloxy)perylene-3,4:9,10-tetracarboxydiimide
• 英文别名: PDI-Br；11-Bromo-7,18-dicyclohexyl-22-dodecoxy-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
• CAS: 935660-63-2
• 化学式: C₄₈H₅₃BrN₂O₅
• 分子量: 817.863
• InChiKey: RJVBJTARCCCIGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (N,N'-dicyclohexyl-1-bromo-7-dodecyloxy)perylene-3,4:9,10-tetracarboxydiimide 、 十二硫醇 在 十六烷基三甲基溴化铵 、 potassium carbonate 作用下， 以 邻二甲苯 为溶剂， 反应 5.0h， 以80%的产率得到(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
• 作为产物：
  描述：

  十二烷醇 、 N,N'-dicyclohexyl-1,7-dibromoperylene-3,4:9,10-tetracarboxylic dianhydride 在 sodium hydride 作用下， 反应 24.25h， 以44%的产率得到(N,N'-dicyclohexyl-1-bromo-7-dodecyloxy)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

• Synthesis and quantum chemical study of PDI derivatives with phenylalkynyl groups at the bay position
  作者：Delou Wang、Yan shi、Chuntao Zhao、Baolong Liang、Xiyou Li

  DOI：10.1016/j.molstruc.2009.09.035

  日期：2009.12

  Six new perylenetetracarboxylic dimide (PDI) compounds were prepared by introducing alkynyl or alkynylphenyl groups with different length to the bay position of PDI ring. The UV-vis absorption and emission spectra of these new compounds were recorded The red-shift on the maximum absorption and emission peaks revealed the efficient participation of the side conjugation chain to the whole conjugation system. The molecular structure, the frontier molecular orbital and the energy gaps between the highest occupied orbital (HOMO) and the lowest un-occupied orbital (LUMO) were calculated with DFT method. The results show good consistent with the experimental results. The absorption and emission spectra of these six compounds were also simulated with TD-B3lyp/6-31g(d) and TD-PBE1PBE/6-31g(d) methods The simulated results for the compounds with short side conjugation chain show better response to the experimental results However. the quantum calculation on the compounds with long conjugated side chain do not give satisfied results because of the significant electron transfer characteristics in the excited states (C) 2009 Elsevier B.V All rights reserved
• 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.