4-(1-methyl-5-indol-5-yl)-[1,3]dithiol-2-one | 1338778-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(1-methyl-5-indol-5-yl)-[1,3]dithiol-2-one
• 英文别名: 4-(1-Methylindol-5-yl)-1,3-dithiol-2-one
• CAS: 1338778-09-8
• 化学式: C₁₂H₉NOS₂
• 分子量: 247.342
• InChiKey: ZWQUWSGGVSIVBC-UHFFFAOYSA-N

物化性质

• 沸点：
  478.3±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-methyl-5-indol-5-yl)-[1,3]dithiol-2-one 、 [Ni(4,4’-diethylcarboxy-bpy)Cl₂].H₂O 在 sodium ethanolate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 以62%的产率得到Ni(4,4′-ethylcarboxy-bpy)(mi-5edt)
  参考文献：
  名称：

  吸电子羧基增强α-二亚胺二硫代latonickel（II）配合物的非线性光学性质

  摘要：

  我们报告了三个二亚胺二硫代镍配合物[Ni（4,4'-R 2羧基-bpy ）（L）]的合成，表征，非线性光学（NLO）性质和密度泛函理论（DFT）计算[R =甲基，L ＝ 1，2-苯二硫代酸酯（bdt），1；R =乙基，L = 5,6-二氢-1,4-二巯基-2,3-二硫代酸酯（dddt），2 ; R ＝乙基，L ＝ 1-（N-甲基吲哚-5-基）乙烯-1,2-二硫代酸酯（mi-5edt），3 ]。1的晶体结构示出了镍离子和键距的平方平面配位，与该配合物的二亚氨基二硫代酸酯描述相符。对于所有络合物，循环伏安法测量均显示出两个可逆的还原过程（分别为-1.353 / –1.380 V和−0798 / –0.830 V）和一个阳极波（+ 0.372 / + 0.601 V）。紫外可见光谱在600-700 nm处出现一个波段（ε= 4880-6000 dm 3 mol –1 cm –1）主要归因于电荷转

  DOI：

  10.1021/ic5002094
• 作为产物：
  描述：

  5-溴-1-甲基吲哚 在 偶氮二异丁腈 、 potassium tert-butylate 、 magnesium 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 25.0h， 生成 4-(1-methyl-5-indol-5-yl)-[1,3]dithiol-2-one
  参考文献：
  名称：

  Formation of stable neutral copper bis-dithiolene thin films by potentiostatic electrodeposition

  摘要：

  中性二硫代铜薄膜已通过恒电位电沉积法制备。该方法使得近红外（NIR）活性物种以可用形式被分离出来，而这些物种通常是传统化学方法无法获得的。

  DOI：

  10.1039/c1cc12344k

文献信息

• Indole-substituted nickel dithiolene complexes in electronic and optoelectronic devices
  作者：Simon Dalgleish、John G. Labram、Zhe Li、Jianpu Wang、Christopher R. McNeill、Thomas D. Anthopoulos、Neil C. Greenham、Neil Robertson

  DOI：10.1039/c1jm12466h

  日期：——

  The synthesis and full characterisation of a novel indole-substituted nickel dithiolene [Ni(mi-5edt)2] (3) is reported, and compared to its alkyl-substituted analogue [Ni(mi-5hdt)2] (4) that has been previously communicated [Dalgleish et al., Chem. Commun., 2009, 5826] [mi-5edt = 1-(N-methylindol-5-yl)-ethene-1,2-dithiolate; mi-5hdt = 1-(N-methylindol-5-yl)-hex-1-ene-1,2-dithiolate)]. Both complexes are shown to undergo oxidative electropolymerisation, yielding polymer films that retain the redox and optical properties of the monomer. The more soluble analogue 4 is shown to form high quality thin films by spin coating, which have been utilised to fabricate field-effect transistors (FETs) and bulk heterojunction photovoltaic devices (BHJ-PVs). From FET studies, the material shows ambipolar charge transport behaviour, with a maximum carrier mobility of ∼10−6 cm2 V−1s−1 for electrons. By using 4 simultaneously as the electron acceptor as well as a NIR sensitiser in BHJ-PVs, the complex is shown to contribute to the photocurrent, extending light harvesting into the NIR region.

  报道了新型吲哚取代的镍二硫烯[Ni(mi-5edt)2](3)的合成及其全面特性，并与之前报道的烷基取代的类似物[Ni(mi-5hdt)2](4)[Dalgleish等，Chem. Commun.，2009，5826][mi-5edt = 1-(N-甲基吲哚-5-基)-乙烯-1,2-二硫醇；mi-5hdt = 1-(N-甲基吲哚-5-基)-己-1-烯-1,2-二硫醇]进行了比较。这两种配合物均表现出氧化电聚合反应，生成的聚合物膜保留了单体的氧化还原和光学性质。溶解性更好的类似物4通过旋涂形成高质量薄膜，这些薄膜已被用于制造场效应晶体管（FETs）和大体积异质结光伏器件（BHJ-PVs）。从FET研究中，该材料显示出双极性载流子传输行为，电子的最大载流子迁移率约为10−6 cm2 V−1s−1。通过同时将4用作BHJ-PVs中的电子受体以及近红外敏化剂，该配合物被证明有助于光电流，将光捕获扩展到近红外区域。
• Tuning the LUMO energy of 1,10-phenanthroline in α-diimine–dithiolate Ni(II) complex and enhancement of nonlinear optical properties
  作者：Luca Pilia、Maddalena Pizzotti、Francesca Tessore、Neil Robertson

  DOI：10.1016/j.ica.2015.03.002

  日期：2015.5

  The synthesis, characterization, nonlinear optical properties and DFT calculations for a new Ni-diiminedithiolate complex [Ni(Cl-4-phen)(mi-5edt)] (Cl-4-phen = 3,4,7,8-tetrachloro-1,10-phenanthroline; mi-5edt = 1-(N-methylindol-5-yl)-ethene-1,2-dithiolate), are reported. The UV-Vis spectrum shows a solvatochromic absorption at 700 nm in DMF (epsilon = 5520 mol(-1) dm(3) cm(-1)) due to a charge-transfer (CT) highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) transition, typical of push-pull complexes. The CT character of this electronic transition is confirmed by DFT calculations with the HOMO mainly centered on the mi-5edt moiety and the LUMO on the Cl-4-phen ligand. By comparison with the unsubstituted analogue compound, computational studies confirm the role of the chlorination enhancing the optical properties of this complex. The second order nonlinear optical properties were measured by EFISH technique (at 1.907 mu m), giving values of -2030 and -810 x 10(-48) esu for mu beta(1.907) and mu beta(0), respectively. These values are among the highest reported so far for the class of d(8) square-planar push-pull compounds. (C) 2015 Elsevier B.V. All rights reserved.