N,N'-di(5-hydroxypentyl)-1,7-dibromoperylene-3,4:9,10-perylenetetracarboxylic diimide | 1314078-28-8

• 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(5-hydroxypentyl)-1,7-dibromoperylene-3,4:9,10-perylenetetracarboxylic diimide
• 英文别名: N,N'-bis(5-hydroxypentyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
• CAS: 1314078-28-8
• 化学式: C₃₄H₂₈Br₂N₂O₆
• 分子量: 720.414
• InChiKey: YHTDQYCKCGDLIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-di(5-hydroxypentyl)-1,7-dibromoperylene-3,4:9,10-perylenetetracarboxylic diimide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q
• 作为产物：
  描述：

  在 甲醇 、 氨 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N,N'-di(5-hydroxypentyl)-1,7-dibromoperylene-3,4:9,10-perylenetetracarboxylic diimide
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q

文献信息

• Retention of perylene diimide optical properties in solid-state materials through tethering to nanodiamonds
  作者：Asia R. Y. Almuhana、Philipp Langer、Sarah L. Griffin、Rhys W. Lodge、Graham A. Rance、Neil R. Champness

  DOI：10.1039/d1tc02577e

  日期：——

  The synthesis of nanodiamond-perylene diimide composites is reported. Suitably hydroxyl-functionalised perylene diimides (PDIs) are reacted with carboxylic acid functionalised nanodiamonds (NDs) through ester formation. The ND-PDI nanocomposite materials were characterised using a variety of different techniques confirming retention of the ND cores and interestingly the dye properties of the PDIs.

  报道了纳米金刚石-苝二酰亚胺复合材料的合成。合适的羟基官能化苝二酰亚胺 (PDI) 与羧酸官能化纳米金刚石 (ND) 通过酯形成反应。ND-PDI 纳米复合材料使用各种不同的技术进行表征，证实了 ND 核的保留，有趣的是 PDI 的染料特性。特别是，荧光测量表明，与 ND 相连的 PDI 保留了溶液相 PDI 的特性，而不是与固态 PDI 相关的光学特性，后者通常会因聚集而改变。我们相对简单的方法提供了一种机制来维持固态材料中 PDI 的溶液相特性。