2,9-Dimethyl-4,7-bis(2-phenylethynyl)-1,10-phenanthroline | 1414364-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2,9-Dimethyl-4,7-bis(2-phenylethynyl)-1,10-phenanthroline
• 英文别名: 2,9-dimethyl-4,7-bis(2-phenylethynyl)-1,10-phenanthroline
• CAS: 1414364-63-8
• 化学式: C₃₀H₂₀N₂
• 分子量: 408.502
• InChiKey: JRBDWRDBXKLGMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,9-Dimethyl-4,7-bis(2-phenylethynyl)-1,10-phenanthroline 、 苯乙炔 、 4,7-dichloro-2,9-dimethyl-1,10-phenanthroline 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper(l) iodide 、 三乙胺 作用下， 以 苯 、 二氯甲烷 、 水 为溶剂， 反应 72.5h， 生成 4,7-bis(phenylethinyl)-1,10-phenanthroline
  参考文献：
  名称：

  Synthesis, crystal structure, and conjugation properties of phenanthroline copper phosphine complexes

  摘要：

  Facial synthetic method of 4,7-position conjugation extended phenanthrolines and X-ray structure of copper phosphine phenanthroline complexe were reported. The crystal structures showed pi-stacking and hydrogen bonding, and a small torsional angle between phen and phenylacetylene. These complexes exhibited strong conjugation dependant MLCT luminescence. The electronic and fluorescence spectra displayed a gradual red shift of the MLCT band as the conjugation increased. The presence of the phenyl groups reduced the energy of the pi* state in the d-pi* MLCT transition, allowing for the red shift. The electron-donating tri-isopropylsilyl (TIPS) groups on the ethynyl moiety increased the energy of the MLCT charge vector, allowing for the blue shift at the luminescence. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.09.028
• 作为产物：
  描述：

  苯乙炔 、 4,7-dichloro-2,9-dimethyl-1,10-phenanthroline 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三乙胺 作用下， 以 苯 为溶剂， 反应 72.0h， 以75%的产率得到2,9-Dimethyl-4,7-bis(2-phenylethynyl)-1,10-phenanthroline
  参考文献：
  名称：

  4,7-二取代共轭-扩展1,10-菲咯啉的简便合成

  摘要：

  公州教育大学科学教育系,公州314-711,韩国2012年5月22日接收,2012年6月22日接受关键词:交叉偶联,菲咯啉,取代,炔烃,共轭1,10-菲咯啉(phen) is a ubiquitous用于螯合过渡金属的配体。

  DOI：

  10.5012/bkcs.2012.33.9.3133

文献信息

• Synthesis, crystal structure, and conjugation properties of phenanthroline copper phosphine complexes
  作者：Hyungsock Suh、Dominick J. Casadonte、Louisa Hope-Weeks、Han-Je Kim、Beomsik Kim、Taesun Chang

  DOI：10.1016/j.ica.2012.09.028

  日期：2013.1

  Facial synthetic method of 4,7-position conjugation extended phenanthrolines and X-ray structure of copper phosphine phenanthroline complexe were reported. The crystal structures showed pi-stacking and hydrogen bonding, and a small torsional angle between phen and phenylacetylene. These complexes exhibited strong conjugation dependant MLCT luminescence. The electronic and fluorescence spectra displayed a gradual red shift of the MLCT band as the conjugation increased. The presence of the phenyl groups reduced the energy of the pi* state in the d-pi* MLCT transition, allowing for the red shift. The electron-donating tri-isopropylsilyl (TIPS) groups on the ethynyl moiety increased the energy of the MLCT charge vector, allowing for the blue shift at the luminescence. (C) 2012 Elsevier B. V. All rights reserved.
• Facile Synthesis of 4,7-Disubstituted Conjugation-Extended 1,10-Phenanthrolines
  作者：Hyung-Sock Suh、Fernando Hung-Low、Dominick Casadonte、Han-Je Kim、Beom-Sik Kim、Tae-Sun Chang

  DOI：10.5012/bkcs.2012.33.9.3133

  日期：2012.9.20

  Department of Science Education, Gongju National University of Education, Gongju 314-711, KoreaReceived May 22, 2012, Accepted June 22, 2012Key Words : Cross-coupling, Phenanthroline, Substitution, Alkynes, Conjugation1,10-Phenanthroline (phen) is a ubiquitous ligand for thechelation of transition metals.

  公州教育大学科学教育系,公州314-711,韩国2012年5月22日接收,2012年6月22日接受关键词:交叉偶联,菲咯啉,取代,炔烃,共轭1,10-菲咯啉(phen) is a ubiquitous用于螯合过渡金属的配体。