9-butyl-3,6-diiodo-9H-carbazole | 551934-69-1

• 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: 9-butyl-3,6-diiodo-9H-carbazole
• 英文别名: 3,6-diiodo-N-butylcarbazole；9-butyl-3,6-diiodocarbazole
• CAS: 551934-69-1
• 化学式: C₁₆H₁₅I₂N
• 分子量: 475.111
• InChiKey: ODLAUPCYNTVLKX-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  502.4±43.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-butyl-3,6-diiodo-9H-carbazole 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 75.0h， 生成 4-[6-ethynyl-9-butylcarbazol-3-yl]-2-methylbut-3-yn-2-ol
  参考文献：
  名称：

  Novel Diethynylcarbazole Macrocycles:  Synthesis and Optoelectronic Properties

  摘要：

  Diethynylcarbazole macrocycles 1b and 2b have been synthesized by oxidative coupling of appropriate precursors. In particular, macrocycle 2b was prepared by bimolecular Pd-catalyzed oxidative coupling in 35% isolated yield. The spectroscopic properties of these macrocycles and their precursors were measured in detail. The films of these macrocycles by the dipping method and the Langmuir-Blodgett technique were fabricated to study their photoinduced charge-transfer properties. A rapid and steady cathodic photocurrent of these films was produced in a three-electrode cell when irradiated with white light. A possible mechanism of the photoinduced electron-transfer pathway was suggested.

  DOI：

  10.1021/jo0611869
• 作为产物：
  描述：

  咔唑 在 N-碘代丁二酰亚胺 、 四丁基溴化铵 、 溶剂黄146 、 sodium hydroxide 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 6.0h， 生成 9-butyl-3,6-diiodo-9H-carbazole
  参考文献：
  名称：

  咔唑连接的卟啉镊子的合成与表征

  摘要：

  本文报道了3,6-二取代咔唑镊子的合成，光谱表征，双光子吸收和电化学性质。在二乙炔基-咔唑间隔基和5-溴-三芳基卟啉之间的Sonogashira偶联反应过程中，分离了Glaser偶合产生的二聚体，并将该原始化合物的性质与3,6-二取代咔唑双卟啉镊子进行了比较。本文报道的二元组在920 nm处具有最大的两个光子吸收，且两个光子的吸收截面在1200 GM范围内。尽管在Soret区有很强的线性吸收和适度的荧光量子产率，但它们均导致达到30 000 M -1  cm -1的高亮度 。

  DOI：

  10.1002/chem.201501619

文献信息

• Synthesis and Photophysical Properties of Aza[<i>n</i>]helicenes
  作者：Gourav M. Upadhyay、Harish R. Talele、Ashutosh V. Bedekar

  DOI：10.1021/acs.joc.6b01395

  日期：2016.9.2

  Synthesis and study of aza[7]helicene and aza[9]helicene is presented in this paper. Photo-dehydrocyclization of the 3,6-bis-styryl derivative of carbazole leading to sterically less demanding aza[7]helicene resulted in smooth reaction, and only the desired angular–angular product was detected. However, in the case of aza[9]helicene, along with the expected angular–angular cyclization, three other

  本文介绍了氮杂[7]螺旋和氮杂[9]螺旋的合成与研究。咔唑的3,6-双苯​​乙烯基衍生物的光脱氢环化导致空间需求量较小的氮杂[7] ic烯导致反应平稳，并且仅检测到所需的角-角产物。然而，在氮杂[9]螺旋烯的情况下，连同预期的角-角环化反应，还分离并鉴定了涉及线性环化模式的其他三种产物。在这种情况下，螺旋化合物aza [9] helicene主要在较低浓度下形成，而其他异构体则在较高浓度下得到。完全表征了由角-角，角-线性和线性-线性环化模式形成的所有化合物，并研究了它们的光物理性质。
• A conjugated hyperbranched polymer constructed from carbazole and tetraphenylethylene moieties: convenient synthesis through one-pot “A2 + B4” Suzuki polymerization, aggregation-induced enhanced emission, and application as explosive chemosensors and PLEDs
  作者：Wenbo Wu、Shanghui Ye、Lijin Huang、Li Xiao、Yingjie Fu、Qi Huang、Gui Yu、Yunqi Liu、Jingui Qin、Qianqian Li、Zhen Li

  DOI：10.1039/c2jm16514g

  日期：——

  In this paper, tetraphenylethylene (TPE) units, a well-known aggregation-induced emission (AIE) active group, are utilized to construct the hyperbranched polymer HP-TPE-Cz with carbazole moieties, a good hole-transporting and electroluminescent group, through an “A2 + B4” approach by using a one-pot Suzuki polycondensation reaction. For comparison, its analog linear polymer LP-TPE-Cz, also constructed from these two moieties, was prepared. These two polymers exhibit interesting aggregation-induced emission enhanced (AIEE) behavior and act as explosive chemosensors with high sensitivity both as nanoparticles and in solid state, due to the presence of TPE units. Also, the HP-TPE-Cz PLED device exhibited a remarkably enhanced current efficiency (2.13 cd A−1) and luminescence efficiency (5914 cd m−2), compared with its analog linear polymer LP-TPE-Cz (1.04 cd A−1, 1654 cd m−2).

