5-(4-methoxyphenyl)-2-(thiophen-2-yl)thiazol-4-ol | 1376711-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methoxyphenyl)-2-(thiophen-2-yl)thiazol-4-ol
• 英文别名: 5-(4-Methoxyphenyl)-2-thiophen-2-yl-1,3-thiazol-4-ol；5-(4-methoxyphenyl)-2-thiophen-2-yl-1,3-thiazol-4-ol
• CAS: 1376711-56-6
• 化学式: C₁₄H₁₁NO₂S₂
• 分子量: 289.379
• InChiKey: AXEAVJZHRDPUOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)-2-(thiophen-2-yl)thiazol-4-ol 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 6.0h， 生成 5-(4-ethoxy-5-(4-methoxyphenyl)thiazol-2-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  小分子作为长波长荧光团：推挽取代4-烷氧基-1,3-噻唑

  摘要：

  专用于瓦尔德马亚当教授在他的80之际个生日 抽象的 已经合成了一系列供体-π-受体（D-π-A）取代的4-羟基噻唑。给电子基团（4-甲氧基苯基和4-二甲基氨基苯基）安装在噻唑的5-位；将噻吩/吡啶桥联的受体（甲酰基及其Knoevenagel缩合产物）置于2位。通过UV / Vis和荧光光谱研究了D-π-A特性对光物理性质和电子结构的影响。 已经合成了一系列供体-π-受体（D-π-A）取代的4-羟基噻唑。给电子基团（4-甲氧基苯基和4-二甲基氨基苯基）安装在噻唑的5-位；将噻吩/吡啶桥联的受体（甲酰基及其Knoevenagel缩合产物）置于2位。通过UV / Vis和荧光光谱研究了D-π-A特性对光物理性质和电子结构的影响。

  DOI：

  10.1055/s-0036-1588581
• 作为产物：
  描述：

  噻吩-2-硫代甲酰胺 、 2-溴-2-(4-甲氧基苯基)乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到5-(4-methoxyphenyl)-2-(thiophen-2-yl)thiazol-4-ol
  参考文献：
  名称：

  4-Methoxy-1,3-thiazole based donor-acceptor dyes: Characterization, X-ray structure, DFT calculations and test as sensitizers for DSSC

  摘要：

  Four donor-(pi-conjugated-bridge)-acceptor type dyes A-D were designed and synthesized. These new compounds use an unconventional 4-hydroxy-1,3-thiazole building block as an additional chromophore for light harvesting and to extend the pi-conjugated system of the molecules. The synthetic route involved a double N-arylation Hartwig-Buchwald reaction using Pd(dba)(2) as precatalyst and P(Bu-t)(3) as ligand. Two different triarylamines and a 4-methoxyphenyl group were used as electron donor moieties. The electron acceptor (anchoring) group was 2-cyanoacrylic acid for all dyes, whereas the pi-spacer was varied and the influence was investigated. The dyes were thoroughly characterized using photophysical and electrochemical methods and by density functional theory calculations. Additionally, they were evaluated in nanocrystalline TiO2-based dye-sensitized solar cells (DSSCs). The DSSCs were prepared with and without deoxycholic acid (DCA) as a co-adsorbent to inhibit dye aggregation. The efficiencies obtained were low for DSSCs fabricated without DCA, but were significantly improved for DCCS with co-adsorbed DCA. Additionally, the X-ray structure of dye D was obtained, demonstrating the stereochemistry and planar geometry of the molecule. The DSSC based on dye A showed an efficiency of eta = 1.70% (J(sc) = 4.49 mA cm(-2), V-OC = 0.61 V, FF = 0.62) under 100 mW cm(-2) simulated AM 1.5 G solar irradiation compared to eta = 4.1% of the standard N-3 obtained under same conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.02.014