4-((5-carboxy-3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((5-carboxy-3,3-dimethyl-1-octylindolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate | 1351395-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-((5-carboxy-3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((5-carboxy-3,3-dimethyl-1-octylindolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate
• 英文别名: VG1-C8；SQ-5；SQ-3；(4Z)-4-[(5-carboxy-3,3-dimethyl-1-octylindol-1-ium-2-yl)methylidene]-2-[(E)-(5-carboxy-3,3-dimethyl-1-octylindol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
• CAS: 1351395-51-1
• 化学式: C₄₄H₅₆N₂O₆
• 分子量: 708.938
• InChiKey: SHMZAIUMIPNOPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  52
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-((5-carboxy-3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((5-carboxy-3,3-dimethyl-1-octylindolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate 、 、 氨基乙醛缩二甲醇 在 2,4,6-三甲基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以100 mg的产率得到
  参考文献：
  名称：

  具有三个同轴电荷传输通路的定向表面结构

  摘要：

  我们报告了一种直接在固体表面上构建具有三个同轴 π 堆栈的定向架构的合成方法。该方法使用正交动态键、二硫化物和腙、自组织表面引发聚合 (SOSIP) 和模板化堆叠交换 (TSE)。已证实与萘二亚胺、苝二亚胺、方酸、富勒烯、低聚噻吩和三苯胺的相容性。与由两个同轴通道组成的光系统相比，安装第三个通道可将光电流产生增加多达 10 倍。限制涉及无法进入 SOSIP 架构的巨型堆叠交换器（例如，被三个富勒烯包围的酞菁），以及可以提供折叠或交叉指型电荷转移架构而不是三个同轴通道的平面三元组。报道的三通道表面架构与今天一样复杂，其结构的方向性保证了对每个单独通道中具有多分量梯度的多通道架构的通用访问。报道的方法将使我们能够系统地解开表面结构中分子二元组和三元组的超快光物理学，并可能对开发概念上的创新光电器件有用。

  DOI：

  10.1021/ja405776a
• 作为产物：
  描述：

  4-肼基苯甲酸 在 喹啉 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 正丁醇 、 苯 为溶剂， 反应 29.0h， 生成 4-((5-carboxy-3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((5-carboxy-3,3-dimethyl-1-octylindolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate
  参考文献：
  名称：

  DYE-SENSITIZED SOLAR CELL, PHOTOELECTRIC CONVERSION ELEMENT, AND DYE FOR USE IN THE SOLAR CELL AND THE ELEMENT

  摘要：

  提供一种具有羧基吲哚啉结构和N-烷基取代基的方酰胺染料，以及使用该方酰胺染料制备的在近红外区域具有高光电转换效率的光电转换元件和染料敏化太阳能电池。光电转换元件或染料敏化太阳能电池使用代表式（1）所示的化合物作为方酰胺染料。在式（1）中，R1和R2代表取代或未取代的C5至C30烷基；X代表C(CH3)2；A和B代表羧基。

  公开号：

  US20120029206A1

文献信息

• Symmetric vs. asymmetric squaraines as photosensitisers in mesoscopic injection solar cells: a structure–property relationship study
  作者：Jinhyung Park、Claudia Barolo、Frédéric Sauvage、Nadia Barbero、Caterina Benzi、Pierluigi Quagliotto、Salvatore Coluccia、Davide Di Censo、Michael Grätzel、Md. K. Nazeeruddin、Guido Viscardi

  DOI：10.1039/c2cc17187b

  日期：——

  A symmetric squaraine and its related non-symmetric structure are shown to have comparable efficiencies in DSCs, but with undoubtedly advantages in the low cost and easiness of synthesis for the symmetrical structure.

  结果显示，对称四氢吖啶与相关的非对称结构在染料敏化太阳能电池（DSCs）中具有相近的效率，但无可置疑的是，对称结构在低成本和合成简易性方面具有优势。
• Near‐Infrared Squaraine Dyes as Bright Fluorescent Probes: A Structure–Activity Photophysical Investigation in Liposomes
  作者：Giacomo Renno、Francesca Cardano、Viktoria Ilieva、Guido Viscardi、Andrea Fin

  DOI：10.1002/ejoc.202200833

  日期：2022.10.7

  unsymmetrical red emitting squaraine dyes is reported, varying the substituents to modulate the hydrophilic/hydrophobic ratio of the fluorescent probes. Their ability to stain cellular membranes is assessed by studying their interactions with liposomal model systems, screening the key features for the design of squaraine-based cell membrane probes.

