4,5-bis(hexylthio)-1,2-diimino-isoindoline | 144255-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4,5-bis(hexylthio)-1,2-diimino-isoindoline
• 英文别名: 5,6-bis(hexylthio)-1,3-diimino-isoindoline；5,6-bis(hexylthio)isoindoline-1,3-diimine；4,5-bis(hexylthio)-1,2-dicyanobenzene；5,6-Bis(hexylsulfanyl)-1-imino-1H-isoindol-3-amine；5,6-bis(hexylsulfanyl)-3-iminoisoindol-1-amine
• CAS: 144255-63-0
• 化学式: C₂₀H₃₁N₃S₂
• 分子量: 377.618
• InChiKey: GRTGHYUBZSJXLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1,3-三氯异吲哚 、 4,5-bis(hexylthio)-1,2-diimino-isoindoline 在 三乙胺 、 sodium methylate 、 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以8%的产率得到2,3,16,17-tetra(hexylthio)phthalocyanine
  参考文献：
  名称：

  ABAB准双（酞菁氨基）镧系元素（III）配合物：原始的八极设计导致巨大的二次超极化性。

  摘要：

  八极立方体是一个T d对称立方体，在其四角处呈现交替电荷，是任何八极分子的通用点电荷模板。迄今为止，尚未实现转座成真实分子结构。我们在这里报告了迈向完全立方八极体系结构的第一步。一系列八极双（2,3,16,17-四（己硫基）酞菁氨基）镧系元素双层配合物[Pc 2 Ln]，Ln = Nd（1），Eu（2），Dy（3），Y（4）和Lu（5）进行了描述，其原始三维结构显示了立方体一个面所需的ABAB类型交替以及两个环之间的离域近似于沿着立方体边缘的电子交互作用。报道了合成，X射线晶体结构以及光学性质和第一分子超极化性β的研究。镧系元素（III）中心离子的大小可调节环与环之间的距离以及两个酞菁环之间的偶联程度。结果，这些八极发色团的光学性质，尤其是由于两个环之间的间隔跃迁而引起的强近红外吸收，也取决于中心镧系元素（III）离子。配合物的第一个氧化态和还原态，在保持相似的八极结构的同时，与中性态相比

  DOI：

  10.1021/ic4031188
• 作为产物：
  描述：

  1,2-dicyano-4,5-bis(hexylthio)benzene 在 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到4,5-bis(hexylthio)-1,2-diimino-isoindoline
  参考文献：
  名称：

  ABAB均质双（酞菁）镥（III）配合物：走向真正的八极立方体和巨大的二次超极化

  摘要：

  八极分子的概念通过提供对 2D 和 3D 结构的访问，大大扩展了二阶非线性光学材料的工程。然而，如果八极对称的原型是在角落处具有交替供体和受体基团的立方体，那么迄今为止还没有实现将这种理想结构转化为真正的分子。这可以通过设计双（酞菁）镥（III）双层复合物来实现，该复合物具有带有交替电子供体和电子受体基团的横向 ABAB 酞菁。在本次交流中，我们展示了实现这一目标的第一步，包括合成、晶体结构测定和通过谐波光扩散测量分子一级超极化率 β，原始镥 (III) 夹心复合物的图像，显​​示立方体的一个面所需的 ABAB 型交替。这种结构的特点是由于间隔跃迁而在近红外区域有强烈吸收，并且表现出有史以来报道的八极分子最高的二次超极化率，√ = 5750 × 10(-30) esu。

  DOI：

  10.1021/ja211064a

文献信息

• Synthesis, characterization, and electrical and electrochemical properties of sandwich dilutetium tetraphthalocyanine
  作者：Saziye Abdurrahmanoglu、Ahmet Altindal、Ali Riza Özkaya、Mustafa Bulut、Özer Bekaroglu

  DOI：10.1039/b406739h

  日期：——

  Lu2Pc2 and lithium hexylthio-phthalocyanine have been used to synthesize [Lu2(Pc)4] which exhibits variable range hopping conductivity as inorganic semiconductors and also observed electrochromic effect from cyclic voltammetric (CV) measurement.

