9-(2-(4-bromophenyl)ethenyl)anthracene | 68790-31-8

• 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: (E)-9-(4-bromostyryl)anthracene；9-[2-(4-bromophenyl)vinyl]anthracene；trans-1-(p-Brom-phenyl)-2-(9-anthryl)-ethylene；Ethene, 1-(anthracen-9-yl)-2-(4-bromophenyl)-, (E)-；9-[(E)-2-(4-bromophenyl)ethenyl]anthracene
• CAS: 68790-31-8
• 化学式: C₂₂H₁₅Br
• 分子量: 359.265
• InChiKey: NDLYUMWWNZQQPD-SDNWHVSQSA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethanol (64-17-5))
• 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 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
• 作为产物：
  描述：

  9-蒽醇 在 potassium tert-butylate 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 9-(2-(4-bromophenyl)ethenyl)anthracene
  参考文献：
  名称：

  Synthesis and spectroscopy of anthracene-containing linear and ‘T’-shaped π-conjugated ligands

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2005.12.024

文献信息

• Exploring the potential of anthracene derivatives as fluorescence emitters for biomedical applications
  作者：Murat Aydemir、Gulcin Haykir、Harun Selvitopi、Ozge Caglar Yildirim、Mehmet Enes Arslan、Bahattin Abay、Figen Turksoy

  DOI：10.1039/d3tb00449j

  日期：——

  of the compounds. Moreover, cell viability analyses put forth that synthesized molecules do not exhibit significant cytotoxicity under 125 μg mL−1 concentration on the human dermal fibroblast cell line (HDFa). Moreover, both of the compounds showed great potential in cellular imaging of HDFa cells. Compared to Hoechst 33258, a common fluorescent dye used for nuclear staining, the compounds showed higher

  合成了两种新型蒽衍生物，并使用各种光谱技术进行了详细的光物理和生物学研究。发现氰基 (-CN) 取代的效果可有效改变电荷数和前沿轨道能级密度泛函理论 (DFT) 计算。特别是，引入与蒽核相连的苯乙烯基和三苯胺基团有助于增加相对于蒽部分的共轭。结果表明，这些分子具有分子内电荷转移 (ICT) 特性，发生在溶液中从给电子三苯胺到接受电子蒽部分。此外，光物理性质强烈依赖于氰基，其中氰基取代的 ( E / Z )-(2-anthracen-9-yl)-3-(4'-(diphenylamino)biphenyl-4yl)acrylonitrile 分子与 ( E )-4'-(2-(anthracen-9-yl)vinyl)- N相比，由于增强的内部空间位阻，显示出更强的电子亲和力，N-二苯基联苯-4-胺分子，导致较低的光致发光量子产率 (PLQY) 值和较短的分子寿命。此外，分子对接方法用于研究可能
• Gupta, K. C.; Pathak, P. K.; Saxena, B. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 196 - 198
  作者：Gupta, K. C.、Pathak, P. K.、Saxena, B. K.、Srivastava, Nirupma

  DOI：——

  日期：——
• Two trans-1-(9-anthryl)-2-phenylethene derivatives as blue-green emitting materials for highly bright organic light-emitting diodes application
  作者：Nonglin Zhou、Xiaona Shao、Shirong Wang、Yin Xiao、Xianggao Li

  DOI：10.1016/j.orgel.2017.07.054

  日期：2017.11

  1-(9-Anthryl)-2-phenylethene (t-APE) is a blue-green material with high fluorescence quantum yield (.f 0.44). However, it is easily crystallized. Herein, Two asymmetric blue-green emitting materials based on t-APE, (E)-9-(4-(2-(anthracen-9-yl) vinyl) phenyl)-10-(naphthalen-1-yl) anthracene (6) and (E)-9-(4-(2(anthracen-9-yl) vinyl) phenyl)-10-(naphthalen-2-yl) anthracene (7) were firstly designed and synthesized. The two compounds possess high thermal stability, morphological durability, and bipolar characteristics. The non-doped blue-green organic light-emitting diodes (OLEDs) using 6 and 7 as emitting layers showed emission at 495 nm, full width at half maximum of 80 nm, maximum brightness of 13,814, 10,579 cd m(-2), maximum current efficiency of 3.62, 7.16 cd A(-1), and Commission Internationale de L'Eclairage (CIE) coordinate of (0.20, 0.43), respectively. Furthermore, when employing 6 and 7 as bluegreen emitting layers and rubrene doped in tris-(8-hydroxyquinolinato) aluminum (Alq3) as the orange emitting layers to fabricate white OLEDs (WOLEDs), the WOLEDs exhibit a maximum brightness of 10,984, 14,652 cd m(-2), maximum current efficiency of 2.04, 2.70 cd A(-1), and CIE coordinate of (0.30, 0.40), (0.37, 0.47), Color Rendering Index (CRI) of 65, 60, stable EL spectra, respectively. This study demonstrates that the t-APE-type derivatives have the excellent properties for the emitting materials of OLEDs. (C) 2017 Published by Elsevier B.V.
• Gupta, K. C.; Srivastava, N.; Nigam, R. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. <B> 20, # 9, p. 802 - 803
  作者：Gupta, K. C.、Srivastava, N.、Nigam, R. K.

  DOI：——

  日期：——
• Tewari,R.S.; Gupta,K.C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16B, p. 665 - 667
  作者：Tewari,R.S.、Gupta,K.C.

  DOI：——

  日期：——