2,3,7,8,12,13-hexabromo-5,10,15-tridodecyl-10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene | 1034498-01-5

• 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: 2,3,7,8,12,13-hexabromo-5,10,15-tridodecyl-10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene
• 英文别名: 2,3,7,8,12,13-hexabromo-5,10,15-tris(dodecyl)-10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole；2,3,7,8,12,13-hexabromo-5,10,15-tridodecyl-10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole
• CAS: 1034498-01-5
• 化学式: C₆₀H₈₁Br₆N₃
• 分子量: 1323.75
• InChiKey: LAOOMINYSBQXKL-UHFFFAOYSA-N

物化性质

• 沸点：
  1048.8±65.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  24.35
• 重原子数：
  69.0
• 可旋转键数：
  33.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  14.79
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3,7,8,12,13-hexabromo-5,10,15-tridodecyl-10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene 在 甲酸 、 palladium 10% on activated carbon 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到5,10,15-tridodecyl-10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole
  参考文献：
  名称：

  基于星形八极三氮杂并苯的双光子吸收发色团的合成与表征

  摘要：

  一系列星形八极triazatruxenes的（的TAT，1 - 6）与分子内的“推-拉”结构的合成和它们的光物理性质进行了系统的研究。这些生色团表现出明显的溶剂变色作用，即，发射光谱的显着红移和在极性更大的溶剂中观察到较大的斯托克斯位移，这主要是由于光诱导的分子内电荷转移（ICT）所致。通过在甲苯和THF中的双光子激发荧光（2PEF）测量来确定双光子吸收（2PA）的横截面值。这些生色团在近红外（NIR）区域表现出大的双光子吸收截面，范围从280到1620 GM。化合物6显示最大2PA动作的横截面（σ 2 Φ）564 GM的和可能是潜在的双光子荧光（2PF）探针。此外，化合物1 - 6所有显示良好的热稳定性和光稳定性。

  DOI：

  10.1021/jo1017926
• 作为产物：
  描述：

  1-碘十二烷 、 hexabromo-triazatruxene 在 氢氧化钾 、 四丁基硫酸氢铵 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以91%的产率得到2,3,7,8,12,13-hexabromo-5,10,15-tridodecyl-10,15-dihydro-5H-5,10,15-triaza-diindeno[1,2-a;1',2'-c]fluorene
  参考文献：
  名称：

  Synthesis and Self-Association Properties of Functionalized C₃-Symmetric Hexakis(p-substituted-phenylethynyl)triindoles

  摘要：

  A number of differently substituted phenylethynyl triindoles has been synthesized by 6-fold Sonogashira coupling in a key step. This new series of hexaalkynyl triindoles self-associate through arene-arene interactions in solution. The electronic communication of the external substituents with the central electron-rich triindole core has been demonstrated by means of cyclic voltammetry and optical absorption. A study of the effect of the electronic character of peripheral substituents on their self-association behavior is presented in an effort to shed light on the nature of the pi-stacking interactions.

  DOI：

  10.1021/ja8025399

文献信息

• New Discotic Mesogens Based on Triphenylene-Fused Triazatruxenes: Synthesis, Physical Properties, and Self-Assembly
  作者：Baomin Zhao、Bo Liu、Rui Qi Png、Kai Zhang、Kheng Aik Lim、Jing Luo、Jinjun Shao、Peter K. H. Ho、Chunyan Chi、Jishan Wu

  DOI：10.1021/cm903555s

  日期：2010.1.26

  efficient charge injection from electrodes such as gold electrodes. Their thermal behavior and self-assembly were studied by different techniques such as thermogravimetric analysis, differential scanning calorimetry, polarizing optical microscopy, and variable-temperature X-ray diffraction. These new discotic mesogens have very good thermal stability and show thermotropic liquid crystalline behavior. Ordered

