N,N'-bis(1-heptyloctyl)-1,6,9,14-tetrabromoterrylene-3,4:11,12-tetracarboxylic acid diimide | 1135063-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N,N'-bis(1-heptyloctyl)-1,6,9,14-tetrabromoterrylene-3,4:11,12-tetracarboxylic acid diimide
• 英文别名: N,N'-bis-(1-heptyloctyl)-1,6,9,14-tetrabromoterrylene tetracarboxdiimide；1,6,9,14-tetrabromo-N,N'-di(1-heptyloctyl)terrylene-3,4:11,12-tetracarboximide；11,26,34,36-Tetrabromo-7,22-di(pentadecan-8-yl)-7,22-diazadecacyclo[14.14.2.22,5.217,20.03,12.04,9.013,31.018,27.019,24.028,32]hexatriaconta-1(31),2(36),3,5(35),9,11,13,15,17(34),18,20(33),24,26,28(32),29-pentadecaene-6,8,21,23-tetrone
• CAS: 1135063-37-4
• 化学式: C₆₄H₇₀Br₄N₂O₄
• 分子量: 1250.89
• InChiKey: QLUWYQFMWLERSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.06
• 重原子数：
  74.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(1-heptyloctyl)-1,6,9,14-tetrabromoterrylene-3,4:11,12-tetracarboxylic acid diimide 、 copper(l) cyanide 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以70%的产率得到N,N'-bis(1-heptyloctyl)-1,6,9,14-tetracyanoterrylene-3,4:11,12-tetracarboxylic acid diimide
  参考文献：
  名称：

  Ortho- vsBay-Functionalization: A Comparative Study on Tetracyano-Terrylenediimides

  摘要：

  In this paper n‐type semiconductors synthesized via selective fourfold cyanation of the ortho‐ and bay‐positions (2,5,10,13‐ and 1,6,9,14‐positions respectively) of teyrrylenediimides are reported. A detailed study about the impact of the diverse functionalization topologies on the optoelectronic properties, self‐organization from solution, solid‐state packing, and charge carrier transport in field‐effect transistors is presented. The ortho‐substitution preserves the planarity of the core and favors high order in solution processed films. However, the strong intermolecular interactions lead to a microstructure with large aggregates and pronounced grain boundaries which lower the charge carrier transport in transistors. In contrast, the well‐soluble bay‐functionalized terrylenediimide forms only disordered films which surprisingly result in n‐type average mobilities of 0.17 cm2/Vs after drop‐casting with similar values in air. Processing by solvent vapor diffusion enhances the transport to 0.65 cm2/Vs by slight improvement of the order and surface arrangement of the molecules. This mobility is comparable to highest n‐type conductivities measured for solution processed PDI derivatives demonstrating the high potential of TDI‐based semiconductors.

  DOI：

  10.1002/adfm.201401573
• 作为产物：
  描述：

  8-十五烷胺 在 碘 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium t-butanolate 作用下， 以 喹啉 、 diethylene glycol diethyl ether 、 水 、 氯苯 为溶剂， 反应 25.0h， 生成 N,N'-bis(1-heptyloctyl)-1,6,9,14-tetrabromoterrylene-3,4:11,12-tetracarboxylic acid diimide
  参考文献：
  名称：

  LIQUID CRYSTALLINE RYLENE TETRACARBOXYLIC ACID DERIVATIVES AND USE THEREOF

  摘要：

  本发明涉及液晶芳纶四羧酸衍生物，其制备方法以及作为n型有机半导体用于制造有机场效应晶体管和太阳能电池的用途。

  公开号：

  US20110042651A1

文献信息

• Core-Extended Terrylene Tetracarboxdiimide: Synthesis and Chiroptical Characterization
  作者：Christian Lütke Eversloh、Zhihong Liu、Beate Müller、Michael Stangl、Chen Li、Klaus Müllen

