(E)-2-cyano-3-(4-((E)-2-(2-(pyrrolidin-1-yl)naphthalen-1-yl)vinyl)phenyl)acrylic acid | 1404196-50-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-cyano-3-(4-((E)-2-(2-(pyrrolidin-1-yl)naphthalen-1-yl)vinyl)phenyl)acrylic acid
• 英文别名: (E)-2-cyano-3-[4-[(E)-2-(2-pyrrolidin-1-ylnaphthalen-1-yl)ethenyl]phenyl]prop-2-enoic acid
• CAS: 1404196-50-4
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: PAAUDTOYSFRAES-YJSWJZPXSA-N

物化性质

• 沸点：
  641.5±55.0 °C(predicted)
• 密度：
  1.286±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴苯甲醛乙烯醛 在 正丁基锂 、 potassium tert-butylate 、 ammonium acetate 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 magnesium 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 16.0h， 生成 (E)-2-cyano-3-(4-((E)-2-(2-(pyrrolidin-1-yl)naphthalen-1-yl)vinyl)phenyl)acrylic acid
  参考文献：
  名称：

  Structure–property relationship of naphthalene based donor–π–acceptor organic dyes for dye-sensitized solar cells: remarkable improvement of open-circuit photovoltage

  摘要：

  设计并合成了四种新的供体-π-受体有机染料（YF01–04），这些染料以含有萘取代胺的化合物作为电子供体，以氰基丙烯酸作为电子受体，并对其光物理性质及染料敏化太阳能电池（DSCs）的性能进行了表征。具有2,6-二取代萘框架的染料YF02和YF04在入射光电流转换效率（IPCE）和总太阳能转电效率（η）方面优于其类似染料YF03和YF01，后者具有1,2-二取代萘基团。基于YF02的DSC，其供体为二苯胺基团，显示出5.29%的最高η，而类似染料YF04（供体为哌咯啶）的η为4.03%。在具有二苯胺供体的YF02和YF03中，惊人地达到了0.799–0.807 V的高开路光电压（Voc）。为了更好地理解DSC应用中的结构-性质关系，对YF01–04进行了分子建模，并使用长程修正的能量泛函WB97XD和CAM-B3LYP在DGDZVP基组水平上计算了垂直电子激发，这与实验结果非常一致。此外，使用混合能量泛函B3LYP和DGDZVP基组在密度泛函理论（DFT）水平上计算了染料YF01–04的平衡分子几何结构。YF02和YF03中萘基与二苯胺供体之间的扭转角（θ）比YF01和YF04（哌咯啶供体染料）的扭转角更大，从而阻碍了高效的分子间π-π电荷转移，导致高Voc。与参考染料TA-St-CA相比，该染料以二苯胺作为电子供体与苯环连接，YF02实现了更高的Voc，这表明用二苯胺取代的萘在延缓电荷复合方面更为有效。

  DOI：

  10.1039/c2jm34363k

文献信息

• Structure–property relationship of naphthalene based donor–π–acceptor organic dyes for dye-sensitized solar cells: remarkable improvement of open-circuit photovoltage
  作者：Fan Yang、Md. Akhtaruzzaman、Ashraful Islam、Tienan Jin、Ahmed El-Shafei、Chuanjiang Qin、Liyuan Han、Khalid A. Alamry、Samia A. Kosa、Mahmoud A. Hussein、Abdullah Mohamed Asiri、Yoshinori Yamamoto

  DOI：10.1039/c2jm34363k

  日期：——

  Four new donor–π–acceptor organic dyes (YF01–04), containing naphthalene-substituted amines as an electron donor and cyanoacrylic acid as an electron acceptor, were designed and synthesized, and their photophysical properties and dye-sensitized solar cells (DSCs) performances were characterized. Dyes YF02 and YF04, with 2,6-disubstituted naphthalene frameworks, were superior than their analog dyes YF03 and YF01, having 1,2-disubstituted naphthalene moiety, in incident-photo-to-current conversion efficiency (IPCE) and total solar-to-electric conversion efficiency (η). The DSCs based on YF02, comprised of diphenylamine moiety as the donor, produced the highest η of 5.29% compared to 4.03% of the analog dye YF04, which has pyrrolidine as the donor. Remarkably, a high open-circuit photovoltage (Voc) of 0.799–0.807 V was achieved in the cases of YF02–03, which have diphenylamine-donors. To better understand the structure–property relationship for DSCs application, molecular modelling was performed on YF01–04 and vertical electronic excitations were calculated using long-range corrected energy functional WB97XD and CAM-B3LYP at the basis set level DGDZVP, which were in excellent agreement with the experimental results. Moreover, the equilibrium molecular geometries of dyes YF01–04 were calculated at the density function theory (DFT) level using the hybrid energy functional B3LYP and basis set DGDZVP. The torsion angles (θ) between the naphthalene moiety and diphenylamine donor in YF02 and YF03 were more twisted than that of the pyrrolidine-donor dyes YF01 and YF04, precluding efficient intermolecular π–π charge transfer, which translated into high Voc. Compared to the reference dye TA-St-CA, which is based on diphenylamine as an electron donor linked to a phenyl ring, YF02 achieved higher Voc, which indicated that naphthalene substituted with diphenylamine is more efficient in retarding charge recombinations.

  设计并合成了四种新的供体-π-受体有机染料（YF01–04），这些染料以含有萘取代胺的化合物作为电子供体，以氰基丙烯酸作为电子受体，并对其光物理性质及染料敏化太阳能电池（DSCs）的性能进行了表征。具有2,6-二取代萘框架的染料YF02和YF04在入射光电流转换效率（IPCE）和总太阳能转电效率（η）方面优于其类似染料YF03和YF01，后者具有1,2-二取代萘基团。基于YF02的DSC，其供体为二苯胺基团，显示出5.29%的最高η，而类似染料YF04（供体为哌咯啶）的η为4.03%。在具有二苯胺供体的YF02和YF03中，惊人地达到了0.799–0.807 V的高开路光电压（Voc）。为了更好地理解DSC应用中的结构-性质关系，对YF01–04进行了分子建模，并使用长程修正的能量泛函WB97XD和CAM-B3LYP在DGDZVP基组水平上计算了垂直电子激发，这与实验结果非常一致。此外，使用混合能量泛函B3LYP和DGDZVP基组在密度泛函理论（DFT）水平上计算了染料YF01–04的平衡分子几何结构。YF02和YF03中萘基与二苯胺供体之间的扭转角（θ）比YF01和YF04（哌咯啶供体染料）的扭转角更大，从而阻碍了高效的分子间π-π电荷转移，导致高Voc。与参考染料TA-St-CA相比，该染料以二苯胺作为电子供体与苯环连接，YF02实现了更高的Voc，这表明用二苯胺取代的萘在延缓电荷复合方面更为有效。