9-hexyl-9H-carbazole-3,6-dicarbaldehyde | 262291-69-0

• 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-hexyl-9H-carbazole-3,6-dicarbaldehyde
• 英文别名: 9-hexylcarbazole-3,6-dicarbaldehyde
• CAS: 262291-69-0
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: NCBOYZMHOSWKBG-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  454.3±38.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-hexyl-9H-carbazole-3,6-dicarbaldehyde 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 (2E,2'E)-3,3'-(9-hexyl-9H-carbazole-3,6-diyl)bis(2-(5-formylthiophen-2-yl)acrylonitrile)
  参考文献：
  名称：

  Bi-anchoring organic sensitizers of type D-(π-A) 2 comprising thiophene-2-acetonitrile as π-spacer and malonic acid as electron acceptor for dye sensitized solar cell applications

  摘要：

  Two new bi-anchoring organic sensitizers of type D-(pi-A)(2) comprising the identical pi-spacer (thiophene-2-acetonitrile) and electron acceptor (malonic acid) but different aryl amine as electron donors (diphenylamine and carbazole) were synthesized, characterized and fabricated metal free dye-sensitized solar cell devices. The intra molecular charge transfer property and electrochemical property of these dyes were investigated by molecular absorption, emission, cyclic voltammetric experiments and in addition, quantum chemical calculation studies were performed to provide sufficient driving force for the electron injection into the conduction band of TiO2 which leads to efficient charge collection. Among the fabricated devices, carbazole based device exhibits high current conversion efficiency (eta = 4.7%) with a short circuit current density (J(SC)) 15.3 mA/cm(2), an open circuit photo voltage (V-OC) of 0.59 V and a fill factor of 0.44 under AM 1.5 illumination (85 mW/cm(2)) compared to diphenylamine based device. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.03.032
• 作为产物：
  描述：

  N-hexylcarbazole 在 三氯氧磷 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 15.0h， 生成 9-hexyl-9H-carbazole-3,6-dicarbaldehyde
  参考文献：
  名称：

  基于咔唑和红色吸收性阳离子吲哚的单支和双支有机染料用于p型染料敏化太阳能电池：结合实验和理论研究

  摘要：

  已经为p型染料敏化太阳能电池合成了一系列新颖的单支和双支咔唑基红色吸收阳离子染料，不含（CSI和CDI），不含（CST和CDT）噻吩间隔基（p-DSSC）。吸收红光的阳离子受体/噻吩间隔基的引入导致吸收最大值从CSI的600 nm起始到CDT的800 nm扩展和红移，并提高了摩尔吸收率。双支/噻吩间隔基的引入降低了CDI，CST和CDT的最低空位分子轨道（LUMO）水平，使其电势比CSI更强。其中，双支CDI的转化效率最高，为0.112％。此外，在相似的制造条件下测得的所有染料均优于标准C343染料（0.062％）。尽管由于噻吩间隔基的引入导致光伏性能下降，但总体而言，与单支链染料的SC和V OC值相比。电化学阻抗谱分析表明，双支化染料比单支化染料具有更低的电荷转移电阻和更长的空穴寿命。进行密度泛函理论（DFT）和与时间有关的DFT计算，以从理论上表征合成染料的光学和电化学性质。

  DOI：

  10.1016/j.dyepig.2017.09.042

文献信息

• High hole mobilities in carbazole-based glass-forming hydrazones
  作者：Jolita Ostrauskaite、Viktoras Voska、Jacek Antulis、Valentas Gaidelis、Vygintas Jankauskas、Juozas V. Grazulevicius

  DOI：10.1039/b209732j

  日期：2002.11.29

  The properties of a series of carbazole-based dihydrazones are reported. The dependence of their thermal and glass-forming properties on their chemical structure is discussed. The hydrazones having phenyl substituents at the N atom of the hydrazine moiety form glasses and their amorphous films on the glass or polyester substrates can be prepared by casting from solutions. The ionization potentials of the synthesized hydrazones measured by the electron photoemission technique range from 5.24 to 5.50 eV. Hole drift mobilities of some newly synthesized carbazole-based dihydrazones appproach 10−2 cm2 V−1 s−1 at an electric field of 6.4×105 V cm−1, at 22 °C.

  报道了一系列以咔唑为基础的二肼酮的性质。讨论了它们的热特性和玻璃形成特性与化学结构之间的依赖关系。具有苯基取代基的肼酮在肼部分的氮原子上形成玻璃，其在玻璃或聚酯基材上的无定形薄膜可以通过从溶液中铸造来制备。合成的肼酮通过电子光电子发射技术测得的电离势在5.24到5.50电子伏特之间。在6.4×10^5 V cm^−1的电场下，某些新合成的以咔唑为基础的二肼酮的孔迁移率在22°C时接近10−2 cm² V−1 s−1。
• Effect of different acceptors on N-hexyl carbazole moiety for dye-sensitized solar cells: design, characterization, molecular structure, and DSSC fabrications
  作者：Moustafa S. Abusaif、M. A. Abu-Saied、M. Fathy、Ahmed A. El-Sherif、A. B. Kashyout、Mohamed R. Selim、Yousry A. Ammar

