[4-((E)-2-Anthracen-9-yl-vinyl)-phenyl]-dimethyl-amine | 60949-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [4-((E)-2-Anthracen-9-yl-vinyl)-phenyl]-dimethyl-amine
• 英文别名: 4-(2-anthracen-9-ylethenyl)-N,N-dimethylaniline
• CAS: 60949-20-4
• 化学式: C₂₄H₂₁N
• 分子量: 323.437
• InChiKey: YATJOUUMQREMEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [4-((E)-2-Anthracen-9-yl-vinyl)-phenyl]-dimethyl-amine 在 palladium on activated charcoal 氢气 作用下， 以 苯 为溶剂， 反应 30.0h， 以60.6%的产率得到9-<2-(4-Dimethylaminophenyl)-ethyl)-anthracen
  参考文献：
  名称：

  分子内异准分子系统的皮秒激光光谱。p-(CH3)2NC6H4–(CH2)n–(9-Anthryl),p-(CH3)2NC6H4–(1-Pyrenyl) 系统和 9,9'-Bianthryl 的时间分辨荧光研究

  摘要：

  为了阐明光化学电荷转移和异源准分子形成过程的基本过程的细节，也为了将获得的结果与瞬态吸收光谱测量的结果进行比较，我们通过 ps 时间分辨方法检查了以下分子内异源准分子系统使用锁模 Nd3+ 进行荧光测量：YAG 激光器和条纹相机：p-(CH3)2–NC6H4–(CH2)n–(9-蒽基) (n=0, 1, 2, 3), p-( CH3)2NC6H4–(CH2)n-(1-芘基) (n=1, 2, 3) 和 9,9'-联蒽基。已经清楚地证明了亚甲基链长、溶剂极性和粘度对分子内电荷转移过程的影响。得出的结论是，在 n=3 化合物中均未识别出在基态具有夹心构型的分子，由于采用夹心构型所需的广泛构象变化，在己烷中形成异源准分子需要几纳秒。构象变化和溶剂重新定向都涉及...

  DOI：

  10.1246/bcsj.54.3304
• 作为产物：
  描述：

  [4-((E)-2-Anthracen-9-yl-vinyl)-phenyl]-dimethyl-amine 以 甲苯 为溶剂， 生成 [4-((E)-2-Anthracen-9-yl-vinyl)-phenyl]-dimethyl-amine
  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

• Picosecond Laser Spectroscopy of Intramolecular Heteroexcimer Systems. Time-resolved Fluorescence Studies of<i>p</i>-(CH₃)₂NC₆H₄–(CH₂)<i>_n</i>–(9-Anthryl),<i>p</i>-(CH₃)₂NC₆H₄–(1-Pyrenyl) Systems and 9,9′-Bianthryl
  作者：Masahito Migita、Tadashi Okada、Noboru Mataga、Yoshiteru Sakata、Soichi Misumi、Nobuaki Nakashima、Keitaro Yoshihara

  DOI：10.1246/bcsj.54.3304

  日期：1981.11

  9′-bianthryl. Effects of methylene chain length, solvent polarity and viscosity upon the intramolecular charge transfer processes have been clearly demonstrated. It is concluded that molecules with sandwich configuration in the ground state are not recognized in both n=3 compounds, and it takes a few ns for the heteroexcimer formation in hexane because of an extensive conformation change necessary to

  为了阐明光化学电荷转移和异源准分子形成过程的基本过程的细节，也为了将获得的结果与瞬态吸收光谱测量的结果进行比较，我们通过 ps 时间分辨方法检查了以下分子内异源准分子系统使用锁模 Nd3+ 进行荧光测量：YAG 激光器和条纹相机：p-(CH3)2–NC6H4–(CH2)n–(9-蒽基) (n=0, 1, 2, 3), p-( CH3)2NC6H4–(CH2)n-(1-芘基) (n=1, 2, 3) 和 9,9'-联蒽基。已经清楚地证明了亚甲基链长、溶剂极性和粘度对分子内电荷转移过程的影响。得出的结论是，在 n=3 化合物中均未识别出在基态具有夹心构型的分子，由于采用夹心构型所需的广泛构象变化，在己烷中形成异源准分子需要几纳秒。构象变化和溶剂重新定向都涉及...
• 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.