5-carboxy-1-hexyl-2,3,3-trimethyl-3H-indolium iodide | 1236069-09-2

• 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: 5-carboxy-1-hexyl-2,3,3-trimethyl-3H-indolium iodide
• 英文别名: 1-Hexyl-2,3,3-trimethylindol-1-ium-5-carboxylic acid;iodide
• CAS: 1236069-09-2
• 化学式: C₁₈H₂₆NO₂*I
• 分子量: 415.314
• InChiKey: WJWQCMQGCKGHFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(3-hexyl-5-methoxybenzothiazol-2(3H)-ylidene)methyl]-4-hydroxy-3-cyclobutene-1,2-dione 、 5-carboxy-1-hexyl-2,3,3-trimethyl-3H-indolium iodide 以 正丁醇 、 苯 为溶剂， 反应 20.0h， 生成 5-carboxy-2-({3-[(3-hexyl-5-methoxybenzothiazol-2(3H)-ylidene)-methyl]-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene}methyl)-1-hexyl-3,3-dimethyl-3H-indolium
  参考文献：
  名称：

  Molecular Design of Near-IR Harvesting Unsymmetrical Squaraine Dyes

  摘要：

  The functionalized unsymmetrical benzothiazole squaraine organic sensitizers 5-carboxy-2-({3-[(3-hexylbenzothiazol-2(3H)-ylidene}methyl]-2-hydroxy-4-oxo-2-cyclobuten-l-ylidenelmethyl)-1-hexy1-3,3-dimethyl-3H-indolium (hereafter named as SK-11) and 5-carboxy-2-0-[(3-hexyl-5-methoxybenzothiazol-2(311)-ylidene)methyl]-2-hydroxy-4-oxo-2cyclobuten- 1-ylidenelmethyl)-1-hexy1-3,3-dimethyl-3H-indolium (coded as SK-I2) are designed and developed to observe an intense and wider absorption band in the red/NIR wavelength region. DFT/TDDFT calculations have been performed on the two unsymmetrical squaraine sensitizers to gain insight into their electronic and optical properties. The utility of these dyes in solid state dye sensitized solar cells (SS-DSSCs) is demonstrated.

  DOI：

  10.1021/la101257b
• 作为产物：
  描述：

  4-肼基苯甲酸 在 sodium acetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 144.0h， 生成 5-carboxy-1-hexyl-2,3,3-trimethyl-3H-indolium iodide
  参考文献：
  名称：

  二甲基和三甲基花青基染料的合成、光物理、电化学和计算研究

  摘要：

  通过羧酸吲哚盐与三种不同的供体N, N-二甲基苯胺、咔唑和吲哚衍生物的缩合反应得到了三种新型花青基染料( D1 - D3 )。这些染料的化学结构已通过 IR、NMR 和 HRMS 得到确认和充分表征。进行了紫外-可见光谱、荧光光谱和循环伏安法，以初步了解它们的光电特性。一般来说，所有合成的染料在可见光区域都表现出明确的吸收，具有高吸收率和低带隙，给出 λ Ex。最大值(516–564 nm)、ε (45279–141011 M -1 cm -1 ) 和 E 0-0(2.11–2.21 eV)。所有染料都观察到明显的斯托克斯位移，其中含二甲炔花青的咔唑供体D2的值最高（2752 cm -1）。溶剂化显色研究表明，随着溶剂极性的增加，会产生减色效应并增加斯托克斯位移。另一方面，电化学研究显示其 HOMO 和 LUMO 能级分别为 <-5.46 和 > -3.58 eV，表明它们适合作为染料敏化太阳能电池中的敏化剂。使用密度泛函理论

  DOI：

  10.1016/j.jphotochem.2022.114189

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。
• Heterotriangulene-based unsymmetrical squaraine dyes: synergistic effects of donor moieties and out-of-plane branched alkyl chains on dye cell performance
  作者：Neeta Karjule、Munavvar Fairoos M. K.、Jayaraj Nithyanandhan

