5-carboxy-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide | 126442-85-1

• 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: 5-carboxy-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide
• 英文别名: 5-carboxy-2,3,3-trimethyl-1-ethyl-3H-indolium iodide；1-ethyl-2,3,3-trimethylindol-1-ium-5-carboxylic acid;iodide
• CAS: 126442-85-1
• 化学式: C₁₄H₁₈NO₂*I
• 分子量: 359.207
• InChiKey: BAJVUMUXZFKZMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  233-234 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.31
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-carboxy-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide 在 potassium acetate 、 乙酸酐 、 N,N-二异丙基乙胺 、 原甲酸三乙酯 、 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (E)-2-(2-(9-(2-carboxyphenyl)-6-(diethylamino)-2,3-dihydro-1H-xanthen-4-yl)vinyl)-1-ethyl-3,3-dimethyl-5-((2-morpholinoethyl)carbamoyl)-3H-indol-1-ium perchlorate
  参考文献：
  名称：

  Design of an Acidic pH‐Activated NIR Fluorescent Convertible Rhodamine−Hemicyanine Probe‐Peptide Conjugate for Living Cancer Cell Active Targeted Selective Tracking of Lysosomes

  摘要：

  We have synthesized an acidic pH‐activatable dual targeting ratiometric fluorescent probe‐peptide conjugate using the SPPS protocol on resin. Living carcinoma cell specific active targeting, successive cell penetration, and selective staining of lysosomes are accomplished. Real‐time monitoring of lysosomes, 3D, and multicolor cancer cell imaging are attained. The de novo design consists of the integration of multifunctionality into a single molecular scaffold, e.g., RGDS peptide to target cancer cell overexpressed receptor αVβ3 integrin, live‐cell penetrating  rhodamine−hemicyanine chromophore comprising a lysosome targeting morpholine group, and an acidic pH openable spiro‐lactam ring for a visible‐to‐NIR switchable ratiometric response. Water‐soluble probe‐peptide conjugate exhibits intramolecular spirolactamization at basic pH through Arg amide N. The visible spirolactam state predominantly exists at physiological and basic pH and can be switched to the highly conjugated NIR open amide state (λem=735 nm) through spiro‐lactam ring opening triggered by acidic pH with a huge bathochromic shift (Δλabs=336 nm, ΔλFL=265 nm). pH‐sensitive ratiometric switching is achieved. This in situ acidic cancer cell lysosome activatable multifunctional fluorophore‐peptide conjugate shows augmented molar absorptivity, enhanced quantum yield, and improved fluorescence lifetime at acidic lysosomal pH; negligible cytotoxicity; and dual targeted ratiometric imaging capability of living cancer cell selective lysosomes with pKa value of 5.1.

  DOI：

  10.1002/chem.202402146
• 作为产物：
  描述：

  4-肼基苯甲酸 在 溶剂黄146 、 potassium hydroxide 作用下， 以 乙腈 为溶剂， 生成 5-carboxy-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide
  参考文献：
  名称：

  一种基于吲哚盐的比色荧光探针，用于100％水溶液中氰化物的检测

  摘要：

  我们报道了一种新型的基于吲哚盐的比色和荧光探针N1，用于氰化物。探针N1显示出漂白溶液和荧光猝灭朝向CN -在超过其它阴离子100％的水溶液。在紫外可见和荧光光谱法中，观察到大的蓝移（261nm），颜色漂白和荧光猝灭。在探针的荧光响应的最低检测限N1朝CN -为3.34×10 -7 摩尔/升。该探头N1通过分子内电荷转移（ICT）机制运作，因为CN的亲核攻击-对吲哚ÇN，通过改变颜色和荧光猝灭阻止了ICT的发展，这通过1 H NMR，MS和DFT研究得到了进一步证实。因此，合成的探针将是用于检测氰化物的有前途的设备。

  DOI：

  10.1016/j.dyepig.2019.04.059

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。
• Efficient near infrared fluorescence detection of elastase enzyme using peptide-bound unsymmetrical squaraine dye
  作者：Maryala Saikiran、Daisuke Sato、Shyam S. Pandey、Shuzi Hayase、Tamaki Kato

