2,7-diiodo-9H-carbazole | 353276-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,7-diiodo-9H-carbazole
• 英文别名: 2,7-diiodocarbazole；2,7-diiodo-carbazole；2,7-Dijod-carbazol
• CAS: 353276-21-8
• 化学式: C₁₂H₇I₂N
• 分子量: 419.003
• InChiKey: WJHDOZKVIHANFK-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C(Solv: benzene (71-43-2))
• 沸点：
  498.3±25.0 °C(Predicted)
• 密度：
  2.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,7-diiodo-9H-carbazole 在 四(三苯基膦)钯 、 三氟化硼乙醚 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 49.0h， 生成 2,7-di(thiophen-2-yl)-9H-carbazole
  参考文献：
  名称：

  A new multi-electrochromic 2,7 linked polycarbazole derivative: Effect of the nitro subunit

  摘要：

  A new poly-2,7-di-2-thienyl-9H-carbazole derivative (poly(TCT-N)) bearing nitro (-NO2) subunit has been reported. The electrochemical and optical properties of TCT-N monomer and its polymer have been compared to the 9-phenyl-2,7-di-2-thienyl-9H-carbazole (TCT) standard molecule. Cyclic voltammetry revealed that TCT-N and TCT have excellent polymerization activity; due to extended conjugation with the attached thiophene unit and also their low oxidation potentials. The oxidation potential of TCT-N is higher than that of TCT, because of electro-withdrawing effect of -NO2 moiety. Besides, the TCT-N polymeric film prepared via electrochemical process exhibits a multi-electrochromic behavior compared with TCT standard molecule. The electroactive orange color of poly-TCT-N film converted respectively to green, turquoise and dark blue upon applied positive potentials. Consequently, the polymeric electrochrome exhibits multi-electrochromic behavior, high redox stability, high coloration efficiency and reasonable response time for electrochromic applications. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.06.023
• 作为产物：
  描述：

  4,4-二碘联苯 在 硝酸 、 溶剂黄146 作用下， 反应 18.5h， 生成 2,7-diiodo-9H-carbazole
  参考文献：
  名称：

  A Novel Three-Step Synthesis of N-(2-Ethylhexyl)-2,7-diiodocarbazole

  摘要：

  本文介绍了一种新的、短而高效的N-(2-乙基己基)-2,7-二碘咔唑合成方法。将4,4′-二碘联苯硝化，得到4,4′-二碘-2-硝基联苯，然后通过弗里曼对卡多根环的修饰将其转化为2,7-二碘咔唑，最后一步将其烷基化。该合成方法大大简化了已报道的五步合成方法。

  DOI：

  10.1055/s-0030-1258474

文献信息

• Novel Fluorescent Carbazolyl−Pyridinyl Alternating Copoloymers:  Synthesis, Characterization, and Properties
  作者：Xiaoyong Pan、Shouping Liu、Hardy S. O. Chan、Siu-Choon Ng

  DOI：10.1021/ma050425b

  日期：2005.9.1

  A novel series of AB-type polymers comprised of alternating carbazolyl and pyridinyl units were synthesized using palladium(0)-catalyzed Suzuki cross-coupling reaction in good to high yields. In this series of alternating copolymers, the electron-rich 2,7-(N-(2-ethylhexyl)carbazolyl) unit was used as a light-emitting unit, and the electron-deficient unit of pyridinyl was introduced to tune the wavelength

  使用钯（0）催化的Suzuki交叉偶联反应以良好至高收率合成了由咔唑基和吡啶基单元交替组成的一系列新型AB型聚合物。在这一系列交替共聚物中，将富电子的2,7-（N-（2-乙基己基）咔唑基）单元用作发光单元，并引入吡啶基的缺电子单元来调节发光并改善其电子传输。这些聚合物的特征在于1 H NMR和13C NMR，凝胶渗透色谱（GPC），热分析，UV-vis，荧光光谱和循环伏安法（CV）。这些聚合物的玻璃化转变温度范围为120至150°C，并且在氮气中，聚合物的分解温度范围为370-400°C，显示出高的热稳定性。共聚物主链中吡啶基单元的不同连接方式对溶液相和薄膜相中的电子和光学性质有重大影响。对于纯蓝色发射并防止聚合物链的聚集，聚合物主链中吡啶基单元的间位键状结构（3,5-和2,6-键）比对位键状结构（2,5-吡啶基单元）。N-辛基]咔唑基]及其衍生物呢。7a
• 2, 7-Substituted carbazoles and oligomers, polymers and co-polymers thereof
  申请人：Iraqi Ahmed

