N,N'-di(2-ethylhexyl)-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide | 318293-22-0

• 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: N,N'-di(2-ethylhexyl)-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide
• 英文别名: N,N′-di(2-ethylhexyl)-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxydiimide；Anthra[2,1,9-def:6,5,10-d'e'fa(2)]diisoquinoline-1,3,8,10(2H,9H)-tetrone, 5,6,12,13-tetrakis[4-(1,1-dimethylethyl)phenoxy]-2,9-bis(2-ethylhexyl)-；11,14,22,26-tetrakis(4-tert-butylphenoxy)-7,18-bis(2-ethylhexyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• CAS: 318293-22-0
• 化学式: C₈₀H₉₀N₂O₈
• 分子量: 1207.6
• InChiKey: LSQHKVHESPHKFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.8
• 重原子数：
  90
• 可旋转键数：
  24
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-di(2-ethylhexyl)-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide 在 potassium hydroxide 作用下， 以 叔丁醇 为溶剂， 以83 %的产率得到1,6,7,12-四叔丁基苯氧基苝-3,4,9,10-四甲酸二酐
  参考文献：
  名称：

  Metal-free FRET macrocycles of perylenediimide and aza-BODIPY for multifunctional sensing

  摘要：

  多色团金属无荧光共振能量转移大环M1 [1+1]和M2 [2+2]由PDI和ABDP组成，已经合成并表现出对温度和氧化还原电位变化的明显刺激响应性。

  DOI：

  10.1039/d2cc06225a
• 作为产物：
  描述：

  2-乙基己胺 、 1,6,7,12-四叔丁基苯氧基苝-3,4,9,10-四甲酸二酐 以 丙酸 为溶剂， 反应 10.0h， 以83%的产率得到N,N'-di(2-ethylhexyl)-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures

  摘要：

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.

  DOI：

  10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

文献信息

• Tri-Petal Lilac-Like Perylene: Asymmetrical Substituted Platform for Regioselective Ether-Exchange Reaction
  作者：Dapeng Cao、Qifang Li、Manxi Zhou、Lei Zhu、Zhimin Sun、Zhenqing Yang

  DOI：10.1055/s-0036-1590808

  日期：2017.10

  An asymmetrical tri-petal lilac-like platform based on perylene bisimide (PBI) was designed and synthesized to further perform the ether-exchange reaction, while common tetraphenoxy PBI analogue cannot do it. We found that the tri-petal lilac-like platform strategy not only avoids the regioisomers of difunctionalized PBI, but also is a precise and facile way to achieve regioselective introduction of

  设计并合成了一种基于苝双酰亚胺 (PBI) 的不对称三瓣紫丁香样平台，以进一步进行醚交换反应，而普通的四苯氧基 PBI 类似物无法做到这一点。我们发现，三瓣紫丁香样平台策略不仅避免了双官能化 PBI 的区域异构体，而且是实现将烷氧基、烷硫基和 C=C 双键末端取代基区域选择性引入到 1 位的一种精确而简便的方法不使用和去除保护基团的苝湾。由于可调的光电特性和位于海湾位置的官能团，这些 n 型 PBI 衍生物是用于光伏和超分子应用的有前途的材料。
• Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures
  作者：Frank Würthner、Christoph Thalacker、Armin Sautter、Wolfgang Schärtl、Wolfram Ibach、Olaf Hollricher

  DOI：10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

  日期：2000.11.3

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.
• Metal-free FRET macrocycles of perylenediimide and aza-BODIPY for multifunctional sensing
  作者：Kavita Rani、Sanchita Sengupta

  DOI：10.1039/d2cc06225a

  日期：——

  Multichromophoric metal-free FRET macrocycles M1 [1+1] and M2 [2+2] composed of PDI and ABDP have been synthesized and showed distinct stimuli responsiveness towards temperature and redox potential variation.

  多色团金属无荧光共振能量转移大环M1 [1+1]和M2 [2+2]由PDI和ABDP组成，已经合成并表现出对温度和氧化还原电位变化的明显刺激响应性。