(E)-1-(4-bromophenyl)-2-(4-nitrophenyl)ethene | 24325-71-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(4-bromophenyl)-2-(4-nitrophenyl)ethene
• 英文别名: trans-1-(4-bromostyryl)-4-nitrobenzene；trans-4-(4-bromostyryl)-nitrobenzene；trans-4-bromo-4'-nitrostilbene；4-bromo-4'-nitrostilbene；4-bromo-4'-nitro-trans-stilbene；4-Brom-4'-nitro-trans-stilben；1-[(E)-2-(4-bromophenyl)ethenyl]-4-nitrobenzene
• CAS: 24325-71-1
• 化学式: C₁₄H₁₀BrNO₂
• 分子量: 304.143
• InChiKey: DFAOJKUHONBIMN-OWOJBTEDSA-N

物化性质

• 熔点：
  198-201 °C
• 沸点：
  393.7±11.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-bromophenyl)-2-(4-nitrophenyl)ethene 在 1,1'-双(二苯基膦)二茂铁 、 tris(dibenzylideneacetone)dipalladium (0) 、 tin(ll) chloride 、 sodium t-butanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 42.0h， 生成 trans-4-(N,N-bis(2-pyridyl)amino)-4'-bromostilbene
  参考文献：
  名称：

  Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in N,N-Bis(2-pyridyl)amino-Substituted Arenes

  摘要：

  The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4'-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a pi-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 Could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (C-ph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong "push-pull" character. Nonetheless, the degree of pi-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced pi-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn(II)-induced fluorescence quenching for 1DPA as well as 3DPA.

  DOI：

  10.1021/jo049902z
• 作为产物：
  描述：

  1-[2-(4-bromophenyl)ethenyl]-4-nitrobenzene 在 碘 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 (E)-1-(4-bromophenyl)-2-(4-nitrophenyl)ethene
  参考文献：
  名称：

  Zn(II)-Induced Ground-State π-Deconjugation and Excited-State Electron Transfer in N,N-Bis(2-pyridyl)amino-Substituted Arenes

  摘要：

  The synthesis and X-ray crystal structures of two N,N-bis(2-pyridyl)amino (dpa)-substituted aromatic systems (Ar-dpa) 1 (Ar = 4,4'-disubstituted trans-stilbene) and 2 (Ar = 1,4-disubstituted benzene) and their ZnCl2 complexes (1/ZnCl2 and 2/ZnCl2) are reported. The fluoroionophoric behavior of 1-2 in response to Zn(II) in acetonitrile also has been investigated. In addition, compound 3DPA has been prepared and served as a pi-deconjugated model for 1DPA. The observed crystal structures for 1/ZnCl2 and 2/ZnCl2 Could be divided into two distinct types, the planar and the twisted forms, depending on the aryl-dpa (C-ph-NC3) dihedral angle. The twisted form is more favorable for these complexes unless the arene has a strong "push-pull" character. Nonetheless, the degree of pi-conjugation between the N-pyridyl and the N-aryl group is reduced in both complex forms when compared with the free ligands. Such a Zn(II)-induced pi-deconjugation not only directly affects the internal charge transfer (ICT) fluorescence of the dpa-substituted stilbenes but also facilitates the occurrence of photoinduced electron transfer (PET) from the stilbene donor to the dpa/Zn(II) acceptor. The PET process is particularly important in accounting for the observed Zn(II)-induced fluorescence quenching for 1DPA as well as 3DPA.

  DOI：

  10.1021/jo049902z

文献信息

• Direct C≡C Triple Bond Formation from the C=C Double Bond and Direct Hydroxylation into the<i>o</i>-Position of a Nitro Group on the Benzene Nucleus with Potassium<i>t</i>-Butoxide in<i>N</i>,<i>N</i>-Dimethylformamide in the Air
  作者：Shuzo Akiyama、Kunihiko Tajima、Shin’ichi Nakatsuji、Kenichiro Nakashima、Kazuko Abiru、Miwa Watanabe

  DOI：10.1246/bcsj.68.2043

  日期：1995.7

  4-diethylamino-4′ -nitrostilbene was measured to identify an anion radical species expected for explanation of the mechanism of the dehydrogenation reaction. Further, cyclic voltammetric measurements of a series of stilbenes and diphenylacetylenes were carried out in connection with the above mechanism. In many cases, interestingly, the use of a large excess of t-BuOK brought about succeeding hydroxylation

