4,7-dibromo-2-(3,4,5-trifluorophenyl)-2H-benzotriazole | 1092706-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,7-dibromo-2-(3,4,5-trifluorophenyl)-2H-benzotriazole
• 英文别名: 4,7-Dibromo-2-(3,4,5-trifluorophenyl)-2H-benzo[d][1,2,3]triazole；4,7-dibromo-2-(3,4,5-trifluorophenyl)benzotriazole
• CAS: 1092706-90-5
• 化学式: C₁₂H₄Br₂F₃N₃
• 分子量: 406.987
• InChiKey: JXQXYRPVFCLXNP-UHFFFAOYSA-N

物化性质

• 沸点：
  453.1±55.0 °C(Predicted)
• 密度：
  2.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-dibromo-2-(3,4,5-trifluorophenyl)-2H-benzotriazole 在 sodium nitrate 、 四(三苯基膦)钯 、 硫酸 、 甲基三辛基氯化铵 、 铁粉 、 sodium hydride 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 甲苯 、 mineral oil 为溶剂， 反应 212.67h， 生成 2-(3,5-difluoro-4-(2-octyldodecyloxy)phenyl)-4,9-bis(5'-hexyl-2,2'-bithiophen-5-yl)-6,7-bis(3-methoxyphenyl)-2H-triazolo[4,5-g]quinoxaline
  参考文献：
  名称：

  Thiophene-2-aryl-2H-benzotriazole-thiophene Oligomers with Adjustable Electronic Properties

  摘要：

  The synthesis and the optical and electrochemical properties of 2-aryl-2H-benzotriazole based thiophene oligomers with chemical modifications either on the phenyl side group or on the backbone are presented. All data, supported by DFT calculations, show that modification on the backbone has a major impact on the electronic properties while the side groups can fine-tune the electronic properties. In addition, one compound exhibits a thermotropic mesophase.

  DOI：

  10.1021/ol2005853

文献信息

• Photovoltaic response to structural modifications on a series of conjugated polymers based on 2-aryl-2H-benzotriazoles
  作者：Felix M. Pasker、Michael F. G. Klein、Monamie Sanyal、Esther Barrena、Uli Lemmer、Alexander Colsmann、Sigurd Höger

  DOI：10.1002/pola.24959

  日期：2011.12.1

  The synthesis, characterization, and photovoltaic properties of a series of four conjugated polymers containing 2‐aryl‐2H‐benzotriazoles and “bis(thiopheno)dialkylfluorenes” is described. The polymers were obtained via Suzuki‐polycondensation and comprise alternating electron rich and electron poor building blocks. The impact of systematic structural changes on the electronic and morphological properties

  一系列包含2-芳基-2 H的四种共轭聚合物的合成，表征和光伏性质描述了苯并三唑和“双（噻吩基）二烷基芴”。这些聚合物是通过Suzuki缩聚反应获得的，包含富电子和贫电子的交替结构单元。研究了系统结构变化对电子和形态学特性以及器件效率的影响。这些聚合物用作有机太阳能电池中的光收集和电子给体材料，使用PCBM衍生物作为电子接受材料，导致功率转换效率高达1.8％。原始聚合物的性质和器件性能均表明，更远离主链的取代的影响可忽略不计，而直接在主链上的取代则具有重大影响。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年。
• Synthesis of fluorinated benzotriazole (BTZ)- and benzodithiophene (BDT)-based low-bandgap conjugated polymers for solar cell applications
  作者：Murali Krishna Pola、Karunakara Moorthy Boopathi、Harihara Padhy、Putikam Raghunath、Ashutosh Singh、Ming-Chang Lin、Chih-Wei Chu、Hong-Cheu Lin

  DOI：10.1016/j.dyepig.2016.12.007

  日期：2017.4

  were investigated. These polymers possessed the highest occupied molecular orbital (HOMO) levels ranged −5.38 to −5.6 eV and the lowest unoccupied molecular orbital (LUMO) levels ranged −3.55 to −3.57 eV, which covered broad absorption ranges with low optical bandgaps. The bulk heterojunction (BHJ) polymer solar cell (PSC) devices containing an active layer of D-A polymers blended with different weight

