SQ-4 | 1351395-52-2

• 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: SQ-4
• 英文别名: 4-[(5-Carboxy-1-dodecyl-3,3-dimethylindol-1-ium-2-yl)methylidene]-2-[(5-carboxy-1-dodecyl-3,3-dimethylindol-2-ylidene)methyl]-3-oxocyclobuten-1-olate；4-[(5-carboxy-1-dodecyl-3,3-dimethylindol-1-ium-2-yl)methylidene]-2-[(5-carboxy-1-dodecyl-3,3-dimethylindol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
• CAS: 1351395-52-2
• 化学式: C₅₂H₇₂N₂O₆
• 分子量: 821.153
• InChiKey: UDZFIMAHSKBLSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  60
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-carboxy-1-dodecyl-2,3,3-trimethyl-3H-indol-1-ium iodide 、 方酸 以 甲苯 、 正丁醇 为溶剂， 生成 SQ-4
  参考文献：
  名称：

  Design, Synthesis, and Photophysical Characterization of Multifunctional Far‐Red Squaraine Dyes for Dye‐Sensitized Solar Cells

  摘要：

  本研究设计了新型远红敏感对称方碱（SQ）染料，旨在通过烷基链末端修饰实现控制染料聚集、促进分子自组装和引入电解质功能等多功能特性。成功合成、表征并详细研究了新设计的无端修饰染料（SQ-5）以及碘（SQ-77）和咪唑（SQ-79）烷基端修饰染料。碘端修饰（SQ-77）导致摩尔消光系数、染料聚集、染料负载和在二氧化钛表面的结合力增强，而咪唑（SQ-79）端修饰后则恰恰相反。在没有碘和酚去氧胆酸的情况下，SQ-77 和 SQ-79 的光伏性能几乎相似，这验证了它们除了作为光敏剂的主要作用外，还分别具有电解质功能和防止染料聚集的多功能作用。以 SQ-5 为敏化剂制造的染料敏化太阳能电池显示出高效的远红外至近红外光敏化和光子收集功能，其短路光电流密度、开路电压和填充因子分别为 11.98 mA cm-2、0.61 V 和 0.57，在模拟太阳辐照下的光电转换效率为 4.2%。

  DOI：

  10.1002/pssa.202300254

文献信息

• 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.