4,5-dimethyl-3-phenyl-1,3-thiazole-2(3H)-thione | 51655-89-1

• 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: 4,5-dimethyl-3-phenyl-1,3-thiazole-2(3H)-thione
• 英文别名: N-phenyl-4,5-dimethyl-1,3-thiazole-2-thione；4,5-dimethyl-3-phenylthiazole-2-thione；2-Thio-3-phenyl-4,5-dimethyl-Δ⁴-thiazolin；4,5-Dimethyl-3-phenyl-thiazolin-Δ⁴-thion-(2)；4,5-dimethyl-3-phenyl-3H-thiazole-2-thione；4,5-Dimethyl-3-phenyl-3H-thiazol-2-thion；4,5-Dimethyl-3-phenyl-1,3-thiazole-2-thione
• CAS: 51655-89-1
• 化学式: C₁₁H₁₁NS₂
• 分子量: 221.347
• InChiKey: DOMBNTYUIQDNHU-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  324.5±25.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-3-phenyl-1,3-thiazole-2(3H)-thione 在 双氧水 、 溶剂黄146 、 sodium perchlorate monohydrate 作用下， 以 水 、 甲醇 为溶剂， 反应 16.5h， 以71.7%的产率得到4,5-dimethyl-3-phenyl-1,3-thiazolium perchlorate
  参考文献：
  名称：

  新材料的光致发光：环金属化的C∧C*噻唑-2-亚甲基铂（II）配合物

  摘要：

  A new class of platinum(II) compounds, the 4,5-dimethyl-3-aryl-thiazole-2-ylidene platinum(II) acetylacetonato complexes, are described. Their efficient phosphorescent emission at room temperature makes them suitable for potential applications in organic light-emitting diodes. A new synthetic pathway that allows the preparation of a broad range of different N-arylthiazole-2-thiones and their subsequent conversion into the corresponding N-arylthiazolium perchlorate and hexafluorophosphate salts has been developed. Not only electron-rich (4-OMe, 4-Me, 3-Me) N-arylthiazoles but also electron-deficient ligands with a cyano or an ester group could be synthesized. From commercially available anilines N-arylthiazolium perchlorate and hexafluorophosphate salts were synthesized via ring closure of in situ generated N-aryldithiocarbamate salts followed by a sulfur-oxidation/-substitution protocol to the air-stable carbene precursors. All reactions were performed in multigram scale in good yields. The synthesis of the corresponding platinum(II) complexes involves generating the corresponding N-arylthiazole-silver(I)-carbene complexes, transmetalation to platinum, cyclometalation, and reaction with acetylacetonate (acac). Solid-state structures of two N-arylthiazole-2-thiones, one Narylthiazolium salt, and three N-arylthiazole-2-ylidene-platinum(II) complexes complement the analytic characterization including Pt-195 NMR. The unsubstituted complex 4,5-dimethyl-3-phenylthiazole-2-ylidene-platinum(II)-acac was additionally characterized by 2D-NMR techniques (COSY, HSQC, HMBC, NOESY). Photoluminescence measurements were performed in amorphous poly(methyl methacrylate) films and revealed bluish-green emission maxima (similar to 500 nm) independent of the electronic structure of the thiazoles, whereas the variation of the substitution pattern at the cyclometalating aryl system led to excellent quantum efficiencies and decay lifetimes of 8.1-21.4 mu s.

  DOI：

  10.1021/acs.organomet.5b00991
• 作为产物：
  描述：

  phenyl-dithiocarbamic acid 1-methyl-2-oxo-propyl ester 生成 4,5-dimethyl-3-phenyl-1,3-thiazole-2(3H)-thione
  参考文献：
  名称：

  Bachetti, Gazzetta Chimica Italiana, 1956, vol. 86, p. 316,323

  摘要：

  DOI：

文献信息

• ORGANIC LIGHT EMITTING ELEMENT, DISPLAY DEVICE, IMAGE INFORMATION PROCESSING DEVICE, LIGHTING DEVICE, IMAGE FORMING DEVICE, EXPOSURE DEVICE, AND ORGANIC PHOTOELECTRIC CONVERSION ELEMENT
  申请人：CANON KABUSHIKI KAISHA

  公开号：US20170012215A1

  公开（公告）日：2017-01-12

  The present disclosure provides an organic light emitting element which has a pair of electrodes and an organic compound layer disposed therebetween and in which the organic compound layer contains an organic compound represented by the following general formula [1], wherein in the formula [1], Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group or a heteroaromatic ring group, R 1 to R 4 are each independently selected from a hydrogen atom or a substituent, R 1 and R 2 and R 3 and R 4 each may form a benzene ring, wherein the benzene ring may have at least one substituent.

