5,5',10,10',15,15'-hexahexyl-2-bromotruxene | 1155921-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5,5',10,10',15,15'-hexahexyl-2-bromotruxene
• 英文别名: 2-bromo-5,5',10,10',15,15'-hexahexyltruxene；6-Bromo-9,9,18,18,27,27-hexahexylheptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12,14,16,19,21,23,25-dodecaene；6-bromo-9,9,18,18,27,27-hexahexylheptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1,3(8),4,6,10,12,14,16,19,21,23,25-dodecaene
• CAS: 1155921-24-6
• 化学式: C₆₃H₈₉Br
• 分子量: 926.304
• InChiKey: MDNDJFLKRKHVSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.4
• 重原子数：
  64
• 可旋转键数：
  30
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,5',10,10',15,15'-hexahexyl-2-bromotruxene 在 正丁基锂 、 N,N-二甲基甲酰胺 、 盐酸 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 反应 1.0h， 以55%的产率得到2-carbaldehyde-5,5,10,10,15,15-hexahexyltruxene
  参考文献：
  名称：

  Singlet and Triplet Energy Transfers in Tetra-(meso-truxene)zinc(II)- and Tetra-(meso-tritruxene)zinc(II) Porphyrin and Porphyrin-Free Base Dendrimers

  摘要：

  The synthesis, optical properties, and energy transfer features of four dendrimers composed of meso-tetrasubstituted zinc(II) porphyrin (ZnP) or a free base (P) central core, where the substituents are four truxene (Tru) or four tritruxene dendrons (TriTru), TruP, TriTruP, TruZnP, and TriTruZnP, are reported. Selective excitation of the truxene donors results in a photoinduced singlet energy transfer from the truxenes to the porphyrin acceptor. The rates for singlet energy transfer (k(ET)), evaluated from the change in the fluorescence lifetime of the donors (Tru and TriTru) in the presence and absence of the acceptor (P or ZnP) for TruP, TruZnP, TriTruP, and TriTruZnP, are 5.9, 1.2, 0.87, and 0.74 (ns)(-1) at 298 K and 2.6, 2.6, 2.7, and 1.2 (ns)(-1) at 77 K, respectively. A slow triplet-triplet energy transfer from tnixene to porphyrin cores in glassy 2MeTHF at 77 K is also reported with rates of 1.3 x 10(3) and 0.10 X 10(2) s(-1) for TruZnP and TriTruZnP, respectively. Tithe Dexter mechanism for the triplet energy transfers is considered, these slow rates are easily explained by a poor orbital overlap between the truxene and porphyrin pi systems. The fluorescence quantum yields (Phi(F)) are 0.20 and 0.16 for TruP and TriTruP and 0.08 and 0.10 for TruZnP and TriTruZnP, respectively at 298 K At 298 K, a phosphorescence from TruZnP at 795 nm was also observed and is associated with the ZnP chromophore.

  DOI：

  10.1021/ic2013667
• 作为产物：
  描述：

  三聚茚 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5,5',10,10',15,15'-hexahexyl-2-bromotruxene
  参考文献：
  名称：

  Shape-persistent poly-porphyrins assembled by a central truxene: synthesis, structure, and singlet energy transfer behaviors

  摘要：

  我们制备了由一个中心三烯和一个或三个 β 取代的锌（II）卟啉（ZnP：TruZnP (7) 和 TruTriZnP (9)）或游离碱（H2P：TruP (6) 和 TruTriP (8)）。β-甲基基团的存在通过卟啉平面和三甲苯平面所成的准直角将π-共轭作用减至最小，并使这些二元化合物相对坚硬。吸收和发射 0-0 峰的位置证实了三并烯和卟啉分别作为能量供体和受体的作用。楚克森的选择性激发导致高效的单线能量转移（S1 ET）从楚克森转移到卟啉单元。S1 ET 的速率（k ET ）是从受体存在和不存在时三红烯荧光寿命的变化中提取出来的，与温度无关（TruP (6)、TruTriP (8)、TruZnP (7) 和 TruTriZnP (9) 在 298 K 时分别为 5.0、1.4、1.0 和 1.4，在 77 K 时分别为 5.9、1.3、2.6 和 0.86 (ns)-1），这与它们的相对刚性是一致的。这些 k ET 与我们其中一人报告的其他相关但更灵活的系统相似（Inorg.）在建模的基础上，假定 k ET 的时间尺度与由于己基-己基的立体相互作用导致的三叉蒽-卟啉 C-C 键旋转受阻有关。这项研究证实了之前的结论是正确的。

  DOI：

  10.1142/s1088424612501271

文献信息

• π-Conjugated Dendrimers as Stable Pure-Blue Emissive Materials: Photophysical, Electrochemical, and Electroluminescent Properties
  作者：Yang Jiang、Lei Wang、Yan Zhou、Yu-Xin Cui、Jian Wang、Yong Cao、Jian Pei

  DOI：10.1002/asia.200800329

  日期：2009.4.6

  stronger, better: A family of giant π‐conjugated dendrimers has been developed as pure‐blue active materials for organic light‐emitting diodes. The dendrimer‐generation number has little effect on the photophysical, electrochemical, and EL properties, and device efficiency of G0 and G1. The preliminary OLED devices achieve pure‐blue color with stable CIE chromaticity coordinates (0.16, 0.08) for both

  更大，更强，更好：已开发出一系列巨大的π共轭树枝状大分子，作为有机发光二极管的纯蓝色活性材料。树枝状大分子的生成数对光物理，电化学和EL性质以及G0和G1的器件效率影响很小。初步的OLED器件对于G0和G1均具有稳定的CIE色度坐标（0.16，0.08）的纯蓝色。
• Cationic Iridium Dendrimers: Synthesis and Photophysical Properties
  作者：Bin Du、Si-Chun Yuan、Jian Pei

