5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)thiophene-2-carbaldehyde | 1354569-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)thiophene-2-carbaldehyde
• CAS: 1354569-62-2
• 化学式: C₁₉H₂₄O₂S
• 分子量: 316.464
• InChiKey: GPMYPQQMMAXXCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)thiophene-2-carbaldehyde 、 氰乙酸 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以60%的产率得到SFO-346
  参考文献：
  名称：

  New D−π–A-Conjugated Organic Sensitizers Based on 4H-Pyran-4-ylidene Donors for Highly Efficient Dye-Sensitized Solar Cells

  摘要：

  We have synthesized a series of four new promising D-pi-A conjugated organic sensitizers with a proaromatic 4H-pyran-4-ylidene as a donor, a thiophene ring in the bridge, and 2-cyanoacrilic acid as acceptor. Comparison between different donor substituents and the modification of the thiophene ring resulted in molar extinction coefficients as high as 36399 M-1 cm(-1) at 551 nm. The photovoltaic properties of the DSSCs demonstrate power conversion efficiencies as high as 5.4%.

  DOI：

  10.1021/ol203298r
• 作为产物：
  描述：

  2,5-噻吩二甲醛 、 (2,6-Di-tert-butyl-4H-pyran-4-yl)tributylphosphonium perchlorate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 hexanes 为溶剂， 反应 15.25h， 以20%的产率得到5-((2,6-di-tert-butyl-4H-pyran-4-ylidene)methyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  New D−π–A-Conjugated Organic Sensitizers Based on 4H-Pyran-4-ylidene Donors for Highly Efficient Dye-Sensitized Solar Cells

  摘要：

  We have synthesized a series of four new promising D-pi-A conjugated organic sensitizers with a proaromatic 4H-pyran-4-ylidene as a donor, a thiophene ring in the bridge, and 2-cyanoacrilic acid as acceptor. Comparison between different donor substituents and the modification of the thiophene ring resulted in molar extinction coefficients as high as 36399 M-1 cm(-1) at 551 nm. The photovoltaic properties of the DSSCs demonstrate power conversion efficiencies as high as 5.4%.

  DOI：

  10.1021/ol203298r

文献信息

• Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4<i>H</i>-Pyranylidene Donor: Synthesis and Optical Properties
  作者：Víctor Tejeda-Orusco、Raquel Andreu、Jesús Orduna、Belén Villacampa、Santiago Franco、Alba Civera

  DOI：10.1021/acs.joc.0c02438

  日期：2021.2.19

  bearing 4H-pyranylidene as electron donor group and a variety of acceptors were designed. On one hand, one-dimensional chromophores with a thiophene ring (series 1H) or 5-dimethylaminothiophene moiety (series 1N) as an auxiliary donor, non-coplanar with the π-conjugated system, were synthesized. On the other hand, related two-dimensional (2D) Y-shaped chromophores (series 2) were also prepared to compare

  设计了以4 H-亚吡喃为电子供体基团和多种受体的三个系列推挽式衍生物。一方面，合成了具有噻吩环（系列1H）或 5-二甲氨基噻吩部分（系列1N）作为辅助供体，与 π 共轭体系不共面的一维发色团。另一方面，相关的二维 (2D) Y 形发色团（系列2) 还准备比较不同的架构如何影响电化学、线性和二阶非线性光学 (NLO) 特性。5-二甲氨基噻吩部分存在于吡喃基单元的环外 C=C 键中，导致氧化电位极低，并且其衍生物的质子化（用过量的三氟乙酸）导致出现新的蓝色-紫外可见光谱中的位移带。对带有和不带有额外噻吩环的衍生物性质的分析表明，这种辅助供体导致更高的 NLO 响应，同时提高了透明度。系列2的 Y 形发色团呈现蓝移吸收、更高的摩尔消光系数和更高的E ox值与其线性扭曲对应物相比。就 NLO 特性而言，二维 Y 形结构会产生稍低的 μβ 值（硫代巴比妥酸盐衍生物除外）。
• Push–pull systems bearing a quinoid/aromatic thieno[3,2-b]thiophene moiety: synthesis, ground state polarization and second-order nonlinear properties
  作者：A. Belén Marco、Raquel Andreu、Santiago Franco、Javier Garín、Jesús Orduna、Belén Villacampa、Beatriz E. Diosdado、Juan T. López Navarrete、Juan Casado

  DOI：10.1039/c3ob41278d

  日期：——

  first time the reactivity of this system towards aldehydes. Their ground state polarization and linear and second-order nonlinear optical (NLO) properties have been determined by a combined experimental and theoretical study, and compared to those of analogous compounds featuring an aromatic thienothiophene unit. Due to the gaining of aromaticity, quinoid systems have been found to display more polarized

  已经合成了以醌型形式 带有2-二氰基亚甲基噻吩并[3,2- b ]噻吩部分的发色团，这是首次探索该体系对醛的反应性。通过结合实验和理论研究，确定了它们的基态极化以及线性和二阶非线性光学（NLO）特性，并将其与具有芳香族噻吩并噻吩单元的类似化合物进行了比较。由于获得了芳香性，已发现醌类系统相对于其芳香族对应物显示出更多的极化电子基态和更高的NLO响应。
• Polarization, second-order nonlinear optical properties and electrochromism in 4H-pyranylidene chromophores with a quinoid/aromatic thiophene ring bridge
  作者：A. Belén Marco、Paula Mayorga Burrezo、Laura Mosteo、Santiago Franco、Javier Garín、Jesús Orduna、Beatriz E. Diosdado、Belén Villacampa、Juan T. López Navarrete、Juan Casado、Raquel Andreu

  DOI：10.1039/c4ra12791a

  日期：——

  between compounds that only differ in the character (quinoid or aromatic) of the thiophene unit shows a more efficient ICT for the quinoid thiophene-containing chromophore, which influences the second-order NLO response. Furthermore, the thienyl ring has been also found to play a significant role in the ICT process for the analogous aromatic derivative.

  制备了推挽系统，其中原芳香族的4 H-吡喃亚基电子供体通过作为电子继电器的一部分的喹啉噻吩与二氰基亚甲基受体共轭，并且已将其性能与母体化合物的性能进行了比较。具有芳族噻吩部分。不同的实验技术（X射线衍射，1 H NMR，IR，拉曼，紫外可见，循环伏安法，光谱电化学和NLO测量）与理论计算相结合已用于发色团的研究。quinoidal衍生物虽然是中性的，但显示出强烈的极化结构，具有正的μβ值和分子内电荷转移（ICT）在加长π间隔物时逐渐增加。仅在噻吩单元的特征（喹啉或芳族）方面不同的化合物之间的比较显示，含醌噻吩的生色团的信息通信技术效率更高，这会影响二阶NLO反应。此外，还发现噻吩基环在ICT过程中对于类似的芳族衍生物起着重要的作用。