1-dodecyl-1H-pyrrole-2-carbaldehyde | 359643-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-dodecyl-1H-pyrrole-2-carbaldehyde
• 英文别名: 1-(dodecyl)-pyrrole-2-carbaldehyde；1-dodecylpyrrole-2-carbaldehyde
• CAS: 359643-81-5
• 化学式: C₁₇H₂₉NO
• 分子量: 263.423
• InChiKey: LJGZHSPRNRSQQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-二苯肼盐酸盐 、 1-dodecyl-1H-pyrrole-2-carbaldehyde 在 咪唑 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以89%的产率得到2-((2,2-diphenylhydrazineylidene)methyl)-1-dodecyl-1H-pyrrole
  参考文献：
  名称：

  Efficient Squaraine-Based Solution Processable Bulk-Heterojunction Solar Cells

  摘要：

  We report the fabrication of organic bulk-heterojunction solar cells based, for the first time, on squaraine/PCBM Wends. The most efficient device, solution-processed in air, exhibits J(sc) = 5.70 mA/cm(2), V-oc = 0.62 V, fill-factor = 0.35, and power conversion efficiency = 1.24%, one of the highest to date for a small molecule solution-processed bulk-heterojunction cell.

  DOI：

  10.1021/ja8067879
• 作为产物：
  描述：

  1-dodecyl-1H-pyrrole 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-dodecyl-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  二茂铁修饰的新型方酸菁染料的合成与性能

  摘要：

  摘要通过（E）-1-十二烷基-2-二茂铁基乙烯基-1H-吡咯和方酸合成了一种新型的二茂铁修饰的方酸染料（SQ）。通过1 H NMR，13 C NMR，MS和元素分析对SQ的分子结构进行了表征。SQ在普通溶剂中高度可溶。在不同溶剂中SQ的最大吸收在708-734 nm范围内，随着溶剂极性的增加，表现出正溶剂溶变色。SQ的光学和电学性质表明，它是用于体-异质结有机太阳能电池的有前途的电子供体材料。

  DOI：

  10.1016/j.cclet.2011.05.039

文献信息

• Fluorescent bispyrroles. New building blocks for novel π-conjugated polymers
  作者：J Eldo、E Arunkumar、A Ajayaghosh

  DOI：10.1016/s0040-4039(00)01039-x

  日期：2000.8

  Several bispyrroles which are bridged through conjugated aromatic moieties were synthesized by the Wittig-Horner-Emmons reaction. Photophysical and electrochemical data of these highly fluorescent monomers reveal that they are useful building blocks for the design of a wide variety of novel pi-conjugated polymers, which may find application as potential optoelectronic materials. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A Ratiometric Fluorescence Probe for Selective Visual Sensing of Zn²⁺
  作者：Ayyappanpillai Ajayaghosh、Priya Carol、Sivaramapanicker Sreejith

  DOI：10.1021/ja054149s

  日期：2005.11.1

  A simple ratiometric fluorescence probe based on vinylpyrrole end-capped bipyridine for the visual sensing of Zn2+ under aqueous physiological pH (6.8-7.4) is described. The fluorophores 3a-c showed strong emission around 537 nm in acetonitrile with a quantum yield of 0.4. In buffered (HEPES, pH 7.2) acetonitrile-water mixture (9:1 v/v), titration of transition metal salts to 3c showed strong quenching of the emission at 547 nm except in the case of Zn2+, which resulted in a red-shifted emission at 637 nm. Alkali and alkaline earth metal salts could not induce any considerable changes to the emission behavior of 3a-c. The binding of Zn2+ was highly selective in the presence of a variety of other metal ions. Though Cu2+ quenches the emission of 3c, in the presence of Zn2+, a red emission prevails, indicating the preference of 3c toward Zn2+. Job plot and Benesi-Hildebrand analysis revealed a 1:1 complexation between the probe and the metal ion. The selective visual sensing of Zn2+ with a red emission is ideally suited for the imaging of biological specimens.
• A Novel Approach Toward Low Optical Band Gap Polysquaraines
  作者：A. Ajayaghosh、J. Eldo

  DOI：10.1021/ol016284p

  日期：2001.8.9

  [GRAPHICS]Polycondensation of 2,5-dialkoxydivinylbenzene-bridged bispyrroles and squaric acid resulted in extensively conjugated polymers with strong near-infrared (NIR) absorption around 800-1000 nm, which is a signature of their low band gap (E-g). Conjugated polymers with such a strong NIR absorption are rare. One of the synthesized polysquaraines showed a significantly low E-g of 0.79 eV with an intrinsic conductivity of 5.3 X 10(-4) S/cm.
• Synthesis and properties of a novel squaraine dye modified by ferrocene
  作者：Yang Wei Huang、Nan Yan Fu

  DOI：10.1016/j.cclet.2011.05.039

  日期：2011.11

  Abstract A novel squaraine dye (SQ) modified by ferrocene has been synthesized through (E)-1-dodecyl-2-ferrocenyl vinyl-1H-pyrrole and squaric acid. The molecular structure of SQ was characterized by 1H NMR, 13C NMR, MS and elemental analysis. SQ is high soluble in common solvents. The maximum absorptions of SQ in different solvents are in the range of 708−734 nm, exhibiting positive solvatochromism

  摘要通过（E）-1-十二烷基-2-二茂铁基乙烯基-1H-吡咯和方酸合成了一种新型的二茂铁修饰的方酸染料（SQ）。通过1 H NMR，13 C NMR，MS和元素分析对SQ的分子结构进行了表征。SQ在普通溶剂中高度可溶。在不同溶剂中SQ的最大吸收在708-734 nm范围内，随着溶剂极性的增加，表现出正溶剂溶变色。SQ的光学和电学性质表明，它是用于体-异质结有机太阳能电池的有前途的电子供体材料。
• Efficient Squaraine-Based Solution Processable Bulk-Heterojunction Solar Cells
  作者：Fabio Silvestri、Michael D. Irwin、Luca Beverina、Antonio Facchetti、Giorgio A. Pagani、Tobin J. Marks

  DOI：10.1021/ja8067879

  日期：2008.12.31

  We report the fabrication of organic bulk-heterojunction solar cells based, for the first time, on squaraine/PCBM Wends. The most efficient device, solution-processed in air, exhibits J(sc) = 5.70 mA/cm(2), V-oc = 0.62 V, fill-factor = 0.35, and power conversion efficiency = 1.24%, one of the highest to date for a small molecule solution-processed bulk-heterojunction cell.