9-heptyl-9H-carbazole-3,6-dicarbaldehyde | 173483-07-3

• 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-heptyl-9H-carbazole-3,6-dicarbaldehyde
• 英文别名: 3,6-diformyl-9-(n-heptyl)carbazole；3,6-diformyl-9-heptylcarbazole；9-Heptyl-3,6-diformylcarbazole；N-heptyl-3,6-diformyl-carbazole；N-heptyl-3,6-Diformylcarbazole；9-heptylcarbazole-3,6-dicarbaldehyde
• CAS: 173483-07-3
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: SWQTVAKPCJPGPW-UHFFFAOYSA-N

物化性质

• 沸点：
  466.0±38.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-heptyl-9H-carbazole-3,6-dicarbaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 [9-Heptyl-6-[6-[4-(4-pentoxyphenyl)phenoxy]hexanoyloxymethyl]carbazol-3-yl]methyl 6-[4-(4-pentoxyphenyl)phenoxy]hexanoate
  参考文献：
  名称：

  Design and Synthesis of Novel Calamitic and Discotic Materials Based on the Photorefractive Carbazole Unit

  摘要：

  The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over conventional electrical poling of photorefractive polymers. Thus, a series of symmetric 3,6-disubstituted carbazole derivatives with well-known biphenyl and triphenylene liquid-crystalline moieties was synthesized and characterized. These modifications were achieved by the esterification of bishydroxy carbazole derivatives with monoalkylated biphenyl carboxylic acids and alkylation of bisacylated bromo- derivatives of carbazole with monohydroxy pentaalkoxy triphenylene. The pure compounds are not liquid-crystalline, even when doped with trinitrofluorenone (TNF), unlike triphenylene/carbazole materials that we reported previously. These compounds, although not liquid-crystalline, may be of interest in the field of photorefractivity.

  DOI：

  10.1080/15421400903568054
• 作为产物：
  描述：

  咔唑 在 sodium hydroxide 、 苄基三乙基氯化铵 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 88.0h， 生成 9-heptyl-9H-carbazole-3,6-dicarbaldehyde
  参考文献：
  名称：

  A new synthetic approach to macrocyclic molecules and main-chain polymers containing carbazole moieties

  摘要：

  通过Knoevenagel缩合反应合成了含有两个受体基团取代的咔唑的新大环分子和主链聚合物。

  DOI：

  10.1039/cc9960000621

文献信息

• Synthesis of a new carbazole cyclic dimer via Knoevenagel condensation
  作者：Yadong Zhang、Tatsuo Wada、Hiroyuki Sasabe

  DOI：10.1016/0040-4039(96)01274-9

  日期：1996.8

  The synthesis of a carbazole cyclic dimer and a main-chain polymer is reported. Knoevenagel condensation of 3,6-diformyl-9-heptylcarbazole and 1,4-bis(cyanoacetoxymethyl)-benzene using 4-(N,N-dimethylamino)pyridine as a base could yield a carbazole cyclic dimer or a carbazole main-chain polymer as a main product depending on the reaction conditions.

  报道了咔唑环二聚体和主链聚合物的合成。以4-（N，N-二甲基氨基）吡啶为碱的3,6-二甲酰基-9-庚基咔唑与1,4-双（氰基乙酰氧基甲基）苯的Knoevenagel缩合反应可产生咔唑环二聚体或咔唑主链聚合物作为主要产物取决于反应条件。
• Carbazole based charge transport compounds
  申请人：——

  公开号：US20030207188A1

  公开（公告）日：2003-11-06

  Improved organophotoreceptors have: (a) a charge transport compound having the formula 1 where R 1 is hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, or an aryl group; and R 2 and R 3 independently have a structure of: 2 in which Ar is selected form the group consisting of; 3 R 4 is a hydrogen, or an aromatic group; (b) a charge generating compound; and (c) an electrically conductive substrate.

