(2E)-methyl 2-(2-tert-butyl-6-methyl-4H-pyran-4-ylidene)-2-cyanoacetate | 1383052-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2E)-methyl 2-(2-tert-butyl-6-methyl-4H-pyran-4-ylidene)-2-cyanoacetate
• CAS: 1383052-30-9
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: SQIXLJFPBPGGDQ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E)-methyl 2-(2-tert-butyl-6-methyl-4H-pyran-4-ylidene)-2-cyanoacetate 在 哌啶 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 29.0h， 生成 (2E)-2-(2-(4-(dimethylamino)styryl)-6-tert-butyl-4H-pyran-4-ylidene)-2-cyanoacetic acid
  参考文献：
  名称：

  New pyran dyes for dye-sensitized solar cells

  摘要：

  Although ruthenium-based dyes have been extensively used in dye-sensitized solar cells (DSSCs) as photosensitizers, they have several shortcomings such as high costs and potential environmental toxicities. This has stimulated the development of highly efficient organic dyes as photosensitizers. We report the synthesis and photophysical, electrochemical and theoretical properties of novel pyran-based organic dyes (D1, D2, and D3) as well as their applications in DSSCs for the first time. The designed dyes possess a cyanoacrylic acid group as an acceptor and arylamine group as a donor group in a D-pi-A configuration. The introduction of varying donor groups resulted in correspondingly different photophysical and electrochemical properties. The DSSCs fabricated using dye D1 showed the highest photovoltaic performance: a maximum incident photon-to-current conversion efficiency (IPCE) of 42%, a short-circuit current density (Jsc) of 4.76 mA cm(-2), an open circuit voltage (Voc) of 0.68 V, and a fill factor (FF) of 0.67, corresponding to an overall conversion efficiency of 2.17% under 100 mW cm(-2) irradiation. The synthesized dyes with a pyran chromophore and arylamine donor groups showed potentials for applications in DSSCs. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.09.014
• 作为产物：
  描述：

  乙酰丙酮 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙酸酐 为溶剂， 反应 12.92h， 生成 (2E)-methyl 2-(2-tert-butyl-6-methyl-4H-pyran-4-ylidene)-2-cyanoacetate
  参考文献：
  名称：

  New pyran dyes for dye-sensitized solar cells

  摘要：

  Although ruthenium-based dyes have been extensively used in dye-sensitized solar cells (DSSCs) as photosensitizers, they have several shortcomings such as high costs and potential environmental toxicities. This has stimulated the development of highly efficient organic dyes as photosensitizers. We report the synthesis and photophysical, electrochemical and theoretical properties of novel pyran-based organic dyes (D1, D2, and D3) as well as their applications in DSSCs for the first time. The designed dyes possess a cyanoacrylic acid group as an acceptor and arylamine group as a donor group in a D-pi-A configuration. The introduction of varying donor groups resulted in correspondingly different photophysical and electrochemical properties. The DSSCs fabricated using dye D1 showed the highest photovoltaic performance: a maximum incident photon-to-current conversion efficiency (IPCE) of 42%, a short-circuit current density (Jsc) of 4.76 mA cm(-2), an open circuit voltage (Voc) of 0.68 V, and a fill factor (FF) of 0.67, corresponding to an overall conversion efficiency of 2.17% under 100 mW cm(-2) irradiation. The synthesized dyes with a pyran chromophore and arylamine donor groups showed potentials for applications in DSSCs. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.09.014