2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]thiophene | 626254-03-3

• 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: 2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]thiophene
• 英文别名: [5-(Hydroxymethyl)thiophen-2-yl]-(4-methylphenyl)methanol
• CAS: 626254-03-3
• 化学式: C₁₃H₁₄O₂S
• 分子量: 234.319
• InChiKey: NQSRTJOWKJQGPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]thiophene 在 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 5-bromo-10,15,20-tri(p-tolyl)-21-thiaporphyrin
  参考文献：
  名称：

  Effects of Core-modification on Porphyrin Sensitizers to the Efficiencies of Dye-sensitized Solar Cells

  摘要：

  AbstractTo study dye‐sensitized solar cells (DSSCs) with core‐modified porphyrins as the sensitizing dyes, three porphyrins with an ethynyl benzoic acid as an anchoring group are prepared. The properties of free‐base regular porphyrin (N4), thiaporphyrin (N3S) and oxaporphyrin (N3O) were thoroughly studied by spectroscopic methods, DFT calculations, and photovoltaic measurements. Replacing one of the porphyrinic core nitrogen atoms by oxygen or sulfur considerably changes the absorption spectra. The Soret band of the N3O and N3S observed bathochromic shifts of 3‐9 nm while the Q band reaches 700 nm to the near‐infrared region. The overall conversion efficiencies of the DSSCs based on these porphyrins are in the order N4 (3.66%) ≫ N3S (0.22%) > N3O (0.01%). The time‐correlated single photon counting observed short fluorescence lifetimes for N3O adsorbed both on TiO2 and Al2O3 which explicates the poor efficiency of DSSC using N3O as the photosensitizer.

  DOI：

  10.1002/jccs.201300525
• 作为产物：
  描述：

  2-噻吩甲醇 、 对甲基苯甲醛 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以41%的产率得到2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]thiophene
  参考文献：
  名称：

  N3S、N3O、N2S2、N2O2、N2SO 和 N2OS 卟啉与 Onemeso 未取代碳的合成

  摘要：

  报道了一种简单直接的 N3S、N2S2、N2O2、N2SO 和 N2OS 卟啉合成方法，以及一种合成具有一个中间未取代碳原子的 N3O 卟啉的改进方法。内消旋未取代碳原子的反应性通过进行溴化和 Heck 偶联反应来证明。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300697

文献信息

• Thiaporphyrins with One, Two and Four Unsubstitutedmeso-Carbons: Synthesis and Functionalization
  作者：Neeraj Agarwal、C.-H. Hung、M. Ravikanth

  DOI：10.1002/ejoc.200300333

  日期：2003.10

  Thiaporphyrins with one, two and four unsubstituted meso carbons were synthesized from easily available thiophene diols. The reactivity at these carbons was demonstrated by carrying out series of reactions and some very useful functional groups were introduced. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  从容易获得的噻吩二醇合成具有 1、2 和 4 个未取代的内碳原子的硫卟啉。通过进行一系列反应并引入了一些非常有用的官能团，证明了这些碳的反应性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of N3S, N3O, N2S2, N2O2, N2SO and N2OS Porphyrins with Onemeso-Unsubstituted Carbon
  作者：Sokkalingam Punidha、Neeraj Agarwal、Ritwik Burai、Mangalampalli Ravikanth

  DOI：10.1002/ejoc.200300697

  日期：2004.5

  A simple straightforward synthesis of N3S, N2S2, N2O2, N2SO and N2OS porphyrins and an improved method for the synthesis of an N3O porphyrin with one meso-unsubstituted carbon atom are reported from readily available precursors. The reactivity of the meso-unsubstituted carbon atom was demonstrated by carrying out bromination followed by Heck coupling reactions. (© Wiley-VCH Verlag GmbH & Co. KGaA,

  报道了一种简单直接的 N3S、N2S2、N2O2、N2SO 和 N2OS 卟啉合成方法，以及一种合成具有一个中间未取代碳原子的 N3O 卟啉的改进方法。内消旋未取代碳原子的反应性通过进行溴化和 Heck 偶联反应来证明。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Effects of Core-modification on Porphyrin Sensitizers to the Efficiencies of Dye-sensitized Solar Cells
  作者：Sandeep B. Mane、Liyang Luo、Gao-Fong Chang、Eric Wei-Guang Diau、Chen-Hsiung Hung

  DOI：10.1002/jccs.201300525

  日期：2014.5

  AbstractTo study dye‐sensitized solar cells (DSSCs) with core‐modified porphyrins as the sensitizing dyes, three porphyrins with an ethynyl benzoic acid as an anchoring group are prepared. The properties of free‐base regular porphyrin (N4), thiaporphyrin (N3S) and oxaporphyrin (N3O) were thoroughly studied by spectroscopic methods, DFT calculations, and photovoltaic measurements. Replacing one of the porphyrinic core nitrogen atoms by oxygen or sulfur considerably changes the absorption spectra. The Soret band of the N3O and N3S observed bathochromic shifts of 3‐9 nm while the Q band reaches 700 nm to the near‐infrared region. The overall conversion efficiencies of the DSSCs based on these porphyrins are in the order N4 (3.66%) ≫ N3S (0.22%) > N3O (0.01%). The time‐correlated single photon counting observed short fluorescence lifetimes for N3O adsorbed both on TiO2 and Al2O3 which explicates the poor efficiency of DSSC using N3O as the photosensitizer.