SQ-3 | 1351395-50-0

• 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-3
• 英文别名: SQ-1；(4Z)-4-[(5-carboxy-1-ethyl-3,3-dimethylindol-1-ium-2-yl)methylidene]-2-[(E)-(5-carboxy-1-ethyl-3,3-dimethylindol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
• CAS: 1351395-50-0
• 化学式: C₃₂H₃₂N₂O₆
• 分子量: 540.616
• InChiKey: IXVNDCIXHBWGQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  SQ-3 、 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以57.5%的产率得到
  参考文献：
  名称：

  一种用于检测有机磷酸酯的荧光试剂及其制备方法

  摘要：

  本发明属于化学分析测试领域，具体涉及一种用于检测有机磷酸酯的荧光试剂及其制备方法。该试剂为基于8‑氨基喹啉骨架的对称方酸菁化合物。以4‑肼基苯甲酸为原料，与3‑甲基‑2‑丁酮成环，再接碘乙烷，得到的产物与3,4‑二羟基‑3‑环丁烯‑1,2‑二酮反应得到荧光染料。再8‑氨基喹啉与氯乙酰氯反应，将产物与对苯二胺反应得到识别部分。最后荧光染料和识别部分在N,N‑二异丙基乙胺碱性条件下，在2‑(7‑氮杂苯并三氮唑)‑N,N,N',N'‑四甲基脲六氟磷酸酯催化下得到最终化合物。本发明化合物具有优良的光学性能和离子选择性，在Zn2+参与下，能够对有机磷酸酯进行荧光响应识别检测。

  公开号：

  CN113735829B
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚-5-羧酸 以 甲苯 、 乙腈 、 正丁醇 为溶剂， 反应 0.67h， 生成 SQ-3
  参考文献：
  名称：

  近红外方酸染料作为明亮的荧光探针：脂质体的结构-活性光物理研究

  摘要：

  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。

  DOI：

  10.1002/ejoc.202200833

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。
• The effect of bis-carboxylic groups of squarylium dyes on the efficiency of dye-sensitized solar cells
  作者：Sultan A. Al-horaibi、Eman M. Garoon、Narendra A. Bhise、Suresh T. Gaikwad、Anjali S. Rajbhoj

  DOI：10.1007/s11696-019-00978-5

  日期：2020.6

  TiO2, resulting in improved dye-sensitized solar cell efficiency compared to SQIND2. Hence, the SQIND1 sensitized exhibit better photovoltaic performance. Although, the absence of any linker groups in the SQIND1, then SQIND1 was perfect efficiently sensitized on porous TiO2 with the long UV–Vis and NIR region up to 800 nm of the spectrum and showed higher remarkable performance of values, such as η

  合成了具有双羧基的对称方酸染料（SQIND1），并与非官能化的类似物基团（SQIND2）进行了比较，研究了光电化学性质。实验结果表明，在SQIND1敏化剂中引入锚定羧基可与纳米颗粒TiO 2更紧密地接触，从而增加了从SQIND1转移至半导体的电荷载流子的数量。理论计算和吸光度结果表明，SQIND1的LUMO电子密度在整个发色团中都离域化，从而导致SQIND1敏化剂与TiO 2导带之间的强电子耦合。与SQIND2相比，可提高染料敏化太阳能电池的效率。因此，敏化的SQIND1表现出更好的光伏性能。虽然，由于没有在SQIND1任何连接基团，然后SQIND1是完美的有效敏化的多孔的TiO 2与长紫外-可见和NIR区域到光谱为800nm和显示值的更高显着的性能，如η的3.3％，J sc为7.6mA / cm 2，V oc为0.59，FF为0.73。
• 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.