N,N'-di(1,8-nonadien-5-yl)-perylene-3,4,9,10-tetracarboxylic bisimide | 1395396-58-3

• 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(1,8-nonadien-5-yl)-perylene-3,4,9,10-tetracarboxylic bisimide
• 英文别名: 7,18-Bis(nona-1,8-dien-5-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone；7,18-bis(nona-1,8-dien-5-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 1395396-58-3
• 化学式: C₄₂H₃₈N₂O₄
• 分子量: 634.775
• InChiKey: FKZSMMGEIPOLIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  790.7±60.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-di(1,8-nonadien-5-yl)-perylene-3,4,9,10-tetracarboxylic bisimide 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 、 zinc diacetate 作用下， 以 喹啉 、 甲苯 、 叔丁醇 为溶剂， 反应 6.0h， 生成 N-(1,9-di(1,1,1,3,3,pentamethylsioxanyl)nonane-5-yl)-N′-(3,6,9-trioxodecane-1-yl)perylene-3,4,9,10-tetracarboxylicbisimi
  参考文献：
  名称：

  带有三环氧乙烷链的液晶per四羧酸双酰亚胺衍生物和该衍生物与Li阳离子的络合

  摘要：

  液晶（LC） 苝合成了带有三环氧乙烷链和两个五甲基二硅氧烷链的四羧酸双酰亚胺（PTCBI）衍生物。该化合物在室温下表现出有序的层状相，当样品冷却至-100°C时，LC相得以保留。由于存在延伸的π共轭per环，因此在层状相中发生有效的电子传输，并且在室温下电子迁移率超过1×10 -3 cm 2 V -1 s -1。而且，这种PTCBI衍生物可以与三氟甲磺酸锂 因为极性的三环氧乙烷链。 三氟甲磺酸锂可以与之混合的比例最高为3摩尔％。在此浓度以下，层状LC结构和电子传输性能不会受到离子种类的干扰。

  DOI：

  10.1039/c3dt51435h
• 作为产物：
  描述：

  在 zinc diacetate 、 一水合肼 作用下， 以 喹啉 、 甲醇 为溶剂， 反应 6.0h， 生成 N,N'-di(1,8-nonadien-5-yl)-perylene-3,4,9,10-tetracarboxylic bisimide
  参考文献：
  名称：

  PERYLENE TETRACARBOXYLIC ACID BISIMIDE DERIVATIVE, n-TYPE SEMICONDUCTOR, PROCESS FOR PRODUCING n-TYPE SEMICONDUCTOR, AND ELECTRONIC DEVICE

  摘要：

  公开号：

  EP2695885B1

文献信息

• A liquid-crystalline perylene tetracarboxylic bisimide derivative bearing trisiloxan-2-yl moieties: influence on mesomorphic properties and electron transport
  作者：Masahiro Funahashi、Nozomi Takeuchi、Akinari Sonoda

  DOI：10.1039/c5ra23119a

  日期：——

  Mesomorphic and electron transport properties are compared for liquid-crystalline perylene tetracarboxylic bisimide derivatives bearing linear disiloxane and trisiloxane chains, as well as trisiloxan-2-yl groups.

  液晶苯并四酰亚胺衍生物的介质和电子输运性质进行了比较，其中包含线性二硅氧烷和三硅氧烷链，以及三硅氧烷-2-基团。
• Liquid-crystalline perylene tetracarboxylic bisimide derivatives bearing cyclotetrasiloxane moieties
  作者：Masahiro Funahashi、Mika Yamaoka、Kaede Takenami、Akinari Sonoda

  DOI：10.1039/c3tc31567c

  日期：——

  Liquid-crystalline perylene tetracarboxylic bisimide derivatives bearing heptamethylcyclotetrasiloxane moieties have been synthesized. Compound 2 bearing four heptamethylcyclotetrasiloxane moieties exhibits a rectangular columnar phase at room temperature. In the columnar phase, the cyclotetrasiloxane rings interdigitate into neighbouring columns and their interaction promotes the formation of the columnar mesomorphic structure. A time-of-flight measurement reveals that the electron mobility in the columnar phase of compound 2 is on the order of 10−2 cm2 V−1 s−1 at room temperature. Compound 2 is soluble in various organic solvents except for alcohol.

