4-[(E)-2-[4-(二甲氨基)苯基]乙烯基]苯甲腈 | 2844-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-[(E)-2-[4-(二甲氨基)苯基]乙烯基]苯甲腈
• 英文名称: 4-(dimethylamino)-4'-cyanostilbene
• 英文别名: (E)-4-[2-(4-(dimethylamino)phenyl)vinyl]benzonitrile；trans-4-[2-(4-dimethylaminophenyl)vinyl]benzonitrile；4-[2-(4-dimethylaminophenyl)vinyl]benzonitrile；trans-4-(4-(dimethylamino)styryl)benzonitrile；trans-4-(dimethylamino)-4'-cyanostilbene；4-(4-(dimethylamino)styryl)benzonitrile；Benzonitrile, 4-(2-(4-(dimethylamino)phenyl)ethenyl)-, (E)-；4-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]benzonitrile
• CAS: 2844-17-9
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: HELBVOVIIVIHNT-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(E)-2-[4-(二甲氨基)苯基]乙烯基]苯甲腈 以 乙腈 为溶剂， 22.0 ℃ 、100.0 kPa 条件下， 生成 cis-4-[2-(4-dimethylaminophenyl)vinyl]benzonitrile
  参考文献：
  名称：

  Ipichev, Yurii V.; Zachariasse, Klaas A., Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics, 1997, vol. 101, # 3, p. 625 - 635

  摘要：

  DOI：
• 作为产物：
  描述：

  对氰基溴化苄 以 xylene 为溶剂， 生成 4-[(E)-2-[4-(二甲氨基)苯基]乙烯基]苯甲腈
  参考文献：
  名称：

  Manecke,G.; Luettke,S., Chemische Berichte, 1970, vol. 103, p. 700 - 707

  摘要：

  DOI：

文献信息

• Inhibition of Purified and Membrane-Bound Flavin-Containing Monooxygenase 1 by (<i>N</i>,<i>N</i>-Dimethylamino)stilbene Carboxylates
  作者：Bernd Clement、Matthias Weide、Daniel M. Ziegler

  DOI：10.1021/tx950145x

  日期：1996.1.1

  (approximately equal to 0.1 mM) in the assay medium. Of the three carboxylic acid analogs, (E)-4-[2-(4(dimethylamino)phenyl)vinyl]benzoic acid had no detectable water solubility at pH 7.4, and measurements were restricted to (E)-3-[2-(4-(dimethylamino)phenyl)vinyl]benzoic acid (DS3CO) and (E)-2-[2-(4-(dimethylamino)phenyl)vinyl]benzoic acid (DS2CO). While DS3CO and DS2CO were substrates, they also inhibited

  合成在2'，3'或4'位置带有腈或羧基的（E）-[2-（2-（4-（二甲基氨基）苯基）乙烯基]苯]苯并用含纯化猪肝黄素的底物活性进行测试单加氧酶（FMO1）。尽管腈衍生物在pH 7.4时不易溶解，无法饱和催化位点，但它们似乎是在测定介质中K（m）略高于其最大溶解度（约等于0.1 mM）的底物。在这三种羧酸类似物中，（E）-4- [2-（4（二甲基氨基）苯基）乙烯基]苯甲酸在pH 7.4时没有可检测到的水溶性，因此测量仅限于（E）-3- [2- （4-（二甲基氨基）苯基）乙烯基]苯甲酸（DS3CO）和（E）-2- [2-（2-（4-（二甲基氨基）苯基）乙烯基]苯甲酸（DS2CO）。尽管DS3CO和DS2CO是底物，但它们也抑制了FMO1转换。DS3CO是更有效的抑制剂，在2 mM时，它抑制FMO1和微粒体催化的甲巯咪唑（N-甲基-2-巯基咪唑）氧化80-90％。动力学研究表明，氨基二苯乙烯羧
• Catalytic Amide–Base System of TMAF and N(TMS)₃ for Deprotonative Coupling of Benzylic C(sp³)–H Bonds with Carbonyls
  作者：Masanori Shigeno、Kunihito Nakaji、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.9b00550

  日期：2019.4.19

  methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.

