11,22-Bis[2-(6,11-dihexoxy-3-methoxytriphenylen-2-yl)ethynyl]-7,18-bis[2,6-di(propan-2-yl)phenyl]-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 | 1361488-87-0

• 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: 11,22-Bis[2-(6,11-dihexoxy-3-methoxytriphenylen-2-yl)ethynyl]-7,18-bis[2,6-di(propan-2-yl)phenyl]-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
• 英文别名: 11,22-bis[2-(6,11-dihexoxy-3-methoxytriphenylen-2-yl)ethynyl]-7,18-bis[2,6-di(propan-2-yl)phenyl]-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: 1361488-87-0
• 化学式: C₁₁₄H₁₁₄N₂O₁₀
• 分子量: 1672.17
• InChiKey: NGQZAKSODOVJBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  32
• 重原子数：
  126
• 可旋转键数：
  36
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-ethynyl-6,11-bis(hexyloxy)-3-methoxytriphenylene 、 1,7-二溴代苝二酰亚胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以35%的产率得到11,22-Bis[2-(6,11-dihexoxy-3-methoxytriphenylen-2-yl)ethynyl]-7,18-bis[2,6-di(propan-2-yl)phenyl]-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
  参考文献：
  名称：

  Synthesis and optical properties of perylene diimide derivatives with triphenylene-based dendrons linked at the bay positions through a conjugated ethynyl linkage

  摘要：

  A number of groups including trimethylsilyl, phenyl, triphenylene, and triphenylene-based dendron have been linked to the bay positions of a perylene diimide (PDI) core through an ethynyl bridge. The photophysical properties of the resulting bay-substituted PDI derivatives have been carefully studied in different solvents and as thin films. Without any capping group, the two ethynyl bay-substituted PDI derivates PAT and PRT both aggregate strongly even in dilute solutions but in different perylene-perylene pi-pi stacking modes; PRT aggregates through slipped (or longitudinal) stacking while PAT selfassembles by rotational (or cross) stacking. With capping groups, the perylene core stacking is completely blocked for PATS in both solution and solid film. For PRTS, the slipped stacking is observed only for its film sample, while for PTB, association only occurs after excitation (excimer formation). When triphenylene or triphenylene-based G1 dendron is attached to the acetylene bridge, the resulting donor-acceptor systems (PTG0 and PTG1) exhibit strong electronic coupling between the dendritic donors and the PDI acceptor, leading to significantly red-shifted absorption bands. The conjugated linkage also facilitates photoinduced electron transfer from the triphenylene or triphenylene dendron to the PDI core, effectively quenching fluorescence emissions of both the donor and the acceptor. The significantly red-shifted absorption bands and the efficient photoinduced electron transfer observed on PTG0 and PTG1 indicate that these new PDI derivatives may find applications in solar cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.008

文献信息

• Synthesis and optical properties of perylene diimide derivatives with triphenylene-based dendrons linked at the bay positions through a conjugated ethynyl linkage
  作者：Mahuya Bagui、Tanmoy Dutta、Haizhen Zhong、Shaohua Li、Sanjiban Chakraborty、Andrew Keightley、Zhonghua Peng

  DOI：10.1016/j.tet.2012.02.008

  日期：2012.4

  A number of groups including trimethylsilyl, phenyl, triphenylene, and triphenylene-based dendron have been linked to the bay positions of a perylene diimide (PDI) core through an ethynyl bridge. The photophysical properties of the resulting bay-substituted PDI derivatives have been carefully studied in different solvents and as thin films. Without any capping group, the two ethynyl bay-substituted PDI derivates PAT and PRT both aggregate strongly even in dilute solutions but in different perylene-perylene pi-pi stacking modes; PRT aggregates through slipped (or longitudinal) stacking while PAT selfassembles by rotational (or cross) stacking. With capping groups, the perylene core stacking is completely blocked for PATS in both solution and solid film. For PRTS, the slipped stacking is observed only for its film sample, while for PTB, association only occurs after excitation (excimer formation). When triphenylene or triphenylene-based G1 dendron is attached to the acetylene bridge, the resulting donor-acceptor systems (PTG0 and PTG1) exhibit strong electronic coupling between the dendritic donors and the PDI acceptor, leading to significantly red-shifted absorption bands. The conjugated linkage also facilitates photoinduced electron transfer from the triphenylene or triphenylene dendron to the PDI core, effectively quenching fluorescence emissions of both the donor and the acceptor. The significantly red-shifted absorption bands and the efficient photoinduced electron transfer observed on PTG0 and PTG1 indicate that these new PDI derivatives may find applications in solar cells. (C) 2012 Elsevier Ltd. All rights reserved.