(2E,5E)-19,19,49,49-tetramethyl-19H,49H-2,3,5,6-tetraaza-1,4(4,5)-dixanthenacyclohexaphane-2,5-diene | 868785-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2E,5E)-19,19,49,49-tetramethyl-19H,49H-2,3,5,6-tetraaza-1,4(4,5)-dixanthenacyclohexaphane-2,5-diene
• CAS: 868785-43-7
• 化学式: C₃₀H₂₄N₄O₂
• 分子量: 472.546
• InChiKey: FIYASCJBCMYZLP-FMWAKIAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.69
• 重原子数：
  36.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2E,5E)-19,19,49,49-tetramethyl-19H,49H-2,3,5,6-tetraaza-1,4(4,5)-dixanthenacyclohexaphane-2,5-diene 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Photoinduced Hinge-Like Molecular Motion:  Studies on Xanthene-Based Cyclic Azobenzene Dimers

  摘要：

  Molecular devices incorporating azobenzene units represent active components of smart systems, as they are capable of exhibiting photoregulated cooperative molecular motion. Herein, we describe the synthesis, X-ray crystal analysis, and photochemical and thermal studies of a xanthene based cyclic azobenzene dimer and its precursor. The trans-trans isomer of the azobenzene dimer upon photoirradiation transforms to the cis-cis isomer through an intermediate trans-cis isomer. The X-ray crystal structures of the trans-trans isomer (open) and the cis-cis isomer (closed) provide unambiguous proof for the hinge-like molecular motion in this class of molecules. The inferences drawn from photochemical and thermal studies shed light on the effect of varied substitution and cyclic structures on the different transitions. The lifetime of the cis-cis isomer is estimated to be 6.43 years, whereas the trans-cis isomer is short-lived (2.73 min) at 303 K. A rational explanation for the relative stability of the different isomers is derived from the isokinetic plot and theoretical calculations.

  DOI：

  10.1021/jo0513616
• 作为产物：
  描述：

  9,9-dimethyl-9H-xanthene-4,5-dicarboxylic acid 在 manganese(IV) oxide 、 氢氧化钾 、 二苯基膦叠氮化物 、 potassium tert-butylate 、 氧气 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 134.0h， 生成 (2E,5E)-19,19,49,49-tetramethyl-19H,49H-2,3,5,6-tetraaza-1,4(4,5)-dixanthenacyclohexaphane-2,5-diene
  参考文献：
  名称：

  Photoinduced Hinge-Like Molecular Motion:  Studies on Xanthene-Based Cyclic Azobenzene Dimers

  摘要：

  Molecular devices incorporating azobenzene units represent active components of smart systems, as they are capable of exhibiting photoregulated cooperative molecular motion. Herein, we describe the synthesis, X-ray crystal analysis, and photochemical and thermal studies of a xanthene based cyclic azobenzene dimer and its precursor. The trans-trans isomer of the azobenzene dimer upon photoirradiation transforms to the cis-cis isomer through an intermediate trans-cis isomer. The X-ray crystal structures of the trans-trans isomer (open) and the cis-cis isomer (closed) provide unambiguous proof for the hinge-like molecular motion in this class of molecules. The inferences drawn from photochemical and thermal studies shed light on the effect of varied substitution and cyclic structures on the different transitions. The lifetime of the cis-cis isomer is estimated to be 6.43 years, whereas the trans-cis isomer is short-lived (2.73 min) at 303 K. A rational explanation for the relative stability of the different isomers is derived from the isokinetic plot and theoretical calculations.

  DOI：

  10.1021/jo0513616