  本文描述了由四甲基氟化铵（TMAF）和N（TMS）3原位产生的酰胺基催化苄基C（sp 3）-H键与羰基的去质子偶联，形成对苯二甲酸酯。多种甲基杂芳烃（2-甲基苯并噻吩，2-甲基苯并呋喃和2-，3-或4-甲基吡啶）用作亲核试剂。还显示了使用DMF作为亲电试剂在烯胺合成中的应用。本系统对于具有低反应性的甲苯（4-苯基-，4-溴-，2-溴和4-氯甲苯）是有效的。
• Comparison Between Organic Sensitizers Containing Stilbene and Azo Group as Bridging Unit for Dye Sensitized Solar Cells
  作者：Se Woong Park、Jin Woong Namgoong、Il Keun Kwon、Jae Pil Kim

  DOI：10.1166/jnn.2014.9554

  日期：2014.10.1

  While azo dyes have been widely used in dye industry, the azo dyes have been seldom applied as sensitizers to dye sensitized solar cells. In this study, new metal-free organic sensitizers, ST and AZ, which are same structures except bridging units, were synthesized and evaluated. ST containing stilbene as bridging unit gave higher energy conversion efficiency than AZ containing azo group as bridging unit. As a result of density functional theory (DFT) calculations, ST displayed more localized frontier molecular orbitals at lowest unoccupied molecular orbital (LUMO) states than AZ.

  虽然偶氮染料在染料工业中得到了广泛的应用，但很少将其作为敏化剂用于染料敏化太阳能电池。在这项研究中，我们合成了两种新的无金属有机敏化剂ST和AZ，这两种物质除了桥连单元外具有相同的结构，并对它们进行了评估。与桥连单元为偶氮基团的AZ相比，桥连单元为二苯乙烯的ST具有更高的能量转换效率。根据密度泛函理论（DFT）计算的结果，ST在最低未占分子轨道（LUMO）态下表现出比AZ更局域的前沿分子轨道。
• An improved efficiency/transparency trade-off for second-harmonic generation by extending the π-electron bridge of an optically nonlinear dye
  作者：Geoffrey J. Ashwell、Anne J. Whittam、Mukhtar A. Amiri、Richard Hamilton、Andrew Green、Ulrich-Walter Grummt

  DOI：10.1039/b009911m

  日期：——

  The second-harmonic intensity from Langmuir–Blodgett films of 5-4-[2-(4-dimethylaminophenyl)vinyl]benzylidene}-2-octadecyl-5,6,7,8-tetrahydroisoquinolinium octadecyl sulfate(1), interleaved with poly(tert-butyl methacrylate), increases quadratically with thickness to more than 100 bilayers. The susceptibility, molecular hyperpolarisability, thickness, refractive indices and chromophore tilt angle, relative to the substrate normal, are χzzz(2) = 45 ± 5 pm V−1 at 1064 nm, β = 8 × 10−38 m4 V−1, l = 3.65 ± 0.12 nm bilayer−1, nω = 1.53 ± 0.01, n2ω = 1.56 ± 0.01 and φ = 44 ± 2°. The moderately high susceptibility arises from an optimised transparency/efficiency trade-off, the alternate-layer LB film being transparent at 1064 nm and having a very slight absorbance of 3.5 × 10−4 bilayer−1 at 532 nm. In contrast, alternate-layer films of the corresponding 7-diethylamino-2-oxo-2H-chromen-3-ylmethylene (2) and 3-(dimethylaminophenyl)prop-2-enylidene (3) derivatives, also reported, have absorbances of 1.1 × 10−3 and 1.5 × 10−3 bilayer−1 at 532 nm and resonantly enhanced susceptibilities of 60 and 95 pm V−1 respectively.

