1-(3-溴苯基)-3,4-二氢异喹啉 | 143576-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 中文名称: 1-(3-溴苯基)-3,4-二氢异喹啉
• 英文名称: 1-(3-bromophenyl)-3,4-dihydroisoquinoline
• CAS: 143576-15-2
• 化学式: C₁₅H₁₂BrN
• 分子量: 286.171
• InChiKey: QWPYVLPFYUOLNX-UHFFFAOYSA-N

物化性质

• 沸点：
  377.1±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-溴苯基)-3,4-二氢异喹啉 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 、 均三甲苯 为溶剂， 反应 27.0h， 生成 1-(3-(N-carbazolyl)biphenyl)lisoquinoline
  参考文献：
  名称：

  Bipolar iridium dendrimers containing carbazolyl dendron and 1,2,4-triazole unit for solution-processed saturated red electrophosphorescence

  摘要：

  Two solution-processable, carbazole-based iridium dendrimers (Ir-1 and Ir-2) were synthesized and characterized. The presence of carbazolyl substituent on the cyclometallated ligand resulted in improved solubility, good control over intermolecular interactions, and improved hole transport properties. The triazole ancillary ligand led to improved electron transport properties. When the dendrimers were employed as host-free light-emitting layers in the OLEDs, the devices exhibited a low turn-on voltage of 5.4 V. The maximal external quantum efficiencies and luminous efficiency of the devices obtained from Ir-1 and Ir-2 were 5.1% and 3.3 cd A(-1) and 7.9% and 4.4 cd A(-1), respectively, both with saturated red emission (CIE coordinates, 0.663, 0.332). The devices have a structure of indium tin oxide/poly(3,4-ethylenedioxythio phene)/dendrimer/1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene/cesium fluoride/aluminum. Given ease of synthesis and good device performance, these iridium dendrimers can be used to fully exploit the potential of low-cost OLEDs, leading to more applications in high-efficiency OLEDs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.04.020
• 作为产物：
  描述：

  3-溴苯甲酰氯 在 四磷十氧化物 、 三乙胺 、 三氯氧磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 生成 1-(3-溴苯基)-3,4-二氢异喹啉
  参考文献：
  名称：

  Bipolar iridium dendrimers containing carbazolyl dendron and 1,2,4-triazole unit for solution-processed saturated red electrophosphorescence

  摘要：

  Two solution-processable, carbazole-based iridium dendrimers (Ir-1 and Ir-2) were synthesized and characterized. The presence of carbazolyl substituent on the cyclometallated ligand resulted in improved solubility, good control over intermolecular interactions, and improved hole transport properties. The triazole ancillary ligand led to improved electron transport properties. When the dendrimers were employed as host-free light-emitting layers in the OLEDs, the devices exhibited a low turn-on voltage of 5.4 V. The maximal external quantum efficiencies and luminous efficiency of the devices obtained from Ir-1 and Ir-2 were 5.1% and 3.3 cd A(-1) and 7.9% and 4.4 cd A(-1), respectively, both with saturated red emission (CIE coordinates, 0.663, 0.332). The devices have a structure of indium tin oxide/poly(3,4-ethylenedioxythio phene)/dendrimer/1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene/cesium fluoride/aluminum. Given ease of synthesis and good device performance, these iridium dendrimers can be used to fully exploit the potential of low-cost OLEDs, leading to more applications in high-efficiency OLEDs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.04.020

文献信息

• Photochromism of tetrahydroindolizines. Part XXVI: Mechanochemical synthesis, tunable photophysical properties and combined experimental and theoretical studies of novel photochromic tetrahydroindolizines
  作者：Saleh A. Ahmed、Nizar El Guesmi、Anas A.B. Alsulami、Ziad Moussa、Abdullah Y.A. Alzahrani、Rami J. Obaid、François Maurel、Aboel-Magd A. Abdel-Wahab

  DOI：10.1016/j.jphotochem.2022.114439

  日期：2023.3

  substituents in region C (base part) which include both electron donating and withdrawing groups in the ortho, meta and para positions of the phenyl ring. The absorption maxima (λmax) of both closed form (THI) and the colored form (betaine, after UV-irradiation) were spectrophotometrically determined in dichloromethane solution. The colored betaines displayed two absorption maxima, one between 472 and 485 nm

