4-(4-硝基-苯基乙炔基)-苯胺 | 7431-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-硝基-苯基乙炔基)-苯胺
• 英文名称: 4-(4-nitro-phenylethynyl)-aniline
• 英文别名: 4-(4-Nitro-phenylaethinyl)-anilin；Benzenamine, 4-[(4-nitrophenyl)ethynyl]-；4-[2-(4-nitrophenyl)ethynyl]aniline
• CAS: 7431-22-3
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: UVJKCOKIGXAEGP-UHFFFAOYSA-N

物化性质

• 沸点：
  446.3±30.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-硝基-苯基乙炔基)-苯胺 在 盐酸 、 锌 作用下， 生成 双(4-氨基苯基)乙炔
  参考文献：
  名称：

  Veschambre,H. et al., Bulletin de la Societe Chimique de France, 1967, p. 134 - 139

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-4-硝基苯 在 potassium fluoride 、 copper-palladium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-(4-硝基-苯基乙炔基)-苯胺
  参考文献：
  名称：

  Twieg, R.; Ebert, M.; Jungbauer, D., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1992, vol. 217, p. 19 - 24

  摘要：

  DOI：

文献信息

• The electronic structure and second-order nonlinear optical properties of donor-acceptor acetylenes: a detailed investigation of structure-property relationships
  作者：Albert E. Stiegman、Eva Graham、Kelly J. Perry、Lutfur R. Khundkar、L. T. Cheng、Joseph W. Perry

  DOI：10.1021/ja00020a030

  日期：1991.9

  increases in the magnitude of beta. For this class of molecules, the increase is dominated by the energy of the intramolecular charge-transfer transition, while factors such as the ground to excited-state dipole moment change and the transition-moment integral are much less important. Increasing the conjugation length from one to two acetylene linkers did not result in an increase in the value of beta;

  合成了一系列供体-受体乙炔化合物，其中共轭长度和供体-受体强度都发生了系统变化。研究了这些结构变化对分子光谱和电子特性的影响，并最终对测得的二阶分子超极化率 (beta) 产生了影响。发现供体-受体强度的增加导致β量级的增加。对于这类分子，增加主要由分子内电荷转移跃迁的能量决定，而诸如基态到激发态偶极矩变化和跃迁矩积分等因素则不那么重要。将共轭长度从 1 个乙炔接头增加到两个乙炔接头不会导致 β 值增加；然而，β 从两个乙炔变成三个乙炔急剧增加。这种增加归因于几个几乎等能的激发态的叠加。
• Unusual structural distortions induced by charge-transfer interactions through conjugated molecules: crystal structures of NH2(C6H4)(C.tplbond.C)n(C6H4)NO2 (n = 0-3)
  作者：Eva M. Graham、Vincent M. Miskowski、Joseph W. Perry、Daniel R. Coulter、A. E. Stiegman、William P. Schaefer、Richard E. Marsh

  DOI：10.1021/ja00206a001

  日期：1989.11

  A detailed structural analysis of the series of donor-acceptor molecules O2NC6H4(C~C),C6H4NH2 (n = 0-3) has been performed in order to investigate ground-state donor-acceptor interactions through a conjugated framework. The results of the investigation reveal an unusual bonding pattern that is not adequately explained by a simple quinonoid resonance structure resulting from bond migration through the

  对一系列供体-受体分子 O2NC6H4(C~C)、C6H4NH2 (n = 0-3) 进行了详细的结构分析，以通过共轭框架研究基态供体-受体相互作用。研究结果揭示了一种不寻常的键合模式，该模式无法通过键迁移通过共轭骨架产生的简单醌型共振结构充分解释。相反，电荷转移特性仅通过硝基苯基和氨基苯基官能团本身的醌类扭曲表现出来。提供了表明电荷转移的分子内起源的证据。必须参与电荷迁移的乙炔桥本身在结构上没有改变。这些观察得出的结论是，基态中的电荷转移特性不是高度离域的，而是导致电荷集中在受体轨道中。从 n = 1-3 的化合物中观察到弱粉末二次谐波的产生。这是相对于单晶 X 射线结构进行讨论的。
• Litwinenko; Lewtschenko; Androssow, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2046
  作者：Litwinenko、Lewtschenko、Androssow

  DOI：——

  日期：——
• Small-Molecule Labeling of Live Cell Surfaces for Three-Dimensional Super-Resolution Microscopy
  作者：Marissa K. Lee、Prabin Rai、Jarrod Williams、Robert J. Twieg、W. E. Moerner

  DOI：10.1021/ja508028h

  日期：2014.10.8

  Precise imaging of the cell surface of fluorescently labeled bacteria requires super-resolution methods because the size-scale of these cells is on the order of the diffraction limit. In this work, we present a photocontrollable small-molecule rhodamine spirolactam emitter suitable for non-toxic and specific labeling of the outer surface of cells for three-dimensional (3D) super-resolution (SR) imaging. Conventional rhodamine spirolactams photoswitch to the emitting form with UV light; however, these wavelengths can damage cells. We extended photoswitching to visible wavelengths >400 nm by iterative synthesis and spectroscopic characterization to optimize the substitution on the spirolactam. Further, an N-hydroxysuccinimide-functionalized derivative enabled covalent labeling of amines on the surface of live Caulobacter crescentus cells. Resulting 3D SR reconstructions of the labeled cell surface reveal uniform and specific sampling with thousands of localizations per cell and excellent localization precision in x, y, and z. The distribution of cell stalk lengths (a sub-diffraction-sized cellular structure) was quantified for a mixed population of cells. Pulse-chase experiments identified sites of cell surface growth. Covalent labeling with the optimized rhodamine spirolactam label provides a general strategy to study the surfaces of living cells with high specificity and resolution down to 10-20 nm.
• A series of donor-acceptor molecules of the form NH2(C6H4)(C.tplbond.C)n(C6H4)NO2. Unusual effects of varying n
  作者：A. E. Stiegman、Vincent M. Miskowski、Joseph W. Perry、Daniel R. Coulter

  DOI：10.1021/ja00253a070

  日期：1987.9

表征谱图