N,N'-bis(3-azidopropyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-bis(dicarboximide) | 1353346-36-7

• 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'-bis(3-azidopropyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-bis(dicarboximide)
• CAS: 1353346-36-7
• 化学式: C₃₀H₁₆Cl₄N₈O₄
• 分子量: 694.32
• InChiKey: LRUUXQZWEGQCMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.94
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  172.28
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-azidopropyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-bis(dicarboximide) 、 2-ethyl-2-(1-pentyn-5-yl)barbituric acid 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到5,6,12,13-tetrachloro-2,9-bis(3-(4-(3-(5-ethyl-2,4,6-trioxohexahydropyrimidin-5-yl)propyl)-1H-1,2,3-triazol-1-yl)propyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone
  参考文献：
  名称：

  Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties

  摘要：

  The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (la-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.096
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 氯磺酸 、 碘 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 N,N'-bis(3-azidopropyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-bis(dicarboximide)
  参考文献：
  名称：

  Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties

  摘要：

  The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (la-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.096