5-(4-nitrophenyl)-2-(thiophen-2-yl)thiazol-4-ol | 1376711-44-2

• 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: 5-(4-nitrophenyl)-2-(thiophen-2-yl)thiazol-4-ol
• 英文别名: 5-(4-Nitrophenyl)-2-thiophen-2-yl-1,3-thiazol-4-ol
• CAS: 1376711-44-2
• 化学式: C₁₃H₈N₂O₃S₂
• 分子量: 304.35
• InChiKey: QJZIJASMAOADKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-nitrophenyl)-2-(thiophen-2-yl)thiazol-4-ol 在 三叔丁基膦 、 potassium tert-butylate 、 一水合肼 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 72.5h， 生成 4-(4-methoxy-2-(thiophen-2-yl)thiazol-5-yl)-N,N-dip-tolylaniline
  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
• 作为产物：
  描述：

  噻吩-2-硫代甲酰胺 、 ethyl α-bromo-p-nitrophenylacetate 以 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到5-(4-nitrophenyl)-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

文献信息

• Small Molecules as Long-Wavelength Fluorophores: Push-Pull Substituted 4-Alkoxy-1,3-thiazoles
  作者：Rainer Beckert、Stefanie Habenicht、Philip Rohland、Jeaninne Reichel、Tarita Biver、Pierpaolo Minei、Dörthe Jakobi、Andrea Pucci、Dieter Weiß、Helmar Görls

  DOI：10.1055/s-0036-1588581

  日期：2018.1

  investigated by means of UV/Vis and fluorescence spectroscopy. A series of donor-π-acceptor (D-π-A) substituted 4-hydroxythiazoles have been synthesized. Electron-donating groups (4-methoxyphenyl and 4-dimethylaminophenyl) were installed in the 5-position of the thiazole; thiophene/pyridine-bridged acceptors (formyl groups and their Knoevenagel condensation products) were placed in the 2-position. The influence

  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。
• Synthesis, properties and quantum chemical evaluation of solvatochromic pyridinium-phenyl-1,3-thiazol-4-olate betaine dyes
  作者：Roberto Menzel、Stephan Kupfer、Ralf Mede、Helmar Görls、Leticia González、Rainer Beckert

  DOI：10.1016/j.tet.2012.12.016

  日期：2013.2

  The syntheses and characterizations of four zwitterionic betaines are presented. These dyes possess an uncommon heterocyclic 1,3-thiazol-4-olate donor moiety. The natures of the HOMO/LUMO transitions and of the intramolecular charge-transfer state were assigned with the help of quantum chemical calculations. Multiple intermolecular solute/solvent interactions were discussed using linear solvation energy relationship (LSER) with Kamlet-Taft and Catalan parameters. The dyes show a pronounced negative solvatochromism ranging from lambda(max) 392 nm in TFE to 820 nm in THF (Delta lambda=428 nm or 1.65 eV). The X-ray structures of one of the tetrafluoroborate salts and of one of the betaines are discussed. (c) 2013 Elsevier Ltd. All rights reserved.