3-[4-(N-phenylanilino)phenyl]prop-2-ynal | 1209009-00-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[4-(N-phenylanilino)phenyl]prop-2-ynal
• CAS: 1209009-00-6
• 化学式: C₂₁H₁₅NO
• 分子量: 297.356
• InChiKey: VDDSIWKYBNLESW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[4-(N-phenylanilino)phenyl]prop-2-ynal 、 苄基苯基砜 在 氯磷酸二乙酯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以78.2%的产率得到
  参考文献：
  名称：

  Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes

  摘要：

  A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of p-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescence. The emission underwent a large bathochromic shift in polar solvent because of stabilization of their charge-separated excited states. Analyses of fluorescence life times of aminoacetylenes revealed that radiationless process was suppressed in the polar solvent CH2Cl2, resulting in high quantum yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.023
• 作为产物：
  描述：

  3-(4-(diphenylamino)phenyl)prop-2-yn-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以59%的产率得到3-[4-(N-phenylanilino)phenyl]prop-2-ynal
  参考文献：
  名称：

  推挽生色团的多足排列：影响其电子和光学性质的基本参数†

  摘要：

  已经准备了一系列具有线性，四极和三脚架排列的模型推挽分子，一个取代的氨基供体，两个受体和一个部分扩展的π系统。两个外围电子受体，即N，N使用了'-二丁基巴比妥酸和双氰基乙烯基。通过差示扫描量热法，电化学，单光子吸收光谱法，光致压电技术研究了24种推挽发色团的基本性质，并得到DFT计算的支持。阐明了彻底的结构-性质关系，同时揭示了结构排列/分支对电子和光学性质的重大影响。推挽式分子的基本光电特性受其排列方式（线性/四极/三脚架），外围受体的附着，π系统的延伸和平面化以及辅助N取代基的类型的影响。

  DOI：

  10.1039/c6nj02994a

文献信息

• Synthesis and spectroscopic study of phenylene–(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic π-systems
  作者：Jing-Kun Fang、De-Lie An、Kan Wakamatsu、Takeharu Ishikawa、Tetsuo Iwanaga、Shinji Toyota、Shin-ichi Akita、Daisuke Matsuo、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tet.2010.05.016

  日期：2010.7

  To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic pi-systems, phenylene-(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of beta-substituted sulfones. These substituted phenyleneethynylenes showed large molar absorption coefficients epsilon, and emitted strong fluorescence upon UV light irradiation. Phenylene (poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields Phi(F) as their polyethynylene motifs -(C C)(n)- expanded. The drastic decrease of fluorescence quantum yields Phi(F) were explained in terms of increasing nonradiative reaction rate constants k(nr), which had been determined by the corresponding fluorescence quantum yields Phi(F) and lifetime values tau. The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state. Comparison of slope values rho in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylene (poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic pi-systems with cyano group did little. (C) 2010 Elsevier Ltd. All rights reserved.