  利用 Lu2Pc2 和六硫代酞菁锂合成了[Lu2(Pc)4]，这种无机半导体具有可变范围的跳变电导率，而且还通过循环伏安法（CV）测量观察到了电致变色效应。
• Synthesis, characterization, and electrochemical and electrochromic properties of sandwich dilutetium tetraphthalocyanine
  作者：Şaziye Abdurrahmanoğlu、Ali Riza Özkaya、Mustafa Bulut、Özer Bekaroğlu

  DOI：10.1039/b412029a

  日期：——

  A new sandwich-tpype dilutetium tetraphthalocyanine 4 has been synthesized by the reaction of dimeric lutetium(III) phthalocyanine 3 with two equiv. of dilithium octakishexylthiophthalocyanine in amyl alcohol. Compound 3 was prepared from 4′,5′,4″,5″-tetraiminoisoindoline(1,4,7,10-tetrathia-12-crown-4) 1, 4,5-bis(hexylthio)-1,2-diiminoisoindoline 2 and lutetium acetate in amyl alcohol. Compounds 3 and 4 were characterized by elemental analysis, UV/visible, IR, 1H NMR and ESR spectroscopy. The electrochemical and electrochromic properties of 3 and 4 have been examined by cyclic voltammetry. Both 3 and 4 displayed well-defined electrochromic behavior.

  通过二聚镥(III)酞菁3与2当量的反应，合成了一种新型夹心型稀四酞菁4。戊醇中的八己基硫代酞菁二锂。化合物3由4',5',4",5"-四亚氨基异吲哚啉(1,4,7,10-四硫基-12-冠-4) 1, 4,5-双(己硫基)-1,2-制备二亚氨基异吲哚啉 2 和乙酸镥的戊醇溶液。通过元素分析、紫外/可见光、红外、1H NMR 和 ESR 光谱对化合物 3 和 4 进行了表征。 3和4的电化学和电致变色性质已通过循环伏安法进行了检查。 3 和 4 都表现出明确的电致变色行为。
• Synthesis, characterization, and electrochemical, electrical and gas sensing properties of a novel tert-butylcalix[4]arene bridged bis double-decker lutetium(III) phthalocyanine
  作者：Tanju Ceyhan、Ahmet Altındal、Ali Rıza Özkaya、Mehmet K. Erbil、Özer Bekaroğlu

  DOI：10.1016/j.poly.2006.07.035

  日期：2007.1

  A novel tert-butylcalix[4]arene bridged bis double-decker lutetium(III) phthalocyanine (Lu2Pc4) (5) has been synthesized by the reaction of dimeric lutetium(III) phthalocyanine (4) with two equiv. of dilithium octakis hexylthiophthalocyanine in amyl alcohol. The phthalonitrile derivative 1 was obtained through the displacement reaction of 4-nitrophthalonitrile with 1,3-dimethoxy-4-tert-butyl-calix[4]arene and was converted to the isoindoline derivative 2 by bubbling ammonia gas in dry MeOH. Compound 4 was prepared from 2, 4,5-bis(hexylthio)-1,2-diimilioisoindoline (3), and lutetium acetate in dry DMF. The new compounds and phthalocyanines were characterized by elemental analysis, IR, UV-Vis, H-1 NMR, ESR and MALDI-TOF MS spectra. The electrochemical properties of 4 and 5 have been examined by cyclic voltammetry, and compared. Distinctive differences between the voltammetric behaviour of 4 and 5 were detected. These differences were compatible with the structures of the compounds. A detailed study of the effect of temperature on the d.c. conductivity and impedance spectra (40-10(5) Hz) of spin coated films of 4 and 5 at temperatures between 290 K and 420 K was carried out. By analyzing the d.c. electrical behaviour of the 5 film, it was found that the experimental data are described by a thermally activated conductivity dependence on temperature with an activation energy of 0.77 eV. The a.c. results give a power law behaviour, sigma(a.c.) = A(T)omega(s), in which the frequency exponent s decreases with temperature. The sensing behaviour of the film for the online detection of volatile organic solvent vapors was investigated by utilizing an AT-cut quartz crystal resonator. It was observed that the adsorption of the target molecules on the coating surface cause a reversible negative frequency shift of the resonator. Thus, a variety of solvent vapors can be detected by using the 5 film as sensitive coating, with sensitivity in the ppm and response times in the order of several seconds depending on the dipole moment of the organic solvent. (c) 2006 Elsevier Ltd. All rights reserved.