4,5,9,10-四溴-2,7-二(2,6-二异丙苯基)苯并[LMN][3,8]邻菲罗啉-1,3,6,8(2H,7H)-四酮 | 943148-75-2

• 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
• 中文名称: 4,5,9,10-四溴-2,7-二(2,6-二异丙苯基)苯并[LMN][3,8]邻菲罗啉-1,3,6,8(2H,7H)-四酮
• 英文名称: N,N'-bis-(2,6-diisopropylphenyl)-2,3,6,7-tetrabromo-1,4,5,8-naphthalenetetracarboxylic acid diimide
• 英文别名: N,N′-bis-(2′,6′-diisopropylphenyl)-2,3,6,7-tetrabromo-naphthalenetetracarboxylic acid diimide；N,N'-di(2,6-diisopropylphenyl)-2,3,6,7-tetrabromonaphthalene-1,8;4,5-tetracarboximide；2,3,9,10-Tetrabromo-6,13-bis[2,6-di(propan-2-yl)phenyl]-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8,10,15-pentaene-5,7,12,14-tetrone
• CAS: 943148-75-2
• 化学式: C₃₈H₃₄Br₄N₂O₄
• 分子量: 902.315
• InChiKey: RCHCPEPJHNBOOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  4,5,9,10-四溴-2,7-二(2,6-二异丙苯基)苯并[LMN][3,8]邻菲罗啉-1,3,6,8(2H,7H)-四酮 在 palladium diacetate 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 N,N′-bis(2,6-diisopropylphenyl)-5H,8H-carbazolo[2,3-b]carbazole[6,7:13,14]tetracarboxylic acid diimide
  参考文献：
  名称：

  파이-연장된 나프탈렌 디이미드의 제조 및 반도체로서의 그의 용도

  摘要：

  本发明提供了化学式为1或2的化合物以及包含这些化合物的电子装置。

  公开号：

  KR20150142043A
• 作为产物：
  描述：

  2,6-二异丙基苯胺 、 四(4-甲酰基苯基)硅烷 在 溶剂黄146 作用下， 反应 6.0h， 以29%的产率得到4,5,9,10-四溴-2,7-二(2,6-二异丙苯基)苯并[LMN][3,8]邻菲罗啉-1,3,6,8(2H,7H)-四酮
  参考文献：
  名称：

  Naphthalenetetracarboxylic Aicd Derivatives and their Use as Semiconductors

  摘要：

  本发明涉及萘四羧酸衍生物，其制备方法及其用途，特别是作为n型半导体。

  公开号：

  US20080300405A1

文献信息

• Regioselectivity in Sequential Nucleophilic Substitution of Tetrabromonaphthalene Diimides
  作者：Sabin-Lucian Suraru、Frank Würthner

  DOI：10.1021/jo400320a

  日期：2013.6.7

  Nucleophilic substitution of tetrabromosubstituted naphthalene diimides (NDIs) with aniline was studied in detail to explore the regioselectivity as three different diamino-substituted regioisomeric products can be formed. We found that the regioselectivity of the nucleophilic disubstitution of 2,3,6,7-tetrabromonaphthalene diimide with aniline is dependent on reaction solvents and additives. In dichloromethane

  详细研究了用苯胺对四溴取代的萘二酰亚胺（NDI）进行亲核取代，以探索区域选择性，因为可以形成三种不同的二氨基取代的区域异构体。我们发现2,3,6,7-四溴萘二酰亚胺与苯胺的亲核性解离的区域选择性取决于反应溶剂和添加剂。在没有添加剂的二氯甲烷和氯仿中，2,7-二氨基-3,6-二溴-NDI异构体是区域选择性形成的，而在DMF中，在相似的反应条件下，可以观察到2,3-二氨基-6,7-二溴异构体为主要的区域异构体。如果可能的话，形成第三种可能的区域异构体2，6-二氨基-3，7-二溴产物的量很小。四丁基氟化铵（TBAF）添加剂对该反应的区域选择性具有显着影响，因为在没有TBAF的二氯甲烷中，2,7-二氨基异构体是区域选择性形成的，而在没有TBAF的二氯甲烷中，仅形成2,3-二氨基异构体。TBAF的显着效果可以合理化，如在此顺序反应的第一步中生成的单氨基-三溴-NDI的去质子化作用，作为氟离子的中间产
• Core-Substituted Naphthalene Diimides: Influence of Substituent Conformation on Strong Visible Absorption
  作者：Samuel Quinn、E. Stephen Davies、Constance R. Pfeiffer、William Lewis、Jonathan McMaster、Neil R. Champness

