2,12-Dibromo-7-phenyl-5,6,8,9-tetrahydrodibenzacridine | 118656-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,12-Dibromo-7-phenyl-5,6,8,9-tetrahydrodibenzacridine
• 英文别名: 2,12-dibromo-7-phenyl-5,6,8,9-tetrahydro-dibenzo[c,h]acridine；6,20-dibromo-13-phenyl-2-azapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4(9),5,7,13,17(22),18,20-nonaene
• CAS: 118656-33-0
• 化学式: C₂₇H₁₉Br₂N
• 分子量: 517.263
• InChiKey: DLWOQGOEYHBGMB-UHFFFAOYSA-N

物化性质

• 熔点：
  245-248 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  641.2±55.0 °C(Predicted)
• 密度：
  1.550±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,12-Dibromo-7-phenyl-5,6,8,9-tetrahydrodibenzacridine 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 以60%的产率得到2,12-diiodo-7-phenyl-5,6,8,9-tetrahydro-dibenzo[c,h]acridine
  参考文献：
  名称：

  Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups

  摘要：

  A molecular tweezer bearing two pentafluorophenyl groups 2b and its o-methylated aryl homologue 2c were newly synthesized by the slight modification of the known procedure. The low yield in the introduction of pentafluorophenyl group to the precursor dibromide 6 was improved by application of the modified Suzuki-Miyaura coupling reaction using C6F5B(OH)(2) with Pd-2(dba)(3)/P(t-Bu)(3)/CsF/Ag2O catalytic system, which was recently developed by us. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.007
• 作为产物：
  描述：

  7-溴-3,4-二氢萘-1(2H)-酮 、 (E)-2-benzylidene-7-bromo-1-tetralone 在 三氟化硼乙醚 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 以47%的产率得到2,12-Dibromo-7-phenyl-5,6,8,9-tetrahydrodibenzacridine
  参考文献：
  名称：

  Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups

  摘要：

  A molecular tweezer bearing two pentafluorophenyl groups 2b and its o-methylated aryl homologue 2c were newly synthesized by the slight modification of the known procedure. The low yield in the introduction of pentafluorophenyl group to the precursor dibromide 6 was improved by application of the modified Suzuki-Miyaura coupling reaction using C6F5B(OH)(2) with Pd-2(dba)(3)/P(t-Bu)(3)/CsF/Ag2O catalytic system, which was recently developed by us. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.007

文献信息

• Rigid molecular tweezers: preorganized hosts for electron donor-acceptor complexation in organic solvents
  作者：Steven C. Zimmerman、Craig M. VanZyl、Gregory S. Hamilton

  DOI：10.1021/ja00186a035

  日期：1989.2

  synthesized which are capable of acting as molecular tweezers. These molecules are 7-aryl-2,12-bis(9-acridinyl)dibenz(c,h)acridines, which when unsymmetrically substituted exhibit atropisomerism. In addition to being rigid and providing a ca. 7 A interchromophore distance, the dibenz(c,h)acridine spacer is the first to enforce a syn cofacial orientation of the complexing chromophores. 'H NMR studies indicate

  新的非大环受体分子 1 和 7 已被合成，它们能够充当分子镊子。这些分子是 7-芳基-2,12-双（9-吖啶基）二苯并（c，h）吖啶，当不对称取代时表现出阻转异构现象。除了刚性和提供约。7 发色团间距离，二苯并（c，h）吖啶间隔物是第一个强制复合发色团同步共面取向的间隔物。'H NMR 研究表明 1 和 7 有开放的裂缝。这些预先组织的裂缝在 CDCl3 中与 2,4,7-三硝基芴酮 (TNF) 形成高度定向的包合物，由 1 H NMR 监测。络合具有强的电子供体-受体成分。因此，TNF 的结合常数取决于宿主的 *-碱性，范围从 149 M-' 对于叔丁基取代的 7b 到 697 M-) 对于二甲氨基取代的 7f (CDCl)。单吖啶和柔韧的双吖啶在相同条件下与 TNF 的结合非常弱（Kd,,,, < 5 Ml）。
• Single-Molecule Magnetoluminescence from a Spatially Confined Persistent Diradical Emitter
  作者：Ryota Matsuoka、Shojiro Kimura、Tomoaki Miura、Tadaaki Ikoma、Tetsuro Kusamoto

  DOI：10.1021/jacs.3c01076

  日期：2023.6.28

  have been limited to systems in which radicals are randomly doped in host crystals or polymerized through metal complexation. This study shows that a covalently linked luminescent radical dimer (diradical) can exhibit ML as a single-molecular property. This facilitates detailed elucidation of the requirements for and mechanisms of ML in radicals and can aid the rational design of ML-active radicals

  发光自由基是一类新兴材料，由于其开壳层电子结构，具有闭壳层分子所没有的独特光功能。特别有前途的是自由基的自旋和发光相关的光函数。例如，当磁场可以影响发光（即磁致发光，ML）时。这些光函数在自旋光子学这一新科学中可能很有用。然而，之前对自由基中ML的观察仅限于自由基随机掺杂在主体晶体中或通过金属络合聚合的系统。这项研究表明，共价连接的发光自由基二聚体（双自由基）可以表现出 ML 作为单分子特性。