tris(4-bromophenyl)(phenyl)silane | 1201099-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tris(4-bromophenyl)(phenyl)silane
• 英文别名: Phenyltris(4-bromophenyl)silane；tris(4-bromophenyl)-phenylsilane
• CAS: 1201099-09-3
• 化学式: C₂₄H₁₇Br₃Si
• 分子量: 573.196
• InChiKey: IQRYMGAVQCQZBN-UHFFFAOYSA-N

物化性质

• 沸点：
  524.8±50.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tris(4-bromophenyl)(phenyl)silane 在 三氯异氰尿酸 、 叔丁基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 5.67h， 生成 tris[4-(diisopropylhydroxysilyl)phenyl]phenylsilane
  参考文献：
  名称：

  Cyclic trimer of tripodal trisilanol with new hydrogen bonding motif

  摘要：

  Tripodal trisilanols tris[4-(diisopropylhydroxysilyl)phenyll-phenylsilane and -methylsilane (3a and 3h) as well as 1,3,5-tris(diisopropylhydroxysilylmethyl)-2,4,6-triethylbenzene (3c) were synthesized by treatment of the corresponding tribromide with alkyl lithium or magnesium, followed by silylation with diisopropylchlorosilane, halogenation with trichloroisocyanuric acid (TCCA) or N-bromosuccinimide (NBS), and subsequent alkaline hydrolysis.X-ray analyses of the tripodal silanols (3a c) revealed the first example of a cyclic trimer in the silanol hydrogen bonding pattern. The connectivity of silanol hydrogen bonding in the silanol products was found to produce a 1D network, based on X-ray packing structures. Substituent effects for this new mode of silanol hydrogen bonding were estimated by hydrogen bonding energy [Efi_bond] based on DFT calculations. Other new silanol hydrogen bonding features were characterized using Bader's Atom in Molecules (AIM) analyses. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.09.041
• 作为产物：
  描述：

  1,4-二溴苯 、 苯基三乙氧基硅烷 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以93%的产率得到tris(4-bromophenyl)(phenyl)silane
  参考文献：
  名称：

  多孔烃笼的合成后改性得到离散的 Co24 有机金属络合物**

  摘要：

  使用不可逆的炔偶联反应合成了坚固的多孔笼。与八羰基二钴的反应得到12个炔单元的彻底金属化，从而在单锅中得到笼的Co 24 (CO) 72加合物。

  DOI：

  10.1002/chem.202200958

文献信息

• Novel violet emitting material synthesized by stepwise chemical reactions
  作者：Xiangyang Tang、Liang Yao、He Liu、Fangzhong Shen、Shitong Zhang、Yunan Zhang、Huanhuan Zhang、Ping Lu、Yuguang Ma

  DOI：10.1039/c4tc00456f

  日期：——

  In this paper, we report the design and synthesis of a novel bipolar violet emitting molecule CzPySiSF. The carbazole and pyridine moieties are employed to facilitate charge injection and balance carrier transport, whereas the spirofluorene is used as the violet emitter. The three functional groups, i.e., carbazole, pyridine and spirofluorene, are connected to tetraphenylsilane in a stepwise fashion using classical coupling reactions such as Suzuki and Ullmann. The resultant bipolar molecule CzPySiSF exhibits very stable thermal properties and a uniform amorphous morphology. The introduction of spirofluorene greatly enhances the fluorescence quantum efficiency of the molecule; moreover the PL spectrum of CzPySiSF in THF is mainly located in the violet region. The EL spectrum of CzPySiSF matches well with the PL spectrum with a maximum at 408 nm. The violet OLED of CzPySiSF exhibits the maximum external quantum efficiency of 0.59%.

  本文报道了一种新型双极性紫光发射分子CzPySiSF的设计与合成。咔唑和吡啶基团用于促进电荷注入和平衡载流子传输，而螺二芴则作为紫光发射体。三个功能团，即咔唑、吡啶和螺二芴，通过经典的偶联反应如铃木反应和乌尔曼反应逐步连接到四苯基硅烷上。所得双极性分子CzPySiSF表现出非常稳定的热性质和均匀的非晶形态。螺二芴的引入大大提高了该分子的荧光量子效率；此外，CzPySiSF在THF中的PL光谱主要位于紫光区域。CzPySiSF的EL光谱与PL光谱吻合良好，最大值在408 nm处。CzPySiSF的紫光OLED显示出最大的外部量子效率为0.59%。
• New cyano functionalized silanes: Synthesis, characterization and diphenylamine detection
  作者：Linlin Wang、Dengxu Wang、Hua Wang、Shengyu Feng

  DOI：10.1016/j.jorganchem.2014.05.039

  日期：2014.9

  A series of novel tetrahedral silicon-centered cyano functionalized silanes, bis(4-cyanodiphenyl)dimethylsilane (1), bis(4-cyanodiphenyl)diphenylsilane (2), tri(4-cyandiphenyl)methylsilane (3), tri(4-cyandiphenyl)phenylsilane (4), and tetra(4-cyandiphenyl) silane (5), have been synthesized by Suzuki coupling reactions. They all display high thermal stability, and are fluorescent with strong emission

