2-cyano-3-{4-[2-(4-diphenylaminophenyl)vinyl]phenyl}acrylic acid | 849680-56-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-3-{4-[2-(4-diphenylaminophenyl)vinyl]phenyl}acrylic acid
• 英文别名: 2-Cyano-3-{4-[2-(4-diphenylaminophenyl)vinyl]phenyl}acrylic acid；2-cyano-3-[4-[2-[4-(N-phenylanilino)phenyl]ethenyl]phenyl]prop-2-enoic acid
• CAS: 849680-56-4
• 化学式: C₃₀H₂₂N₂O₂
• 分子量: 442.517
• InChiKey: QZBRCSFGVAKGJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-3-{4-[2-(4-diphenylaminophenyl)vinyl]phenyl}acrylic acid 在 3-甲氧基丙腈 、 水 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  染料敏化太阳能电池中基于氰基丙烯酸的有机增敏剂的降解

  摘要：

  由于其良好的性能，灵活的结构修改和低成本，有机染料已广泛用于染料敏化太阳能电池（DSSC）中。为了提高基于有机染料的DSSC的光稳定性，我们对基于氰基丙烯酸的有机敏化剂在DSSC中的降解机理进行了全面研究。结果表明，在水和紫外光的协同作用下，敏化剂可从TiO 2表面脱附，敏化剂的氰基丙烯酸单元转化为醛基。还观察到水含量对降解过程有很大的影响。我们的实验是使用18O标记的水表明在降解的染料中鉴定出的醛基的氧原子来自DSSC中的溶剂水。因此，在DSSC制造过程中控制含水量，良好的电池密封性以及过滤UV光对于生产更耐用，更坚固的DSSC至关重要。

  DOI：

  10.1002/cssc.201200949
• 作为产物：
  描述：

  二苯胺 在 哌啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2,6-二叔丁基-4-甲基苯酚 、 phosphan 、 sodium carbonate 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 42.0h， 生成 2-cyano-3-{4-[2-(4-diphenylaminophenyl)vinyl]phenyl}acrylic acid
  参考文献：
  名称：

  [EN] STILBENE DERIVATIVES FOR THE TREATMENT OF CNS AND OTHER DISORDERS
  [FR] DÉRIVÉS DE STILBÈNE À UTILISER POUR LE TRAITEMENT DE TROUBLES DU SNC ET D'AUTRES TROUBLES

  摘要：

  本申请公开了stilbene衍生物化合物和组合物，以及使用所述化合物和组合物治疗患者的眼部疾病、神经系统疾病和蛋白聚集相关疾病的方法。

  公开号：

  WO2018208709A1

文献信息

• Ultra-fast co-sensitization and tri-sensitization of dye-sensitized solar cells with N719, SQ1 and triarylamine dyes
  作者：Peter J. Holliman、Moneer Mohsen、Arthur Connell、Matthew L. Davies、Kareem Al-Salihi、Mateusz B. Pitak、Graham J. Tizzard、Simon J. Coles、Ross W. Harrington、William Clegg、Carlos Serpa、Octávio H. Fontes、Cecile Charbonneau、Matthew J. Carnie

  DOI：10.1039/c2jm31314f

  日期：——

  This paper describes the synthesis of a new, yellow triphenylamine dye, 4-[2-(4-diphenylaminophenyl)vinyl]benzoic acid] (6), with a sorption maximum at 380 nm in solution for which EQE data show shifts to 420 nm on sorption to TiO2. The performance of this dye has been measured in dye-sensitized solar cell (DSC) devices, showing η = 2.6% for 1 cm2 devices. Light soaking of (6) shows excellent long-term stability with <10% variation in device performance over 1800 h. Full characterization data are reported for (6) and the intermediates used in its synthesis including single-crystal X-ray structural analysis of all compounds. The paper also describes the ultra-fast dye sensitization and co-sensitization of TiO2 photo-electrodes in 5 minutes using one or two dyes and the first example of ultra-fast tri-sensitization. The dyes tested include the ruthenium dye N719, the squaraine dye SQ1, the red triphenylamine dye 2-cyano-3-4-[2-(4-diphenylaminophenyl)vinyl]phenyl}acrylic acid (5) and (6). DSC efficiencies of 7.5% have been achieved for 1 cm2 devices co-sensitized using (6) and N719. These efficiencies exceed those recorded for single dye devices and EQE measurements confirm efficient photon capture from two or more dyes in a single photo-electrode. Photo-acoustic calorimetry (PAC) has also been used to measure the energy of the charge separation states formed for (6) and N719, showing a larger value (1.47 eV) for (6) compared to N719 (1.08 eV), whilst a TiO2 film co-sensitized with both (6) and N719 gave an intermediate value (1.28 eV). These data have been used to calculate dye HOMO, LUMO and λmax levels for (6) and N719 leading to important insights for future successful co-sensitization.

