cyano-(2,6-dimethyl-4H-pyran-4-ylidene)-acetic acid methyl ester | 49810-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyano-(2,6-dimethyl-4H-pyran-4-ylidene)-acetic acid methyl ester
• 英文别名: methyl-2-cyano-2-(2,6-dimethyl-4H-pyran-ylidene) acetate；cyano-(2,6-dimethyl-pyran-4-ylidene)-acetic acid methyl ester；Methyl 2-cyano-2-(2,6-dimethylpyran-4-ylidene)acetate；methyl 2-cyano-2-(2,6-dimethylpyran-4-ylidene)acetate
• CAS: 49810-74-4
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: MXFSZNYQBSUYHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  295.6±40.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyano-(2,6-dimethyl-4H-pyran-4-ylidene)-acetic acid methyl ester 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 2-(2,6-bis(4-(dimethylamino)styryl)-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 6.0h， 生成 cyano-(2,6-dimethyl-4H-pyran-4-ylidene)-acetic acid methyl ester
  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

文献信息

• Investigation of ¹H NMR Chemical Shifts of Organic Dye with Hydrogen Bonds and Ring Currents
  作者：Sung Soo Park、Yong Sun Won、Woojin Lee、Jae Hong Kim

  DOI：10.1021/jp110176c

  日期：2011.4.7

  computed for the organic dyes 2-(2,6-dimethyl-4H-pyran-4-ylidene)-malononitrile (1), cyano-(2,6-dimethyl-4H-pyran-4-ylidene)-acetic acid methyl ester (2), 2-(2,6-bis(4-(dimethylamino)styryl)-4H-pyran-4-ylidene)-malononitrile (3), and methyl 2-(2,6-bis(4-(dimethylamino)styryl)-4H-pyran-4-ylidene)-2-cyanoacetate (4) at the GIAO/B3LYP/6-311++G(d,p)//B3LYP/6-311++G(d,p) level of theory. Moreover, the intramolecular

  理论上计算了有机染料2-（2,6-二甲基-4 H-吡喃-4-亚烷基）-丙二腈（1），氰基-（2,6-二甲基-4 H-吡喃）的1 H NMR化学位移-4-亚烷基）-乙酸甲酯（2），2-（2,6-双（4-（二甲基氨基）苯乙烯基）-4 H-吡喃-4-亚烷基）-丙二腈（3）和甲基2- （2,6-双（4-（二甲基氨基）苯乙烯基）-4 H-吡喃-4-亚烷基）-2-氰基乙酸酯（4）的理论水平为GIAO / B3LYP / 6-311 ++ G（d，p）// B3LYP / 6-311 ++ G（d，p）。此外，计算了分子的分子内旋转势垒以评估相对于扭转自由度的内部挠性，并采用独立于核的化学位移（NICS）分析环电流。根据分子内的氢键和分子的环电流来解释差异。的1 1 H NMR光谱通过实验与计算上构造的数据比较再现。我们的研究结果为使用计算方法解释1 H NMR化学位移提供了很好的指导，并且为设计分子结构提供了可靠的视角。