9-octyl-3-vinyl-9H-carbazole | 1374308-57-2

• 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-octyl-3-vinyl-9H-carbazole
• 英文别名: 3-Ethenyl-9-octylcarbazole；3-ethenyl-9-octylcarbazole
• CAS: 1374308-57-2
• 化学式: C₂₂H₂₇N
• 分子量: 305.463
• InChiKey: IGCTYACHOQSRHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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-octyl-3-vinyl-9H-carbazole 在 potassium tert-butylate 、 四丁基溴化铵 、 甲基三苯基碘化膦 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 4-((1E)-2-(4-((E)-2-(9-octyl-9H-carbazol-6-yl)vinyl)phenyl)vinyl)-N-(4-((1E)-2-(4-((E)-2-(9-octyl-9H-carbazol-6-yl)vinyl)phenyl)vinyl)phenyl)-N-(4-vinylphenyl)benzenamine
  参考文献：
  名称：

  Branched benzothiadiazole-cored oligomers with terminal carbazoles: Synthesis and fluorescence probing nitroaromatics

  摘要：

  New branched benzothiadiazole-cored conjugated oligomers with terminal carbazoles 1 and 2 have been synthesized. It was found that no obvious shifts of the maximal absorption bands for 1 and 2 were detected in the films compared with those in solutions, indicating weak pi-pi stacking occurred in the solid states on account of site isolation effect of the branched architectures. Hence, the synthesized oligomers could emit strong red light in the films. Notably, the emission of the films based on 1 and 2 could be quenched obviously upon exposed to gaseous TNT and DNT. The fluorescence quenching efficiency of the oligomer 2-based film reached 91% when exposed to the saturated vapor of DNT for 3 min at 55 degrees C. The linear Stern-Volmer plot and the decrease of the fluorescence lifetime of 2 induced by DNT suggested the fluorescence sensing mechanism was due to the photo-induced electron transfer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.01.009
• 作为产物：
  描述：

  9-正辛基咔唑 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 14.33h， 生成 9-octyl-3-vinyl-9H-carbazole
  参考文献：
  名称：

  轴向咔唑基乙烯基 萘二甲酰亚胺官能化的磷（v）卟啉的合成及其光物理性质†

  摘要：

  我们已经合成了新的DAD型磷（V）卟啉衍生物1和2，它们被轴向的咔唑基乙烯基萘二甲酰亚胺单元官能化。所获得的磷（V）卟啉的吸收带在250–640 nm范围内，具有高摩尔吸收系数，意味着很强的光收集能力。值得注意的是，发现具有[ITO / PEDOT：PSS /有机活性膜/ LiF / Al]的构型的基于磷（V）卟啉的器件具有入射光子-电流转换效率（IPCE）响应。 。基于化合物2的设备的最大IPCE值达到2.76％，远高于化合物1的0.20％。原因可能是由于化合物2中轴向单元的扩大共轭作用导致的低氧化电位和强大的集光能力。因此，我们推论在带有轴向共轭给体单元的磷（V）卟啉中发生了光诱导的电子转移，这使其成为可用于太阳能电池的光伏材料的良好候选者。

  DOI：

  10.1039/c2ob26478a

文献信息

• Aggregation-induced emission and reversible mechanochromic luminescence of carbazole-based triphenylacrylonitrile derivatives
  作者：Yong Zhan、Peng Gong、Peng Yang、Zhe Jin、Ying Bao、Ying Li、Yongnan Xu

  DOI：10.1039/c6ra03310e

  日期：——

  Conjugated organic molecules exhibiting AIE are characterized by the strongly twisted conjugated skeleton, which could provide loose intermolecular stacking and weak π–π interactions in the solid state to generate stimuli-responsive materials.

