1-hexyl-2,3,3-trimethyl-3H-indol-1-ium iodide

• 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: 1-hexyl-2,3,3-trimethyl-3H-indol-1-ium iodide
• 英文别名: 1-Hexyl-2,3,3-trimethylindol-1-ium;iodide；1-hexyl-2,3,3-trimethylindol-1-ium;iodide
• 化学式: C₁₇H₂₆N*I
• 分子量: 371.305
• InChiKey: ALNGJUVEOALCKZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-hexyl-2,3,3-trimethyl-3H-indol-1-ium iodide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Regioselective Synthesis of 1,2- vs 1,3-Squaraines

  摘要：

  Squaraines have been known for many decades as very stable and versatile vis-NIR absorbing dyes. They have found applications for example as sensitizers in organic photovoltaics and photodetectors. The most common squaraine structure is the 1,3-regioisomer. Their 1,2-regiolsomers are seldom mentioned and unanimously regarded as side products. A facile direct synthesis of 1,2-squaraines, highlighting the role played by reaction conditions and electronic factors, is described. The first electrochemical characterization of these dyes is also shown.

  DOI：

  10.1021/ol201093t
• 作为产物：
  描述：

  1-hexyl-2,3,3-trimethyl-3H-indol-1-ium bromide 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以99%的产率得到1-hexyl-2,3,3-trimethyl-3H-indol-1-ium iodide
  参考文献：
  名称：

  N-Alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles. Potential lead compounds in the fight against Saccharomyces cerevisiae infections

  摘要：

  The synthesis of a variety of N-alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles is reported herein. Their potential as antifungal agents is evaluated by preliminary screening against Saccharomyces cerevisiae (S. cerevisiae), Schizosaccharomyces pombe (S. pombe), and Candida albicans (C albicans). Statistical analyses illustrate a strong relationship between chain length and growth inhibition for S. cerevisiae and S. pombe (p < 0.0001 in every case).Of particular interest is the activity of both sets of compounds against S. cerevisiae, as this is emerging as an opportunistic pathogen, especially in immunosuppressed and immunocompromised patients. Bioassays were set up to compare the efficacy of our range of N-alkylated compounds against classic antifungal agents; Amphotericin B and Thiabendazole. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.031

文献信息

• [EN] SQUARAINE DYES AND APPLICATIONS THEREOF<br/>[FR] COLORANTS SQUARAÏNE ET LEURS APPLICATIONS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2018020518A1

  公开（公告）日：2018-02-01

  The present invention disclosed a squaraine dye of formula (I) and process for the preparation thereof. Further, the present invention disclosed to an electronic device comprising dye of formula (I).

  本发明揭示了一种式（I）的方酮染料以及其制备方法。此外，本发明还揭示了一种包括式（I）染料的电子设备。
• Panchromatic squaraine compounds for broad band light harvesting electronic devices
  作者：Luca Beverina、Riccardo Ruffo、Matteo M. Salamone、Elisabetta Ronchi、Maddalena Binda、Dario Natali、Marco Sampietro

  DOI：10.1039/c2jm16240g

  日期：——

  Squaraine compounds are currently investigated as high performance active components in both organic and hybrid photovoltaic devices as well as in photodetectors. Their most valuable features include a particularly efficient optical absorption in the Vis-NIR region, high polarizability, and a remarkable chemical stability. Their full exploitation is somewhat limited by a negligible absorption in the UV-Vis region (prototypical squaraines basically do not absorb below 500 nm). The aim of the present paper is the design and synthesis of truly panchromatic squaraines to be effectively employed as the photoactive materials in Vis operating optoelectronic devices. Our strategy involves the design of squaraines that are both nonsymmetric and core-substituted with suitable electron-withdrawing groups. We show the effect of such a design strategy by means of UV-Vis spectroscopy, cyclic voltammetry and prototypical device performances rationalization.

  方形烯化合物目前正被研究用作有机和混合光伏器件以及光电探测器中的高性能活性组分。它们最宝贵的特性包括在可见-近红外区域具有特别高效的光学吸收、高极化性以及显著的化学稳定性。它们完全开发利用受到一定限制，原因是其在紫外-可见光区域几乎没有吸收（典型的方形烯基本在500 nm以下不吸收）。本文的目标是设计并合成真正全光谱的方形烯，以便在可见光工作的光电设备中有效地用作光活性材料。我们的策略涉及设计既非对称又以适当吸电子基团为核心取代的方形烯。我们通过紫外-可见光谱、循环伏安法以及典型器件性能的合理化来展示这种设计策略的效果。
• Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines
  作者：A. Pardal、S. Ramos、P. Santos、L. Reis、P. Almeida