  在本文中，利用四苯乙烯（TPE）单元，这是一种众所周知的聚集诱导发光（AIE）活性基团，通过“一锅法”铃木聚缩合反应，构建了具有良好孔导电性和电致光发射特性的胺基喹啉（HP-TPE-Cz）超支化聚合物。作为对比，其类似的线性聚合物LP-TPE-Cz也由这两种基团构建而成。这两种聚合物表现出有趣的聚集诱导发光增强（AIEE）行为，并由于TPE单元的存在，作为纳米颗粒和固态均具有高灵敏度的爆炸性化学传感器。此外，HP-TPE-Cz PLED器件展现出显著提高的电流效率（2.13 cd A⁻¹）和发光效率（5914 cd m⁻²），相比于其类似线性聚合物LP-TPE-Cz（1.04 cd A⁻¹, 1654 cd m⁻²）。
• Carbazole-bridged double D–A dye for efficient dye-sensitized solar cell
  作者：Songyos Pramjit、Utt Eiamprasert、Panida Surawatanawong、Pattida Lertturongchai、Supavadee Kiatisevi

  DOI：10.1016/j.jphotochem.2014.09.007

  日期：2015.1

  donors such as arylamino and carbazole units. The double donor–acceptor dye CBZ-3 is linked by a carbazole unit as a secondary donor which increases the donor–acceptor strength of the dye and proved to increase the η and Jsc values of the photovoltaic cell compared to the corresponding mono-anchoring system CBZ-2 and the monodonor dye CBZ-1. With the non-planar structure of the arylamino group and the alkyl

  一种基于受体-π间隔基-供体-次级供体-施主-π间隔基-受体结构基序的双锚定有机染料已被合成，并用作染料敏化太阳能电池（DSSC）的敏化剂。新的合成方法使用两个π间隔基，两个受体和两个不同的供体，例如芳基氨基和咔唑单元。双给体-受体染料CBZ-3通过咔唑单元作为辅助供体连接，与相应的单锚定相比，该咔唑单元增加了染料的给体-受体强度，并证明可提高光伏电池的η和J sc值系统CBZ-2和单给体染料CBZ-1。由于芳基氨基和烷基链的非平面结构有效地防止了染料聚集体的形成，该染料显示出650 mV的高开路光电压（V oc），短路光电流密度（J sc）为7.20 mA cm -2，太阳能-电转换效率（η）为3.23％。
• Enantioselective Recognition of Mandelic Acid by a 3,6-Dithiophen-2-yl-9<i>H</i>-carbazole-Based Chiral Fluorescent Bisboronic Acid Sensor
  作者：Yubo Wu、Huimin Guo、Tony D. James、Jianzhang Zhao

  DOI：10.1021/jo200675j

  日期：2011.7.15

  binding with tartaric acid is 3.5-fold at pH 3.0. With the fluorescent bisboronic acid sensor 1, enantioselective recognition of mandelic acid was achieved for the first time. To the best of our knowledge, this is the first time that the mandelic acid has been enantioselectively recognized using a chiral fluorescent boronic acid sensor. Chiral monoboronic acid sensor 2 and bisboronic acid sensor 3 without

  我们准备了以3,6-dithiophen-2-yl-9 H-咔唑为荧光团的手性荧光双硼酸传感器。噻吩部分用于扩展荧光团的π共轭框架，以使荧光发射红移，同时增强荧光团作为光诱导电子转移过程的电子供体的新过程（d-PET）的硼酸传感器；即传感器1的背景荧光与典型的a-PET硼酸传感器（其中荧光团充当光诱导电子转移过程的电子受体）形成鲜明对比的是，酸性pH下的pH值比中性或碱性pH下的弱。d-PET硼酸传感器的优势在于可以在酸性pH值下实现对羟基酸的识别。我们发现噻吩部分是一种有效的π-共轭连接子和电子供体。结果，与先前报道的没有噻吩部分的d-PET传感器相比，pH值变化时传感器的d-PET对比度提高了10倍。在酸性pH条件下，酒石酸的对映选择性识别得以实现，其对映选择性（总响应K d I F d / Kl I F l）是3.3。荧光增强（我˚F样品/我˚F空白传感器） 1在与酒石酸结合是在pH
• Highly Luminescence Anthracene Derivatives as Promising Materials for OLED Applications
  作者：Aneta Slodek、Michal Filapek、Ewa Schab-Balcerzak、Marzena Grucela、Sonia Kotowicz、Henryk Janeczek、Karolina Smolarek、Sebastian Mackowski、Jan Grzegorz Malecki、Agnieszka Jedrzejowska、Grazyna Szafraniec-Gorol、Anna Chrobok、Beata Marcol、Stanislaw Krompiec、Marek Matussek

  DOI：10.1002/ejoc.201600532

  日期：2016.8

  in the range of 77–98 %. OLED devices were fabricated. The AFM images of thin films and blends prepared from all compounds show a uniform and flat surface, indicating excellent film-forming properties. Devices incorporating the anthracene derivative with diphenylamino-fluorene end-capping groups exhibited the highest value of current density (J). All of the fabricated OLED devices emitted yellowish-orange

  通过使用 Sonogashira 交叉偶联，以优异的收率合成了具有庞大的咔唑基-芴、二苯氨基-芴或咔唑基-咔唑单元通过乙炔基桥连接到蒽框架的新型对称蒽衍生物。蒽染料中的乙炔桥增加了 π 电子共轭，而庞大的取代基大大减弱了分子间相互作用。该染料具有高热稳定性、在常见有机溶剂中的巨大溶解度，尤其是在溶液中的光致发光量子产率 (Φf) 高达 77-98%。制造了OLED器件。由所有化合物制备的薄膜和共混物的 AFM 图像显示出均匀和平坦的表面，表明具有出色的成膜性能。包含具有二苯氨基芴封端基团的蒽衍生物的器件表现出最高的电流密度值 (J)。所有制造的 OLED 器件在施加电压下都发出黄橙色光。