  具有AIE特性的共轭有机分子的特征是强烈扭曲的共轭骨架，这可以在固态中提供松散的分子间堆积和弱的π-π相互作用，从而生成对刺激响应的材料。
• Y-shaped dyes based on triphenylamine for efficient dye-sensitized solar cells
  作者：Junhui Jia、Kaiyu Cao、Pengchong Xue、Yuan Zhang、Huipeng Zhou、Ran Lu

  DOI：10.1016/j.tet.2012.02.077

  日期：2012.5

  Three new triphenylamine-based dyes with Y-shaped conformation bearing triphenylamino-vinyl, 10-octy1-10H-phenothiazine-vinyl and 9-octy1-9H-carbazole-vinyl as arms (TT, TP, and TC) have been synthesized. From electrochemical investigations it is found that they can be employed in DSSCs due to the balanced HOMO and LUMO energy levels. Notably, the photo-to-electrical conversion efficiency of the DSSCs sensitized with branched TT, TP, and TC reach 5.12%, 4.84%, and 3.63%, which are higher than that sensitized with T (2.79%), and the DSSC sensitized with TT shows higher IPCE response and better photovoltaic performances (J(sc)=12.37 mA/cm(,)(2) V-oc=0.72 V and ff=0.58) than others. These results reveal that the introduction of branched Y-shaped extended pi-conjugated donors to D-pi-A dyes cannot only enlarge the spectral response range, but also suppress the molecular aggregation on TiO2 films to a certain extent, which would enhance the performance of DSSCs. (C) 2012 Elsevier Ltd. All rights reserved.
• Donor-acceptor type π-conjugated diphenylsulfone derivatives showing diverse fluorescence response to mechanical force
  作者：Feng Zhao、Ting Sun、Yu Wang、Wenjun Yang、Yong Zhan

  DOI：10.1016/j.dyepig.2021.109542

  日期：2021.10
• Synthesis and photophysical properties of phosphorus(v) porphyrins functionalized with axial carbazolylvinylnaphthalimides
  作者：Yong Zhan、Kaiyu Cao、Chenguang Wang、Junhui Jia、Pengchong Xue、Xingliang Liu、Xuemei Duan、Ran Lu

  DOI：10.1039/c2ob26478a

  日期：——

  have synthesized new D-A-D type phosphorus(V) porphyrin derivatives 1 and 2 functionalized with axial carbazolylvinylnaphthalimide units. The absorption bands of the obtained phosphorus(V) porphyrins were in the range 250–640 nm with high molar absorption coefficients, meaning strong light-harvesting abilities. Notably, it is found that the devices based on phosphorus(V) porphyrins with a configuration

  我们已经合成了新的DAD型磷（V）卟啉衍生物1和2，它们被轴向的咔唑基乙烯基萘二甲酰亚胺单元官能化。所获得的磷（V）卟啉的吸收带在250–640 nm范围内，具有高摩尔吸收系数，意味着很强的光收集能力。值得注意的是，发现具有[ITO / PEDOT：PSS /有机活性膜/ LiF / Al]的构型的基于磷（V）卟啉的器件具有入射光子-电流转换效率（IPCE）响应。 。基于化合物2的设备的最大IPCE值达到2.76％，远高于化合物1的0.20％。原因可能是由于化合物2中轴向单元的扩大共轭作用导致的低氧化电位和强大的集光能力。因此，我们推论在带有轴向共轭给体单元的磷（V）卟啉中发生了光诱导的电子转移，这使其成为可用于太阳能电池的光伏材料的良好候选者。
• Branched benzothiadiazole-cored oligomers with terminal carbazoles: Synthesis and fluorescence probing nitroaromatics
  作者：Jiang Peng、Kaiqi Ye、Jingbo Sun、Yong Zhan、Junhui Jia、Pengchong Xue、Gonghe Zhang、Zhenqi Zhang、Ran Lu

  DOI：10.1016/j.dyepig.2015.01.009

  日期：2015.5

  New branched benzothiadiazole-cored conjugated oligomers with terminal carbazoles 1 and 2 have been synthesized. It was found that no obvious shifts of the maximal absorption bands for 1 and 2 were detected in the films compared with those in solutions, indicating weak pi-pi stacking occurred in the solid states on account of site isolation effect of the branched architectures. Hence, the synthesized oligomers could emit strong red light in the films. Notably, the emission of the films based on 1 and 2 could be quenched obviously upon exposed to gaseous TNT and DNT. The fluorescence quenching efficiency of the oligomer 2-based film reached 91% when exposed to the saturated vapor of DNT for 3 min at 55 degrees C. The linear Stern-Volmer plot and the decrease of the fluorescence lifetime of 2 induced by DNT suggested the fluorescence sensing mechanism was due to the photo-induced electron transfer. (C) 2015 Elsevier Ltd. All rights reserved.