  一系列供体-受体（DA）聚合物（P1 - P3通过Stille偶联聚合法设计并合成了基于苯并二噻吩（BDT）和含噻吩连接基的电子接受性苯并三唑（BTZ）单元。研究了具有多个氟化BTZ基团的聚合物对其热，光学，电化学和光伏性质的影响。这些聚合物的最高占据分子轨道（HOMO）水平在-5.38至-5.6 eV范围内，最低未占据分子轨道（LUMO）水平在-3.55至-3.57 eV范围内，涵盖了宽吸收范围和低光学带隙。体异质结（BHJ）聚合物太阳能电池（PSC）器件，包含掺有不同重量比的电子受体[6,6]-苯基-C 71的DA聚合物活性层-丁酸甲酯（PC 71 BM）在100 mW cm -2的AM 1.5白光照明下进行了探索，其中最大功率转换效率（PCE）值为3％（J sc  = 7.70 mA / cm 2， 在由聚合物P3组成的PSC装置中获得FF  ＝ 54.04，并且V oc＝ 0.72V
• New benzotriazole-based D–A–D type solvatochromic dyes for water content detection in organic solvents
  作者：Fang Hou、Xiaolei Liu、Xueying Hao、Guofei Li、Futai Lu、Qiliang Deng

  DOI：10.1016/j.dyepig.2021.109667

  日期：2021.11

  structured organic dyes (LM1 and LM2) based on methoxy substituted triphenylamine (MeO-TPA) as the electron donor, N-aryl benzotriazole as the electron acceptor have been designed and synthesized for water content detection in organic solvents. Both dyes exhibit large stoke shift with solvatochromic properties and display apparent fluorescence quenching upon the addition of different amount of water in organic

  设计并合成了两种以甲氧基取代三苯胺 (MeO-TPA) 为电子供体、N-芳基苯并三唑为电子受体的新型 DAD 结构有机染料（LM1和LM2），用于有机溶剂中的水含量检测。两种染料都表现出较大的斯托克位移和溶剂化变色特性，并在有机溶剂中加入不同量的水时显示出明显的荧光猝灭。与LM1、LM2相比具有更强吸电子受体的氟化苯并三唑具有红移吸收和荧光发射，增强的分子内电荷转移（ICT）特性和更强的氢键相互作用，导致水的检测限（LOD）更低。LM2 的THF 和 1,4-二恶烷的 LOD分别为 0.009% 和 0.024%，表明其在检测有机溶剂中的水含量方面具有巨大的应用潜力。
• Carbazole–Phenylbenzotriazole Copolymers as Absorber Material in Organic Solar Cells
  作者：Michael F. G. Klein、Felix M. Pasker、Stefan Kowarik、Dominik Landerer、Marina Pfaff、Matthias Isen、Dagmar Gerthsen、Uli Lemmer、Sigurd Höger、Alexander Colsmann

  DOI：10.1021/ma400440q

  日期：2013.5.28

  An alternating copolymer comprising a 2,7-functionalized carbazole donor and a 2-phenyl-2H-benzotriazole acceptor with an octyldodecyloxy substituent was synthesized. The polymer was blended with [6,6]-phenyl C-71-butyric acid methyl ester (PC71BM) and incorporated as absorber layer into solution processed organic solar cells. By adding the processing additive 1,8-diiodooctane (DIO) to the host solvent 1,2-dichlorobenzene (DCB), the solar cell fill factor increased to remarkable 70% and the power conversion efficiency approached 4.6%. Low energy scanning transmission electron microscopy (low-keV STEM) investigations indicated a finer bulk morphology of the active layer upon deposition from DCB:DIO. Further, the low-energy shoulder of the absorption spectrum was enhanced, indicating stronger polymer aggregation. According to external quantum efficiency measurements, the enhanced absorption also promoted better photon harvesting. Grazing incidence X-ray diffraction experiments revealed face-on polymer aggregates being beneficial for the vertical hole transport.
• CN116621786
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