9-(2-(4-bromophenyl)ethenyl)anthracene | 400717-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(2-(4-bromophenyl)ethenyl)anthracene
• 英文别名: 9-anthryl-1-bromostilbene；9-[2-(4-Bromophenyl)ethenyl]anthracene
• CAS: 400717-16-0
• 化学式: C₂₂H₁₅Br
• 分子量: 359.265
• InChiKey: NDLYUMWWNZQQPD-UHFFFAOYSA-N

物化性质

• 沸点：
  520.3±25.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  2
• 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：

  9-(2-(4-bromophenyl)ethenyl)anthracene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 33.17h， 生成 4-(((anthracen-9-yl)vinylphenyl)ethynyl)-N,N-(di(4-formylphenyl))aniline
  参考文献：
  名称：

  用于 p 沟道高性能 OFET 的蒽和芘封端三芳基胺的合成

  摘要：

  合成了具有 D-π-D' 结构的蒽和芘封端的乙炔基苯乙烯基桥联三芳基胺，以探索供体基序对 OFET 特性的影响。制造的 BGTC 器件表现出p沟道行为，具有高迁移率和高达 2.6 cm 2 /Vs 和 10 7的开/关电流比，以及 -9 V 的低阈值电压。

  DOI：

  10.1002/ejoc.202200825
• 作为产物：
  描述：

  9-(2-(4-bromophenyl)ethenyl)anthracene 以 甲基环己烷 为溶剂， 生成 9-(2-(4-bromophenyl)ethenyl)anthracene
  参考文献：
  名称：

  具有给电子和受电子取代基的反式-1-（9-蒽基）-2-（4-R-苯基）乙烯的激发态性质[R = N（CH3）2，OCH3，CH3，Br，CN，和NO2]

  摘要：

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.

  DOI：

  10.1021/j100145a012

文献信息

• Preparation of Functionalized Polystyrene-<i>b</i><i>lock</i>-polyisoprene Copolymers and Their Luminescence Properties
  作者：Sijian Hou、Wai Kin Chan

  DOI：10.1021/ma0107206

  日期：2002.1.1

  A series of block copolymers functionalized with aromatic 1,3,4-oxadiazole and stilbene, derivatives have been synthesized by the palladium catalyzed reaction between polystyrene-block-polyisoprene and different functional units. These polymers exhibited different emission properties in solution and in the solid state. In chloroform solution, they showed relatively narrow and featured emission bands while, in the solid state, the emission band was broadened and showed a significant red shift. These observations were attributed to the formation of aggregates between the luminophores. After some oxadiazole functionalized copolymers were annealed at elevated temperature, such aggregation was enhanced and there were further changes in the emission spectra. For the bifunctional copolymers, such a shift in the emission band was not significant because the presence of two different chemical species in the same block may prevent the same type of luminophores from aggregating together.
• Synthesis and spectroscopy of anthracene-containing linear and ‘T’-shaped π-conjugated ligands
  作者：Ian Cade、Nicholas J. Long、Andrew J.P. White、David J. Williams

  DOI：10.1016/j.jorganchem.2005.12.024

  日期：2006.3

  A range of new it-conjugated ethynyl- and diethynyl-benzene ligands has been synthesised and their spectroscopic characterisation carried out, most notably via IR and H-1 NMR. X-ray crystal structures were obtained for three of these ligands and one unusual ruthenium complex. Both the 4-ethynyl- and 2,5-diethynyl-benzene cores of these compounds have been functionalised through organic transformations by addition of an 9-anthracenyl. This has been attached via a range of linker moieties that vary in both their length and degree of pi-conjugation. This has given rise to two groups of compounds with either a linear, e.g., 9-(2-(4-ethynylphenyl)ethynediyl)anthracene and 9-(2-(4-ethynylphenyl)ethyl)anthracene, or 'T'-shaped morphologies, e.g., 9-(2-(2,5-diethylnylphenyl)ethyl)anthracene. (c) 2005 Elsevier B.V. All rights reserved.
• Excited-state properties of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes with electron-donating and -accepting substituents [R = N(CH3)2, OCH3, CH3, Br, CN, and NO2]
  作者：Licheng Sun、Helmut Goerner

  DOI：10.1021/j100145a012

  日期：1993.10

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.
• Synthesis of Anthracene and Pyrene End‐Capped Triarylamines for p <i>‐</i> Channel High‐Performance OFETs
  作者：Panneerselvam Devibala、Balu Balambiga、Predhanekar Mohamed Imran、Nattamai S. P. Bhuvanesh、Samuthira Nagarajan

  DOI：10.1002/ejoc.202200825

  日期：2022.11.25

  Anthracene and pyrene end-capped ethynyl styrylene bridged triarylamines with D-π-D’ architectures were synthesized to explore the influence of donor motifs on OFET properties. The fabricated BGTC device exhibited p-channel behavior with high mobility and on/off current ratio up to 2.6 cm2/Vs and 107 and a low threshold voltage of −9 V, respectively.

  合成了具有 D-π-D' 结构的蒽和芘封端的乙炔基苯乙烯基桥联三芳基胺，以探索供体基序对 OFET 特性的影响。制造的 BGTC 器件表现出p沟道行为，具有高迁移率和高达 2.6 cm 2 /Vs 和 10 7的开/关电流比，以及 -9 V 的低阈值电压。