(E)-4-(4-bromostyryl)-N,N-diphenylaniline | 925674-50-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-4-(4-bromostyryl)-N,N-diphenylaniline
• 英文别名: {4-[2-(4-bromophenyl)vinyl]phenyl}diphenylamine；4-(4-Bromostyryl)-N,N-diphenylaniline；4-[(E)-2-(4-bromophenyl)ethenyl]-N,N-diphenylaniline
• CAS: 925674-50-6
• 化学式: C₂₆H₂₀BrN
• 分子量: 426.356
• InChiKey: ZYDLDMVHUXTEEE-VAWYXSNFSA-N

物化性质

• 沸点：
  549.9±29.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-bromostyryl)-N,N-diphenylaniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 生成 (E)-4-(4-ethynylstyryl)-N,N-diphenylaniline
  参考文献：
  名称：

  Functionalized Ruthenium Dialkynyl Complexes with High Second-Order Nonlinear Optical Properties and Good Potential as Dye Sensitizers for Solar Cells

  摘要：

  Various dipolar p-delocalized Ru(II) dialkynyl complexes were prepared and characterized. Their second-order nonlinear optical (NLO) properties were investigated by the electric-field-induced second harmonic generation (EFISH) technique working in CH2Cl2 solution with an incident wavelength of 1907 nm, whereas the dipole moments were determined by density functional theory (DFT) calculations. All the investigated complexes are characterized by a negative value of mu beta 1.907 EFISH, in agreement with a negative value of Delta mu eg (difference of the dipole moment in the excited and ground state) upon excitation. Their second-order NLO response can be easily modulated by the nature of the alkynyl substituents. Besides, the most promising pushpull ruthenium diacetylide complex, adequately functionalized for anchoring to TiO2, was tested as photosensitizer in dye-sensitized solar cells (DSSCs).

  DOI：

  10.1021/om5009378
• 作为产物：
  描述：

  对溴溴苄 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 (E)-4-(4-bromostyryl)-N,N-diphenylaniline
  参考文献：
  名称：

  三价硼在供体-π-受体型化合物中作为单光子和双光子激发荧光的受体。

  摘要：

  一系列新的供体-pi-受体（D-pi-A）型化合物的合成，结构和荧光性质，三价硼由两个均三基团保护，作为受体，并带有各种典型的供体和不同的pi报道了共轭桥。所有这些稳定的有机硼化合物在从蓝色到绿色的宽光谱范围内均显示出强烈的单光子激发荧光（SPEF）和双光子激发荧光（TPEF），SPEF的光谱峰位置与TPEF。在两种化合物的X射线晶体结构中显示出非常强的Cbond; B（mesityl）（2）键和良好共轭的pi系统，表明基态的某些电荷转移特征。同时，光谱数据表明，在激发态下，从供体到受体的电荷转移大大增强。根据典型的结构数据和全面的光谱数据，可以得出以下结构性质关系：1）中度芳基氨基供体比强烷基氨基供体能更有效地增强SPEF和TPEF强度；2）二苯乙烯具有比苯乙烯基噻吩更好的pi桥，因为它具有增强和蓝移相应D-pi-A化合物的SPEF和TPEF的能力；和3）与无硼前体和其他类似物相比，-B

  DOI：

  10.1002/chem.200304833

文献信息

• Molecular Engineering of UV/Vis Light-Emitting Diode (LED)-Sensitive Donor-π-Acceptor-Type Sulfonium Salt Photoacid Generators: Design, Synthesis, and Study of Photochemical and Photophysical Properties
  作者：Xingyu Wu、Ming Jin、Jianchao Xie、Jean-Pierre Malval、Decheng Wan

  DOI：10.1002/chem.201703414

  日期：2017.11.7

  of branches through molecular engineering. These PAGs can effectively decompose under UV/Vis irradiation from a light‐emitting diode (LED) light source because of the matching absorption and emitting spectra of the LEDs. The absorption and acid‐generation properties of these sulfonium salts were elucidated by UV/Vis spectroscopy and so forth. Results indicated that the PAG performance benefited from

  通过系统地改变供电子基团，π共轭体系，吸电子基团和分支数量，通过分子工程设计和合成了一系列供体-π-受体型sulf盐光酸产生剂。由于LED的吸收光谱和发射光谱匹配，因此这些PAG可以在UV / Vis照射下从发光二极管（LED）光源有效分解。通过紫外/可见光谱等方法阐明了这些sulf盐的吸收和产酸特性。结果表明，PAG的性能受益于强供电子基团，特定的π共轭结构，某些吸电子基团或二分支结构的引入。
• Photophysical Properties of Silyl‐Substituted Stilbene Derivatives
  作者：Hajime Maeda、Ryo Horikoshi、Minoru Yamaji、Taniyuki Furuyama、Masahito Segi

  DOI：10.1002/ejoc.202000397

  日期：2020.6.23

  Absorption and fluorescence properties of silyl‐substituted stilbenes were investigated. The derivative in which four Me3Si groups were introduced at the ortho positions did not fluoresce at room temperature. The para bis‐Me3SiC≡C‐substituted analog has a high fluorescence quantum yield (0.95). The stilbene containing Ph2N and Me3SiC≡C groups exhibited solvatofluorochromism while maintaining a good

