8-(9H-carbazol-9-yl)octanoic acid | 391276-77-0

• 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: 8-(9H-carbazol-9-yl)octanoic acid
• 英文别名: 8-Carbazol-9-yl-octanoic acid；8-carbazol-9-yloctanoic acid
• CAS: 391276-77-0
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: NEONZDXIWJKQQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3,6,7,10,11-pentapentyloxytriphenylene 、 8-(9H-carbazol-9-yl)octanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以56%的产率得到8-Carbazol-9-yl-octanoic acid 3,6,7,10,11-pentakis-pentyloxy-triphenylen-2-yl ester
  参考文献：
  名称：

  摘要：

  The synthesis of 13 discotic mesogens is described in which the well-known hexakis( pentyloxy) triphenylene liquid crystalline material has been chemically modified to incorporate one, two, three and six carbazole moieties. These modifications have been achieved by the alkylation or esterification of mono-, di-, tri- and hexa-hydroxytriphenylene derivatives with alkyl bromides and carboxylic acids incorporating the carbazole moiety. The pure compounds are not liquid crystalline in nature but when doped with TNF, hexagonal columnar mesophases are induced, as shown by DSC, OPM and X-ray diffraction. These mesophases exist below room temperature. The mesophase clearing temperatures are dependent on several factors including the chain length separating the carbazole moiety from the triphenylene core, and the nature of the ether or ester linkage, and the degree of TNF doping. The data suggest that the most stable mesophases (highest clearing temperatures) are formed when a 2 : 1 complex is formed between the carbazole derivatives and the TNF, respectively. The correlation length obtained from X-ray diffraction reveals that the columnar order for one of the ether derivatives decreases, whereas the correlation length increases for one of the ester derivatives. This result suggests that the TNF is not only partaking in pi-pi noncovalent bonding interactions, but also in polar interactions with the C=O bond. Such mesogenic carbazole derivatives may have advantageous photorefractive properties over the amorphous polymeric materials.

  DOI：

  10.1039/b103052n
• 作为产物：
  描述：

  methyl 8-carbazol-9-yloctanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以100%的产率得到8-(9H-carbazol-9-yl)octanoic acid
  参考文献：
  名称：

  摘要：

  The synthesis of 13 discotic mesogens is described in which the well-known hexakis( pentyloxy) triphenylene liquid crystalline material has been chemically modified to incorporate one, two, three and six carbazole moieties. These modifications have been achieved by the alkylation or esterification of mono-, di-, tri- and hexa-hydroxytriphenylene derivatives with alkyl bromides and carboxylic acids incorporating the carbazole moiety. The pure compounds are not liquid crystalline in nature but when doped with TNF, hexagonal columnar mesophases are induced, as shown by DSC, OPM and X-ray diffraction. These mesophases exist below room temperature. The mesophase clearing temperatures are dependent on several factors including the chain length separating the carbazole moiety from the triphenylene core, and the nature of the ether or ester linkage, and the degree of TNF doping. The data suggest that the most stable mesophases (highest clearing temperatures) are formed when a 2 : 1 complex is formed between the carbazole derivatives and the TNF, respectively. The correlation length obtained from X-ray diffraction reveals that the columnar order for one of the ether derivatives decreases, whereas the correlation length increases for one of the ester derivatives. This result suggests that the TNF is not only partaking in pi-pi noncovalent bonding interactions, but also in polar interactions with the C=O bond. Such mesogenic carbazole derivatives may have advantageous photorefractive properties over the amorphous polymeric materials.

  DOI：

  10.1039/b103052n

文献信息

• Functionalized tails influence photoluminescence emissions for advanced applications in the fiel of time-resolved information input and erasure
  作者：Haowen Huang、Yasong Cao、Zhonghua Zhao、Jiatong Xu、Cheng Zeng、Richao Shen、Jiawei Lv、Ziqiang Lei、Hengchang Ma

  DOI：10.1039/d4nj01438c

  日期：——

  chemical structures is a reliable way to achieve these emission properties. In this study, five carbazole derivatives with different functional groups were obtained via C–N coupling reactions: Cz–C8, Cz–C8–Br, Cz–C8–OH, Cz–C8–Tu and Cz–C7–COOH. Our results reveal that small differences in functionalized tail groups can produce a huge contrast in photoluminescence behavior. Obviously, more polar tails

  对具有不同分子结构但具有相同发光核心、产生荧光、磷光或延迟荧光的有机小分子的研究是令人着迷的。当然，精细化学结构的调控是实现这些排放特性的可靠方法。本研究通过C-N偶联反应得到了5种具有不同官能团的咔唑衍生物：Cz–C 8 、Cz–C 8 –Br、Cz–C 8 –OH、Cz–C 8 –Tu 和 Cz–C 7 –COOH。我们的结果表明，功能化尾基的微小差异可以在光致发光行为中产生巨大的差异。显然，更多的极性尾部，例如-Tu和-COOH，对高性能有机室温磷光材料的贡献更大。 –H 的非极性尾部有利于延迟荧光，而 –OH 的中间极性基团则在 Cz–C 8 –OH 中实现磷光和延迟荧光。这两种不同的行为可以通过外部刺激（例如光激活和热退火）进行人为调节。内部机制研究表明，分子间相互作用和分子聚集状态是影响光致发光性能的主要因素。最后，利用时间分辨技术阐述了数据加密、数据存储和防伪领域的高级应用。