3-(4-bromophenyl)-4,5-dimethyl-1,3-thiazole-2(3H)-thione | 51656-12-3

• 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-(4-bromophenyl)-4,5-dimethyl-1,3-thiazole-2(3H)-thione
• 英文别名: 3-(4-bromophenyl)-4,5-dimethyl-1,3-thiazol-2-thione；2-Thio-3(p)bromphenyl-4,5-dimethyl-Δ⁴-thiazolin；3-(4-bromo-phenyl)-4,5-dimethyl-3H-thiazole-2-thione；3-(4-Bromophenyl)-4,5-dimethyl-1,3-thiazole-2-thione
• CAS: 51656-12-3
• 化学式: C₁₁H₁₀BrNS₂
• 分子量: 300.243
• InChiKey: CYYMWMVUSKOYHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 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：

  3-(4-bromophenyl)-4,5-dimethyl-1,3-thiazole-2(3H)-thione 在 双氧水 、 溶剂黄146 、 六氟磷酸钾 作用下， 以 水 、 甲醇 为溶剂， 反应 16.5h， 以30.5%的产率得到3-(4-bromophenyl)-4,5-dimethyl-1,3-thiazolium hexafluorophosphate
  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：

  ammonium N-(p-bromophenyl)dithiocarbamate 、 丁酮 在 溴 作用下， 以 乙醇 为溶剂， 生成 3-(4-bromophenyl)-4,5-dimethyl-1,3-thiazole-2(3H)-thione
  参考文献：
  名称：

  Tripathy,H. et al., Journal of the Indian Chemical Society, 1973, vol. 50, p. 417 - 419

  摘要：

  DOI：

文献信息

• Phosphorescent C^∧C* Cyclometalated Thiazol-2-ylidene Iridium(III) Complexes: Synthesis, Structure, and Photophysics
  作者：Hendrik Leopold、Ivana Císařová、Thomas Strassner

  DOI：10.1021/acs.organomet.7b00421

  日期：2017.8.28

  The synthesis and characterization of the first cyclometalated arylthiazole-based iridium(III) phosphorescent emitters of the general structure IrL2(acac) with L = 3-(4-bromophenyl)-4,5-dimethyl-1,3-thiazol-2-ylidene and 3-(4-methylphenyl)-4,5-dimethyl-1,3-thiazol-2-ylidene and acac = acetylacetonato is presented. All complexes were isolated isomerically pure and were unambiguously assigned by a solid-state

  具有L = 3-（4-溴苯基）-4,5-二甲基-1,3-噻唑-2的一般结构IrL 2（acac）的第一个基于环金属化芳基噻唑的铱（III）磷光发光体的合成和表征提出了亚乙基和3-（4-甲基苯基）-4,5-二甲基-1,3-噻唑-2-亚烷基，acac =乙酰丙酮。所有的配合物都是同分异构纯的，并通过固态结构，DFT计算和2D NMR研究明确分配。对它们的发射行为的研究显示出在495±5 nm处的最大发射。使用量子化学计算来计算可能的异构体之间的能量差并了解发射行为。