9-(4-N,N-dimethylaminophenyl)phenanthrene | 147648-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-(4-N,N-dimethylaminophenyl)phenanthrene
• 英文别名: 4-(9-phenanthryl)-N,N-dimethylaniline；N,N-Dimethyl-4-(phenanthren-9-YL)aniline；N,N-dimethyl-4-phenanthren-9-ylaniline
• CAS: 147648-01-9
• 化学式: C₂₂H₁₉N
• 分子量: 297.4
• InChiKey: LIINMAHNIYWECN-UHFFFAOYSA-N

物化性质

• 沸点：
  469.1±24.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  C₂₂H₁₉N 在 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以44%的产率得到9-(4-N,N-dimethylaminophenyl)phenanthrene
  参考文献：
  名称：

  2炔基联芳基的Brønsted酸催化的碳环化

  摘要：

  邻炔基联芳基在催化量的布朗斯台德酸存在下反应，在温和的条件下以高收率得到菲。该转化的活性和选择性由二芳基炔基部分的取代模式决定。在嗜碳性路易斯和布朗斯台德酸催化的环异构化过程中，炔烃活化存在选择性变化。

  DOI：

  10.1002/adsc.201801526

文献信息

• Radiative Depopulation of the Excited Intramolecular Charge-Transfer State of 9-(4-(<i>N</i>,<i>N</i>-Dimethylamino)phenyl)phenanthrene
  作者：A. Onkelinx、F. C. De Schryver、L. Viaene、M. Van der Auweraer、K. Iwai、M. Yamamoto、M. Ichikawa、H. Masuhara、M. Maus、W. Rettig

  DOI：10.1021/ja953697a

  日期：1996.1.1

  Intramolecular photoinduced electron transfer in 9-(p-N,N-dimethylanilino)phenanthrene (9DPhen) has been studied in solution. The solvent dependence of the fluorescence spectra of 9DPhen indicates that the emission occurs from a highly polar excited state. The quantum yield of fluorescence (Phi(f)) of 9DPhen is quite high and increases with increasing solvent polarity. The radiative rate constant (k(f)), however, shows a maximum for solvents of intermediate polarity, e.g., in butyl acetate a value of 2.3 x 10(8) s(-1) is attained. These results are difficult to explain within the ''TICT'' (twisted intramolecular charge transfer) model, which predicts a strongly forbidden fluorescence caused by a minimum overlap of the orbitals involved in the transition. The above-mentioned trend as a function of the solvent polarity is observed in particular donor-acceptor substituted arenes where the L(b) State of the corresponding arenes is lower in energy than the L(a) state. The quantum chemical calculations actually could explain this behavior on the basis of an ICT state which interacts with the lower lying (1)L(a) and (1)L(b) states of the acceptor. The quantum mechanical mixing of states can occur by two pathways, namely orbital mixing and mixing of configurations, and is modified by geometrical changes and by solvent polarity. The single exponential fluorescence decay, obtained with time-correlated single-photon-timing, suggests emission from an excited charge-transfer state, resulting from a solvent-induced rapid relaxation of the initial delocalized excited state of 9DPhen, obtained immediately after picosecond pulsed excitation. Picosecond transient absorption spectra in acetonitrile show a rapid decay within a few picoseconds from a less polar but delocalized excited state toward a more polar ICT state. Even the triplet state of 9DPhen in isopentane at 77 K shows a significant polar character. As a reference compound, 9-phenylphenanthrene (9PhPhen) was also examined by means of stationary and time-resolved fluorescence measurements as well as transient absorption experiments.