4,6,4'',6''-Tetraphenyl-2,2':6',2''-terpyridine | 221055-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,6,4'',6''-Tetraphenyl-2,2':6',2''-terpyridine
• 英文别名: 4,6,4'',6''-tetraphenyl-[2,2';6',2'']terpyridine；2,6-Bis<4,6-diphenylpyrid-2-yl>pyridin；2-[6-(4,6-Diphenylpyridin-2-yl)pyridin-2-yl]-4,6-diphenylpyridine；2-[6-(4,6-diphenylpyridin-2-yl)pyridin-2-yl]-4,6-diphenylpyridine
• CAS: 221055-92-1
• 化学式: C₃₉H₂₇N₃
• 分子量: 537.663
• InChiKey: XGQLVHRXWSVZJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 [trichloro(4'-tolyl-2,2':6',2''-terpyridine)ruthenium(III)] 、 4,6,4'',6''-Tetraphenyl-2,2':6',2''-terpyridine 在 AgBF₄ 作用下， 以 丙酮 为溶剂， 以68%的产率得到[Ru(4,6,4'',6''-tetraphenyl-2,2':6',2''-terpyridine)(4'-p-tolyl-2,2':6',2''-terpyridine)](PF6)2*H2O
  参考文献：
  名称：

  Ru(II) complexes of polyarylated terpyridines: unexpected side-chain C-metallation and photosensitization of electron transfer

  摘要：

  The new ligands 4,4 " -diphenyl-6,6 " -di(4-ethoxycarbonylphenyl)-2,2':6',2 " -terpyridine (H4), its non-carboxylated 4,6,4 " ,6 " -tetraphenyl analogue (H5) and the 4,4 " -diphenyl-6,6 " -di(4-methoxyphenyl) analogue were prepared in high yields via double Krohnke reactions. Reactions with activated (ttpy)RuCl3 (ttpy is 4'-p-tolyl-2,2':6',2 " -terpyridine) provided the symmetrical N-6-coordinated complexes, [Ru(H4)(ttpy)](PF6)(2) and [Ru(H5)(ttpy)](PF6)2, along with the novel, unsymmetrical C-metallated analogues [Ru(4)(ttpy)]PF6 and [Ru(5)(ttpy)]PF6, in which an unprecedented side-chain metallation occurred in lieu of incomplete substitution. A crystallographic analysis of [Ru(5)(ttpy)]NO3 confirmed the N5C donor set in these products and revealed a distorted binding of 5(-) as well as 'pi -stacking' between its uncoordinated pyridine and the ttpy ligand. The diester [Ru(H4)(ttpy)](PF6)(2) was hydrolyzed to the diacid complex [Ru(H(2)3)(ttpy)PF6)(2) (H(2)3 is 4,4 " -diphenyl-6,6 " -di(4-carboxyphenyl)2,2':6',2 " -terpyridine). Measurements of the photogeneration of methyl viologen cation radical with [Ru(H5)(ttpy)](PF6)(2) and [Ru(H(2)3)(ttpy)](PF6)(2) as sensitizers showed that the presence of carboxyl groups in the latter provided a distinct benefit, owing to the formation of the neutral form [Ru(3)(ttpy)](0) but this was insufficient to overcome the detrimental effect of inter-ligand repulsions. (C) 2001 Published by Elsevier Science B.V.

  DOI：

  10.1016/s0020-1693(01)00626-0
• 作为产物：
  描述：

  N-苯甲酰甲基溴吡啶 、 1,1'-(2,6-pyridylene)bis(3-phenyl-2-propen-1-one) 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以71%的产率得到4,6,4'',6''-Tetraphenyl-2,2':6',2''-terpyridine
  参考文献：
  名称：

  Constable, Edwin C.; Baum, Gerhard; Bill, Eckhard, Chemistry - A European Journal, 1999, vol. 5, # 2, p. 498 - 508

  摘要：

  DOI：

文献信息

• Constable, Edwin C.; Baum, Gerhard; Bill, Eckhard, Chemistry - A European Journal, 1999, vol. 5, # 2, p. 498 - 508
  作者：Constable, Edwin C.、Baum, Gerhard、Bill, Eckhard、Dyson, Raylene、Van Eldik, Rudi、Fenske, Dieter、Kaderli, Susan、Morris, Darrell、Neubrand, Anton、Neuburger, Markus、Smith, Diane R.、Wieghardt, Karl、Zehnder, Margareta、Zuberbuehler, Andreas D.

  DOI：——

  日期：——
• Ru(II) complexes of polyarylated terpyridines: unexpected side-chain C-metallation and photosensitization of electron transfer
  作者：Charles Mikel、Pierre G. Potvin

  DOI：10.1016/s0020-1693(01)00626-0

  日期：2001.12

  The new ligands 4,4 " -diphenyl-6,6 " -di(4-ethoxycarbonylphenyl)-2,2':6',2 " -terpyridine (H4), its non-carboxylated 4,6,4 " ,6 " -tetraphenyl analogue (H5) and the 4,4 " -diphenyl-6,6 " -di(4-methoxyphenyl) analogue were prepared in high yields via double Krohnke reactions. Reactions with activated (ttpy)RuCl3 (ttpy is 4'-p-tolyl-2,2':6',2 " -terpyridine) provided the symmetrical N-6-coordinated complexes, [Ru(H4)(ttpy)](PF6)(2) and [Ru(H5)(ttpy)](PF6)2, along with the novel, unsymmetrical C-metallated analogues [Ru(4)(ttpy)]PF6 and [Ru(5)(ttpy)]PF6, in which an unprecedented side-chain metallation occurred in lieu of incomplete substitution. A crystallographic analysis of [Ru(5)(ttpy)]NO3 confirmed the N5C donor set in these products and revealed a distorted binding of 5(-) as well as 'pi -stacking' between its uncoordinated pyridine and the ttpy ligand. The diester [Ru(H4)(ttpy)](PF6)(2) was hydrolyzed to the diacid complex [Ru(H(2)3)(ttpy)PF6)(2) (H(2)3 is 4,4 " -diphenyl-6,6 " -di(4-carboxyphenyl)2,2':6',2 " -terpyridine). Measurements of the photogeneration of methyl viologen cation radical with [Ru(H5)(ttpy)](PF6)(2) and [Ru(H(2)3)(ttpy)](PF6)(2) as sensitizers showed that the presence of carboxyl groups in the latter provided a distinct benefit, owing to the formation of the neutral form [Ru(3)(ttpy)](0) but this was insufficient to overcome the detrimental effect of inter-ligand repulsions. (C) 2001 Published by Elsevier Science B.V.