  报道了一个小型对称和不对称红色发射方酸染料库的有效制备，通过改变取代基来调节荧光探针的亲水/疏水比。通过研究它们与脂质体模型系统的相互作用来评估它们对细胞膜染色的能力，筛选基于方酸的细胞膜探针设计的关键特征。
• Synthesis and characterization of squaric acid based NIR dyes for their application towards dye-sensitized solar cells
  作者：Takafumi Inoue、Shyam S. Pandey、Naotaka Fujikawa、Yoshihiro Yamaguchi、Shuji Hayase

  DOI：10.1016/j.jphotochem.2010.04.015

  日期：2010.6

  Synthesis of novel cyan-colored sensitizing dyes bearing squaric acid core and 2,3,3-trimethyl-indole as terminal moieties has been conducted in order to fabricate dye-sensitized solar cells based on nanoporous TiO2. It has been found that position of COOH functionality utilized for anchoring with TiO2 surface has a marked effect on solar cell performance. Carboxylic acid group directly substituted to indole ring gave about 5-fold higher conversion efficiency as compared to the dye when it was substituted in alkyl chain of the indole ring. Efficiency has been found to be hampered due to aggregation and enhancement in the efficiency was observed when dyes were used with chenodeoxycholic acid (CDCA). Using COCA and long alkyl substituent at the N-position of indole ring to prevent aggregation and enhanced TiO2 surface passivation, respectively, has achieved a solar conversion efficiency of 3.15% with a short circuit current density of 7.26 mA/cm(2), an open circuit voltage of 0.64 V and a fill factor of 0.68 for SQ-5 under standard AM 1.5 solar irradiation. (C) 2010 Elsevier B.V. All rights reserved.
• Substituent effect in direct ring functionalized squaraine dyes on near infra-red sensitization of nanocrystalline TiO2 for molecular photovoltaics
  作者：Shyam S. Pandey、Takafumi Inoue、Naotaka Fujikawa、Yoshihiro Yamaguchi、Shuji Hayase

  DOI：10.1016/j.jphotochem.2010.07.010

  日期：2010.8

  We have synthesized a series of novel blue colored symmetrical squaraine sensitizers with variable alkyl chain length for their application towards the fabrication of dye-sensitized solar cells (DSSCs). It has been found that an increase in the alkyl chain length substituted at N-position of indole ring exhibits enhanced electron diffusion length and electron life-time resulting in better passivation of nanocrystalline TiO2 surface leading to enhancement in the cell performance. Based on HOMO and LUMO energy measurement of squaraine dyes, it has been demonstrated that about 0.16 eV energy barrier is sufficient for electron injection from LUMO of dye to TiO2 conduction band and dye regeneration after photo-excitation. Performances of DSSCs using model squaraine dyes indicate that dodecyl alkyl substituent is optimum giving highest Voc and use of chenodeoxycholic acid along with the dye SQ-4 shows a photoconversion efficiency of 3.5% under AM 1.5 irradiation. (C) 2010 Elsevier B.V. All rights reserved.
• Microwave-Assisted Synthesis of Near-Infrared Fluorescent Indole-Based Squaraines
  作者：Nadia Barbero、Claudio Magistris、Jinhyung Park、Davide Saccone、Pierluigi Quagliotto、Roberto Buscaino、Claudio Medana、Claudia Barolo、Guido Viscardi

  DOI：10.1021/acs.orglett.5b01453

  日期：2015.7.2

  A microwave-assisted method for the preparation of a wide color range of 2,3,3-trimethylindolenine-based squaraines and their intermediates is described. This practical approach allows the rapid preparation of both symmetrical and nonsymmetrical Squaraine dyes, reducing reaction time from days to minutes with more than 2-fold improvement in product yields when compared to,conventional methods.