  DOI：10.1021/ol202254c

  日期：2011.10.21

  The novel 1,16:6,7:8,9:14,15-tetranaphthoterrylene tetracarboxdiimide was synthesized via a straightforward route, yielding optically active atropisomers with a high racemization barrier. Absorption, fluorescence, and circular dichroism measurements revealed high absorption coefficients and fluorescence quantum yields and enabled the stereochemical assignment in combination with quantum mechanical calculations.
• US8481736B2
  申请人：——

  公开号：US8481736B2

  公开（公告）日：2013-07-09
• [DE] FLÜSSIG-KRISTALLINE RYLENTETRACARBONSÄUREDERIVATE UND DEREN VERWENDUNG<br/>[EN] LIQUID CRYSTALLINE RYLENE TETRACARBOXYLIC ACID DERIVATIVES AND USE THEREOF<br/>[FR] DÉRIVÉS D'ACIDE RYLÈNE-TÉTRACARBOXYLIQUE CRISTALLINS LIQUIDES ET UTILISATION
  申请人：BASF AG

  公开号：WO2007116001A2

  公开（公告）日：2007-10-18

  [EN] The invention relates to liquid crystalline rylene tetracarboxylic acid derivatives, method for production and use thereof as organic semiconductors of type n for the production of organic field effect transistors and solar cells.
  [FR] L'invention concerne des dérivés d'acide rylène-tétracarboxylique cristallins liquides, des procédés de fabrication de ces composés et leur utilisation en tant que semi-conducteurs organiques de type N pour la fabrication de transistors à effet de champ organiques et de cellules solaires.
  [DE] Die vorliegende Erfindung betrifft flüssig-kristalline Rylentetracarbonsäurederivate, Verfahren zu ihrer Herstellung und deren Verwendung als organische Halbleiter vom n-Typ zur Herstellung von organischen Feldeffekttransistoren und von Solarzellen.
• LIQUID CRYSTALLINE RYLENE TETRACARBOXYLIC ACID DERIVATIVES AND USE THEREOF
  申请人：Koenemann Martin

  公开号：US20110042651A1

  公开（公告）日：2011-02-24

  The present invention relates to liquid-crystalline rylenetetracarboxylic acid derivatives, to processes for their preparation and to their use as n-type organic semiconductors for producing organic field-effect transistors and solar cells.

  本发明涉及液晶芳纶四羧酸衍生物，其制备方法以及作为n型有机半导体用于制造有机场效应晶体管和太阳能电池的用途。
• <i>Ortho</i>- vs<i>Bay</i>-Functionalization: A Comparative Study on Tetracyano-Terrylenediimides
  作者：Glauco Battagliarin、Sreenivasa Reddy Puniredd、Sebastian Stappert、Wojciech Zajaczkowski、Suhao Wang、Chen Li、Wojciech Pisula、Klaus Müllen

  DOI：10.1002/adfm.201401573

  日期：2014.12

  In this paper n‐type semiconductors synthesized via selective fourfold cyanation of the ortho‐ and bay‐positions (2,5,10,13‐ and 1,6,9,14‐positions respectively) of teyrrylenediimides are reported. A detailed study about the impact of the diverse functionalization topologies on the optoelectronic properties, self‐organization from solution, solid‐state packing, and charge carrier transport in field‐effect transistors is presented. The ortho‐substitution preserves the planarity of the core and favors high order in solution processed films. However, the strong intermolecular interactions lead to a microstructure with large aggregates and pronounced grain boundaries which lower the charge carrier transport in transistors. In contrast, the well‐soluble bay‐functionalized terrylenediimide forms only disordered films which surprisingly result in n‐type average mobilities of 0.17 cm2/Vs after drop‐casting with similar values in air. Processing by solvent vapor diffusion enhances the transport to 0.65 cm2/Vs by slight improvement of the order and surface arrangement of the molecules. This mobility is comparable to highest n‐type conductivities measured for solution processed PDI derivatives demonstrating the high potential of TDI‐based semiconductors.