7,18-Bis[2,6-di(propan-2-yl)phenyl]-11,22-diethynyl-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 | 1361488-86-9

• 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: 7,18-Bis[2,6-di(propan-2-yl)phenyl]-11,22-diethynyl-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: 7,18-bis[2,6-di(propan-2-yl)phenyl]-11,22-diethynyl-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: 1361488-86-9
• 化学式: C₅₂H₄₂N₂O₄
• 分子量: 758.916
• InChiKey: QLYBPEIDPKWXTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  己基叠氮化物 、 7,18-Bis[2,6-di(propan-2-yl)phenyl]-11,22-diethynyl-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 在 铜 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  研究 Curtin-Hammett 控制下大环化合物的非对映选择性合成

  摘要：

  这项工作为含有扭曲芳香单元的手性大环化合物的立体选择性合成提供了新的思路，这是用于识别、传感和光电子学的有价值的π共轭材料。我们首次利用科廷-哈米特原理研究手性大环化反应，揭示了超分子 π-π 相互作用指导动态动力学解析结果的潜力，有利于产生与可逆热力学下预期相反的大环产物受控条件。具体来说，动态外消旋苝二酰亚胺染料 (1 : 1 P : M ) 与对映体纯 ( S )-1,1'-bi-2-萘酚基团 ( P -BINOL) 结合，形成两个非对映体大环产物，即同手性大环 ( PP ) 和异手性物种 ( PM )。我们发现PM大环具有显着的选择性 (dr = 4 : 1)，这是通过大环化过程中P -BINOL π 供体和M -PDI π 受体之间分子内芳香族非共价相互作用的动力学模板合理化的反应。

  DOI：

  10.1039/d3sc05715a
• 作为产物：
  描述：

  2,9-bis(2,6-diisopropylphenyl)-5,12-bis((trimethylsilyl)ethynyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)tetraone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以52%的产率得到7,18-Bis[2,6-di(propan-2-yl)phenyl]-11,22-diethynyl-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.
• Investigating the diastereoselective synthesis of a macrocycle under Curtin–Hammett control
  作者：Angus Yeung、Martijn A. Zwijnenburg、Georgia R. F. Orton、Jennifer H. Robertson、Timothy A. Barendt

  DOI：10.1039/d3sc05715a

  日期：2024.4.17

  that expected under reversible, thermodynamically controlled conditions. Specifically, a dynamic, racemic perylene diimide dye (1 : 1 P : M) is strapped with an enantiopure (S)-1,1′-bi-2-naphthol group (P-BINOL) to form two diastereomeric macrocyclic products, the homochiral macrocycle (PP) and the heterochiral species (PM). We find there is notable selectivity for the PM macrocycle (dr = 4 : 1), which

  这项工作为含有扭曲芳香单元的手性大环化合物的立体选择性合成提供了新的思路，这是用于识别、传感和光电子学的有价值的π共轭材料。我们首次利用科廷-哈米特原理研究手性大环化反应，揭示了超分子 π-π 相互作用指导动态动力学解析结果的潜力，有利于产生与可逆热力学下预期相反的大环产物受控条件。具体来说，动态外消旋苝二酰亚胺染料 (1 : 1 P : M ) 与对映体纯 ( S )-1,1'-bi-2-萘酚基团 ( P -BINOL) 结合，形成两个非对映体大环产物，即同手性大环 ( PP ) 和异手性物种 ( PM )。我们发现PM大环具有显着的选择性 (dr = 4 : 1)，这是通过大环化过程中P -BINOL π 供体和M -PDI π 受体之间分子内芳香族非共价相互作用的动力学模板合理化的反应。