1-(4-bromophenyl)-1,2-closo-carborane | 12081-05-9

• 英文名称: 1-(4-bromophenyl)-1,2-closo-carborane
• 英文别名: 1-(4-bromophenyl)-o-carborane；p-(o-carboranyl)-bromobenzene；1-(4-Br-C6H4)-1,2-C2HB10H10；4-bromo-o-carboranylbenzene；p-(o-carboran-1-yl)bromobenzene
• CAS: 12081-05-9
• 化学式: C₈H₁₅B₁₀Br
• 分子量: 299.221
• InChiKey: ROBCGJNLQXUFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-1,2-closo-carborane 、 2-(三甲基甲锡烷基)吡啶 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 2-{p-(2-H-1,2-carboran-1-yl)phenyl}pyridine
  参考文献：
  名称：

  Iridium Cyclometalates with Tethered o-Carboranes: Impact of Restricted Rotation of o-Carborane on Phosphorescence Efficiency

  摘要：

  Iridium(III) cyclometalates (1c and 2c) in which the two carborane units on the 4- or 5-positions of 2-phenylpyridine (ppy) ligands were tethered by an alkylene linker were prepared to investigate the effect of free rotation of o-carborane on phosphorescence efficiency. In comparison with the unlinked complex, tethering the o-carboranes to the 5-positions of ppy ligands (2c) enhanced phosphorescence efficiency by over 30-fold in polar medium (Phi(PL) = 0.37 vs 0.011 in THF), while restricting the rotation of o-carborane at the 4-positions (1c) negatively affected the phosphorescence efficiency. The different effects of restricted rotation of o-carborane on phosphorescence efficiency were likely a result of the different variations of the carboranyl C-C bond distances in the excited state.

  DOI：

  10.1021/jacs.5b04576
• 作为产物：
  描述：

  (4-溴苯基)乙炔 、 癸硼烷 在 乙硫醚 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 1-(4-bromophenyl)-1,2-closo-carborane
  参考文献：
  名称：

  邻甲硼烷取代对环金属铱配合物的磷光颜色调节

  摘要：

  杂（Ç ∧ Ñ）2的Ir（ACAC）（ç ∧ Ñ = 4- CBppy（1）; 5- CBppy（2），4- fppy（4）CB =邻-methylcarborane; PPY = 2-苯基-C 2，N，4- fppy = 2-（4-氟苯基）吡啶-C 2，N，ACAC =乙酰丙酮化物）的制备和表征复合物。虽然1展示了一个以531 nm为中心的磷光带，但与未取代的磷光带相比，该光带发生了红移（ppy）2 Ir（acac）（3）（λem = 516 nm），发射光谱2显示在503 nm处出现蓝移带。与4-氟取代的4（λem = 493 nm）的发射谱带的比较表明，1中存在显着的红移。电化学和理论研究表明，尽管在苯环的4位上进行碳硼烷取代会降低3 MLCT能量，这主要归因于最低的未占据分子轨道（LUMO）离域化，从而将最低的三重态1定义为[d π（IR）→π*（ç ∧ ñ）]由于具有3 MLCT

  DOI：

  10.1021/ic3015699

文献信息

• Electron-donating abilities and luminescence properties of tolane-substituted nido-carboranes
  作者：Kenta Nishino、Yasuhiro Morisaki、Kazuo Tanaka、Yoshiki Chujo

  DOI：10.1039/c7nj02438j

  日期：——

  The luminescence properties of nido-carborane (7,8-dicarba-nido-carborate anion)-substituted tolane derivatives were investigated. It was shown that the nido-carborane unit acted as an electron-donating group in all derivatives, and their emission colors can be tuned by the substituents at the tolane moiety. According to theoretical investigation, it was proposed that frontier orbitals were distinctly