  本文描述了一种新型黄色三苯胺染料 4-[2-(4-二苯氨基苯基)乙烯基]苯甲酸] (6) 的合成，在溶液中最大吸收波长为 380 nm，EQE 数据显示偏移至 420 nm TiO2 的吸附。该染料的性能已在染料敏化太阳能电池 (DSC) 装置中进行了测量，结果显示 1 cm2 装置的 η = 2.6%。 (6) 的光浸泡表现出优异的长期稳定性，1800 小时内器件性能变化 <10%。报告了 (6) 及其合成中使用的中间体的完整表征数据，包括所有化合物的单晶 X 射线结构分析。该论文还描述了使用一种或两种染料在 5 分钟内实现 TiO2 光电极的超快速染料敏化和共敏化，以及超快速三敏化的第一个示例。测试的染料包括钌染料N719、方酸菁染料SQ1、红色三苯胺染料2-氰基-3-4-[2-(4-二苯氨基苯基)乙烯基]苯基}丙烯酸(5)和(6)。使用 (6) 和 N719 共同敏化的 1 cm2 器件的 DSC 效率达到 7.5%。这些效率超过了单染料设备记录的效率，EQE 测量证实了单个光电极中两种或多种染料的有效光子捕获。光声量热法 (PAC) 也已用于测量 (6) 和 N719 形成的电荷分离态的能量，与 N719 (1.08 eV) 相比，(6) 显示出更大的值 (1.47 eV)，而与 (6) 和 N719 共同敏化的 TiO2 薄膜给出了中间值 (1.28 eV)。这些数据已用于计算 (6) 和 N719 的染料 HOMO、LUMO 和 λmax 水平，从而为未来成功的共敏化提供重要见解。
• Fluorine substituent effect on organic dyes for sensitized solar cells
  作者：Yan-Duo Lin、Tahsin J. Chow

  DOI：10.1016/j.jphotochem.2011.12.013

  日期：2012.2

  Two sets of organic dyes containing a stilbene backbone with fluorine substituents were designed for a study on the quantum efficiency of dye-sensitized solar cells (DSSCs). The results revealed that adding a fluorine substituent on the phenyl group ortho to the cyanoacrylate can enhance the light-harvesting performance in comparison with the unsubstituted one. However, when the two ortho-positions were both substituted by fluorine atoms, the performance of DSSCs was substantially reduced. The reason was mainly ascribed to a distortion from a planar geometry caused by steric hindrance. The pi-conjugation was therefore disturbed, and the result led to a substantial reduction of the short-circuit photocurrent density (J(sc)). Another effect was found that the open-circuit photovoltage (V-oc) of the doubly substituted derivative was lower than that of the mono-substituted one. The more flexible conformation of the difluoro-substituted dyes induced an undesired nonradiative decay, therefore led to a reduction of open-circuit photovoltage. The phenomenon can be verified by electrochemical impendence spectrum. The non-planar geometry was realized by a computation using the density function theory (DFT) model. The slight blue shift of absorption band was also consistent with the calculated transition energy by a time dependent OFT model. (C) 2011 Elsevier B.V. All rights reserved.
• [EN] STILBENE DERIVATIVES FOR THE TREATMENT OF CNS AND OTHER DISORDERS<br/>[FR] DÉRIVÉS DE STILBÈNE À UTILISER POUR LE TRAITEMENT DE TROUBLES DU SNC ET D'AUTRES TROUBLES
  申请人：WARNER BABCOCK INST FOR GREEN CHEMISTRY LLC

  公开号：WO2018208709A1

  公开（公告）日：2018-11-15

  The present application discloses stilbene derivative compounds and compositions, and methods for treating ocular diseases, neurological disorders and protein aggregation-related disorders in patients using the compounds and compositions as disclosed herein.

  本申请公开了stilbene衍生物化合物和组合物，以及使用所述化合物和组合物治疗患者的眼部疾病、神经系统疾病和蛋白聚集相关疾病的方法。
• Degradation of Cyanoacrylic Acid-Based Organic Sensitizers in Dye-Sensitized Solar Cells
  作者：Cheng Chen、Xichuan Yang、Ming Cheng、Fuguo Zhang、Licheng Sun

  DOI：10.1002/cssc.201200949

  日期：2013.7

  Organic dyes have become widely used in dye‐sensitized solar cells (DSSCs) because of their good performance, flexible structural modifications, and low costs. To increase the photostability of organic dye‐based DSSCs, we conducted a full study on the degradation mechanism of cyanoacrylic acid‐based organic sensitizers in DSSCs. The results showed that with the synergy between water and UV light, the

  由于其良好的性能，灵活的结构修改和低成本，有机染料已广泛用于染料敏化太阳能电池（DSSC）中。为了提高基于有机染料的DSSC的光稳定性，我们对基于氰基丙烯酸的有机敏化剂在DSSC中的降解机理进行了全面研究。结果表明，在水和紫外光的协同作用下，敏化剂可从TiO 2表面脱附，敏化剂的氰基丙烯酸单元转化为醛基。还观察到水含量对降解过程有很大的影响。我们的实验是使用18O标记的水表明在降解的染料中鉴定出的醛基的氧原子来自DSSC中的溶剂水。因此，在DSSC制造过程中控制含水量，良好的电池密封性以及过滤UV光对于生产更耐用，更坚固的DSSC至关重要。