trans-1-(p-Anisolyl)-2-(9-anthryl)-ethylene | 68790-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: trans-1-(p-Anisolyl)-2-(9-anthryl)-ethylene
• 英文别名: Ethene, 1-(anthracen-9-yl)-2-(4-methoxyphenyl)-, (E)-；9-[(E)-2-(4-methoxyphenyl)ethenyl]anthracene
• CAS: 68790-33-0
• 化学式: C₂₃H₁₈O
• 分子量: 310.395
• InChiKey: OOLQOXSVWDFFLH-NTCAYCPXSA-N

物化性质

• 熔点：
  174-175 °C(Solvent: Ethanol)
• 沸点：
  519.1±25.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-1-(p-Anisolyl)-2-(9-anthryl)-ethylene 以 甲苯 为溶剂， 生成 1-<4-Methoxy-phenyl>-2-
  参考文献：
  名称：

  具有给电子和受电子取代基的反式-1-（9-蒽基）-2-（4-R-苯基）乙烯的激发态性质[R = N（CH3）2，OCH3，CH3，Br，CN，和NO2]

  摘要：

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.

  DOI：

  10.1021/j100145a012
• 作为产物：
  描述：

  9-氯甲基蒽 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 trans-1-(p-Anisolyl)-2-(9-anthryl)-ethylene
  参考文献：
  名称：

  具有给电子和受电子取代基的反式-1-（9-蒽基）-2-（4-R-苯基）乙烯的激发态性质[R = N（CH3）2，OCH3，CH3，Br，CN，和NO2]

  摘要：

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.

  DOI：

  10.1021/j100145a012

文献信息

• Gupta, K. C.; Pathak, P. K.; Saxena, B. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 196 - 198
  作者：Gupta, K. C.、Pathak, P. K.、Saxena, B. K.、Srivastava, Nirupma

  DOI：——

  日期：——
• Gupta, K. C.; Srivastava, N.; Nigam, R. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. <B> 20, # 9, p. 802 - 803
  作者：Gupta, K. C.、Srivastava, N.、Nigam, R. K.

  DOI：——

  日期：——
• Tewari,R.S.; Gupta,K.C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16B, p. 665 - 667
  作者：Tewari,R.S.、Gupta,K.C.

  DOI：——

  日期：——
• GUPTA K. C.; PATHAK P. K.; SAXENA B. K.; SRIVASTAVA NIRUPMA, INDIAN J. CHEM., 25,(1986) N 2, 196-198
  作者：GUPTA K. C.、 PATHAK P. K.、 SAXENA B. K.、 SRIVASTAVA NIRUPMA

  DOI：——

  日期：——
• Excited-state properties of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes with electron-donating and -accepting substituents [R = N(CH3)2, OCH3, CH3, Br, CN, and NO2]
  作者：Licheng Sun、Helmut Goerner

  DOI：10.1021/j100145a012

  日期：1993.10

  The der-ay pathways of the lowest excited singlet state (1t*) of trans-1-(9-anthryl)-2-(4-R-phenyl)ethylenes (trans-R-StAs, where R = N(CH3)2, OCH3, CH3, Br, CN, and NO2 On the 4-Position of the styryl) were studied in solution at room and low temperatures. Fluorescence lifetime (tau(f)) and quantum yield (PHI(f)) as well as the yield (PHI(T)) and spectral and kinetic properties of the lowest triplet state were determined by steady-state and transient techniques. The solvent polarity has a large effect on the Stokes shift for (H3C)2N- and O2N-StA, the two derivatives with the strongest electron-donating and -accepting substituents. The smallest changes in PHI(f) and PHI(T), in comparison with the case of parent 9-StA, are caused by the Br or CH3 groups. For O2N- and (H3C)2N-StA, and to a lesser degree for NC- and H3CO-StA, PHI(f) and tau(f) become significantly smaller with increasing solvent polarity. Efficient deactivation by charge transfer via an excited singlet state with essentially trans configuration (A*) is proposed for these derivatives. The 1t* --> A* relaxation pathway in polar solvents is activated and competes with fluorescence and intersystem crossing. For NC-, H3CO-, and (H3C)2N-StA at room temperature trans --> cis photoisomerization occurs with substantial quantum yield (PHI(t --> c)) in those solvents in which the presence of the postulated A*-state efficiency reduces fluorescence and intersystem crossing. A contribution of a triplet mechanism to trans --> cis photoisomerization can be excluded throughout. A special case is O2N-StA, which exhibits virtually no photochemistry in both nonpolar and polar solvents, but PHI(t --> c) is up to 0.2 in slightly polar solvents, e.g., toluene.