2,2'-(4,5,6,7-tetrahydro-2-benzotellurophene-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) | 1428449-05-1

• 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: 2,2'-(4,5,6,7-tetrahydro-2-benzotellurophene-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 英文别名: 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-4H-cyclopenta-[c]tellurophene；4,4,5,5-Tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5,6,7-tetrahydro-2-benzotellurophen-1-yl]-1,3,2-dioxaborolane
• CAS: 1428449-05-1
• 化学式: C₂₀H₃₂B₂O₄Te
• 分子量: 485.694
• InChiKey: YGMHBVOPRRYZKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-(4,5,6,7-tetrahydro-2-benzotellurophene-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 在 copper(ll) bromide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  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(h5-cyclopentadienyl)-1,3-bis(4,4,5,5-tetrametyhl-1,3,2-dioxaborolan-2-yl)-4,5,6,7-tetrahydro-2H-benzo[c]zirconacyclopentadiene 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2.588 g的产率得到2,2'-(4,5,6,7-tetrahydro-2-benzotellurophene-1,3-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
  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

• Rapid access to (cycloalkyl)tellurophene oligomer mixtures and the first poly(3-aryltellurophene)
  作者：Bruno T. Luppi、Robert McDonald、Michael J. Ferguson、Lingzi Sang、Eric Rivard

  DOI：10.1039/c9cc07512g

  日期：——

  polymerized to afford new low Eg oligomers and polymers. Specifically, mixtures of (cycloalkyl)tellurophene oligomers (of 5 to 12 repeat units) with ring-fused 5- and 6-membered cyclic side chains were prepared via Yamamoto coupling, with a dramatic narrowing of band gap noted when less bulky 5-membered cycloalkyl side groups were present, due to enhanced tellurophene ring coplanarity. Grignard metathesis

  聚tellurophenes代表了新兴的π共轭聚合物，它们具有柔性电子学的重要特性，例如较窄的HOMO-LUMO间隙（E g）和电荷迁移率比其普遍存在的聚噻吩对应物大几个数量级。在本文中，我们使用连接到碲代芬支架上的频哪醇硼酸酯（BPin）基团的反应性来直接制备新的2,5-二碘代单体，然后将其聚合以提供新的低E g低聚物和聚合物。具体地，制备具有稠环的5-和6-元环侧链的（环烷基）碲低聚物（5〜12个重复单元）的混合物通过YamaMOto偶联，由于增强了碲苯环的共平面性，当存在体积较小的5元环烷基侧基时，带隙显着缩小。Grignard复分解（GRIM）也用于获得具有94％区域规则性，E g为1.3 eV的低Eg并在约40°C时开始吸光的第一个聚（3-芳基鸟嘌呤）。1000纳米
• 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。
• The Marriage of Metallacycle Transfer Chemistry with Suzuki–Miyaura Cross-Coupling To Give Main Group Element-Containing Conjugated Polymers
  作者：Gang He、Le Kang、William Torres Delgado、Olena Shynkaruk、Michael J. Ferguson、Robert McDonald、Eric Rivard

  DOI：10.1021/ja402242z

  日期：2013.4.10

  A versatile and general synthetic route for the synthesis of conjugated main group element-based polymers, previously inaccessible by conventional means, is reported. These polymers contain five-membered chalcogenophene rings based on S, Se, and Te, and we demonstrate that optoelectronic properties can be readily tuned via controlled atom substitution chemistry. In addition, regioregular hybrid th

  报道了一种通用的通用合成路线，用于合成基于共轭主族元素的聚合物，以前无法通过常规手段获得。这些聚合物包含基于 S、Se 和 Te 的五元硫属元素环，并且我们证明可以通过受控原子取代化学轻松调整光电特性。此外，合成了区域规则杂化噻吩-硒吩-碲烯和硒吩-芴共聚物，以进一步说明所提出的金属环转移/交叉偶联聚合方法的范围。
• Using boryl-substitution and improved Suzuki–Miyaura cross-coupling to access new phosphorescent tellurophenes
  作者：Christina A. Braun、Nicole Martinek、Yuqiao Zhou、Michael J. Ferguson、Eric Rivard

  DOI：10.1039/c9dt02095k

  日期：——

  di(isopropoxy)boryl –B(OiPr)2 tellurophene precursor is described, from which several previously inaccessible phosphorescent borylated tellurophenes are formed via exchange of the –OiPr groups. One such tellurophene Mes(iPrO)B-Te-6-B(OiPr)Mes, bearing a sterically encumbered mesityl (Mes) substituent at each boron center, exhibits bright yellow-orange phosphorescence in the solid state at room temperature

  描述了一种新的二（异丙氧基）硼基–B（O i Pr）2碲二苯醚前体，通过–O i Pr基团的交换，从中形成了几个以前难以接近的磷光化硼酸化碲二苯醚。在每个硼中心带有一个空间阻碍的均三甲苯基（Mes）取代基的一种这样的碲二苯醚Mes（i PrO）B-Te-6-B（O i Pr）Mes在室温下以固态呈现明亮的橙黄色磷光在已知的淬灭剂O 2的存在下。此外，使用预催化剂Cl（XPhos）Pd（氨基联苯）检测了新制备的硼酸化碲二苯醚与测试底物2-溴噻吩之间的Suzuki-Miyaura交叉偶联。尽管更多的电子缺陷性的硼基（例如儿茶酚硼基（–Bcat））会产生显着的原去硼硼烷，而不是有效的C–C键形成，但从碲苯中注意到，所需噻吩封端的碲基噻吩噻吩-Te -6-噻吩基的有效形成是容易实现的。频哪醇硼酸酯（–Bpin）和1,8-萘二甲氨基硼酸酯（–Bdan）官能团。这些发现为通过芳烃有效合成芳基碲二酚和聚碲二酚打开了大门。