11,22-bis(trifluoromethyl)-7,18-dioxaheptacyclo[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 | 1080663-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 11,22-bis(trifluoromethyl)-7,18-dioxaheptacyclo[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: 1080663-36-0
• 化学式: C₂₆H₆F₆O₆
• 分子量: 528.32
• InChiKey: IPMMRFXXKQSCLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  11,22-bis(trifluoromethyl)-7,18-dioxaheptacyclo[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 、 正丁胺 在 5,13-bis(trifluoromethyl)anthra[2,1,9-def:6,5,10-d'e'f']diisochromene-1,3,8,10-tetraone 作用下， 以 丙酸 为溶剂， 反应 2.0h， 以64%的产率得到N,N’-bis(n-butyl)-1,7-bis(trifluoromethyl)perylene-3,4:9,10-tetracarboxylic acid diimide
  参考文献：
  名称：

  Core-Perfluoroalkylated Perylene Diimides and Naphthalene Diimides: Versatile Synthesis, Solubility, Electrochemistry, and Optical Properties

  摘要：

  By a strategy featuring perfluoroalkylation of the highly soluble intermediates and their further efficient transformations to target compounds, a versatile synthesis of core-perfluoroalkylated perylene diimides (PDIs) and naphthalene diimides (NDIs) was developed, and PDIs perfluoroalkylated at 1-position or 1,6-positions and core-perfluoroalkylated NDIs were first obtained. By esterification, perfluoroalkylation, hydrolysis, and condensation with amine, 1-perfluorooctyl-PDIs (7b, 7c, and 7e), 1,7-bis(perfluorooctyl)-PDIs (8a-c and 8e-g), 1,6-bis(perfluorooctyl)PDIs (8'e), a mixture of 1,7-bis(trifluoromethyl)-PDIs and 1,6-bis(trifluoromethyl)-PDIs (11b and 11'b), 11d and 11'd, in a ratio of 19:1), 2-perfluorooctyl-NDIs (20a-d), and 2,6-bis(perfluorooctyl)-NDIs (21a-21d) were efficiently synthesized. Five valuable intermediates-1-perfluorooctylperylene dianhydride (5), 1,7-bis(perfluorooctyl)perylene dianhydride (6) 1,6-bis(perfluorooctyl)perylene dianhydride (6'), 2-perfluorooctylnaphthalene dianhydride (18), and 2,6-bis(perfluorooctyl) naphthalene dianhydride (19)-were also obtained, and they can condense with many amines to produce PDIs containing different functional side chains on the imide nitrogen atoms. Solubility, electrochemistry, and optical properties of the above core-perfluoroalkylated PDIs and NDIs were investigated. Core-perfluoroalkylated 8e, 8f, 8'e, mixture of 11d and 11'd, 20b, and 20d with excellent solubility in common organic solvents are competitive as candidates as solution processable semiconductors. Core-perfluoroalkylated PDIs and NDIs with experimental LUMO energy of 4.04-4.34 eV demonstrate strong electron accepting ability. For core-perfluoroalkylated PDIs, the maximum absorptions display blue shifts of 6-18 nm and the maximum molar extinction coefficients decrease obviously relative to those of unsubstituted PDIs, and they inherit the strong fluorescence from the PDIs family, which makes them promising fluorescent dyes.

  DOI：

  10.1021/jo100231j
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 copper(l) iodide 、 1,3-二溴-5,5-二甲基海因 作用下， 生成 11,22-bis(trifluoromethyl)-7,18-dioxaheptacyclo[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：

  Antioxidants Having Aromatic Structures Reacting with Superoxide

  摘要：

  本方法揭示了一种治疗疾病的方法，这些疾病包括：由活性氧自由基介导的、缺血或再灌注相关的、或T细胞介导的，包括自身免疫疾病。该方法是向患者施用含有非酚类芳香结构的活性成分的制剂，这些结构是电子不足的并且能够将超氧自由基转化为O2；和/或将超氧自由基转化为氧气和过氧化氢，或者这些结构的药用盐。还揭示了一种诊断和治疗这类疾病和病况的方法。

  公开号：

  US20160175292A1

文献信息

• Efficient Synthesis of Regioisomerically Pure Bis(trifluoromethyl)-Substituted 3,4,9,10-Perylene Tetracarboxylic Bis(benzimidazole)
  作者：Zhongyi Yuan、Yi Xiao、Zheng Li、Xuhong Qian

  DOI：10.1021/ol9010689

  日期：2009.7.2

  trifluoromethyl groups were efficiently introduced to highly insoluble n-type semiconductor 3,4,9,10-perylene tetracarboxylic bis(benzimidazole) (PTCBI), and for the first time we obtained three pure regioisomers of bis(trifluoromethyl)-substituted PTCBI, whose optical properties are different from one another.

  通过一种新的策略，两个三氟甲基被有效地引入到高度不溶的n型半导体3,4,9,10- tetra四羧酸双（苯并咪唑）（PTCBI）中，并且我们首次获得了三个纯的双（三氟甲基）区域异构体）-取代的PTCBI，其光学性质互不相同。