  本公开提供了一种有一对电极和位于其之间的有机化合物层的有机发光元件，其中所述有机化合物层包含由下述通用式[1]表示的有机化合物， 在通用式[1]中，Ar1和Ar2分别独立表示芳香烃基或杂芳环基，R1至R4分别独立地选自氢原子或取代基，R1和R2以及R3和R4各自可以形成苯环，其中苯环可以具有至少一个取代基。
• Changing the Emission Properties of Phosphorescent C^C*-Cyclometalated Thiazol-2-ylidene Platinum(II) Complexes by Variation of the β-Diketonate Ligands
  作者：Hendrik Leopold、Ute Heinemeyer、Gerhard Wagenblast、Ingo Münster、Thomas Strassner

  DOI：10.1002/chem.201604456

  日期：2017.1.23

  platinum(II) complexes based on the N‐phenyl‐4,5‐dimethyl‐1,3‐thiazol‐2‐ylidene N‐heterocyclic carbene (NHC) ligand and seven different β‐diketonate ligands have been synthesised and investigated for their structural and photophysical properties. The complexes were synthesised in a one‐pot procedure starting with the in situ formation of the corresponding silver(I) carbene and transmetalation to platinum

  基于N-苯基-4,5-二甲基-1,3-噻唑-2-亚烷基N-杂环卡宾（NHC）配体和七个不同的β-二酮基配体的环金属化的噻唑-2-亚烷基铂（II）配合物合成并研究了它们的结构和光物理性质。配合物的合成是通过一锅法进行的，首先在原位形成相应的银（I）卡宾，然后金属转移成铂，然后在碱性条件下与相应的β-二酮酸酯反应。所有化合物均通过标准技术进行了充分表征，包括195种Pt NMR光谱。三种固态结构揭示了完全不同的聚集行为，具体取决于β-二酮结构。报道的络合物在室温下在无定形聚（甲基丙烯酸甲酯）薄膜中显示出强烈的磷光。发现发射波长（约510 nm）与β-二酮酸酯配体无关，但电子多样性的β-二酮酸酯强烈影响观察到的量子产率（QY）和衰变寿命。使用密度泛函理论（DFT）方法的理论研究结果支持了金属-配体电荷转移的结论（3MLCT）作为主要的发射过程，根据报道的光物理特性。使用其中一种配合物使用未经优化
• Improved Protocols for the Synthesis of Precursors of Thiazol-2-ylidene N-Heterocyclic Carbenes
  作者：Eder Tomás-Mendivil、David Martin、Ludivine Delfau、Jacques Pecaut

  DOI：10.1055/a-2284-4798

  日期：——

  We report improved protocols for the synthesis of thiazolium precatalysts from primary amines, carbon disulfide, and α-halo ketones. For N-alkyl-substituted derivatives, yields of the corresponding thiazolethiones can be dramatically improved by isolating the intermediate dithiocarbamates. In most cases, meta-chloroperbenzoic acid can advantageously replace H2O2 in acetic acid for the oxidation of

  我们报告了从伯胺、二硫化碳和 α-卤代酮合成噻唑鎓预催化剂的改进方案。对于N-烷基取代的衍生物，通过分离中间体二硫代氨基甲酸酯可以显着提高相应噻唑硫酮的产率。在大多数情况下，间氯过苯甲酸可以有利地代替乙酸中的H 2 O 2以将噻唑硫酮氧化成噻唑鎓。该方法应用于合成具有 2-金刚烷基N取代基的噻唑鎓、相应的持久卡宾及其二聚体。
• Chemical and Electrochemical Investigations on Thiazolium Salts: a Route to Powerful Donors in the Dithiadiazafulvalene Series.
  作者：Nathalie Bellec、David Guérin、Dominique Lorcy、Albert Robert、Roger Carlier、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0861

  日期：——

  Thiazolium salts have been investigated, chemically and electrochemically, in order to access to the redox properties of dithiadiazafulvalenes (DTDAF). As these donor molecules are oxygen-sensitive, it is more advisable to isolate them in their oxidized form as dicationic salts. Starting from a tetrathiazolium cation including two precursors groups, linked together with a conjugated spacer, a bis-DTDAF was formed and its electrochemical behavior studied.
• Tripathy,H. et al., Journal of the Indian Chemical Society, 1973, vol. 50, p. 417 - 419
  作者：Tripathy,H. et al.

  DOI：——

  日期：——