tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tellurophene | 1613509-24-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tellurophene
• 英文别名: 2,3,4,5-tetrakis(pinacolato)tellurophene；4,4,5,5-Tetramethyl-2-[2,4,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tellurophen-3-yl]-1,3,2-dioxaborolane
• CAS: 1613509-24-2
• 化学式: C₂₈H₄₈B₄O₈Te
• 分子量: 683.528
• InChiKey: XZKWQOKSJAEAKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tellurophene 在 水 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以75%的产率得到3-pinacolatotellurophene
  参考文献：
  名称：

  关于碲化物的溴化物和萘酚硼酸酯基团的选择性放置：光电子应用的新组成部分

  摘要：

  Selective protodeboronation of preformed phosphorescent di- and tetrapinacolboronate (BPin)-substituted tellurophenes controllably affords new tellurophene products that show photoluminescence or, in the case of tellurophenes lacking BPin groups at the 2,5-positions, nonemissive behavior; for comparison the protodeboronation of select thiophene and selenophenes is also reported. The resulting BPin-appended tellurophenes are promising candidates for postfunctionalization via Suzuki-Miyaura cross-coupling and can be effectively converted into their respective brominated tellurophene counterparts via treatment with excess CuBr2. It is expected from prior studies that these brominated tellurophenes will be suitable building blocks (and monomers) for the preparation of conjugated oligomers and polymers featuring narrower optical band gaps in relation to their lighter chalcogen analogues; in this regard preliminary Stille coupling chemistry is reported.

  DOI：

  10.1021/acs.organomet.6b00362
• 作为产物：
  描述：

  bis(cyclopentadienyl)zirconium(1,2-diylidenetetra{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methanide}) 在 6,6-dichloro-6H-6l4-[1,2,5]telluradiazolo[2,3-a:5,4-a']dipyridine-5,7-diium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以2.577 g的产率得到tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tellurophene
  参考文献：
  名称：

  关于碲化物的溴化物和萘酚硼酸酯基团的选择性放置：光电子应用的新组成部分

  摘要：

  Selective protodeboronation of preformed phosphorescent di- and tetrapinacolboronate (BPin)-substituted tellurophenes controllably affords new tellurophene products that show photoluminescence or, in the case of tellurophenes lacking BPin groups at the 2,5-positions, nonemissive behavior; for comparison the protodeboronation of select thiophene and selenophenes is also reported. The resulting BPin-appended tellurophenes are promising candidates for postfunctionalization via Suzuki-Miyaura cross-coupling and can be effectively converted into their respective brominated tellurophene counterparts via treatment with excess CuBr2. It is expected from prior studies that these brominated tellurophenes will be suitable building blocks (and monomers) for the preparation of conjugated oligomers and polymers featuring narrower optical band gaps in relation to their lighter chalcogen analogues; in this regard preliminary Stille coupling chemistry is reported.

  DOI：

  10.1021/acs.organomet.6b00362

文献信息

• Coaxing Solid-State Phosphorescence from Tellurophenes
  作者：Gang He、William Torres Delgado、Devon J. Schatz、Christian Merten、Arash Mohammadpour、Lorenz Mayr、Michael J. Ferguson、Robert McDonald、Alex Brown、Karthik Shankar、Eric Rivard

  DOI：10.1002/anie.201307373

  日期：2014.4.25

  The synthesis of the first examples of tellurophenes exhibiting phosphorescence in the solid state and under ambient conditions (room temperature and in air) is reported. Each of these main‐group‐element‐based emitters feature pinacolboronates (BPin) as ring‐appended side groups. The nature of the luminescence observed was also investigated using computational methods.

  报道了在固态和在环境条件下（室温和空气中）显示出磷光的碲二酚的第一实施例的合成。这些基于主族元素的发射体均具有频哪醇硼酸酯（BPin）作为环附加侧基的特征。还使用计算方法研究了观察到的发光的性质。