  通过微波辅助六溴杂氮杂氮杂苯的6倍Suzuki偶联反应，然后用FeCl 3制备了一种新型的基于三亚苯基稠合的三杂氮杂苯的盘状介晶。介导的氧化环脱氢。与三亚苯基和三氮杂tru烯本身相比，这些盘状分子显示出扩展的π共轭。更重要的是，它们具有理想的HOMO能级，可以从电极（例如金电极）中高效注入电荷。通过热重分析，差示扫描量热法，偏振光学显微镜和可变温度X射线衍射等不同技术研究了它们的热行为和自组装。这些新的盘状介晶具有很好的热稳定性，并显示出热致液晶行为。在这两种化合物中均观察到有序的柱状液晶相和结晶相，其相变温度和中间相宽度可调。对于TP-TATC6和TP-TATC12分别获得2 V -1  s -1）。有趣的是，由于强烈的分子间相互作用，长脂肪链取代的TP-TATC12可以胶凝几种非极性烃溶剂或极性脂族醇和酯溶剂。所有这些特性使这种新型的盘状液晶成为了电子器件（例如场效应晶体管，发光二极管和太阳能电池）的潜在空穴传输材料。
• Room-temperature discotic liquid crystals based on oligothiophenes—attached and fused triazatruxenes
  作者：Jing Luo、Baomin Zhao、Jinjun Shao、Kheng Aik Lim、Hardy Sze On Chan、Chunyan Chi

  DOI：10.1039/b913930c

  日期：——

  A new class of discotic liquid crystals based on oligothiophenes - attached and fused triazatruxenes, were synthesized in high yields. The synthesis was carried out first by microwave-assisted six-fold Stille cross-coupling reactions to yield the hexakis-oligothiophenes - substituted triazatruxenes TAT-T1 and TAT-T2 and followed by successful oxidative cyclodehydrogenation of TAT-T1 to afford the planar TAT-T1-C with an extended core. Their optical properties, electronic properties, thermal behavior and self-assembly were investigated by various techniques. UV-vis absorption and fluorescence spectroscopic measurements demonstrate that TAT-T1-C is a largely delocalized and rigid polycyclic aromatic π-system. All of these disk-like molecules, in particular TAT-T1-C, show a strong π–π interaction in the solid state and exhibit columnar liquid crystalline properties at room temperature with a wide-range mesophase. Elongation of the peripheral oligothiophene arms or expansion of the rigid core size upon cyclization of the neighbouring thiophene moieties gives rise to dramatic increases of both the isotropic temperatures and the mesophase width.

  一种基于低聚噻吩-连接和融合三氮杂三环庚烯的新型盘状液晶被高产率合成。合成首先通过微波辅助的六倍斯蒂尔交叉耦合反应生成六亚甲基寡噻吩-取代的三氮杂环丁烯 TAT-T1 和 TAT-T2，然后成功地对 TAT-T1 进行氧化环化氢化，得到具有扩展核心的平面 TAT-T1-C。研究人员利用各种技术对它们的光学特性、电子特性、热行为和自组装进行了研究。紫外-可见吸收和荧光光谱测量结果表明，TAT-T1-C 在很大程度上是一个去局域化的刚性多环芳香Ï-系统。所有这些盘状分子，尤其是 TAT-T1-C，在固态下都表现出很强的ÏâÏ相互作用，并在室温下表现出柱状液晶特性和宽范围介相。在相邻噻吩分子环化时，外围低聚噻吩臂的伸长或刚性核心尺寸的扩大导致各向同性温度和介相宽度的急剧增加。
• High Charge Mobility in Discotic Liquid-Crystalline Triindoles: Just a Core Business?
  作者：Eva M. García-Frutos、Upendra K. Pandey、Roberto Termine、Ana Omenat、Joaquín Barberá、José L. Serrano、Attilio Golemme、Berta Gómez-Lor

  DOI：10.1002/anie.201005820

  日期：2011.8.1

  The stacking order and distance in columnar phases of triindole‐based liquid crystals is controlled by an ethynyl linker (see picture; orange rod) between the central triindole core (green) and the peripheral flexible chains of a discotic mesogen. Hole (h) mobility is very high even if the stacking distances is not very short and the conjugated system is not particularly extended.