  公开号：US20050119491A1

  公开（公告）日：2005-06-02

  A carbazole of formula I wherein R 1 and R 2 are each independently halo, B(OH) 2 , B(OR 7 ) 2 , Sn(R 6 ), C 1-20 hydrocarbyl, or C 1-20 hydrocarbyl comprising one or more hetero atoms, R 3 is H, halo, C 1-20 hydrocarbyl, C 1-20 hydrocarbyl comprising one or more heteroatoms, or cyano, R 4 and R 5 are each independently H, halo, C 1-20 hydrocarbyl, C l-20 hydrocarbyl comprising one or more heteroatoms, or cyano, and R 7 and R 8 are each independently C 1-20 hydrocarbyl, provided that R 4 and R 5 are not both H when R 3 is n-octyl, and conjugated oligomers, polymers and co-polymers thereof. Embodiments of the oligomers, polymers and co-polymers can, for example, be formed into films which can be incorporated into electronic devices.

  式I中的一个carbazole，其中R1和R2各自独立地是卤素、B（OH）2、B（OR7）2、Sn（R6）、C1-20烃基或含有一个或多个杂原子的C1-20烃基，R3为H、卤素、C1-20烃基、含有一个或多个杂原子的C1-20烃基或氰基，R4和R5各自独立地是H、卤素、C1-20烃基、含有一个或多个杂原子的C1-20烃基或氰基，R7和R8各自独立地是C1-20烃基，但当R3为正辛基时，R4和R5不能同时为H，并且还包括其共轭寡聚物、聚合物和共聚物。例如，这些寡聚物、聚合物和共聚物的实施形式可以形成薄膜，这些薄膜可以用于电子器件中。
• Conjugated poly(2,7-carbazole) derivatives and process for the preparation thereof
  申请人：——

  公开号：US20030092880A1

  公开（公告）日：2003-05-15

  The invention relates to conjugated poly(2,7-carbazole) derivatives comprising repeating, alternating or random units of the formula: 1 wherein R represents a linear or branched alkyl group having 1 to 22 carbon atoms. The conjugated poly(2,7-carbazole) derivatives according to the invention have interesting optical and electrochemical properties which render them suitable for use in the manufacture of diverse electrical, optical and electro-optical devices.

  本发明涉及共轭聚合物（2,7-咔唑）衍生物，包含公式1中的重复、交替或随机单元，其中R代表具有1至22个碳原子的线性或支链烷基。根据本发明，共轭聚合物（2,7-咔唑）衍生物具有有趣的光学和电化学性质，使其适用于制造各种电气、光学和电光设备。
• Conjugated polycarbazole derivatives and process for the preparation thereof
  申请人：——

  公开号：US20020103332A1

  公开（公告）日：2002-08-01

  The invention relates to conjugated polycarbazole derivates comprising repeating or alternating units of the formula: 1 wherein R represents a linear or branched alkyl group having 1 to 22 carbon atoms. The conjugated polycarbazole derivatives according to the invention have interesting optical and electrochemical properties which render them suitable for use in the manufacture of diverse electrical, optical and electro-optical devices.

  该发明涉及共轭聚合物咔唑衍生物，包括公式1的重复或交替单元，其中R代表具有1至22个碳原子的线性或支链烷基。根据本发明的共轭聚合物咔唑衍生物具有有趣的光学和电化学性质，使它们适用于制造各种电气、光学和电光学设备。
• Efficient synthesis of N-alkyl-2,7-dihalocarbazoles by simultaneous carbazole ring closure and N-alkylation
  作者：Drahomír Výprachtický、Ivan Kmínek、Veronika Pokorná、Věra Cimrová

  DOI：10.1016/j.tet.2012.04.044

  日期：2012.6

  The N-alkyl-2,7-dihalocarbazole as the main product was formed by the reaction of 4,4'-dihalo-2-nitrobiphenyl with aromatic nitro compound and trialkyl phosphite. The presence and crucial role of aromatic nitro compound causes simultaneous carbazole ring closure and N-alkylation unlike the Ca-dogan ring closure where non-alkylated carbazole is formed as a main product. In addition, the mixture of aromatic nitro compound and trialkyl phosphite was found to be a possible N-alkylating agent for heterocycles, such as carbazole or indole. (C) 2012 Elsevier Ltd. All rights reserved.