3,5-bis(octyloxy)-N-(4H-1,2,4-triazol-4-yl)benzamide | 890850-20-1

• 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: 3,5-bis(octyloxy)-N-(4H-1,2,4-triazol-4-yl)benzamide
• 英文别名: C8tba；3,5-dioctoxy-N-(1,2,4-triazol-4-yl)benzamide
• CAS: 890850-20-1
• 化学式: C₂₅H₄₀N₄O₃
• 分子量: 444.618
• InChiKey: SICVMAPSNKFTNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iron(II) tetrafluoroborate hexahydrate 、 3,5-bis(octyloxy)-N-(4H-1,2,4-triazol-4-yl)benzamide 以 甲醇 为溶剂， 生成 tris(3,5-bis(octyloxy)-N-(4H-1,2,4-triazol-4-yl)benzamide)iron(II) tetrafluoroborate monohydrate
  参考文献：
  名称：

  One-Dimensional Iron(II) Compounds Exhibiting Spin Crossover and Liquid Crystalline Properties in the Room Temperature Region

  摘要：

  A novel series of 1D Fe(II) metallomesogens have been synthesized using the ligand 5-bis(alkoxy)-N-(4H-1,2,4-triazol-4-yl)benzamide (C-n-tba) and the Fe(X)(2) center dot sH(2)O salts. The polymers obey the general formula [Fe(C-n-tba)(3)]-(X)(2) center dot sH(2)O [X = CF3SO3-, BF4-; n = 4, 6, 8, 10, 12]. The derivatives with n = 4, 6 exhibit spin transition behavior like in crystalline compounds, whereas those with n = 8, 10, 12 present a spin transition coexisting with the mesomorphic behavior in the room-temperature region. A columnar mesophase has been found for the majority of the metallomesogens, but also a columnar lamellar mesophase was observed for other derivatives. [Fe(C-12- tba)(3)](CF3SO3)(2) represents a new example of a system where the phase transition directly influences the spin transition of the Fe(II) ions but is not the driving energy of the spin crossover phenomenon. The compounds display drastic changes of color from violet (low-spin state, LS) to white (high-spin state, HS). The compounds are fluid, and it is possible to prepare thin films from them.

  DOI：

  10.1021/ic8006266
• 作为产物：
  描述：

  4-氨基-1,2,4-三氮唑 、 3,5-bis(octyloxy)benzoic acid 在 (2,3-二氢-2-硫酮-3-苯并唑)膦酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到3,5-bis(octyloxy)-N-(4H-1,2,4-triazol-4-yl)benzamide
  参考文献：
  名称：

  由相变触发的自旋状态切换：自组装铁 (II) 配合物与烷基束缚三唑配体的自旋交叉特性

  摘要：

  具有两个 C12 和 C16 长烷基链的三唑衍生物的铁 (II) 配合物 (C12trz)FeII 和 (C16trz)FeII，作为新型自旋交叉材料，显示出响应相变的自旋态转变。相比之下，具有两个 C8 烷基链 ((C8trz)FeII) 的三唑配合物仅表现出较差的响应。(C16trz)FeII 的 EXAFS 和 XRD 分析表明多核铁 (II) 物种的交叉自组装结构。根据 DSC、VT-IR 和 VT-XRD 谱，自旋态转变是由相互交错的烷基链的熔化触发的，这可能是自旋态的“锁定和释放”特征的原因。由于相变的热可逆性，自旋交叉可以重复而不会恶化。

  DOI：

  10.1021/ja038088e

文献信息

• Switching of Spin States Triggered by a Phase Transition:  Spin-Crossover Properties of Self-Assembled Iron(II) Complexes with Alkyl-Tethered Triazole Ligands
  作者：Tsuyohiko Fujigaya、Dong-Lin Jiang、Takuzo Aida

  DOI：10.1021/ja038088e

  日期：2003.12.1

  self-assembled structure of polynuclear iron(II) species. According to DSC, VT-IR, and VT-XRD profiles, the spin-state transition is triggered by melting of the interdigitating alkyl chains, which is likely responsible for the "lock-and-release" feature of the spin state. By virtue of the thermoreversibility of the phase transition, the spin crossover could be repeated without deterioration.

  具有两个 C12 和 C16 长烷基链的三唑衍生物的铁 (II) 配合物 (C12trz)FeII 和 (C16trz)FeII，作为新型自旋交叉材料，显示出响应相变的自旋态转变。相比之下，具有两个 C8 烷基链 ((C8trz)FeII) 的三唑配合物仅表现出较差的响应。(C16trz)FeII 的 EXAFS 和 XRD 分析表明多核铁 (II) 物种的交叉自组装结构。根据 DSC、VT-IR 和 VT-XRD 谱，自旋态转变是由相互交错的烷基链的熔化触发的，这可能是自旋态的“锁定和释放”特征的原因。由于相变的热可逆性，自旋交叉可以重复而不会恶化。
• One-Dimensional Iron(II) Compounds Exhibiting Spin Crossover and Liquid Crystalline Properties in the Room Temperature Region
  作者：M. Seredyuk、A. B. Gaspar、V. Ksenofontov、Y. Galyametdinov、M. Verdaguer、F. Villain、P. Gütlich

  DOI：10.1021/ic8006266

  日期：2008.11.17

  A novel series of 1D Fe(II) metallomesogens have been synthesized using the ligand 5-bis(alkoxy)-N-(4H-1,2,4-triazol-4-yl)benzamide (C-n-tba) and the Fe(X)(2) center dot sH(2)O salts. The polymers obey the general formula [Fe(C-n-tba)(3)]-(X)(2) center dot sH(2)O [X = CF3SO3-, BF4-; n = 4, 6, 8, 10, 12]. The derivatives with n = 4, 6 exhibit spin transition behavior like in crystalline compounds, whereas those with n = 8, 10, 12 present a spin transition coexisting with the mesomorphic behavior in the room-temperature region. A columnar mesophase has been found for the majority of the metallomesogens, but also a columnar lamellar mesophase was observed for other derivatives. [Fe(C-12- tba)(3)](CF3SO3)(2) represents a new example of a system where the phase transition directly influences the spin transition of the Fe(II) ions but is not the driving energy of the spin crossover phenomenon. The compounds display drastic changes of color from violet (low-spin state, LS) to white (high-spin state, HS). The compounds are fluid, and it is possible to prepare thin films from them.