  改进的有机光感受器具有： (a) 具有以下化学式的电荷传输化合物：其中 R1为氢、支链或直链烷基、支链或直链不饱和碳氢基团、醚基或芳基；而 R2 和 R3 独立具有以下结构：其中 Ar 从以下组合中选取；R4 为氢或芳基； (b) 一个电荷生成化合物；以及 (c) 一个电性导电基底。
• Organophotoreceptors for electrophotography featuring novel charge transport compounds
  申请人：Imation Corp.

  公开号：US06340548B1

  公开（公告）日：2002-01-22

  Organic photoreceptors that include a charge transport compound, a charge generating compound, and an electroconductive support in which the charge transport compound is a novel aryl hydrazone-functional carbazole compound.

  有机光感受器包括一个电荷传输化合物、一个电荷生成化合物，以及一个电导支撑，其中电荷传输化合物是一种新颖的芳基酰肼基咔唑化合物。
• Synthesis and photo physical properties of carbazole based quinoxaline conjugated polymer for fluorescent detection of Ni 2+
  作者：Anjali Upadhyay、S. Karpagam

  DOI：10.1016/j.dyepig.2016.12.019

  日期：2017.4

  A new series of donor-acceptor (P1-P3) conjugated polymers containing carbazole and quinoxaline units have been synthesized through multistep reactions. In the final step, the polymerization was carried out using Wittig reaction. The optical and potential charge –transporting properties of the polymers has been carefully investigated by UV-Vis, fluorescence emission spectroscopy and cyclic voltammetry

  新系列的供体-受体（P1-P3）通过多步反应合成了含有咔唑和喹喔啉单元的共轭聚合物。在最后步骤中，使用维蒂希反应进行聚合。通过紫外可见，荧光发射光谱和循环伏安法已经仔细研究了聚合物的光学和电荷传输性质。还研究了溶剂对这些聚合物的吸收和发射光谱的影响。与溶液和固态聚合物的光谱相比，聚合物的固态显着红移。循环伏安法实验表明，这些聚合物的高HOMO能级范围为-5.57至-5.49 eV，低态LUMO能级范围为3.24至3.30 eV。电化学带隙与光学带隙一致。TGA和AFM分析的结果表明该化合物表现出良好的热稳定性和光滑的粗糙度。此外，还研究了聚合物与电子给体（N，N'-二甲基苯胺）和电子受体（对苯二甲酸二甲酯）的分子相互作用。此外，在各种金属离子（例如锂）中也观察到了感应行为。+，Na +，K +，Mg 2 +，Ca 2 +，Mn 2 +，Ni 2 +，Cd 2 +，Cu 2 +，Zn 2 +，Fe
• Photo- and electroluminescent properties of cyano-substituted styryl derivatives and synthesis of CN–PPV model compounds containing an alkoxy spacer for OLEDs
  作者：Hosuk Ryu、L.R. Subramanian、Michael Hanack

  DOI：10.1016/j.tet.2006.04.051

  日期：2006.6

  substituted acetonitrile derivatives 11,16,17. The influence of the different substituents on the optical properties of the resulting α-cyanostyryl compounds 18–20 was investigated. Another series of dimeric cyano-substituted styryl compounds 26–28 were prepared, in which a flexible, nonconjugated spacer is present between the two cyanostyryl moieties. The spacer isolates the π-conjugated portions of dimeric

  该系列的氰基取代的模型化合物18 - 20为有机发光二极管（OLED）是通过二醛之间的Knoevenagel缩合反应制备3，6，9和不同取代的乙腈衍生物11，16，17。对所得到的α氰基苯乙烯基的光学性质的不同取代基的影响，化合物18 - 20进行了研究。另一系列的二聚氰基取代苯乙烯基化合物26 – 28制备了其中两个氰基苯乙烯基部分之间存在挠性，非共轭的间隔基的化合物。间隔件隔离的二聚化合物的π共轭部分26 - 28，改善了它们在普通有机溶剂中的溶解度，并降低了它们的结晶倾向。这些特征有利于在OLED器件中生产有效的发光膜。