4-methoxy-N-(4-(4-methoxy-2-(thiophen-2-yl)thiazol-5-yl)phenyl)-N-(4-methoxyphenyl)aniline | 1376711-48-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-methoxy-N-(4-(4-methoxy-2-(thiophen-2-yl)thiazol-5-yl)phenyl)-N-(4-methoxyphenyl)aniline
• 英文别名: N,N-bis(4-methoxyphenyl)-4-(4-methoxy-2-thiophen-2-yl-1,3-thiazol-5-yl)aniline
• CAS: 1376711-48-6
• 化学式: C₂₈H₂₄N₂O₃S₂
• 分子量: 500.642
• InChiKey: NPUQPRZGTDMRIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(4-(4-methoxy-2-(thiophen-2-yl)thiazol-5-yl)phenyl)-N-(4-methoxyphenyl)aniline 在 哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 6.5h， 生成 3-(5-(5-(4-(bis(4-methoxyphenyl)amino)phenyl)-4-methoxythiazol-2-yl)thiophen-2-yl)-2-cyanoacrylic acid
  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：

  ethyl α-bromo-p-nitrophenylacetate 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 96.5h， 生成 4-methoxy-N-(4-(4-methoxy-2-(thiophen-2-yl)thiazol-5-yl)phenyl)-N-(4-methoxyphenyl)aniline
  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

• 4-Methoxy-1,3-thiazole based donor-acceptor dyes: Characterization, X-ray structure, DFT calculations and test as sensitizers for DSSC
  作者：Roberto Menzel、Daniel Ogermann、Stephan Kupfer、Dieter Weiß、Helmar Görls、Karl Kleinermanns、Leticia González、Rainer Beckert

  DOI：10.1016/j.dyepig.2012.02.014

  日期：2012.9

  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.