  DOI：10.1016/j.bmcl.2017.07.057

  日期：2017.9

  autofluorescence by biomolecules. Near infra-red (NIR) sensitive and self-quenching fluorescent probe based on the dye-peptide conjugate (SQ 1 PC) was designed and synthesized by facile and efficient one-pot synthetic route for the detection of Elastase activity. In the phosphate buffer solution, there was an efficient quenching of fluorescence of SQ 1 PC (86%) assisted by pronounced dye-dye interaction due to

  由于其深入的组织渗透以及生物分子对自发荧光的干扰最小，因此扩展波长对分析物响应的荧光探针非常需要用于成像应用。设计并合成了一种基于染料-肽结合物（SQ 1 PC）的近红外（NIR）敏感和自猝灭荧光探针，该探针通过简便有效的一锅合成路线来检测弹性蛋白酶的活性。在磷酸盐缓冲溶液中，由于H聚集物的形成，染料与染料之间的相互作用显着，有效抑制了SQ 1 PC（86％）的荧光。通过弹性蛋白酶将这种肽染料偶联物水解后，可以快速有效地恢复SQ 1 PC的这种淬灭荧光（在30 s内> 50％）。
• Visible light-harvesting in covalently-linked porphyrin-cyanine dyes
  作者：Jonathan S. Lindsey、Philip A. Brown、David A. Siesel

  DOI：10.1016/s0040-4020(01)85156-5

  日期：1989.1

  We report the synthesis and properties of three members of a new class of photochemical model compounds containing a covalently-linked porphyrin and a cyanine dye. In compounds 1 and 2 the dye absorbs in the 450–570 nm region and energy transfer occurs with 80% efficiency from the dye to the free base porphyrin. In compound 3 the dye absorbs in the 650–780 nm region and energy transfer occurs with

  我们报告了新型的光化学模型化合物的三个成员的合成和性质，这些化合物包含共价连接的卟啉和花菁染料。在化合物1和2中，染料在450-570 nm范围内吸收，并且从染料到游离碱卟啉的能量转移效率为80％。在化合物3中，染料在650-780 nm范围内吸收，从游离碱卟啉到染料的能量转移效率为80％。锌卟啉染料表现出给体和受体猝灭，只有中等程度的能量转移。这项工作是迈向人工藻胆体发展的第一步。
• Effect of nature of anchoring groups on photosensitization behavior in unsymmetrical squaraine dyes
  作者：Gururaj M. Shivashimpi、Shyam S. Pandey、Rie Watanabe、Naotaka Fujikawa、Yuhei Ogomi、Yoshihiro Yamaguchi、Shuzi Hayase

  DOI：10.1016/j.jphotochem.2013.09.004

  日期：2014.1

  indole based unsymmetrical squaraine dyes bearing various anchoring groups such as carboxylate (SQ-A), cyanoacrylate (SQ-B) and thiophene-bridged cyanoacrylate (SQ-C) were synthesized and evaluated for their performance in dye sensitized solar cells (DSSCs) under similar experimental conditions. Electronic absorption spectral investigation on thin films of these dyes adsorbed on nanoporous TiO2 reveals

  合成了一系列带有各种锚定基团（例如羧酸根（SQ-A），氰基丙烯酸酯（SQ-B）和噻吩桥基氰基丙烯酸酯（SQ-C））的吲哚基不对称方酸染料，并对其在染料敏化太阳能电池中的性能进行了评估（ DSSC）。这些染料薄膜在纳米多孔TiO 2上的电子吸收光谱研究当引入氰基丙烯酸酯官能团作为锚定基团时，其揭示了相对增强的光谱展宽。虽然在主要发色团和锚定基团（SQ-C）之间掺入了噻吩π桥，虽然导致了远红区的红移，但由于染料聚集相对增强，阻碍了光子的收集。直接取代并带有芳族发色团的带有氰基丙烯酸酯锚定基团的不对称方酸染料（SQ-B）表现出最佳的光伏性能，在模拟太阳辐射下的光转换效率为5.03％。