  一系列新颖的以四面体硅为中心的氰基官能化硅烷，双（4-氰基二苯基）二甲基硅烷（1），双（4-氰基二苯基）二苯基硅烷（2），三（4-氰基二苯基）甲基硅烷（3），三（4-氰基二苯基））苯基硅烷（4）和四（4-氰基二苯基）硅烷（5）已经通过Suzuki偶联反应合成。它们均显示出高的热稳定性，并且在紫罗兰色至蓝色区域中具有强烈发射的荧光。此外，1 - 5都显示出与高线性荧光淬灭响应于二苯胺（DPA）结合常数高达1.0×10 6 中号-1 在二氯甲烷溶液中的应用，证明了其在DPA检测中的潜在应用。
• An Efficient AIE‐Active Blue‐Emitting Molecule by Incorporating Multifunctional Groups into Tetraphenylsilane
  作者：Xiangyang Tang、Liang Yao、He Liu、Fangzhong Shen、Shitong Zhang、Huanhuan Zhang、Ping Lu、Yuguang Ma

  DOI：10.1002/chem.201402152

  日期：2014.6.16

  A multifunctional AIE‐active molecule, CzPySiTPE, in which carbazole (Cz) and pyridine (Py) were attached to tetraphenylsilane to facilitate carrier injection has been designed and synthesized. Tetraphenylethene (TPE) was adopted to maintain efficient blue emission. Blue electroluminescent (EL) emission of CzPySiTPE was obtained with CIE coordinates of (0.16, 0.17) and an external quantum efficiency

  设计并合成了一种多功能的AIE活性分子CzPySiTPE，其中咔唑（Cz）和吡啶（Py）连接到四苯基硅烷上，以方便载流子注入。采用四苯乙烯（TPE）来保持有效的蓝色发射。获得CzPySiTPE的蓝色电致发光（EL）发射，其CIE坐标为（0.16，0.17），外部量子效率为1.12％。
• Synthesis and properties of wide bandgap polymers based on tetraphenylsilane and their applications as hosts in electrophosphorescent devices
  作者：Xiaoxiao Li、Qing Bai、Jinyu Li、Fang Lu、Xiaoyi Sun、Ping Lu

  DOI：10.1039/c7nj04213b

  日期：——

  materials. The wide bandgap polymer PFSCPO was synthesized via a Suzuki coupling reaction between diphenylphosphine oxide substituted tetraphenylsilane and carbazole modified dihexylfluorene. PFSC without the diphenylphosphine oxide group was also prepared for comparison. They both show high thermal stabilities and good morphological stabilities. Doped films using these two polymers as hosts and Ir(ppy)3

  宽带隙材料在有机光电领域很重要。在这项研究中，二苯基氧化膦官能化的四苯基硅烷部分被设计并应用于宽带隙材料的构造。宽带隙聚合物PFSCPO是通过二苯膦氧化物取代的四苯基硅烷与咔唑改性的二己基芴之间的Suzuki偶联反应合成的。还制备了没有二苯基膦氧化物基团的PFSC用于比较。它们都显示出高的热稳定性和良好的形态稳定性。使用这两种聚合物作为主机和的Ir（ppy）掺杂薄膜3作为客体制备通过旋涂法。与PFSC相比，具有强吸电子性能的二苯膦氧化物基团降低了PFSCPO的LUMO能级，并促进了OLED中的电子注入。在掺杂PFSC / Ir（ppy）3的器件中，开启电压为7.5 V，在掺杂PFSCPO / Ir（ppy）3的器件中，开启电压降至6.3V 。最大电流效率也从8.83 cd A -1增加到9.33 cd A -1。
• A versatile hybrid polyphenylsilane host for highly efficient solution-processed blue and deep blue electrophosphorescence
  作者：Dianming Sun、Xiaokang Zhou、Huihui Li、Xiaoli Sun、Yonghao Zheng、Zhongjie Ren、Dongge Ma、Martin R. Bryce、Shouke Yan

  DOI：10.1039/c4tc01467g

  日期：——

  solubility, combined with high thermal and morphological stability give amorphous and homogenous PCzSiPh films by solution processing. As a result, using PCzSiPh as host with the guest iridium complex TMP-FIrpic gives blue phosphorescent organic light-emitting diodes (PhOLEDs) with overall performance which far exceeds that of a control device with poly(vinylcarbazole) (PVK) host. Notably, FIrpic-based

  通过在聚四苯基硅烷主链上掺入供电子咔唑作为侧基，设计和合成了用于蓝色和深蓝色磷光体的通用混合聚合物主体（PCzSiPh）。聚合物PCzSiPh（4）具有较宽的带隙和高的三重态能量（E T）是因为四苯基硅烷主链中的硅原子具有四面体的几何形状。具有良好溶解性的独特物理特性，再加上较高的热稳定性和形态稳定性，可通过溶液加工获得无定形和均质的PCzSiPh薄膜。结果，将PCzSiPh与客体铱配合物TMP-FIrpic一起使用，可以提供蓝色磷光有机发光二极管（PhOLED），其总体性能远远超过带有聚乙烯基咔唑（PVK）主机的控制设备。值得注意的是，基于的FIrpic的设备表现出的最大外部量子效率为14.3％（EQE）（29.3光盘-1，10.4流明w ^ -1）可与使用聚合物主体作为蓝色掺杂剂发射器的最新文献数据相媲美。此外，PCzSiPh的多功能性扩展到使用FIr6和FCNIrpic作为掺杂剂的深蓝色PhOLED，其高效率分别为11