6,13-di-tert-butyl-9,10-dihydro-9,10[1',2']benzenoanthra-1,4-quinone | 632621-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6,13-di-tert-butyl-9,10-dihydro-9,10[1',2']benzenoanthra-1,4-quinone
• 英文别名: 6,10-di(tert-butyl)triptycene-1,4-quinone；11,17-Ditert-butylpentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),4,9(14),10,12,15(20),16,18-octaene-3,6-dione；11,17-ditert-butylpentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),4,9(14),10,12,15(20),16,18-octaene-3,6-dione
• CAS: 632621-49-9
• 化学式: C₂₈H₂₈O₂
• 分子量: 396.529
• InChiKey: MTVVUUPLDMLMKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,13-di-tert-butyl-9,10-dihydro-9,10[1',2']benzenoanthra-1,4-quinone 在 sodium dithionite 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以77%的产率得到6,11-di(tert-butyl)triptycene-1,4-hydroquinone
  参考文献：
  名称：

  Molecular Design of Free Volume as a Route to Low-κ Dielectric Materials

  摘要：

  Polymers incorporating the triptycene subunit were prepared for the molecular-level design of low dielectric constant (low-kappa) materials that can be used to manufacture faster integrated circuits. Triptycenes having restricted rotation by multiple point attachment to the polymer backbone are shown to introduce free volume into the films, thereby lowering their dielectric constants. The triptycene containing polymers exhibit a number of desirable properties including low-water absorption and high thermal stability. Systematic studies wherein comparisons are made between two separate classes of triptycene polymers and their non-triptycene containing analogues demonstrate that proper insertion of triptycenes into a polymer backbone can give rise to a reduction in the material's dielectric constant while also improving its mechanical properties. These characteristics are desired by the semiconductor industry for the next generation of microprocessors and memory to provide insulation of the increasingly shrinking features.

  DOI：

  10.1021/ja0360945
• 作为产物：
  描述：

  2,6-二-叔丁基蒽 、 对苯醌 在 溶剂黄146 作用下， 以 2-甲基丁烷 为溶剂， 反应 5.7h， 以60%的产率得到6,13-di-tert-butyl-9,10-dihydro-9,10[1',2']benzenoanthra-1,4-quinone
  参考文献：
  名称：

  单分散低聚（1,4-亚苯基亚乙炔基-alt-1,4-三亚甲基亚乙炔基）s的合成

  摘要：

  单分散低聚（合成p -phenyleneethynylene）类8A Ñ具有交替的2,5-二己基-1,4-亚苯基和-6,14-二-叔-丁基-1,4- triptycylene单元和正交保护的炔端基是报告。从6,14-二叔丁基-1-（2-三异丙基甲硅烷基乙炔基）-4-（2-三甲基甲硅烷基乙炔基）三茂烯（5a），1,4-二己基-2,5-二碘苯（10）和1， 4-二己基-2-碘-5-（3-羟基丙-1-炔基）苯（9），通过以炔基-芳基（Sonogashira-Hagihara）偶联为关键反应的部分发散-收敛路线，制备了具有最多四个重复单元（即八个亚苯基亚乙炔基单元）的低聚物。由三苯并二苯醌通过添加2-三烷基甲硅烷基乙炔基锂，还原和同时消除水，将苯酚转化成三氟甲磺酸酯，以及最后由Pd / Cu催化的与三烷基甲硅烷基乙炔的偶联来制备起始化合物5a。严格的发散-收敛途径对关键化合物的相似途径是6,14-

  DOI：

  10.1021/jo9009744

文献信息

• Conjugation Enhancement of Intramolecular Exciton Migration in Poly(<i>p</i>-phenylene ethynylene)s
  作者：Evgueni E. Nesterov、Zhengguo Zhu、Timothy M. Swager

