(E,E,E)-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene | 36288-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,E,E)-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene
• 英文别名: (E,E,E)-1,6-di(4-cyanophenyl)-1,3,5-hexatriene；(all-E)-1,6-bis(4-cyanophenyl)hexa-1,3,5-triene；CN-DPH；4-[(1E,3E,5E)-6-(4-cyanophenyl)hexa-1,3,5-trienyl]benzonitrile
• CAS: 36288-08-1
• 化学式: C₂₀H₁₄N₂
• 分子量: 282.345
• InChiKey: DINCAEDLHXGDGO-CRQXNEITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,E,E)-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene 反应 4.0h， 以21%的产率得到
  参考文献：
  名称：

  Intermolecular [2+2] Photocycloaddition of Formyl- and Cyano-Substituted Diphenylhexatrienes in the Solid State

  摘要：

  全反式-1,6-双(4-R-苯基)-1,3,5-己三烯（R = CHO和CN）的结晶粉末在三烯的1,2位发生分子间[2+2]光环加成反应，生成镜像对称二聚体。红外光谱和13C CP/MAS NMR光谱表明，甲酰衍生物中存在C–H···O氢键。

  DOI：

  10.1246/cl.2001.410
• 作为产物：
  描述：

  (E)-2-butene-1,4-bis(triphenylphosphonium chloride) 、 4-氰基苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (E,E,E)-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene
  参考文献：
  名称：

  Crystal Structures and Fluorescence Spectroscopic Properties of Cyano-Substituted Diphenylhexatrienes

  摘要：

  The crystal structures and spectroscopic properties of (E,E,E)-1,6-di(x-cyanophenyl)-1,3,5-hexatrienes (2: x = 2, 3: x = 3, 4: x = 4) have been investigated. The single crystal X-ray structure analysis reveals that the molecules are linked via sp(2)-CH center dot center dot center dot N C hydrogen bonds in each crystal. The existence of the sp(2)-CH center dot center dot center dot N C hydrogen bonds in crystals 2-4 is spectroscopically evidenced by the fact that the IR peaks due to C N stretching vibration shift to lower wavenumbers in the solid state relative to those in solution. The molecules of 3 are hydrogen bonded to form orthogonally oriented ribbons, whereas those of 2 and 4 are organized into molecular sheets. The distance and displacements between the nearest stacking molecules are larger in 3 than those in 2 and 4. For each triene, the absorption and fluorescence spectra in the solid state shift to longer wavelengths than those in solution. The magnitude of the red shift is similar for 2-4 in the absorption spectra, but larger for 2 and 4 than for 3 in the fluorescence spectra. We conclude that the origin of the solid-state fluorescence is monomeric for 3 and excimeric for 2 and 4. The relationship between crystal structure and fluorescence properties is discussed.

  DOI：

  10.1021/cg5009363

文献信息

• Photocyclization Reactions of Aryl Polyenes. V. Photochemical Synthesis of Substituted Chrysenes
  作者：Clifford C. Leznoff、Roger J. Hayward

  DOI：10.1139/v72-081

  日期：1972.2.15

  The photocyclization-oxidation reaction of 1,6-di-p-substituted-phenyl-1,3,5-hexatrienes gave 3,9-disubstituted-chrysenes. Similarly, irradiation of 1-p-substituted-phenyl-6-phenyl-1,3,5-hexatrienes yielded 3-substituted-chrysenes. The 3-substituted-chrysenes were independently prepared in a high yield by the photocyclization-oxidation of 1-α-naphthyl-2-p-substituted-phenylethylenes.

  1,6-二对位取代苯基-1,3,5-己三烯的光环化-氧化反应产生了3,9-二取代蒽。类似地，对1-对位取代苯基-6-苯基-1,3,5-己三烯的辐射处理产生了3-取代蒽。通过1-α-萘基-2-对位取代苯乙烯的光环化-氧化，高产率地独立制备了3-取代蒽。
• Diphenylhexatrienes as Photoprotective Agents for Ultrasensitive Fluorescence Detection
  作者：Daniela Pfiffi、Brigitte A. Bier、Christel M. Marian、Klaus Schaper、Claus A. M. Seidel

  DOI：10.1021/jp909033x

  日期：2010.4.1

  explored for enhancing the fluorescence signal by selectively quenching the first excited triplet state of the laser dye Rhodamine 123 (Rh123). The strategy is to quench the T1 state by Dexter triplet energy transfer, while undesired quenching of the singlet state via Förster or Dexter singlet energy transfer and the generation of free radicals through electron transfer should be avoided. Diphenylhexatrienes