  在此，使用成熟的机械化学合成方法成功制备了 18 种新型光致变色四氢二氢吲嗪 (THI)。这些产品的收率非常好，而且纯化过程相对简单，没有任何分离挑战。新的 THI 在 C 区（碱基部分）包含各种取代基，其中包括苯环邻位、间位和对位的给电子基团和吸电子基团。吸收最大值 (λ max) 的封闭形式 (THI) 和有色形式（甜菜碱，在紫外线照射后）在二氯甲烷溶液中通过分光光度法测定。彩色甜菜碱显示出两个吸收最大值，一个在 472 和 485 nm 之间，第二个出现在 658 和 724 nm 之间的白色区域，拖尾延伸到近红外 (NIR) 区域。10'b-苯环中取代基的性质和位置对甜菜碱吸收的影响表明，吸收最大值在 658 和 690 nm 之间的邻位取代导致主要由空间效应引起的向色偏移THI 分子 10'b-苯环邻位取代基与间位和对位取代基的比较-吸收最大值在 700 和 724 nm 之间的
• Enantioselective Synthesis of 1-Aryl-tetrahydroisoquinolines through Iridium Catalyzed Asymmetric Hydrogenation
  作者：Farouk Berhal、Zi Wu、Zhaoguo Zhang、Tahar Ayad、Virginie Ratovelomanana-Vidal

  DOI：10.1021/ol301281s

  日期：2012.7.6

  Asymmetric hydrogenation of 1-aryl-3,4-dihydrolsoquinolines using the [IrCODCl](2)/(R)-3,5-diMe-Synphos catalyst is reported. Under mild reaction conditions, this atom-economical process provides easy access to a variety of enantioenriched 1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives, which are important pharmacophores found in several pharmaceutical drug candidates, in high yields and enantiomeric excesses up to 99% after a single crystallization.
• Application of heteroleptic iridium complexes with fluorenyl-modified 1-phenylisoquinoline ligand for high-efficiency red polymer light-emitting devices
  作者：Bo Liang、Lei Wang、Xuhui Zhu、Huahong Shi、Junbiao Peng、Yong Cao

  DOI：10.1016/j.jorganchem.2009.05.009

  日期：2009.9

  A series of new heteroleptic iridium complexes bearing fluorenyl-modified 1-phenylisoquinoline as the first ligand and different ancillary ligands has been prepared and characterized. These complexes bis(1-(3-(9,9-dimethyl-fluoren-2-yl)phenyl)isoquinoline-C2,N')iridium(III)acetylacetonate(Ir(DMFPQ)(2)acac)), bis(1-(3-(9,9-dimethyl-fluoren-2-yl)phenyl)isoquinoline-C2,N')iridium(III)(3-(pyridin-2-yl)-1,2,4-triazolate)( Ir(DMFPQ)(2)pt) and bis(1-(3-(9,9-dimethyl-fluoren-2-yl)phenyl)isoquinoline-C2,N')iridium(III)(2- (2-pyridyl)benzimidazolate)(Ir(DMFPQ)(2)pbi) showed red phosphorescent emissions of 615-630 nm in dichloromethane solution. The device fabricated with these complexes doped into a host polyfluorene (PFO) blend with 30% of an electron transport material 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD)showed high device efficiencies. Ir(DMFPQ)(2)acac exhibited red emission with an external quantum efficiency(eta(ext)) of 14.3% and luminous efficiency(eta(c)) of 7.8 cd/A at 1.2 mA/cm(2) and the maximum brightness reached 10 006 cd/m(2) (Commission Internationale de I'Eclairage(CIE) chromaticity coordinates: (0.67, 0.32)) at 412 mA/cm(2). Ir(DMFPQ)(2)pt showed a eta(ext) of 13.0% and eta(c) of 9.2 cd/A at 17 mA/cm(2), 1532 cd/m(2), and the maximum brightness reached 15085 cd/m(2) (CIE: 0.64, 0.34) at 360 mA/cm2. (C) 2009 Elsevier B.V. All rights reserved.
• Bipolar iridium dendrimers containing carbazolyl dendron and 1,2,4-triazole unit for solution-processed saturated red electrophosphorescence
  作者：Bo Liang、Sujun Hu、Yanping Liu、Zhiqiang Fan、Xueye Wang、Weiguo Zhu、Hongbin Wu、Yong Cao

  DOI：10.1016/j.dyepig.2013.04.020

  日期：2013.10

  Two solution-processable, carbazole-based iridium dendrimers (Ir-1 and Ir-2) were synthesized and characterized. The presence of carbazolyl substituent on the cyclometallated ligand resulted in improved solubility, good control over intermolecular interactions, and improved hole transport properties. The triazole ancillary ligand led to improved electron transport properties. When the dendrimers were employed as host-free light-emitting layers in the OLEDs, the devices exhibited a low turn-on voltage of 5.4 V. The maximal external quantum efficiencies and luminous efficiency of the devices obtained from Ir-1 and Ir-2 were 5.1% and 3.3 cd A(-1) and 7.9% and 4.4 cd A(-1), respectively, both with saturated red emission (CIE coordinates, 0.663, 0.332). The devices have a structure of indium tin oxide/poly(3,4-ethylenedioxythio phene)/dendrimer/1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene/cesium fluoride/aluminum. Given ease of synthesis and good device performance, these iridium dendrimers can be used to fully exploit the potential of low-cost OLEDs, leading to more applications in high-efficiency OLEDs. (C) 2013 Elsevier Ltd. All rights reserved.