  三吲哚基液晶的柱状相中的堆积顺序和距离是由中心三吲哚核（绿色）和盘状介晶的外围柔性链之间的乙炔基连接基控制的（见图片；橙色棒）。即使堆积距离不是很短并且共轭体系没有特别扩展，空穴（h）的迁移率也非常高。
• Self-Assembly of <i>C</i>₃-Symmetrical Hexaaryltriindoles Driven by Solvophobic and CH−π Interactions
  作者：Eva M. García-Frutos、Gunther Hennrich、Enrique Gutierrez、Angeles Monge、Berta Gómez-Lor

  DOI：10.1021/jo902013v

  日期：2010.2.19

  forces. A study of the influence of the electronic character of peripheral substituents on the self-association behavior in solution has shown that increasing the electron-donor character of the substituents facilitates self-association while derivatives substituted with electron-acceptor substituents do not self-assemble. The electronic nature of the substituents also has an influence in the geometry

  据报道，在溶液和固态下一系列不同取代的星形六芳基三吲哚的合成和聚集性质。尽管这些分子在CDCl 3中没有显示任何明显的分子间聚集，已经有可能通过增加溶剂的极性来诱导聚集，因此促进了疏溶剂力的发生。对外围取代基的电子特性对溶液中自缔合行为的影响的研究表明，增加取代基的电子给体特性有助于自缔合，而被电子受体取代基取代的衍生物不会自组装。取代基的电子性质也影响在固态下观察到的这些衍生物的堆叠的几何形状。未取代的六苯基三吲哚以错开的面对面排列方式自组装时，连接六个氰基官能团会导致胶版堆叠。
• Large core-expanded triazatruxene-based discotic liquid crystals: synthesis, characterization and physical properties
  作者：Qun Ye、Jingjing Chang、Jinjun Shao、Chunyan Chi

  DOI：10.1039/c2jm31684f

  日期：——

  Two new discotic liquid crystals based on the triazatruxene core, TAT-1 and TAT-2, have been constructed using diamine–diketone condensation as the key expansion step with different solubilizing chains attached at the periphery. The new mesogens possess good thermal stability and show columnar liquid crystalline properties. Upon expansion of the core size, TAT-2 is found to have a strong tendency to aggregate both in solution and in thin film. Their optical properties, electronic properties and thermal behaviour are investigated by various techniques. They are found to respond to protons due to protonation of the pyrazine rings in the conjugation system and an obvious colour change is observed upon protonation. These new molecules are also found to possess a weak intramolecular charge transfer (ICT) nature and a weak ICT band can be observed on the UV-vis absorption spectra. The charge transport properties of TAT-1 and TAT-2 have been measured by a space-charge limited-current technique and the highest mobilities obtained for TAT-1 and TAT-2 are 0.14 cm2 V−1 s−1 and 0.69 cm2 V−1 s−1, respectively.

  两种新的基于三氮杂芴核心的圆盘状液晶TAT-1和TAT-2，是通过将二胺-二酮缩合作为关键扩展步骤，并在外围连接不同的增溶链而构建的。新的中间体具有良好的热稳定性，并表现出柱状液晶特性。在扩展核心尺寸后，发现TAT-2在溶液和薄膜中都有很强的聚集倾向。通过多种技术对其光学特性、电子特性和热行为进行了研究。发现它们对质子有反应，这是由于共轭体系中的吡嗪环质子化，并且在质子化后观察到明显的颜色变化。还发现这些新分子具有弱的分子内电荷转移（ICT）性质，并且在紫外-可见吸收光谱上可以观察到弱的ICT带。TAT-1和TAT-2的电荷传输特性已通过空间电荷限制电流技术进行了测量，TAT-1和TAT-2的最高迁移率分别为0.14 cm2 V−1 s−1和0.69 cm2 V−1 s−1。