N,N’-bis(n-butyl)-1,7-bis(trifluoromethyl)perylene-3,4:9,10-tetracarboxylic acid diimide | 1080663-28-0

• 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’-bis(n-butyl)-1,7-bis(trifluoromethyl)perylene-3,4:9,10-tetracarboxylic acid diimide
• 英文别名: 7,18-Dibutyl-11,22-bis(trifluoromethyl)-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: 1080663-28-0
• 化学式: C₃₄H₂₄F₆N₂O₄
• 分子量: 638.566
• InChiKey: VKHPYNLAMMNALO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N’-bis(n-butyl)-1,7-bis(trifluoromethyl)perylene-3,4:9,10-tetracarboxylic acid diimide 、 氰化四乙基铵 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N,N’-bis(n-butyl)-1,7-bis(trifluoromethyl)-5-cyanoperylene-3,4:9,10-tetracarboxylic acid diimide
  参考文献：
  名称：

  通过直接 Bay-andortho-(Poly)trifluoromethylation 设计核心苝二酰亚胺：合成、分离、X 射线结构、光学和电子特性

  摘要：

  我们开发了一种有效的无溶剂和无催化剂的固体苝-3,4,9,10-四羧酸二酐的直接多三氟甲基化，产生了一个新的（多）全氟烷基湾和邻位取代的 PDI，具有两个不同的酰亚胺取代基。CN 基团的直接氢取代导致首次合成氰化全氟烷基 PDI 衍生物。吸收、稳态和时间分辨发射、X 射线衍射、电化学和气相电子亲和性数据允许系统研究新 PDI 中海湾、邻位和酰亚胺位置的取代效应。固态包装显示出对电荷传输和光物理性质很重要的分子间相互作用的显着变化。此外，对 143 种缺电子 PDI 的电化学数据进行分析，

  DOI：

  10.1002/ejoc.201501024
• 作为产物：
  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

文献信息

• Core-Perfluoroalkylated Perylene Diimides and Naphthalene Diimides: Versatile Synthesis, Solubility, Electrochemistry, and Optical Properties
  作者：Zhongyi Yuan、Jing Li、Yi Xiao、Zheng Li、Xuhong Qian

  DOI：10.1021/jo100231j

  日期：2010.5.7

  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.
• Core Perylene Diimide Designs via Direct Bay- and<i>ortho</i>-(Poly)trifluoromethylation: Synthesis, Isolation, X-ray Structures, Optical and Electronic Properties
  作者：Tyler T. Clikeman、Eric V. Bukovsky、Xue-Bin Wang、Yu-Sheng Chen、Garry Rumbles、Steven H. Strauss、Olga V. Boltalina

  DOI：10.1002/ejoc.201501024

  日期：2015.10

  ortho-substituted PDIs with two different imide substituents. Direct hydrogen substitution with CN group led to the synthesis of a cyanated perfluoroalkyl PDI derivative for the first time. Absorption, steady-state and time-resolved emission, X-ray diffraction, electrochemical, and gas-phase electron affinity data allowed for systematic studies of substitution effects at bay, ortho, and imide positions in the

  我们开发了一种有效的无溶剂和无催化剂的固体苝-3,4,9,10-四羧酸二酐的直接多三氟甲基化，产生了一个新的（多）全氟烷基湾和邻位取代的 PDI，具有两个不同的酰亚胺取代基。CN 基团的直接氢取代导致首次合成氰化全氟烷基 PDI 衍生物。吸收、稳态和时间分辨发射、X 射线衍射、电化学和气相电子亲和性数据允许系统研究新 PDI 中海湾、邻位和酰亚胺位置的取代效应。固态包装显示出对电荷传输和光物理性质很重要的分子间相互作用的显着变化。此外，对 143 种缺电子 PDI 的电化学数据进行分析，