  研究了甲硅烷基取代的斯蒂苯酯的吸收和荧光性质。在邻位引入四个Me 3 Si基的衍生物在室温下不发荧光。的对位双-ME 3 SiC≡C取代类似物具有高荧光量子产率（0.95）。含pH值茋2 N和我3 SiC≡C组表现出solvatofluorochromism同时保持良好的发射量子产率（0.50）。
• Pyrene functionalized triphenylamine-based dyes: synthesis, photophysical properties and applications in OLEDs
  作者：Yong Zhan、Jiang Peng、Kaiqi Ye、Pengchong Xue、Ran Lu

  DOI：10.1039/c3ob41185k

  日期：——

  Pyrene functionalized triphenylamine-based dyes TP, TCP and TCCP were synthesized via alternate Heck and Wittig reactions. It was found that they could emit strong green light with high fluorescence yields because the formation of the excimer from a pyrene unit was suppressed completely. Moreover, the non-doped organic light-emitting diodes using TP, TCP and TCCP as the emitters as well as the hole-transporting materials were fabricated, and gave green electroluminescence. Notably, the device based on TP exhibited good performance with a low turn-on voltage of 2.80 V, a high maximum luminance of 29 880 cd m−2 at 9.5 V, a high current efficiency of 3.34 cd A−1, and a high power efficiency of 2.67 lm w−1. It suggested that pyrene functionalized triphenylamine derivatives may have applications in non-doped OLEDs.

  功能化的芘三苯胺基染料TP、TCP和TCCP通过交替的Heck反应和Wittig反应合成。研究发现，由于芘单元形成的激基态（excimer）被完全抑制，这些染料能够发出强烈的绿色光并具有高荧光产率。此外，使用TP、TCP和TCCP作为发光体和孔传输材料的无掺杂有机发光二极管被制造出来，并产生了绿色电致发光。值得注意的是，基于TP的器件展现出良好的性能，具有低的开启电压2.80 V，在9.5 V时的高最大亮度为29,880 cd m−2，高电流效率为3.34 cd A−1，高功率效率为2.67 lm w−1。这表明功能化的芘三苯胺衍生物在无掺杂OLED中可能具有应用前景。
• Synthesis, Structures, and Properties of Two New Two-Photon Photopolymerization Initiators
  作者：Yun-Xing Yan、Xu-Tang Tao、Yuan-Hong Sun、Wen-Tao Yu、Gui-Bao Xu、Chuan-Kui Wang、Hua-Ping Zhao、Jia-Xiang Yang、Xiao-Qiang Yu、Xian Zhao、Min-Hua Jiang

  DOI：10.1246/bcsj.78.300

  日期：2005.2

  Two new two-photon photopolymerization initiators, diphenyl-(4-2-[4-(2-pyridin-4-ylvinyl)phenyl]vinyl}phenyl)amine 3 and 9-(4-2-[4-(2-pyridin-4-ylvinyl)phenyl]vinyl}phenyl)-9H-carbazole 4, have been synthesized and their crystal structures have been determined. One-photon fluorescence, one-photon fluorescence quantum yields, one-photon fluorescence lifetimes, and two-photon fluorescence have been investigated. The results show that they are good two-photon absorbing chromophores and effective two-photon photopolymerization initiators. The calculated two-photon absorption cross sections of molecules 3 and 4 for the lowest excited state are 59.3 × 10−50 and 43.0 × 10−50 cm4 s photon−1, respectively. Two-photon initiating polymerization microfabrication experiments have been studied and the possible photopolymerization mechanisms have been discussed.

  合成了两种新型的双光子光聚合引发剂，二苯基-(4-2-[4-(2-吡啶-4-乙烯基)苯基]乙烯}苯基)胺3和9-(4-2-[4-(2-吡啶-4-乙烯基)苯基]乙烯}苯基)-9H-咔唑4，并确定了它们的晶体结构。研究了单光子荧光、单光子荧光量子产率、单光子荧光寿命和双光子荧光。结果表明，它们是良好的双光子吸收色素和有效的双光子光聚合引发剂。分子3和4在最低激发态下的计算双光子吸收截面分别为59.3 × 10−50和43.0 × 10−50 cm4 s photon−1。研究了双光子引发的聚合微加工实验，并讨论了可能的光聚合机制。
• An acido-triggered reversible luminescent and nonlinear optical switch based on a substituted styrylpyridine: EFISH measurements as an unusual method to reveal a protonation–deprotonation NLO contrast
  作者：Elena Cariati、Claudia Dragonetti、Elena Lucenti、Filippo Nisic、Stefania Righetto、Dominique Roberto、Elisa Tordin

  DOI：10.1039/c3cc48149b

  日期：——

  Diphenyl-(4-2-[4-(2-pyridin-4-yl-vinyl)-phenyl]-vinyl}-phenyl)-amine (DPVPA) constitutes a novel acido-triggered reversible luminescent and nonlinear optical switch. Remarkably, for the first time the Electric-Field Induced Second Harmonic generation (EFISH) technique is used to reveal a protonation–deprotonation NLO contrast.

  二苯基-(4-2-[4-(2-吡啶-4-基-乙烯)-苯基]-乙烯}-苯基)-胺（DPVPA）是一种新型酸触发的可逆发光和非线性光学开关。值得注意的是，首次使用电场诱导二次谐波产生（EFISH）技术揭示了质子化-去质子化的非线性光学对比。