3,7-di([2,2'-bithiophen]-5-yl)-5-(2,4,6-tri-tert-butylphenyl)dibenzo[b,f]borepin | 1279129-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,7-di([2,2'-bithiophen]-5-yl)-5-(2,4,6-tri-tert-butylphenyl)dibenzo[b,f]borepin
• 英文别名: 2-thiophen-2-yl-5-[2-(5-thiophen-2-ylthiophen-2-yl)-11-(2,4,6-tritert-butylphenyl)benzo[b][1]benzoborepin-9-yl]thiophene
• CAS: 1279129-92-8
• 化学式: C₄₈H₄₇BS₄
• 分子量: 762.976
• InChiKey: CLGCRWKWDWRRRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.49
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴-2-碘甲苯 在 四(三苯基膦)钯 正丁基锂 、 potassium tert-butylate 、 三氯化硼 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 104.67h， 生成 3,7-di([2,2'-bithiophen]-5-yl)-5-(2,4,6-tri-tert-butylphenyl)dibenzo[b,f]borepin
  参考文献：
  名称：

  [EN] BORON-CONTAINING PI-ELECTRON MATERIALS INCORPORATING FORMALLY AROMATIC AND NEUTRAL BOREPIN RINGS
  [FR] MATÉRIAUX À PI-ÉLECTRONS CONTENANT DU BORE INCORPORANT DES CYCLES BORÉPINE FORMELLEMENT AROMATIQUES ET NEUTRES

  摘要：

  公开号：

  WO2011127383A3

文献信息

• Boron-Containing PI-Electron Materials Incorporating Formally Aromatic and Neutral Borepin Rings
  申请人：Tovar John Dayton

  公开号：US20130059996A1

  公开（公告）日：2013-03-07

  The synthesis, functionalization and characterization of borepin-based extended pi-electron molecules is disclosed. Bulky substituents shielded the vacant boron p-orbitals thus allowing synthetic manipulation and purification under ambient lab conditions. The presently disclosed borepin-containing compounds displayed reversible cathodic electrochemistry and can be viewed as n-type analogues to bent acene hydrocarbons.

  揭示了基于硼环的扩展π电子分子的合成、功能化和表征。笨重的取代基屏蔽了空的硼p轨道，从而允许在常温实验室条件下进行合成操作和纯化。目前披露的含硼环化合物显示出可逆的阴极电化学性质，可以看作是弯曲芘烃的n型类似物。
• Functionalized Dibenzoborepins as Components of Small Molecule and Polymeric π-Conjugated Electronic Materials
  作者：Anthony Caruso、John D. Tovar

  DOI：10.1021/jo2001726

  日期：2011.4.1

  We present the synthesis and characterization of dibenzo[b,f]borepins (DBBs) functionalized at the para and meta position with respect to the boron center in order to understand how regiochemical issues influence photophysical and electrochemical properties. An expanded synthetic repertoire is presented, using palladium catalysis (to perform Stifle, Suzuki, Buchwald- Hartwig, and Sonogashira cross-coupling reactions) and lithium halogen exchange to synthesize a series of extended a-conjugated DBBs. These chemistries are enabled by the use of a sterically bulky Mes* (2,4,6-tri-tert-butylphenyl) group on boron and the inclusion of reactive bromide handles on the DBB core. Photophysical, electrochemical, and computational analyses of these compounds indicate that relative to the protio-DBB the installation of groups at the meta positions decreases the optical band gap while para substitution raises the electron affinity of the system. Thus, both the HOMO-LUMO gap and specific frontier molecular orbital levels can be tuned by the installation of different conjugated substituents.