4,4'-(bis-phenylethynyl)diethynylbiphenyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-(bis-phenylethynyl)diethynylbiphenyl
• 英文别名: 1-(4-Phenylbuta-1,3-diynyl)-4-[4-(4-phenylbuta-1,3-diynyl)phenyl]benzene
• 化学式: C₃₂H₁₈
• 分子量: 402.495
• InChiKey: RENUDYLRKHMXQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (碘乙炔基)苯 、 4,4'-bis((trimethylstannyl)ethynyl)biphenyl 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以50%的产率得到4,4'-(bis-phenylethynyl)diethynylbiphenyl
  参考文献：
  名称：

  Synthesis of highly ethynylated mono and dinuclear Pt(II) tethers bearing the 4,4′-bis(ethynyl)biphenyl (debp) unit as central core

  摘要：

  Mono and bisubstituted bis(ethynyl)biphenyl Pt(II) complexes, i.e. trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-H)], R = p-NO2C6H4 (3b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (3c), and trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-R)], R = C6H5 (4a), p-NO2C6H4 (4b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (4c), have been synthesized by the dehydrohalogenation reaction from the appropriate Pt monochloro acetylides trans-[(RC equivalent toC)Pt(PPh3)(2)Cl], R = C6H5 (1a), R =p-NO2C6H4 (1b), R = (eta (5)-C5H4)Fe(eta (5)-C5H5) (1c) and HC equivalent toC-p-C6H5-p-C6H5-C equivalent to CH, (4,4'-bis-ethynylbiphenyl), (DEBP) (2). In order to make possible a direct evaluation of the role of Pt centers on the properties of these highly ethynylated complexes, the corresponding species without Pt were prepared, i.e. C6H5-C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC-C6H5, (4,4'-(bis-phenylethynyl)-diethynylbiphenyl) (7), and (eta (5)-C5H5)Fe(eta (5)-C5H4)-(C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC)-(eta (5)-C5H4)Fe(eta (5)-C5H4)Fe(eta (5)-C5H5), (4,4 '-(bis-ferrocenylethynyl)-diethynylbiphenyl) (8). Preparation of the latter compounds was only achieved by the use of the palladium catalyzed Stille coupling reaction, since the dehydrohalogenation route afforded only homocoupled and polymeric products. The electron-donor or electron-withdrawing ligands coordinated to Pt were chosen for the purpose of tuning the optical properties of the complexes through the different charge distribution along the pi -electron conjugation. Characteristic spectroscopic features (UV-vis, FT-IR and NMR) of these complexes are discussed. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00533-7

文献信息

• Synthesis of highly ethynylated mono and dinuclear Pt(II) tethers bearing the 4,4′-bis(ethynyl)biphenyl (debp) unit as central core
  作者：M.V Russo、C Lo Sterzo、P Franceschini、G Biagini、A Furlani

  DOI：10.1016/s0022-328x(00)00533-7

  日期：2001.1

  Mono and bisubstituted bis(ethynyl)biphenyl Pt(II) complexes, i.e. trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-H)], R = p-NO2C6H4 (3b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (3c), and trans-[(R-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-p-C6H4-p-C6H4-C equivalent toC-)Pt(PPh3)(2)(-C equivalent toC-R)], R = C6H5 (4a), p-NO2C6H4 (4b), (eta (5)-C5H5)Fe(eta (5)-C5H4) (4c), have been synthesized by the dehydrohalogenation reaction from the appropriate Pt monochloro acetylides trans-[(RC equivalent toC)Pt(PPh3)(2)Cl], R = C6H5 (1a), R =p-NO2C6H4 (1b), R = (eta (5)-C5H4)Fe(eta (5)-C5H5) (1c) and HC equivalent toC-p-C6H5-p-C6H5-C equivalent to CH, (4,4'-bis-ethynylbiphenyl), (DEBP) (2). In order to make possible a direct evaluation of the role of Pt centers on the properties of these highly ethynylated complexes, the corresponding species without Pt were prepared, i.e. C6H5-C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC-C6H5, (4,4'-(bis-phenylethynyl)-diethynylbiphenyl) (7), and (eta (5)-C5H5)Fe(eta (5)-C5H4)-(C equivalent toC-C equivalent toC-C6H4-C6H4-C equivalent toC-C equivalent toC)-(eta (5)-C5H4)Fe(eta (5)-C5H4)Fe(eta (5)-C5H5), (4,4 '-(bis-ferrocenylethynyl)-diethynylbiphenyl) (8). Preparation of the latter compounds was only achieved by the use of the palladium catalyzed Stille coupling reaction, since the dehydrohalogenation route afforded only homocoupled and polymeric products. The electron-donor or electron-withdrawing ligands coordinated to Pt were chosen for the purpose of tuning the optical properties of the complexes through the different charge distribution along the pi -electron conjugation. Characteristic spectroscopic features (UV-vis, FT-IR and NMR) of these complexes are discussed. (C) 2001 Elsevier Science B.V. All rights reserved.