3,6-bis{(1Z)-1-bromo-2-[4-(dodecyloxy)phenyl]ethenyl}pyridazine | 1147871-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,6-bis{(1Z)-1-bromo-2-[4-(dodecyloxy)phenyl]ethenyl}pyridazine
• 英文别名: 3,6-bis[(Z)-1-bromo-2-(4-dodecoxyphenyl)ethenyl]pyridazine
• CAS: 1147871-90-6
• 化学式: C₄₄H₆₂Br₂N₂O₂
• 分子量: 810.796
• InChiKey: XDNXKLBWGGBMHQ-CSMBQKPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  50
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-bis{(1Z)-1-bromo-2-[4-(dodecyloxy)phenyl]ethenyl}pyridazine 以 环己烷 为溶剂， 生成
  参考文献：
  名称：

  含卤素3,6-二苯乙烯基哒嗪（= 3,6-双（2-苯基乙烯基）哒嗪的液晶成像技术

  摘要：

  Abstractmagnified imageThe 3,6‐bis{(1E)‐2‐[4‐(dodecyloxy)phenyl]ethenyl}pyridazine (1a) was regio‐ and stereoselectively brominated or chlorinated to the (Z,Z)‐compounds 3 and 6, respectively. The conjugated core of these systems represents a mesogen for smectic (and nematic) liquid crystals and, moreover, a chromophore with an absorption at the UV/VIS border. Irradiation and efficient intersystem crossing to the triplet state leads to isomerization reactions (Z,Z)→(E,Z) in solution as well as in the thermotropic LC phases. Since (E,Z)‐configurations are only tolerated to a very small extent by the mesophases, the photoinduced transition S→N→I of 6 can be used as an imaging technique.

  DOI：

  10.1002/hlca.200800249
• 作为产物：
  描述：

  3,6-双{(1E)-2-[4-(十二烷氧基)苯基]乙烯基}哒嗪 在 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 以55%的产率得到3,6-bis{(1Z)-1-bromo-2-[4-(dodecyloxy)phenyl]ethenyl}pyridazine
  参考文献：
  名称：

  含卤素3,6-二苯乙烯基哒嗪（= 3,6-双（2-苯基乙烯基）哒嗪的液晶成像技术

  摘要：

  Abstractmagnified imageThe 3,6‐bis{(1E)‐2‐[4‐(dodecyloxy)phenyl]ethenyl}pyridazine (1a) was regio‐ and stereoselectively brominated or chlorinated to the (Z,Z)‐compounds 3 and 6, respectively. The conjugated core of these systems represents a mesogen for smectic (and nematic) liquid crystals and, moreover, a chromophore with an absorption at the UV/VIS border. Irradiation and efficient intersystem crossing to the triplet state leads to isomerization reactions (Z,Z)→(E,Z) in solution as well as in the thermotropic LC phases. Since (E,Z)‐configurations are only tolerated to a very small extent by the mesophases, the photoinduced transition S→N→I of 6 can be used as an imaging technique.

  DOI：

  10.1002/hlca.200800249

文献信息

• Imaging Technique with Liquid Crystals of Halogen-Containing 3,6-Distyrylpyridazines (=3,6-Bis(2-phenylethenyl)pyridazines)
  作者：Thorsten Lifka、Peter Seus、Annette Oehlhof、Herbert Meier

  DOI：10.1002/hlca.200800249

  日期：2009.2

  Abstractmagnified imageThe 3,6‐bis(1E)‐2‐[4‐(dodecyloxy)phenyl]ethenyl}pyridazine (1a) was regio‐ and stereoselectively brominated or chlorinated to the (Z,Z)‐compounds 3 and 6, respectively. The conjugated core of these systems represents a mesogen for smectic (and nematic) liquid crystals and, moreover, a chromophore with an absorption at the UV/VIS border. Irradiation and efficient intersystem crossing to the triplet state leads to isomerization reactions (Z,Z)→(E,Z) in solution as well as in the thermotropic LC phases. Since (E,Z)‐configurations are only tolerated to a very small extent by the mesophases, the photoinduced transition S→N→I of 6 can be used as an imaging technique.