  DOI：10.1071/ch11143

  日期：——

  Two dendrimers, D1 and D2, containing the cationic iridium complexes (C1 and C2) as cores and truxene-functionalized chromophores as the branches, have been developed by a convergent synthetic strategy. The cationic complexes employ 3-(pyridin-2-yl)-1H-1,2,4-triazole and 2-(pyridin-2-yl)-benzimidazole derivatives as the ancillary ligands. To avoid the change in emission colour arising from the iridium complex, the conjugation between the dendron and the ligand is decoupled by separating them using the alkyl chain. An investigation of their photoluminescent features reveals that efficient energy transfer happens from the dendrons to the core in the solid state. Likewise, the charged dendritic structure is demonstrated to be an efficient method to improve the compatibility between the polar charged iridium complexes and typical hydrophobic hosts with the additional benefit of excellent solution processability. Both dendrimers exhibit strong solvatochromic behaviours in solvents and exclusive green and yellow-orange light in the solid state.

  我们采用聚合合成策略开发出了两种树枝状聚合物 D1 和 D2，它们以阳离子铱络合物（C1 和 C2）为核心，以三烯功能化发色团为分支。阳离子配合物采用 3-(吡啶-2-基)-1H-1,2,4-三唑和 2-(吡啶-2-基)-苯并咪唑衍生物作为辅助配体。为了避免铱配合物引起的发射颜色变化，树枝状化合物和配体之间的共轭作用通过使用烷基链进行分离而解除。对其光致发光特征的研究表明，在固态下，能量从树枝状结构有效地传递到核心。同样，带电树枝状结构也被证明是改善极性带电铱复合物与典型疏水性宿主之间相容性的有效方法，而且还具有优异的溶液加工性。这两种树枝状聚合物在溶剂中都表现出强烈的溶解变色行为，在固态下则表现出独有的绿色和橘黄色光。
• 一种基于芘的多臂结构三并茚基有机光电材料及其制备方法和应用
  申请人：南京邮电大学

  公开号：CN106748625A

  公开（公告）日：2017-05-31

  本发明公开了一种基于芘的多臂结构三并茚基有机光电材料及其制备方法和应用，该有机光电材料是一种以芘为核、三并茚为支臂的多臂结构衍生物。制备方法是以1,3,6,8‑四溴‑芘为原料，和2‑硼酸酯‑三并茚发生偶联反应，获得产物A；以1,3,6,8‑四溴‑芘为原料，和2‑炔基‑三并茚发生偶联反应，获得产物B。因芘、三并茚具有大π共轭结构，具有良好的电子和空穴传输性能，两种产物均表现出优异的光电性能；另外由于三并茚C5,10,15位引入烷基链，使产物具有良好的溶解性能。由于其结构与光电性能的独特性，在光电领域中有着很大的实际应用价值。
• A Mechanically Interlocked [3]Rotaxane as a Light-Harvesting Antenna: Synthesis, Characterization, and Intramolecular Energy Transfer
  作者：Jie-Yu Wang、Ji-Min Han、Jing Yan、Yuguo Ma、Jian Pei

  DOI：10.1002/chem.200802228

  日期：2009.3.23

  Mimicking photosynthesis: The concept of light‐harvesting by using a mechanically interlocked [3]rotaxane is developed through synthesis and characterization. Our results provide a new candidate for light‐harvesting systems and also open up the possibility of creating intelligent or controllable energy‐collecting machines (see figure).

  模仿光合作用：通过机械联锁的[3]轮烷的光收集概念是通过合成和表征而开发的。我们的结果为光收集系统提供了一个新的候选者，也为创建智能的或可控的能量收集机提供了可能性（见图）。
• Singlet and Triplet Energy Transfers in Tetra-(<i>meso</i>-truxene)zinc(II)- and Tetra-(<i>meso</i>-tritruxene)zinc(II) Porphyrin and Porphyrin-Free Base Dendrimers
  作者：Bin Du、Daniel Fortin、Pierre D. Harvey

  DOI：10.1021/ic2013667

  日期：2011.11.21

  The synthesis, optical properties, and energy transfer features of four dendrimers composed of meso-tetrasubstituted zinc(II) porphyrin (ZnP) or a free base (P) central core, where the substituents are four truxene (Tru) or four tritruxene dendrons (TriTru), TruP, TriTruP, TruZnP, and TriTruZnP, are reported. Selective excitation of the truxene donors results in a photoinduced singlet energy transfer from the truxenes to the porphyrin acceptor. The rates for singlet energy transfer (k(ET)), evaluated from the change in the fluorescence lifetime of the donors (Tru and TriTru) in the presence and absence of the acceptor (P or ZnP) for TruP, TruZnP, TriTruP, and TriTruZnP, are 5.9, 1.2, 0.87, and 0.74 (ns)(-1) at 298 K and 2.6, 2.6, 2.7, and 1.2 (ns)(-1) at 77 K, respectively. A slow triplet-triplet energy transfer from tnixene to porphyrin cores in glassy 2MeTHF at 77 K is also reported with rates of 1.3 x 10(3) and 0.10 X 10(2) s(-1) for TruZnP and TriTruZnP, respectively. Tithe Dexter mechanism for the triplet energy transfers is considered, these slow rates are easily explained by a poor orbital overlap between the truxene and porphyrin pi systems. The fluorescence quantum yields (Phi(F)) are 0.20 and 0.16 for TruP and TriTruP and 0.08 and 0.10 for TruZnP and TriTruZnP, respectively at 298 K At 298 K, a phosphorescence from TruZnP at 795 nm was also observed and is associated with the ZnP chromophore.