  研究了Nido -carborane（7,8-dicarba-nido - carborate anion）取代的tolane衍生物的发光特性。结果表明，在所有衍生物中，氨基-碳硼烷单元均作为供电子基团，并且其发射颜色可以通过甲苯部分的取代基进行调节。根据理论研究，提出边界轨道被在Nido- carborane单元上的甲基取代基的扭曲结构明显地分开。因此，在吸收光谱中，由于禁止了HOMO-LUMO跃迁而获得了急剧的变化。这些结构和电取代基效应应作为基于以下条件设计光电子材料的良好指南尼多-碳硼烷。
• Dual emission <i>via</i> remote control of molecular rotation of <i>o</i>-carborane in the excited state by the distant substituents in tolane-modified dyads
  作者：Kenta Nishino、Kyoya Uemura、Kazuo Tanaka、Yoshiki Chujo

  DOI：10.1039/c7nj04283c

  日期：——

  tolane-o-carborane dyad having various substituents at the tolane moiety. A series of o-carborane dyads were synthesized and characterized. It was shown that their luminescent colors were tuned by the substituents at the tolane moiety. Some derivatives with strong electron-donating substituents such as –OMe, –(OMe)3 and –NMe2 simultaneously showed dual emission bands from the locally-excited (LE) state in the parallel

  基于在甲苯部分上具有各种取代基的甲苯-邻-碳氢化合物二聚体，报道了双发射性质及其对环境的响应性。合成并表征了一系列邻-碳二烷。结果表明，它们的发光颜色被甲苯部分的取代基所调节。一些带有强电子给体取代基的衍生物，例如–OMe，–（OMe）3和–NMe 2同时在辛烷溶液中以平行构象显示了来自本地激发（LE）状态的双发射带，在扭曲的状态下显示了分子内电荷转移（ICT）的双发射带。此外，两个发射带之间的强度比通过加热而变化。这些结果意味着可以通过电子共轭通过取代基上的电子给体性质的程度来调节邻-甲硼烷二元体系的电子性质。
• Highly Emissive Organic Single-Molecule White Emitters by Engineering <i>o</i> -Carborane-Based Luminophores
  作者：Deshuang Tu、Pakkin Leong、Song Guo、Hong Yan、Changsheng Lu、Qiang Zhao

  DOI：10.1002/anie.201703862

  日期：2017.9.11

  The development of organic single‐molecule solid‐state white emitters holds a great promise for advanced lighting and display applications. Highly emissive single‐molecule white emitters were achieved by the design and synthesis of a series of o‐carborane‐based luminophores. These luminophores are able to induce multiple emissions to directly emit high‐purity white light in solid state. By tuning both

  有机单分子固态白光发射器的发展对于高级照明和显示应用具有广阔的前景。通过设计和合成一系列o来获得高发射率的单分子白光发射器基于碳烷的发光体。这些发光体能够诱发多种发射，从而以固态直接发射高纯度白光。通过调整分子和聚集体的结构，实现了显着提高的白光效率（绝对量子产率为67％），这是固态的已知有机单分子白光发射器中的最高值。在一个分子骨架中成功完成了从H-到J-和交叉堆积聚集体以及分子间氢键的堆积模式的微调。这些对于固态高发射白光至关重要。
• A carborane-triggered metastable charge transfer state leading to spontaneous recovery of mechanochromic luminescence
  作者：Deshuang Tu、Pakkin Leong、Zhihong Li、Rongrong Hu、Chao Shi、Kenneth Yin Zhang、Hong Yan、Qiang Zhao

  DOI：10.1039/c6cc07093k

  日期：——

  Spontaneous recovery of mechanochromic luminescence was realized by carborane-functionalized anthracene derivatives.

  通过对碳硼烷功能化的蒽衍生物进行处理，实现了机械致变色发光的自发恢复。
• Excitation spectroscopic and synchronous fluorescence spectroscopic analysis of the origin of aggregation-induced emission in <i>N</i>,<i>N</i>-diphenyl-1-naphthylamine-<i>o</i>-carborane derivatives
  作者：So-Yoen Kim、Jong-Dae Lee、Yang-Jin Cho、Mi Rang Son、Ho-Jin Son、Dae Won Cho、Sang Ook Kang

  DOI：10.1039/c8cp02603c

  日期：——

  Excitation spectroscopy is one of the most suitable methods to classify the aggregation patterns in AIE.

  激发光谱是分类AIE聚集模式最合适的方法之一。