  在空气中的 N,N-二甲基甲酰胺中用叔丁醇钾 (t-BuOK) 处理从 C=C 双键直接形成 C≡C 炔键的新方法和简便方法已在 9,10-双(4-取代苯乙烯基)蒽系列、4-取代4'-硝基二苯乙烯系列和1-(对硝基苯基)-4-(对-取代苯基)-1,3-丁二烯系列；已经审查了其范围和局限性。测量针对 4-二乙氨基-4'-硝基二苯乙烯的反应的 ESR 光谱，以确定预期用于解释脱氢反应机理的阴离子自由基种类。此外，结合上述机理进行了一系列二苯乙烯和二苯乙炔的循环伏安测量。在许多情况下，有趣的是，使用大量过量的 t-BuOK 导致后续羟基化到苯核上硝基的邻位。简单的羟基化可用于合成取代的 5-（芳基乙炔基）-2-硝基苯酚，...
• Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes
  作者：Harish R. Talele、Anju R. Chaudhary、Parthiv R. Patel、Ashutosh V. Bedekar

  DOI：10.3998/ark.5550190.0012.902

  日期：——

  developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number

  已开发出一种用于合成菲和螺旋烯的二苯乙烯光脱氢环化的改进程序。该过程涉及使用 THF 作为碘介导的光脱氢环化过程中产生的氢碘酸的清除剂。由于与环氧丙烷相比，THF的沸点更高、成本更低且易于获得，因此使用THF是有利的。该方法用于合成多种菲和螺旋。
• Synthesis, spectroscopy, photophysics and thermal behaviour of stilbene-based triarylamines with dehydroabietic acid methyl ester moieties
  作者：Bárbara Gigante、M. Alexandra Esteves、N. Pires、Matthew L. Davies、Peter Douglas、Sofia M. Fonseca、Hugh D. Burrows、Ricardo A. E. Castro、João Pina、João Seixas de Melo

  DOI：10.1039/b815711a

  日期：——

  Novel stilbene-based triarylamines with dehydroabietic acid methyl ester moieties have been synthesised by palladium catalysed C–N coupling reactions. The presence of the bulky dehydroabietic acid group increases solubility, hinders crystallisation and permits their sublimation while preserving their electronic and optical characteristics. This makes them good candidates for various molecular electronic applications. We report a detailed characterisation of their electrochemical, spectroscopic and photophysical properties. In addition, the thermal stability and behaviour is discussed with reference to the potential for preparation of stable thin films.

  已合成以脱氢松香酸甲酯为取代基的新型苯乙烯基三芳胺，采用钯催化的C–N偶联反应。庞大的脱氢松香酸基团的存在增加了溶解度，抑制了结晶，并使其在保持电子和光学特性的同时能够升华。这使得它们成为各种分子电子应用的良好候选者。我们报告了对其电化学、光谱和光物理特性的详细表征。此外，还讨论了热稳定性和行为，以及制备稳定薄膜的潜力。
• Synthesis and Optical Properties, Including Two-Photon Absorption Cross-Sections, of Differentially Functionalized Starburst-Type π-Conjugated Molecules
  作者：Kenji Kobayashi、Yuto Kita、Motoyuki Shigeiwa、Satoru Imamura、Shuuichi Maeda

  DOI：10.1246/bcsj.82.1416

  日期：2009.11.15

  Differentially functionalized hexakis( p-substituted-phenylethynyl)benzene and hexakis[4-( p-substituted-styryl)phenylethynyl]benzene derivatives with various (D6h, D3h, D2h, and C2v) symmetries were synthesized by Sonogashira cross-coupling reactions. The optical properties of this starburst-type π-conjugated system were investigated. Among them, hexakis[4-( p-dioctylaminostyryl)phenylethynyl]benzene (5) showed the largest two-photon absorption cross-section of δ = 818 GM at 800 nm, which was determined by open aperture Z-scan with 120 fs laser pulses in toluene solution.

