4,4'-(9-hexyl-9H-carbazole-3,6-diyl)dibenzaldehyde | 1105069-46-2

• 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: 4,4'-(9-hexyl-9H-carbazole-3,6-diyl)dibenzaldehyde
• 英文别名: 3,6-di-(4-formylphenyl)-9-hexyl-9H-carbazole；3,6-Di(4-formylphenyl)-9-hexyl-9h-carbazole；4-[6-(4-formylphenyl)-9-hexylcarbazol-3-yl]benzaldehyde
• CAS: 1105069-46-2
• 化学式: C₃₂H₂₉NO₂
• 分子量: 459.588
• InChiKey: FGIGQIOOXXAJQS-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  642.6±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  4,4'-(9-hexyl-9H-carbazole-3,6-diyl)dibenzaldehyde 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到3,6-di-(4-hydroxymethylphenyl)-9-hexyl-9H-carbazole
  参考文献：
  名称：

  Synthesis and Photophysical Properties of 3,6-Diphenyl-9-hexyl-9H-carbazole Derivatives Bearing Electron Withdrawing Groups

  摘要：

  3,6-Diphenyl-9-hexyl-9H-carbazole derivatives bearing electron withdrawing groups, such as the formyl or the nitro-group in 4-positions of the phenyl substituents, were prepared and characterized. Their photophysical properties were evaluated and compared with those of the unsubstituted counterpart 3,6-diphenyl-9-hexyl-9H-carbazole. The electron withdrawing groups bearing compounds exhibited considerable red shifts of the absorption and the emission maxima. While 3,6-di(4-nitrophenyl)-9-hexyl-9H-carbazole emitted in the orange region of the visible spectrum with its emission maximum peaking at 585 nm, 3,6-di(4-formylphenyl)-9-hexyl-9H-carbazole gave a pure blue emission with a luminescence quantum yield of 95% peaking at 450 nm. Observed features were explained using quantum mechanical calculations and organic light emitting diodes using the formylphenyl substituted compound as emissive layer were built demonstrating the practical applicability of this class of compounds.

  DOI：

  10.1007/s00706-007-0774-3
• 作为产物：
  描述：

  溴己烷 在 四(三苯基膦)钯 、 四丁基溴化铵 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 水 、 甲苯 为溶剂， 生成 4,4'-(9-hexyl-9H-carbazole-3,6-diyl)dibenzaldehyde
  参考文献：
  名称：

  Metal-free organic luminophores with ultrastrong dipole moment exhibiting force-induced near-infrared emission (>800 nm) turn-on

  摘要：

  我们展示了具有极强偶极矩（高达22.7 Debye）的无金属有机荧光体，它们在研磨时表现出发射开启峰值为822纳米。

  DOI：

  10.1039/c8cc05616a

文献信息

• A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoresponsive luminescence turn-on
  作者：Ping Wen、Zhixiang Gao、Rong Zhang、Anran Li、Fang Zhang、Jie Li、Jingjuan Xie、Yuezhen Wu、Min Wu、KunPeng Guo

  DOI：10.1039/c7tc00559h

  日期：——

  (h-CPDM) and N-isooctyl substituents (i-CPDM) were synthesized, and both of them presented remarkable dual properties of solvatochromism and mechanoresponsive luminescence (MRL) turn-on. The intrinsic intramolecular charge transfer (ICT) characteristic endowed both luminophors with a prominent solvatochromic effect, with emission color tuning from blue to orange-red by changing the solvent from nonpolar

  合成了两个具有咔唑供体和双氰基乙烯基受体但在N-己基（h -CPDM）和N-异辛基取代基（i -CPDM）上不同的A–π–D–π–A分子，并且它们都表现出显着的双重溶剂变色的性质和机械响应发光（MRL）开启。固有的分子内电荷转移（ICT）特性赋予两种发光体显着的溶剂致变色效应，通过将溶剂从非极性己烷变为极性二甲基亚砜，发光颜色从蓝色变为橙红色。同时，h -CPDM和i -CPDM的非/弱发射原始粉末发出亮橙色（610 nm）和黄色（596 nm）的光，研磨后的光致发光量子产率提高到85倍。研究表明，这种机械响应的发光开启可能是由于机械力对非/弱发射J聚集体中π-π堆积相互作用的干扰。这项工作提供了咔唑衍生物，可用作有机溶剂和机械传感器的敏感荧光指示剂。
• 一种具有信息深度隐藏功能的有机荧光材料、制备及应用
  申请人：太原理工大学

  公开号：CN113121409A

  公开（公告）日：2021-07-16

  本发明涉及信息高阶加密与深度隐藏技术，更具体而言，涉及一种具有信息深度隐藏功能的有机荧光材料、制备及应用，以咔唑为电子给体基团，苯基为共轭桥，1,3‑茚满二酮为电子受体，具有电子受体‑共轭桥‑电子给体‑共轭桥‑电子受体(A‑π‑D‑π‑A)分子结构，在加热刺激作用下能够实现荧光的启亮与淬灭或荧光颜色的多相态转变，在加热刺激作用过程中，可以发生荧光亮暗或颜色的多重变化，且荧光强度和颜色对比度极其明显，非常有利于以荧光信号为载体所传递信息的辨识。
• Carbazole based A-π-D-π-A dyes with double electron acceptor for dye-sensitized solar cell
  作者：K.S.V. Gupta、Thogiti Suresh、Surya Prakash Singh、Ashraful Islam、Liyuan Han、Malapaka Chandrasekharam

  DOI：10.1016/j.orgel.2013.11.020

  日期：2014.1

  Three novel carbazole-based A-pi-D-pi-A-featured dyes (CSG1-CSG3) have been designed, synthesized for applications in dye-sensitized solar cells and fully characterized with NMR, MS, IR, UV-vis and electrochemical measurements. These dyes share the same donor (N-hexylcarbazole) and acceptor/anchoring group (cyanoacrylic acid), but differs in conjugated linkers incorporated, such as benzene, furan or thiophene, to configure the novel A-pi-D-pi-A framework for effective electron flow. The power conversion efficiencies were observed to be sensitive to the p-bridging linker moiety. The photovoltaic experiments showed that dye with a benzene linker exhibited a higher open-circuit voltage (0.699 V) compared to thiophene and furan linker. Among all dyes, CSG2 containing a thiophene linker exhibited the maximum overall conversion efficiency of 3.8% (J(SC) = 8.90 mA cm (2), V-OC = 584 mV, FF = 0.74) under standard global AM 1.5 G solar condition. Under similar fabrication conditions, champion dye N719 exhibited the maximum overall conversion efficiency of 6.4% (J(SC) = 14.74 mA cm (2), V-OC = 606 mV, FF = 0.716). (C) 2013 Elsevier B.V. All rights reserved.