4,5-dibromo-9,10-ditriflatopyrene | 1320215-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4,5-dibromo-9,10-ditriflatopyrene
• 英文别名: 4,5-dibromo-9,10-bis(trifluoromethylsulfonyloxy)pyrene；[9,10-Dibromo-5-(trifluoromethylsulfonyloxy)pyren-4-yl] trifluoromethanesulfonate；[9,10-dibromo-5-(trifluoromethylsulfonyloxy)pyren-4-yl] trifluoromethanesulfonate
• CAS: 1320215-17-5
• 化学式: C₁₈H₆Br₂F₆O₆S₂
• 分子量: 656.172
• InChiKey: WPYZSQKFLMFNIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tributyl(5-butylthiophen-2-yl)stannane 、 4,5-dibromo-9,10-ditriflatopyrene 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 以42%的产率得到4,5,9,10-tetrakis(5-n-butylthien-2-yl)pyrene
  参考文献：
  名称：

  Saddle Shaped Hexaaryl[a,c,fg,j,l,op]tetracenes from 4,5,9,10-Tetrafunctionalized Pyrenes

  摘要：

  A new K-region functionalized pyrene is presented which was used as a building block for the straightforward synthesis of hexaaryl[a,c,fg,j,l, op]tetracene via fourfold Stille coupling and subsequent cyclodehydrogenation. Electronic properties and crystal structures are provided and reveal a saddle conformation for the curved hexaarylated tetracenes.(1)

  DOI：

  10.1021/ol2016516
• 作为产物：
  描述：

  9,10-dibromopyrene-4,5-dione 在 吡啶 、 sodium dithionite 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4,5-dibromo-9,10-ditriflatopyrene
  参考文献：
  名称：

  Saddle Shaped Hexaaryl[a,c,fg,j,l,op]tetracenes from 4,5,9,10-Tetrafunctionalized Pyrenes

  摘要：

  A new K-region functionalized pyrene is presented which was used as a building block for the straightforward synthesis of hexaaryl[a,c,fg,j,l, op]tetracene via fourfold Stille coupling and subsequent cyclodehydrogenation. Electronic properties and crystal structures are provided and reveal a saddle conformation for the curved hexaarylated tetracenes.(1)

  DOI：

  10.1021/ol2016516

文献信息

• A kinetically protected pyrene: molecular design, bright blue emission in the crystalline state and aromaticity relocation in its dicationic species
  作者：Akinobu Matsumoto、Mitsuharu Suzuki、Daiki Kuzuhara、Junpei Yuasa、Tsuyoshi Kawai、Naoki Aratani、Hiroko Yamada

  DOI：10.1039/c4cc03645j

  日期：——

  The aromaticity of sterically congested tetranaphthylpyrene relocates from the biphenyl part to the naphthalene unit upon the two-electron oxidation.

  在空间位阻较大的四萘基芘分子中，经过两电子氧化后，芳香性从联苯部分转移到萘单元。
• Toward the<i>peri</i>-Pentacene Framework
  作者：Lukas Zöphel、Reinhard Berger、Peng Gao、Volker Enkelmann、Martin Baumgarten、Manfred Wagner、Klaus Müllen

  DOI：10.1002/chem.201302859

  日期：2013.12.23

  peri‐pentacene is predicted to suffer from high instability and reactivity. Therefore, a recently developed 4,5,9,10‐tetrafunctionalization of pyrene was utilized to build up a planar and a dragonfly‐shaped derivative in five steps, which only differ in the two outer bonds between the peripheral benzene rings. The planar tetraketone could only be dissolved in strong acids upon protonation, which limited the use

  基于现代芘化学上，向着合成新路线周边五苯框架开发的。首先，tetraketo形式稳定的前驱体有针对性的，因为全芳族围预计并五苯具有很高的不稳定性和反应性。因此，最近开发的4，的4,5,9,10-四官能团被用来分五个步骤构建平面和蜻蜓形的衍生物，仅在外围苯环之间的两个外部键不同。平面四酮只能在质子化后溶于强酸中，这限制了分析方法的使用。相比之下，蜻蜓形的形式表现出优异的有机溶解性。核磁共振波谱的深入研究表明溶液中既有熵异构体并存。通过UV / Vis光谱法和循环伏安法分析光学和电子性质。为了实现芳族共轭，通过使用四丁基硼氢化铵逐步还原溶液。
• Saddle Shaped Hexaaryl[<i>a,c,fg,j,l,op</i>]tetracenes from 4,5,9,10-Tetrafunctionalized Pyrenes
  作者：Lukas Zöphel、Volker Enkelmann、Ralph Rieger、Klaus Müllen

  DOI：10.1021/ol2016516

  日期：2011.9.2

  A new K-region functionalized pyrene is presented which was used as a building block for the straightforward synthesis of hexaaryl[a,c,fg,j,l, op]tetracene via fourfold Stille coupling and subsequent cyclodehydrogenation. Electronic properties and crystal structures are provided and reveal a saddle conformation for the curved hexaarylated tetracenes.(1)