4-((3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((3,3-dimethyl-1-octyl-indolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate

• 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-((3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((3,3-dimethyl-1-octyl-indolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate
• 英文别名: (4E)-4-[(3,3-dimethyl-1-octylindol-1-ium-2-yl)methylidene]-2-[(Z)-(3,3-dimethyl-1-octylindol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
• 化学式: C₄₂H₅₆N₂O₂
• 分子量: 620.919
• InChiKey: OQJKJUVCASMYJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 sodium perchlorate 作用下， 以 喹啉 、 乙醇 、 甲苯 、 正丁醇 为溶剂， 生成 4-((3,3-dimethyl-1-octyl-3H-indolium-2-yl)methylene)-2-((3,3-dimethyl-1-octyl-indolin-2-ylidene)methyl)-3-oxocyclobut-1-enolate
  参考文献：
  名称：

  桥接方酸染料单元的策略和研究

  摘要：

  研究了合成策略和基本分子原理，以使发色团吸收远红色甚至近红外区域的光。因此，合成并表征了一系列新的方酸菁染料。除了单体不对称和对称的方酸染料以外，方酸染料二聚体和低聚物还与亚苯基，芴，异氰酸酯桥联获得了-辛氧基亚苯基和四氟亚苯基或通过缩合反应直接偶联的部分。通过使用基普里亚诺夫偶合染料理论的理论研究支持的紫外可见测量，研究了各种分子染料结构对其吸收性能的影响。关于极限值的迈耶理论，确定了对于最大可能吸收最大值的染料系列重复单元的有效数目。染料的电化学势和带隙的观察趋势和极限值与UV-vis研究一致。最后，计算的二聚体分子结构和前沿轨道验证了光物理和电化学研究的结果。

  DOI：

  10.1016/j.dyepig.2012.06.017

文献信息

• Strategies and investigations on bridging squaraine dye units
  作者：Simon Kuster、Thomas Geiger

  DOI：10.1016/j.dyepig.2012.06.017

  日期：2012.12

  strategies and basic molecular principles were investigated in order to achieve chromophores absorbing light in the far red or even near infrared region. Therefore, a comprehensive series of new squaraine dyes were synthesized and characterized. Beside monomeric unsymmetrical and symmetrical squaraine dyes, also squaraine dye dimers and oligomers bridged with phenylene, fluorene, iso-octyloxy phenylene

  研究了合成策略和基本分子原理，以使发色团吸收远红色甚至近红外区域的光。因此，合成并表征了一系列新的方酸菁染料。除了单体不对称和对称的方酸染料以外，方酸染料二聚体和低聚物还与亚苯基，芴，异氰酸酯桥联获得了-辛氧基亚苯基和四氟亚苯基或通过缩合反应直接偶联的部分。通过使用基普里亚诺夫偶合染料理论的理论研究支持的紫外可见测量，研究了各种分子染料结构对其吸收性能的影响。关于极限值的迈耶理论，确定了对于最大可能吸收最大值的染料系列重复单元的有效数目。染料的电化学势和带隙的观察趋势和极限值与UV-vis研究一致。最后，计算的二聚体分子结构和前沿轨道验证了光物理和电化学研究的结果。
• Synthesis, photophysical study and BSA association of water-insoluble squaraine dyes
  作者：Diego dos Santos Pisoni、Marluza Pereira de Abreu、Cesar Liberato Petzhold、Fabiano Severo Rodembusch、Leandra Franciscato Campo

  DOI：10.1016/j.jphotochem.2012.11.013

  日期：2013.1

  In this work, the synthesis, spectroscopic characterisation, photophysical study and bovine serum albumin association of water-insoluble squaraine dyes are described. The photophysical behaviour of the dyes was investigated using UV-vis and steady-state fluorescence in solution, as well as its association with bovine serum albumin in phosphate buffer solution. No squaraine aggregation was observed in organic solvents, but J-type aggregation could be observed in phosphate buffer solution. In the absence of protein, the J-aggregation promoted the fluorescence quenching; however, upon addition of protein, the fluorescence intensity increased by a factor of up to 80. Additionally, a linear relationship between the fluorescence intensity and the protein concentration could be observed for the squaraine dyes in a concentration range around 0.02-0.10 mu M. (C) 2012 Elsevier B.V. All rights reserved.
• Solid-state fluorescence of squarylium dyes
  作者：Masaki Matsui、Masato Fukushima、Yasuhiro Kubota、Kazumasa Funabiki、Motoo Shiro

  DOI：10.1016/j.tet.2011.12.067

  日期：2012.2

  An N-butyl indolenine squarylium dye could include toluene and p-xylene and exhibited the solid-state fluorescence in near-infrared region (F-max=761 nm) in crystalline form due to inhibition of pi/pi-interactions between the fluorophores. (C) 2011 Elsevier Ltd. All rights reserved.
• 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。