  Langmuir-Blodgett 薄膜的二次谐波强度 5-4-[2-(4-二甲基氨基苯基)乙烯基]亚苄基}-2-十八烷基-5,6,7,8-四氢异喹啉鎓 十八烷基硫酸盐(1), 与聚（甲基丙烯酸叔丁酯）交错，增加 厚度超过 100 个双层的二次方。敏感性， 分子超极化性、厚度、折射率和发色团 相对于基底法线的倾斜角为 Ïzzz(2) = 45±5 pm V – 1 (1064 nm)， β = – 8 – 10 – 38 – m4 – V – 1， l=3.65±0.12nm 双层×1，n×=1.53±0.01，n2×=1.56±0.01 且 θ=44±2°。 适度高的敏感性源于优化的透明度/效率 权衡，交替层 LB 薄膜在 1064 nm 处透明 吸光度非常小，为 3.5 × 10 × 4 532 nm 处双层 1。相比之下，交替层 相应的 7-二乙氨基-2-氧代-2H-苯并-3-基亚甲基 (2) 和 3-(二甲氨基苯基)丙-2-亚烯基 (3) 衍生物的薄膜也有报道，具有吸光度 1.1 × 10 × 3 和 1.5 × 10 × 3 532 nm 处的双层 1 和共振增强的磁化率 分别为下午 60 点和 95 点 V 至 1 点。
• Unconventional Langmuir–Blodgett films: alignment of an optically nonlinear dye where the donor and π-electron bridge are hydrophobic and the acceptor is hydrophilic
  作者：Geoffrey J. Ashwell、Alison A. Maxwell、Andrew Green

  DOI：10.1039/b200565b

  日期：——

  The optically nonlinear dye, 5-4-[2-(4-dibutylaminophenyl)vinyl]benzylidene}-2-(1-ethylpropyl)-5,6,7,8-tetrahydroisoquinolinium bromide (1a), differs from other Langmuir–Blodgett (LB) film-forming materials. The molecule is amphiphilic and, therefore, may be aligned at the air–water interface but, instead of a conventional aliphatic tail, has an extended π-electron bridge. It forms non-centrosymmetric LB films which exhibit second-harmonic generation (SHG) and have a high second-order susceptibility: χ(2)zzz = 40 pm V−1 at 1.064 µm for a monolayer thickness of 1.8 nm and chromophore tilt angle of 55° from the substrate normal. The octadecyl sulfate salt (1b) also forms non-centrosymmetric films but with improved properties: χ(2)zzz = 90 pm V−1 at 1.064 µm for d = 2.4 nm and φ = 33°. Both films exhibit charge-transfer bands at 360 nm but with absorbance cut-off above 560 nm for 1a and 530 nm for 1b. The latter is fully transparent at the fundamental and harmonic wavelengths and its susceptibility is the highest to date for such a film. This results from an optimised packing arrangement, a conjugation enhanced molecular hyperpolarisability of β = 4.3 × 10−38 m4 V−1, and the proximity of the absorption band, albeit non-overlapping at 532 nm. The properties are compared with those of conventional long alkyl tailed materials (2 and 3) of the same chromophore.

  光学非线性染料 5-4-[2-(4-二丁基氨基苯基)乙烯基]亚苄基}-2-(1-乙基丙基)-5,6,7,8-四氢异喹啉溴化物 (1a) 与其他 Langmuir 不同。 Blodgett (LB) 成膜材料。该分子是两亲性的，因此可以在空气-水界面处排列，但不是传统的脂肪族尾部，而是具有延伸的π电子桥。它形成非中心对称的 LB 薄膜，表现出二次谐波产生 (SHG) 并具有高二阶磁化率：Ï(2)zzz = 40 pm V-1 at 1.064 µm，单分子层厚度为 1.8 nm，发色团与基底法线的倾斜角为 55°。十八烷基硫酸盐 (1b) 也形成非中心对称薄膜，但具有改进的性能：Ï(2)zzz = 晚上 90 点 Vâ1 在 1.064 µm 处持续 d = 2.4 nm 和 Ï = 33°。两种薄膜均在 360 nm 处呈现电荷转移带，但 1a 的吸光度截止值高于 560 nm，1b 的吸光度截止值高于 530 nm。后者在基波和谐波波长下是完全透明的，其敏感性是迄今为止此类薄膜中最高的。这是由于优化的堆积排列、共轭增强的 β 分子超极化性所致 = 4.3 × 10−38 m4 V−1，以及吸收带的接近度，尽管在 532 nm 处不重叠。将这些性能与相同发色团的常规长烷基尾材料（2 和 3）的性能进行了比较。