  DOI：10.1039/c6ta08651a

  日期：——

  Unsymmetrical squaraine sensitizers with two different donor moieties, triphenylamine (NSQR) and heterotriangulene (NSQ1–3), for dye-sensitized solar cells (DSSCs) have been designed and synthesized. These dyes utilize the indolium moiety to control charge recombination dynamics at the TiO2-dye-electrolyte interface by connecting linear and branched alkyl functionalities. In the present study, an efficient heterotriangulene (HT) donor and a branched alkyl group at sp3-C atoms were strategically incorporated to increase the power conversion efficiency (PCE) of zwitterionic dyes by improving photo-current density (Jsc) and open-circuit potential (Voc) of the cell. Among these four dyes, NSQ3 exhibited the highest efficiency of 6.73% with a Jsc of 18.74 mA cm−2, Voc of 0.53 V, and fill factor (ff) of 68.3%, without any co-adsorbent under an irradiance of 100 mW cm−2 (simulated AM 1.5G sunlight). In the presence of 3α,7α-dihydroxy-5β-cholanic acid (CDCA), NSQ1, NSQ2 and NSQ3 showed an efficiency of 7.07%, 7.38% and 7.17%, respectively. Despite the low Voc, far red light harvesting efficiency, reduced dye aggregation, long lifetime (τ) of injected electrons and high quantum efficiency of NSQ1–3 played constructive roles in achieving high PCE efficiency. Deceleration of charge recombination for NSQ dye cells was further studied by electrochemical impedance spectroscopy (EIS) and open-circuit photo-voltage decay (OCVD) measurements.

  具有两种不同供体部分的非对称方唑染料敏化剂：三苯胺（NSQR）和杂三环烯（NSQ1–3），已被设计和合成为染料敏化太阳能电池（DSSCs）。这些染料利用吲哚盐部分，通过连接线性和支链烷基功能性来控制TiO2-染料-电解质界面上的电荷复合动力学。在本研究中，通过提高电池的光电流密度（Jsc）和开路电位（Voc），战略性地引入高效的杂三环烯（HT）供体和sp3-C原子上的支链烷基，以提高两性离子染料的功率转换效率（PCE）。在这四种染料中，NSQ3在不加共吸附剂的照射下表现出最高的效率为6.73%，光电流密度为18.74 mA cm-2，开路电位为0.53 V，填充因子（ff）为68.3%，照射强度为100 mW cm-2（模拟AM 1.5G阳光）。在存在3α，7α-二羟基-5β-胆酸（CDCA）的情况下，NSQ1，NSQ2和NSQ3分别表现出7.07%，7.38%和7.17%的效率。尽管开路电位较低，远红光收获效率、减少染料聚集、注入电子的长寿命（τ）和高量子效率的NSQ1–3对实现高PCE效率起到了建设性作用。通过电化学阻抗光谱（EIS）和开路光电压衰减（OCVD）测量进一步研究了NSQ染料电池的电荷复合减速。
• 스쿠아레인 유도체, 염료감응 태양전지용 염료 및 염료감응 태양전지
  申请人：Korea University Research and Business Foundation 고려대학교 산학협력단(220040170680) BRN ▼209-82-08298

  公开号：KR101508564B1

  公开（公告）日：2015-04-07

  본 발명은 스쿠아레인 유도체, 염료감응 태양전지용 염료 및 염료감응 태양전지에 관한 것으로, 구체적으로는 하기의 화학식 1로 표시되는 스쿠아레인 유도체 염료로, 우수한 광변환 효율을 가지고, 넓은 영역의 빛을 흡수하고, 상기 스쿠아레인 유도체를 포함하는 염료를 사용함으로써 고효율의 염료감응 태앙전지를 제공할 수 있다. [화학식 1]

  本发明涉及苯并噻吩导体，染料敏化太阳能电池用染料和染料敏化太阳能电池，具体涉及化学式1所示的苯并噻吩导体染料，具有优异的光电转换效率，能吸收广泛范围的光线，通过使用包含上述苯并噻吩导体的染料，可以提供高效的染料敏化太阳能电池。【化学式1】
• Squaraine dyes and applications thereof
  申请人：Council of Scientific and Industrial Research

  公开号：US11377562B2

  公开（公告）日：2022-07-05

  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).

  本发明公开了一种式(I)的方碱染料及其制备工艺。此外，本发明还公开了一种包含式（I）染料的电子设备。
• SQUARAINE DYES AND APPLICATIONS THEREOF
  申请人：Council of Scientific and Industrial Research

  公开号：US20190270889A1

  公开（公告）日：2019-09-05

  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).