1,1'-bis(ethenyl-4-pyridyl)ferrocene | 222165-10-8

• 英文名称: 1,1'-bis(ethenyl-4-pyridyl)ferrocene
• CAS: 222165-10-8
• 化学式: C₂₄H₂₀FeN₂
• 分子量: 392.283
• InChiKey: PTOGSSGZFZYYQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,1'-bis(ethenyl-4-pyridyl)ferrocene 、 S-1,1'-联-2-萘酚 以 甲醇 为溶剂， 以58%的产率得到1,1'-bis(ethenyl-4-pyridyl)ferrocene * (+/-)-1,1'-binaphtol
  参考文献：
  名称：

  Organometallic−Organic Hybrid Crystals from Ferrocenyl Dipyridine and Binaphthol:  Different Crystal Structures and Nonlinear Optical Properties Depending upon the Reaction Medium and Optical Purity of Binaphthol

  摘要：

  The hydrogen bond directed molecular recognition between 1,1'-bis(ethenyl-4-pyridyl)ferrocene (1) and (+/-)-1,1'-binaphthol (2)/(-)-1,1'-binaphthol ((-)-2) has been studied by cocrystallization in different solvents. Single-crystal X-ray structures reveal that 3:2, 2:1, and 1:1 complexes (3, 4, and 5, respectively) of 1,1'-bis(ethenyl-4-pyridyl)ferrocene (1) and (+/-)-1,1-binaphthol (2) are formed in tetrahydrofuran, methanol, and ethanol, respectively. 5 has a noncentrosymmetric packing arrangement, and an efficiency of 0.3 times that of urea in second-harmonic generation has been measured at 1295 nm. An X-ray crystal structure of 6, 1:1 complex of 1 with (-)-2 in ethanol, reveals that all the molecular dipoles are aligned in the same direction (i.e, a polar crystal), but 6 has modest nonlinear optical properties (ca. 0.4 times that of urea).

  DOI：

  10.1021/om990544d
• 作为产物：
  描述：

  4-甲基吡啶 、 1,1'-二茂铁二甲醛 在 lithium diisopropylamide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到1,1'-bis(ethenyl-4-pyridyl)ferrocene
  参考文献：
  名称：

  Organometallic−Organic Hybrid Crystals from Ferrocenyl Dipyridine and Binaphthol:  Different Crystal Structures and Nonlinear Optical Properties Depending upon the Reaction Medium and Optical Purity of Binaphthol

  摘要：

  The hydrogen bond directed molecular recognition between 1,1'-bis(ethenyl-4-pyridyl)ferrocene (1) and (+/-)-1,1'-binaphthol (2)/(-)-1,1'-binaphthol ((-)-2) has been studied by cocrystallization in different solvents. Single-crystal X-ray structures reveal that 3:2, 2:1, and 1:1 complexes (3, 4, and 5, respectively) of 1,1'-bis(ethenyl-4-pyridyl)ferrocene (1) and (+/-)-1,1-binaphthol (2) are formed in tetrahydrofuran, methanol, and ethanol, respectively. 5 has a noncentrosymmetric packing arrangement, and an efficiency of 0.3 times that of urea in second-harmonic generation has been measured at 1295 nm. An X-ray crystal structure of 6, 1:1 complex of 1 with (-)-2 in ethanol, reveals that all the molecular dipoles are aligned in the same direction (i.e, a polar crystal), but 6 has modest nonlinear optical properties (ca. 0.4 times that of urea).

  DOI：

  10.1021/om990544d

文献信息

• Crystal Engineering with Structurally Flexible 1,1′‐Substituted Ferrocenes for Nonlinear Optical Materials
  作者：Dong Mok Shin、In Su Lee、Young Keun Chung

  DOI：10.1002/ejic.200200596

  日期：2003.6

  Cocrystals derived from 1,1′-bis(ethenyl-4-pyridyl)ferrocene (1) and resorcinol/phloroglucinol and a crystal of 1,1′-bis(ethenyl-4-quinolinyl)ferrocene (5) have been studied with the aim of engineering crystalline NLO materials. X-ray structure analyses revealed a NLO active syn-type molecular conformation of 1 and 5 via hydrogen bonding with resorcinol/phloroglucinol and π-π interaction between quinoline

  衍生自 1,1'-双（乙烯基-4-吡啶基）二茂铁 (1) 和间苯二酚/间苯三酚的共晶以及 1,1'-双（乙烯基-4-喹啉基）二茂铁 (5) 的晶体已与工程晶体 NLO 材料的目标。X 射线结构分析揭示了 1 和 5 的 NLO 活性合成型分子构象，分别通过与间苯二酚/间苯三酚的氢键和喹啉环之间的 π-π 相互作用。对于 5，所有分子偶极子都在同一方向上排列，SHG 效率约为尿素的 4 倍。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)