2,7-bis(hexyloxy)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone | 1335149-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,7-bis(hexyloxy)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
• 英文别名: O,O'-di-n-hexylDHNDI；6,13-Dihexoxy-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone；6,13-dihexoxy-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1335149-95-5
• 化学式: C₂₆H₃₀N₂O₆
• 分子量: 466.534
• InChiKey: PZFLARQENJWVRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 三正丁胺 、 盐酸羟胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 2,7-bis(hexyloxy)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
  参考文献：
  名称：

  O,O′-Disubstituted N,N′-Dihydroxynaphthalenediimides (DHNDI): First Principles Designed Organic Building Blocks for Materials Science

  摘要：

  N,N'-Disubstituted naphthalenedlimIdes (NDIs), planar, electron-deficient building blocks, play an important role in materials and biological sciences. Naphthalene core substituents control the HOMO and LUMO energies, whereas the N-alkyl or aryl substituents affect the solubility, aggregation, and packing propensity in condensed phases. N,N'-Dihydroxynaphthalenedlimide (DHNDI) allows expanding the chemical diversity by O-alkylation, acylation, or sulfonylation; these derivatives also allow fine-tuning of the HOMO/LUMO levels. The synthesis, UV-vis, electrochemical, solid state, and computational prediction of the properties of such derivatives are presented.

  DOI：

  10.1021/ol201906z

文献信息

• <i>O</i>,<i>O′</i>-Disubstituted <i>N</i>,<i>N′</i>-Dihydroxynaphthalenediimides (DHNDI): First Principles Designed Organic Building Blocks for Materials Science
  作者：Eric Assen B. Kantchev、Huei Shuan Tan、Tyler B. Norsten、Michael B. Sullivan

  DOI：10.1021/ol201906z

  日期：2011.10.21

  N,N'-Disubstituted naphthalenedlimIdes (NDIs), planar, electron-deficient building blocks, play an important role in materials and biological sciences. Naphthalene core substituents control the HOMO and LUMO energies, whereas the N-alkyl or aryl substituents affect the solubility, aggregation, and packing propensity in condensed phases. N,N'-Dihydroxynaphthalenedlimide (DHNDI) allows expanding the chemical diversity by O-alkylation, acylation, or sulfonylation; these derivatives also allow fine-tuning of the HOMO/LUMO levels. The synthesis, UV-vis, electrochemical, solid state, and computational prediction of the properties of such derivatives are presented.