  DOI：10.1021/ja051936g

  日期：2005.7.1

  Efficient energy migration in conjugated polymers is critical to their performance in photovoltaic, display, and sensor devices. The ability to precisely control the polymer conformation is a key issue for the experimental investigations and deeper understanding of the nature of this process. We make use of specially designed iptycene-containing poly(p-phenylene ethynylene)s that display chain-extended conformations when dissolved in nematic liquid crystalline solvents. In these solutions, the polymers show a substantial enhancement in the intrachain exciton migration rate, which is attributed to their increased conjugation length and better alignment. The organizational enhancement of the energy transfer efficiency, as determined by site-selective emission from lower energy traps at the polymer termini, is accompanied by a significant increase of the fluorescence quantum yield. The liquid crystalline phase is a necessary requirement for these phenomena to occur, and when the temperature was increased above the nematic-isotropic transition, we observed a dramatic reduction of the energy transfer efficiency and fluorescence quantum yield. The ability to improve the exciton migration efficiency through precise control of the polymer structure with liquid crystalline solutions demonstrates the importance of a polymer's conformation for energy transfer, and provides a way to improve the energy transporting performance of conjugated polymers.
• Synthesis of Monodisperse Oligo(1,4-phenyleneethynylene-alt-1,4-triptycyleneethynylene)s
  作者：Daniela Maag、Tilman Kottke、Miriam Schulte、Adelheid Godt

  DOI：10.1021/jo9009744

  日期：2009.10.16

  The synthesis of monodisperse oligo(p-phenyleneethynylene)s 8an with alternating 2,5-dihexyl-1,4-phenylene and 6,14-di-tert-butyl-1,4-triptycylene units and orthogonally protected alkyne end groups is reported. Starting from 6,14-di-tert-butyl-1-(2-triisopropylsilylethynyl)-4-(2-trimethylsilylethynyl)triptycene (5a), 1,4-dihexyl-2,5-diiodobenzene (10), and 1,4-dihexyl-2-iodo-5-(3-hydroxyprop-1-ynyl)benzene

  单分散低聚（合成p -phenyleneethynylene）类8A Ñ具有交替的2,5-二己基-1,4-亚苯基和-6,14-二-叔-丁基-1,4- triptycylene单元和正交保护的炔端基是报告。从6,14-二叔丁基-1-（2-三异丙基甲硅烷基乙炔基）-4-（2-三甲基甲硅烷基乙炔基）三茂烯（5a），1,4-二己基-2,5-二碘苯（10）和1， 4-二己基-2-碘-5-（3-羟基丙-1-炔基）苯（9），通过以炔基-芳基（Sonogashira-Hagihara）偶联为关键反应的部分发散-收敛路线，制备了具有最多四个重复单元（即八个亚苯基亚乙炔基单元）的低聚物。由三苯并二苯醌通过添加2-三烷基甲硅烷基乙炔基锂，还原和同时消除水，将苯酚转化成三氟甲磺酸酯，以及最后由Pd / Cu催化的与三烷基甲硅烷基乙炔的偶联来制备起始化合物5a。严格的发散-收敛途径对关键化合物的相似途径是6,14-
• Molecular Design of Free Volume as a Route to Low-κ Dielectric Materials
  作者：Timothy M. Long、Timothy M. Swager

  DOI：10.1021/ja0360945

  日期：2003.11.1

  Polymers incorporating the triptycene subunit were prepared for the molecular-level design of low dielectric constant (low-kappa) materials that can be used to manufacture faster integrated circuits. Triptycenes having restricted rotation by multiple point attachment to the polymer backbone are shown to introduce free volume into the films, thereby lowering their dielectric constants. The triptycene containing polymers exhibit a number of desirable properties including low-water absorption and high thermal stability. Systematic studies wherein comparisons are made between two separate classes of triptycene polymers and their non-triptycene containing analogues demonstrate that proper insertion of triptycenes into a polymer backbone can give rise to a reduction in the material's dielectric constant while also improving its mechanical properties. These characteristics are desired by the semiconductor industry for the next generation of microprocessors and memory to provide insulation of the increasingly shrinking features.