  DOI：10.1007/s13738-020-02082-y

  日期：2021.4

  Hexyl carbazole derivatives are one of the most prominent dye scaffolds in the dye-sensitized solar cells (DSSCs). New substituted carbazole dyes such as DRA-HC, DCA-HC, and DTC-HC were synthesized for DSSCs. These dyes are containing hexyl moiety as electron donor and rhodanine-3-acetic acid, cyanoacetic acid and tetracyanoethylene as an electron acceptor linked to carbazole moiety. The relation between dye structures, photophysical/electrochemical, molecular structure and DSSC manufacturing had been discussed. All structures showed more positive ground-state oxidation potential than I−/I−3 and more negative excited state oxidation potential than the conduction band edge of the semiconductor. The highest efficiency of the DSSCs was obtained in the case of DCA-HC dye (η = 1.41%, VOC = 708 mV, FF = 0.81, and JSC = 2.45 mA cm−2 with 100 mW cm−2) compared to other synthesized dyes.

  己基咔唑衍生物是染料敏化太阳能电池（DSSC）中最重要的染料支架之一。为 DSSC 合成了新的取代咔唑染料，如 DRA-HC、DCA-HC 和 DTC-HC。这些染料含有作为电子供体的己基部分和与咔唑部分连接的绕丹宁-3-乙酸、氰基乙酸和四氰乙烯作为电子受体。讨论了染料结构、光物理/电化学、分子结构和DSSC制造之间的关系。所有结构均表现出比 I−/I−3 更大的正基态氧化电位，以及比半导体导带边缘更负的激发态氧化电位。与其他合成染料相比，在 DCA-HC 染料（η = 1.41%，VOC = 708 mV，FF = 0.81，JSC = 2.45 mA cm−2，100 mW cm−2）的情况下，DSSC 的效率最高。染料。
• Lambda-shaped carbazole and main-chain NLO polyurethane containing the same
  申请人：——

  公开号：US20020115869A1

  公开（公告）日：2002-08-22

  The present invention provides a lambda-shaped carbazole based chromophore, and a main-chain NLO polyurethane containing the same. The lambda-shaped structure reduces the plasticization to the main-chain polymers caused by the chromophore and increases temporal stability of the NLO coefficients of the main-chain NLO polyurethane. The NLO coefficients of the main-chain NLO polyurethane are stable because the efficiency of dipole alignment in electric field is increased due to the dipole thereof being perpendicular to the main chain of the polyurethane.

  本发明提供了一种基于咔唑的λ形色团和含有该色团的主链非线性光学聚氨酯。λ形结构减少了色团对主链聚合物的增塑作用，并增加了主链非线性光学聚氨酯的时间稳定性。由于其偶极矢量垂直于聚氨酯的主链，因此在电场中偶极排列的效率提高，从而使主链非线性光学聚氨酯的非线性光学系数稳定。
• Synthesis and characterization of organic dyes bearing new electron-withdrawing group for dye-sensitized solar cells
  作者：A. Salimi Beni、M. Zarandi、A.R. Madram、Y. Bayat、A. Najafi Chermahini、R. Ghahary

  DOI：10.1016/j.electacta.2015.10.172

  日期：2015.12

  Three new carbazole-based dyes (DB-CH, DTB-CH, DT-CH) have been synthesized. The dye structures were built from an aliphatic hexyl which served as an electron donor and barbituric acid, thiobarbituric acid and thiazolidine-2,4-dione moieties which served as acceptors. The photophysical and electrochemical properties of the dyes were investigated by UV spectroscopy and cyclic voltammetry (CV). The barbituric

  已经合成了三种新的咔唑基染料（DB-CH，DTB-CH，DT-CH）。染料结构由用作电子供体的脂族己基和用作受体的巴比妥酸，硫代巴比妥酸和噻唑烷-2,4-二酮部分构成。通过紫外光谱和循环伏安法（CV）研究了染料的光物理和电化学性质。发现巴比妥酸，硫代巴比妥酸和噻唑烷-2,4-二酮衍生物会影响摩尔消光系数和λmax这可能是由于染料的π共轭结构的扩展。在最佳情况下，掺入这些新染料的DSSC在完全阳光照射下的转化效率高达2.16％。我们的研究表明，在染料结构中包含噻唑烷-2,4-二酮作为电子受体可以改善其光电性能。
• Synthesis and characterization of new carbazole-based materials for optoelectronic applications
  作者：Amira Bahy、Mejed Chemli、Béchir Ben Hassine

  DOI：10.1016/j.tetlet.2013.05.091

  日期：2013.7

  New triazolo-carbazole derivatives were synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reactions. The chemical structures of these compounds were confirmed by NMR and FT-IR spectroscopic analysis. The optical properties of the triazolo-carbazoles were investigated by UV–visible absorption and photoluminescence spectroscopy; an emission in the ultraviolet region was observed. The

  通过铜催化的叠氮化物-炔烃环加成（CuAAC）反应合成了新的三唑并咔唑衍生物。这些化合物的化学结构通过NMR和FT-IR光谱分析确认。通过紫外可见吸收和光致发光光谱研究了三唑并咔唑的光学性质。观察到紫外线区域的发射。这些有机材料的能级通过循环伏安法测定，并显示出较高的电子亲和力，表明它们可能是有机发光二极管中电子注入空穴阻挡层的良好候选者。