  我们合成了含有七甲基环四硅氧烷分子的液晶包烯四羧酸二亚胺衍生物。含有四个七甲基环四硅氧烷分子的化合物 2 在室温下呈矩形柱状相。在柱状相中，环四硅氧烷环相互咬合成相邻的柱状，它们之间的相互作用促进了柱状介形结构的形成。飞行时间测量显示，在室温下，化合物 2 柱状相中的电子迁移率约为 10-2 cm2 V-1 s-1。除酒精外，化合物 2 可溶于各种有机溶剂。
• High electron mobility in a columnar phase of liquid-crystalline perylene tetracarboxylic bisimide bearing oligosiloxane chains
  作者：Masahiro Funahashi、Akinari Sonoda

  DOI：10.1039/c2jm35579e

  日期：——

  A liquid-crystalline (LC) semiconductor based on perylene tetracarboxylic bisimide (PTCBI) bearing four 1,1,1,3,3-pentamethyldisiloxane chains was synthesized. This LC PTCBI derivative exhibits ordered columnar phases and the low temperature columnar phase is retained below room temperature. The electron mobility in the ordered columnar phase of this compound at room temperature exceeds 0.1 cm2 V−1 s−1. Moreover, this compound is soluble in various organic solvents, except alcohols, and thin films in which the columnar aggregates are aligned parallel to the substrates are produced by spin-coating. In particular, LC thin films in which the columnar stacks are uniaxially oriented can be produced by a friction transfer method.

  我们合成了一种基于带有四条 1,1,1,3,3 五甲基二硅氧烷链的过四甲酰二亚胺（PTCBI）的液晶半导体。这种 LC PTCBI 衍生物显示出有序的柱状相，而且低温柱状相在室温以下仍保持不变。在室温下，该化合物有序柱状相中的电子迁移率超过 0.1 cm2 V-1 s-1。此外，这种化合物还可溶于除乙醇以外的各种有机溶剂中，并可通过旋涂法制备出柱状聚集体与基底平行排列的薄膜。特别是，柱状堆积物呈单轴定向的 LC 薄膜可通过摩擦转移法生产。
• PERYLENE TETRACARBOXYLIC ACID BISIMIDE DERIVATIVE, N-TYPE SEMICONDUCTOR, A METHOD FOR PRODUCING N-TYPE SEMICONDUCTOR, AND ELECTRONIC DEVICE
  申请人：Funahashi Masahiro

  公开号：US20140024171A1

  公开（公告）日：2014-01-23

  The present invention provides a perylene tetracarboxylic acid bisimide derivative which enables the formation of an n-type semiconductor having high carrier mobility and has superior solubility. The perylene tetracarboxylic acid bisimide derivative is a perylene tetracarboxylic acid bisimide derivative represented by the following chemical formula (I), a tautomer or stereoisomer of the perylene tetracarboxylic acid bisimide derivative, or a salt of the perylene tetracarboxylic acid bisimide derivative or the tautomer or stereoisomer, In the chemical formula (I), R 1 to R 6 each represents a hydrogen atom, organooligosiloxane, or any substituent, at least one of R 1 to R 6 represents a monovalent substituent derived from organooligosiloxane, L 1 and L 2 each represents a single bond or a linking group, R 7 to R 10 each represents a lower alkyl group or a halogen, and o, p, q, and r each represents an integer from 0 to 2.

  本发明提供了一种苝酞菁四羧酸双亚胺衍生物，其能够形成具有高载流子迁移率的n型半导体，并具有优异的溶解性。该苝酞菁四羧酸双亚胺衍生物是由以下化学式（I）所表示的苝酞菁四羧酸双亚胺衍生物，其互变异构体或立体异构体，或者是该苝酞菁四羧酸双亚胺衍生物或其互变异构体或立体异构体的盐。在化学式（I）中，R1至R6分别表示氢原子、有机寡硅氧烷或任何取代基，其中至少一个R1至R6表示来自有机寡硅氧烷的一价取代基，L1和L2分别表示单键或连接基，R7至R10分别表示低碳烷基或卤素，o、p、q和r分别表示0至2的整数。
• Liquid–crystalline perylene tetracarboxylic acid bisimide bearing oligosiloxane chains with high electron mobility and solubility
  作者：Masahiro Funahashi、Akinari Sonoda

  DOI：10.1016/j.orgel.2012.05.027

  日期：2012.9

  Liquid-crystalline perylene tetracarboxylic acid bisimide derivatives 1 and 2 bearing 1,1,1,2,2,3,3-heptamethyltrisiloxane chains at the end of alkyl side-chains have been synthesized. Compound 1 having four trisiloxane chains exhibits a hexagonal columnar phase at room temperature. Time-of-flight measurement reveals that the electron mobility in the columnar phase of compound 1 exceeds 10 (3) cm(2) V (1) s (1) at room temperature. In contrast, compound 2 bearing two trisiloxane chains is not mesomorphic. These two compounds are soluble in various organic solvents except for alcohols and thin films can be produced by a spin-coating method. (C) 2012 Elsevier B. V. All rights reserved.