  通过 Sonogashira 交叉偶联反应合成了不同对称性（D6h、D3h、D2h 和 C2v）的不同官能化六(对取代苯乙炔基)苯和六[4-(对取代苯乙烯基)苯乙炔基]苯衍生物。研究了这种星爆型 π 共轭体系的光学性质。其中，六[4-( 对二辛基氨基苯乙烯基)苯乙炔基]苯（5）在 800 纳米波长处显示出最大的双光子吸收截面δ = 818 GM，这是通过在甲苯溶液中使用 120 fs 激光脉冲进行开孔 Z 扫描测定的。
• Verfahren zur Herstellung von bifunktionellen Z-Stilbenverbindungen, neue bifunktionelle Z-Stilbenverbindungen sowie die Verwendung der Z-Stilbenverbindungen zur Herstellung von Polymeren
  申请人：BAYER AG

  公开号：EP0391212A2

  公开（公告）日：1990-10-10

  Bifunktionelle, mindestens eine Z-konfigurierte Stilben­gruppierung enthaltende Stilbenverbindungen der Formel werden hergestellt, indem man Verbindungen der Formel mit einem Acetylen der Formel HC≡C-R⁴      (III), in Gegenwart eines Palladium-Katalysators und einer Base bei Temperaturen von 30 bis 160°C umsetzt, die erhalte­nen Verbindungen in Gegenwart einer Base in Verbindungen der Formel überführt, danach die Verbindungen der Formel (IV) mit Verbindungen der Formel in Gegenwart eines Palladium-Katalysators und einer Base bei Temperaturen von 30 bis 160°C umsetzt, anschließend die erhaltenen Acetylen-Verbindungen in Gegenwart von Katalysatoren mit Wasserstoff oder mit anderen Reduk­tionsmitteln zu Z-Stilbenverbindungen der Formel reduziert und die funktionellen Gruppen D und D¹ in die obengenannten funktionellen Gruppen Z und Y der Formel (I) in bekannter Weise überführt oder die Z-Stilbenverbindungen der Formel (VI) im Fall daß D und D¹ mindestens für ein Bromatom stehen mit Verbin­dungen der Formel H₂C=CHR⁷      (VII), in Gegenwart eines Palladium-Katalysators und einer Base bei Temperaturen von 30 bis 160°C umsetzt und die funk­tionellen Gruppen D, D¹ und D² in die funktionellen Gruppen Z und Y der Formel (I) in üblicher Weise über­führt oder die Verbindungen der Formel (IV) mit Verbindungen der Formel in Gegenwart eines Palladium-Katalysators und einer Base bei Temperaturen von 30 bis 160°C umsetzt, anschließend die erhaltenen Acetylenverbindungen in Gegenwart von Katalysatoren mit Wasserstoff oder mit anderen Re­duktionsmitteln zu entsprechenden Z-Stilbenverbindungen reduziert und danach die funktionellen Gruppen D in die funktionellen Gruppen Z und Y der Formel (I) in be­kannter Weise überführt.

  含有至少一个式中 Z 构型二苯乙烯基团的双官能团二苯乙烯化合物 通过将式 与式 HC≡C-R⁴ (III)、 在 30 至 160°C 的温度下，在钯催化剂和碱存在下，将生成的化合物在碱存在下转化为 式中化合物 然后将式 (IV) 化合物与式化合物反应 在钯催化剂和碱存在下，在 30 至 160°C 的温度下反应，然后在催化剂存在下用氢气或其他还原剂还原生成的炔化合物，得到式（IV）的 Z-二苯乙烯化合物。 用已知的方法将官能团 D 和 D¹ 转化为上述式 (I) 的官能团 Z 和 Y 或 在 D 和 D¹ 代表至少一个溴原子的情况下，将式（VI）的 Z-二苯乙烯化合物与式中的化合物反应 H₂C=CHR⁷ (VII)、 在钯催化剂和碱存在下，在 30 至 160°C 的温度下，按常规方法将官能团 D、D¹ 和 D² 转化为式 (I) 的官能团 Z 和 Y 或 将式（IV）化合物与式（IV）化合物反应 在钯催化剂和碱存在下，在 30 至 160°C 的温度下反应，然后在催化剂存在下用氢气或其他还原剂还原生成的炔化合物，得到相应的 Z-二苯乙烯化合物，然后按已知方式将官能团 D 转化为式（I）的官能团 Z 和 Y。