  DOI：10.1002/cplu.201700059

  日期：2017.3

  Functionalization of the aromatic core of naphthalene diimide (NDI) chromophores with morpholine substituents leads to molecules with strong absorbance in the visible spectrum. The shift of absorption maxima to lower energy is determined not only by the degree of substitution but also by the relative conformation and orientation of the tertiary amine with respect to the plane of the NDI.

  具有吗啉取代基的萘二酰亚胺（NDI）生色团的芳族核官能团导致分子在可见光谱中具有强吸收性。吸收最大值向较低能量的移动不仅取决于取代程度，还取决于叔胺相对于NDI平面的相对构象和取向。
• Diindole-Annulated Naphthalene Diimides: Synthesis and Optical and Electronic Properties of <i>Syn</i>- and <i>Anti</i>-Isomers
  作者：Sabin-Lucian Suraru、Christian Burschka、Frank Würthner

  DOI：10.1021/jo402365s

  日期：2014.1.3

  Here we report a selective method for the core-extension of naphthalene diimide (NDI) with two annulated indole rings leading to carbazolo[2,3-b]carbazole diimides (CbDIs) with exclusive syn-connectivity based on a regioselective nucleophilic substitution reaction of Br-4-NDI with arylamines, followed by palladium-catalyzed intramolecular C-C coupling. The oxygen analogues of anti-CbDIs, namely anti-benzofurobenzofuran diimides (anti-BfDIs), were obtained from 2,6-Br-2-NDI and 2-bromophenol. The syn- and anti-isomers of CbDIs were unambiguously characterized by single-crystal X-ray analysis. The optical properties of the present core-enlarged NDIs were studied, revealing clear differences in the absorption characteristics of the syn- and anti-isomers of CbDI, on one hand, and CbDI vs BfDI derivatives, on the other hand. Cyclic voltammetry studies showed that the redox properties are dependent on the substituents at the CbDI-core and oxygen atom containing BfDIs are more prone to reduction than the respective nitrogen analogues CbDIs. Vacuum-processed organic field effect transistors reveal CbDI and BfDI derivatives with n-channel, p-channel, as well as ambient transport characteristics with mobility values up to 0.2 cm(2)/(V s).
• Core-Tetrasubstituted Naphthalene Diimides:  Synthesis, Optical Properties, and Redox Characteristics
  作者：Cornelia Röger、Frank Würthner

  DOI：10.1021/jo7015357

  日期：2007.10.1

  [GRAPHICS]2,3,6,7-Tetrabromonaphthalene dianhydride has been synthesized by the bromination of naphthalene dianhydride with dibromoisocyanuric acid in excellent yield. The condensation of this dianhydride with 2,6-diisopropylaniline yielded the corresponding tetrabromo-substituted naphthalene diimide (NDI), which is a versatile precursor for the synthesis of core-tetrafunctionalized NDIs. Nucleophilic substitution of tetrabromo NDI with alkoxy, alkylthio, and alkylamino nucleophiles afforded a series of core-tetrasubstituted NDI chromophores that complete the series of previously reported di- and trifunctionalized NDI derivatives. The effects of electronic nature and number of core substituents on the optical and electrochemical properties of NDIs have been investigated by UV-vis and fluorescence spectroscopy and cyclic voltammetry. The absorption maxima (629-642 nm) of tetraamino NDIs are strongly bathochromically shifted compared to those of other core-functionalized NDIs.
• NAPHTHALINTETRACARBONSÄUREDERIVATE UND DEREN VERWENDUNG ALS HALBLEITER
  申请人：BASF SE

  公开号：EP1966206B1

  公开（公告）日：2016-03-09