  DOI：10.3390/70300320

  日期：——

  The synthesis and spectroscopic characterisation of some representative N-alkyl-substituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzo-selenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine

  描述了从苯并噻唑、苯并恶唑、苯并硒唑、吲哚和喹啉衍生的一些代表性 N-烷基取代季铵盐的合成和光谱表征。这些杂环盐在与氮原子和 N-甲基、-戊基、-己基和-癸基链相关的 2-位带有活化的甲基，是花青染料的典型前体。
• Panchromatic Sensitizer for Dye-Sensitized Solar Cells: Unsymmetrical Squaraine Dyes Incorporating Benzodithiophene π-Spacer with Alkyl Chains to Extend Conjugation, Control the Dye Assembly on TiO₂, and Retard Charge Recombination
  作者：Rajesh Bisht、Munavvar Fairoos M. K.、Ambarish Kumar Singh、Jayaraj Nithyanandhan

  DOI：10.1021/acs.joc.6b02670

  日期：2017.2.17

  (NIR) active unsymmetrical squaraine dyes, RSQ1 and RSQ2, with benzodithiophene (BDT) π-spacer and cyanoacrylic acid acceptor were synthesized by utilizing palladium catalyzed direct (hetero)arylation reaction. Methyl and 2-ethylhexyl groups were strategically placed at the BDT unit for RSQ1 and RSQ2, respectively, to investigate the effect of alkylated π-spacer on dye aggregation on the TiO2 surface and

  利用钯催化的直接（杂）芳基化反应，合成了具有苯并二噻吩（BDT）π间隔物和氰基丙烯酸受体的无金属近红外（NIR）活性不对称方酸方形染料RSQ1和RSQ2。分别在BDT单元的RSQ1和RSQ2上分别策略性地放置了甲基和2-乙基己基，以研究烷基化的π-间隔基对TiO 2表面染料聚集和TiO 2 /染料/电解质界面的重组反应的影响。这些染料具有强吸收性（ε> 10 5 M –1 cm –1）在近红外（NIR）区域具有相同的共轭骨架，因此显示出相似的光学和电化学性质。RSQ2比进行更好RSQ1由于其较高的开路电压（V OC）和填充因子（FF，尽管具有可比较的短路电流密度（的）Ĵ SC）。还观察到两种染料的全色入射光子-电流转换效率（IPCE）响应。RSQ2的功率转换效率（PCE）为6.72％，短路电流密度（J sc）为18.53 mA / cm 2，开路电压（V oc））的0.538 V ）和67
• Biodegradable and pH-Responsive Acetalated Dextran (Ac-Dex) Nanoparticles for NIR Imaging and Controlled Delivery of a Platinum-Based Prodrug into Cancer Cells
  作者：Carolyne B. Braga、Gabriel Perli、Tiago B. Becher、Catia Ornelas

  DOI：10.1021/acs.molpharmaceut.9b00058

  日期：2019.5.6

  encapsulation efficiency, high stability in physiological conditions, and pH responsiveness. Drug-release studies clearly showed that the PtIV prodrug 3 release from Ac-Dex NPs was negligible at pH 7.4, whereas at pH 5.5, this compound was completely released with a controlled rate. Confocal laser scanning microscopy unambiguously showed that the NIR-dye 9/Ac-Dex NPs were efficiently taken up by MCF-7 cells

  基于可生物降解的乙缩醛葡聚糖聚合物（Ac-Dex）的纳米颗粒（NPs）用于近红外（NIR）成像，并控制Pt IV前药向癌细胞的递送。载有疏水性Pt IV前药3（Pt IV / Ac-Dex NPs）和新型疏水性NIR荧光染料9（NIR染料9）的Ac-Dex NP/ Ac-Dex NPs，以及与两种化合物共载的Ac-Dex NP（共载Ac-Dex NP），是使用一种水包油纳米乳液方法组装而成的。动态光散射测量和扫描电子显微镜图像显示，所得Ac-Dex NP是球形的，平均直径为100 nm，它通过增强的渗透和保留效果而适合在肿瘤中蓄积。新的纳米系统显示出高载药能力，高包封效率，在生理条件下的高稳定性和pH响应性。药物释放研究清楚地表明，Pt IV前药3在pH 7.4时，Ac-Dex NPs的释放可忽略不计，而在pH 5.5时，该化合物以受控的速率完全释放。共聚焦激光扫描显微镜清楚地表明，NIR-dye