9-hexadecyl-3-iodo-9H-carbazole | 1381780-84-2

• 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-hexadecyl-3-iodo-9H-carbazole
• 英文别名: N-hexadecyl-3-iodo-carbazole；3-iodo-9-hexadecylcarbazole；N-hexadecyl-3-iodocarbazole；9-Hexadecyl-3-iodocarbazole
• CAS: 1381780-84-2
• 化学式: C₂₈H₄₀IN
• 分子量: 517.537
• InChiKey: HRBJSWRNCCOCEX-UHFFFAOYSA-N

物化性质

• 沸点：
  573.4±32.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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-hexadecyl-3-iodo-9H-carbazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 3-ethynyl-9-hexadecyl-9H-carbazole
  参考文献：
  名称：

  Novel Design of Carbazole-Based Donor–Acceptor Molecules for Fullerene-Free Organic Photovoltaic Devices

  摘要：

  Small molecular weight donor-acceptor molecules composed of the carbazole donor and cyanobased acceptor units were newly synthesized by the Knoevenagel condensation or formal [2 + 2] cycloaddition-retroelectrocyclization reactions. The resulting donor-acceptor molecules were fully characterized by H-1-, C-13-NMR, and IR spectroscopies, MALDI-TOF MS spectrometry, and elemental analysis. The energy levels, determined by electrochemical redox potentials, suggested the deep lowest unoccupied molecular orbital (LUMO) levels, indicating the potential use as an n-type semiconductor. The narrow band gaps were also suggested by the well-defined visible and near-IR absorptions. Therefore, the mixed films of poly(3-hexylthiophene) (P3HT) and the carbazole-based donor-acceptor molecules were investigated. The mixed films were hardly fluorescent due to the energy transfer from P3HT to the donor-acceptor molecules. A preliminary test of the bulk-heterojunction solar cells based on the donor-acceptor molecule prepared by the [2 + 2] cycloaddition-retroelectrocyclization showed a dark current flow, while the device based on the donor-acceptor molecule prepared by the Knoevenagel condensation displayed a weak photoresponsive current.

  DOI：

  10.1166/jnn.2016.11905
• 作为产物：
  描述：

  9-hexadecylcarbazole 在 diphenyliodonium tetrafluoroborate 、 copper(II) sulfate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以82%的产率得到9-hexadecyl-3-iodo-9H-carbazole
  参考文献：
  名称：

  铜（II）催化的咔唑碘化：获得官能化的咔唑

  摘要：

  已经开发了咔唑的铜催化的碘化。Barluenga的试剂IPy2BF4用于生成软的亲电子ha，用于咔唑的碘化。该报告代表了铜催化剂促进咔唑的亲电子卤化的第一个概念。我们展示了这种方法的广泛应用，可用于合成多种咔唑衍生物，即富电子和缺电子系统。

  DOI：

  10.1021/acs.joc.8b02821

文献信息

• A Highly C₇₀Selective Shape-Persistent Rectangular Prism Constructed through One-Step Alkyne Metathesis
  作者：Chenxi Zhang、Qi Wang、Hai Long、Wei Zhang

  DOI：10.1021/ja210418t

  日期：2011.12.28

  and highly efficient approach for building molecules that are usually thermodynamically favored. However, the DCC methods that are efficient enough to construct large, complex molecules, particularly those with three-dimensional (3-D) architectures, are still very limited. Here, for the first time, we have successfully utilized alkyne metathesis, a highly efficient DCC approach, to construct the novel

  动态共价化学 (DCC) 为构建通常在热力学上受青睐的分子提供了一种有趣且高效的方法。然而，足以构建大型复杂分子的 DCC 方法，尤其是那些具有三维 (3-D) 结构的分子，仍然非常有限。在这里，我们第一次成功地利用炔烃复分解，一种高效的 DCC 方法，从易于获得的基于卟啉的前体一步构建新型 3-D 矩形棱柱分子笼 COP-5。COP-5 由刚性的芳香卟啉和咔唑部分以及线性亚乙炔连接器组成，使其具有形状持久性。有趣的是，COP-5 是富勒烯的极好受体。它形成1：1 与 C(60) 和 C(70) 复合，结合常数为 1.4 × 10(5) M(-1) (C(60)) 和 1.5 × 10(8) M(-1) (C(70) ) 在甲苯中。这是迄今为止报道的对纯有机富勒烯受体的最高结合亲和力之一。COP-5 在结合 C(70) 比 C(60) 方面表现出前所未有的高选择性（K(C70)/K(C60)
• A C84 selective porphyrin macrocycle with an adaptable cavity constructed through alkyne metathesis
  作者：Chenxi Zhang、Hai Long、Wei Zhang

  DOI：10.1039/c2cc32571c

  日期：——

  A bisporphyrin macrocycle was constructed from a porphyrin-based diyne monomer in one step through alkyne metathesis. The fullerene binding studies (C(60), C(70) and C(84)) showed the highest binding affinity of the macrocycle for C(84), which is in great contrast to its bisporphyrin four-armed cage analogue that showed the strongest binding with C(70).

  在基于炔烃复分解的一步中，由基于卟啉的二炔单体构建了双卟啉大环。富勒烯结合研究（C（60），C（70）和C（84））显示了大环对C（84）的最高结合亲和力，这与它的双卟啉四臂笼类似物形成了鲜明的对比。与C（70）的结合最强。
• [EN] FULLERENE SEPARATION THROUGH USE OF ORGANIC CAGES<br/>[FR] SÉPARATION DE FULLERÈNE PAR L'UTILISATION DE CAGES ORGANIQUES
  申请人：UNIV COLORADO REGENTS

  公开号：WO2013063368A1

  公开（公告）日：2013-05-02

  Provided herein are compositions useful in the separation of fullerenes from a mixture comprising fullerenes. Also provided herein are methods of making the compositions, as well as methods of using the compositions for fullerene separation.

  本文提供了用于从含有富勒烯的混合物中分离富勒烯的组合物。本文还提供了制备这些组合物的方法，以及利用这些组合物进行富勒烯分离的方法。
• Synthesis and characterization of 1,3,5-triphenylamine derivatives with star-shaped architecture
  作者：Alina Brzeczek、Krzysztof Karon、Heather Higginbotham、Rafał G. Jędrysiak、Mieczyslaw Lapkowski、Krzysztof Walczak、Sylwia Golba

  DOI：10.1016/j.dyepig.2016.05.030

  日期：2016.10

  In this work we report the synthesis, electrochemical and optical properties of five new, star shaped compounds containing both carbazole and triphenylamine moieties, further endcapped with thiophene or 3,4-ethylenedioxythiophene units. Electrochemical, UV–visible spectroscopy and fluorescence methods were employed to study the properties of these compounds as well as their electropolymers. The basic

  在这项工作中，我们报告了五个新的星形化合物的合成，电化学和光学性质，这些化合物同时包含咔唑和三苯胺部分，并进一步用噻吩或3,4-乙撑二氧噻吩单元封端。电化学，紫外可见光谱和荧光方法用于研究这些化合物及其电聚合物的性能。报告并讨论了诸如带隙，HOMO和LUMO值，单体和聚合物的最大吸收和发射最大波长等基本特征。
• FULLERENE SEPARATION THROUGH USE OF ORGANIC CAGES
  申请人：The Regents Of The University Of Colorado, a body corporate

  公开号：US20140301937A1

  公开（公告）日：2014-10-09

  Provided herein are compositions useful in the separation of fullerenes from a mixture comprising fullerenes. Also provided herein are methods of making the compositions, as well as methods of using the compositions for fullerene separation.