N,N'-dibutyl-1,7-dipyrrolidinyl-3,4,9,10-perylenetetracarboxylic diimide | 1321992-61-3

• 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'-dibutyl-1,7-dipyrrolidinyl-3,4,9,10-perylenetetracarboxylic diimide
• 英文别名: 7,18-Dibutyl-11,22-dipyrrolidin-1-yl-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；7,18-dibutyl-11,22-dipyrrolidin-1-yl-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: 1321992-61-3
• 化学式: C₄₀H₄₀N₄O₄
• 分子量: 640.782
• InChiKey: XXJDLSNRKBVQCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-dibutyl-1,7-dipyrrolidinyl-3,4,9,10-perylenetetracarboxylic diimide 在 potassium hydroxide 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 7.0h， 以45%的产率得到1,7-dipyrrolidinyl-perylene-9,10-(N-butyl)-dicarboxyimide-3,4-dicarboxylic anhydride
  参考文献：
  名称：

  Perylenetetracarboxylic Diimide Derivatives Linked with Spirobifluorene

  摘要：

  A series of perylenetetracarboxylic diimide (PDI) compounds linked with spirobifluorene have been prepared. The orthogonal configuration of the PDI subunits efficiently hindered their molecular aggregation in solution. Energy transfer from a 1,7-diphenoxyl group substituted PDI (PO-PDI) to a 1,7-dipyrrolidinyl group substituted PDI (PY-PDI) occurred with a large efficiency when PO-PDI was selectively excited, despite the orthogonal orientation of the two units. This observation was in direct conflict with predictions derived from the Forster theory. More interestingly, this efficient energy transfer also occurred in the solid state.

  DOI：

  10.1021/ol300985h
• 作为产物：
  描述：

  四氢吡咯 、 3,4,9,10-苝四羧酸二酐 、 正丁胺 在 硫酸 、 溴 、 碘 作用下， 以 水 、 异丙醇 为溶剂， 反应 56.0h， 以58%的产率得到N,N'-dibutyl-1,7-dipyrrolidinyl-3,4,9,10-perylenetetracarboxylic diimide
  参考文献：
  名称：

  二哌啶基和二吡咯烷基取代的per四羧酸二酰亚胺的结构和性能比较

  摘要：

  四种化合物1 - 4在已经制备苝酰亚胺（PDI）的托架位置和同分异构体的环氨基与连接1,7-和1,6-取代的PDI的成功通过常规柱色谱分离。通过单晶X射线衍射实验进一步表征了1,7-二吡咯烷基取代的PDI（1）和1,7-二哌啶基取代的PDI（3）的结构。晶体结构表明，分子结构的微小差异已引起吸收光谱和发射光谱以及电化学性质的显着差异。C1的短键长N3与吡咯烷中的氮原子相对于哌啶中的氮原子具有更多sp2杂原子轨道特性，这是造成这种较大的1与3之间的性质差异的原因。版权所有©2010 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1799

文献信息

• Structural and property comparison between the di-piperidinyl- and di-pyrrolidinyl-substituted perylene tetracarboxylic diimides
  作者：Junqian Feng、Delou Wang、Hailong Wang、Daopeng Zhang、Liangliang Zhang、Xiyou Li

  DOI：10.1002/poc.1799

  日期：2011.8

  difference on the absorption and emission spectra as well as the electrochemical properties. The shorter bond length of C1N3, together with the more sp2 hybrid atomic orbital characteristics of the nitrogen atom in pyrrolidine relative to those in piperidine is found to be responsible for this large property difference between 1 and 3. Copyright © 2010 John Wiley & Sons, Ltd.

  四种化合物1 - 4在已经制备苝酰亚胺（PDI）的托架位置和同分异构体的环氨基与连接1,7-和1,6-取代的PDI的成功通过常规柱色谱分离。通过单晶X射线衍射实验进一步表征了1,7-二吡咯烷基取代的PDI（1）和1,7-二哌啶基取代的PDI（3）的结构。晶体结构表明，分子结构的微小差异已引起吸收光谱和发射光谱以及电化学性质的显着差异。C1的短键长N3与吡咯烷中的氮原子相对于哌啶中的氮原子具有更多sp2杂原子轨道特性，这是造成这种较大的1与3之间的性质差异的原因。版权所有©2010 John Wiley＆Sons，Ltd.
• Perylenetetracarboxylic Diimide Derivatives Linked with Spirobifluorene
  作者：Yanan Du、Lilin Jiang、Jun Zhou、Guiju Qi、Xiyou Li、Yanqiang Yang

  DOI：10.1021/ol300985h

  日期：2012.6.15

  A series of perylenetetracarboxylic diimide (PDI) compounds linked with spirobifluorene have been prepared. The orthogonal configuration of the PDI subunits efficiently hindered their molecular aggregation in solution. Energy transfer from a 1,7-diphenoxyl group substituted PDI (PO-PDI) to a 1,7-dipyrrolidinyl group substituted PDI (PY-PDI) occurred with a large efficiency when PO-PDI was selectively excited, despite the orthogonal orientation of the two units. This observation was in direct conflict with predictions derived from the Forster theory. More interestingly, this efficient energy transfer also occurred in the solid state.