  考虑到染料光稳定性对于单分子研究，荧光波动光谱和激光扫描显微镜特别重要，人们探索了精细的策略，通过选择性地淬灭激光染料若丹明123（Rh123）的第一个激发三重态来增强荧光信号。该策略是通过Dexter三重态能量转移淬灭T 1状态，同时应避免通过Förster或Dexter单重态能量转移对单峰态进行不期望的淬灭以及通过电子转移产生自由基。使用荧光相关光谱法在乙醇中测试了二苯基己三烯（DPH）作为一类新型的光保护剂的有益作用。的图书馆合成了具有供电子（二甲基氨基）和吸收性取代基（例如三氟甲基）的DPH，以优化电子性能。量子化学计算，光谱学和循环伏安法被用来确定电子性能。所计算的Ť 1的发射能量的Rh123和T 1的所有的激发能量DPH小号允许放能三重态能量转移到淬灭剂。母体化合物淬灭了几乎受扩散控制的Rh123的T 1状态（4.9×10 9 M -1s -1）。所有电子不足的DPH都通过减少
• Substituent Effect on the cis-trans Photoisomerization of trans,trans,trans-1,6-Diphenyl-1,3,5-hexatrienes
  作者：Yoriko Sonoda、Hisayuki Morii、Masako Sakuragi、Yasuzo Suzuki

  DOI：10.1246/cl.1998.349

  日期：1998.4

  Quantum yield of trans,trans,trans→cis,trans,trans photoisomerization of p,p′-disubstituted 1,6-diphenyl-1,3,5-hexatriene increased as the polarity of substituents increased, regardless of their electron-withdrawing or donating nature. On the contrary, quantum yield of trans,trans,trans→trans,cis,trans isomerization increased with increasing the electron-donating nature of substituents.

  p,p'-二取代的 1,6-二苯基-1,3,5-己三烯的反式、反式、反式→顺式、反式、反式光异构化的量子产率随着取代基极性的增加而增加，无论它们的吸电子或捐赠自然。相反，反，反，反→反，顺，反异构化的量子产率随着取代基给电子性质的增加而增加。
• Solvent effects on the photophysical and photochemical properties of (E,E,E )-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene
  作者：Yoriko Sonoda、Wai Ming Kwok、Zdenék Petrasek、Richard Ostler、Pavel Matousek、Michael Towrie、Anthony W. Parker、David Phillips

  DOI：10.1039/b008711o

  日期：——

  The photophysical and photochemical properties of (E,E,E)-1,6-bis(4-nitrophenyl)hexa-1,3,5-triene [(E,E,E)-1] have been studied in various solvents. The fluorescence emission maxima of (E,E,E)-1 show an increasing Stokes shift with increasing solvent polarity. Picosecond time-resolved fluorescence (TF) and transient absorption (TA) spectra do not show any significant time-dependent shifts in nonpolar solvent whereas, in more polar solvents, large red and blue shifts are observed in the TF and TA spectra, respectively. The fluorescence quantum yield reaches a maximum in moderately polar solvents and the quantum yield of intersystem crossing decreases strongly with increasing solvent polarity. Z–E-Isomerization of triene double bonds is inefficient in all solvents. In contrast, the absorption and fluorescence maxima for (E,E,E)-1,6-bis(4-cyanophenyl)hexa-1,3,5-triene [(E,E,E)-2] are practically solvent-independent. When the solvent polarity is increased, fluorescence quantum yield decreases monotonically and Z–E-isomerization quantum yield increases strongly. The results for (E,E,E)-1 can be understood in terms of an additional charge transfer excited state, which is absent for (E,E,E)-2.

  研究了(E,E,E)-1,6-双（4-硝基苯基）六-1,3,5-三烯[(E,E,E)-1]在各种溶剂中的光物理和光化学特性。随着溶剂极性的增加，(E,E,E)-1 的荧光发射最大值显示出越来越大的斯托克斯偏移。在非极性溶剂中，皮秒时间分辨荧光光谱（TF）和瞬态吸收光谱（TA）没有出现任何明显的时间偏移，而在极性较强的溶剂中，TF 和 TA 光谱分别出现了较大的红色和蓝色偏移。在中等极性溶剂中，荧光量子产率达到最大值，而系统间交叉的量子产率则随着溶剂极性的增加而强烈下降。在所有溶剂中，三烯双键的 Z-E 异构化效率都很低。相反，(E,E,E)-1,6-双（4-氰基苯基）六-1,3,5-三烯[(E,E,E)-2]的吸收和荧光最大值实际上与溶剂无关。当溶剂极性增加时，荧光量子产率单调下降，而 Z-E-异构化量子产率则强烈增加。(E,E,E)-1的结果可以通过额外的电荷转移激发态来理解，而(E,E,E)-2不存在这种激发态。