2-(2-甲基-1,3-苯并噻唑-3-鎓-3-基)乙酸溴化物 | 3121-52-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(2-甲基-1,3-苯并噻唑-3-鎓-3-基)乙酸溴化物
• 中文别名: N-{[2-(二苯基甲亚基)肼基&lt联氨基&gt]羰基}-4,5,7-三甲基-2-羰基-2H-色烯-8-磺酰胺
• 英文名称: 3-(carboxymethyl)-2-methylbenzothiazolium bromide
• 英文别名: 3-(carboxymethyl)-2-methylbenzo[d]thiazol-3-ium bromide；3-carboxymethyl-2-methylbenzothiazole-3-ium bromide；2-(2-Methyl-1,3-benzothiazol-3-ium-3-yl)acetate;hydrobromide；2-(2-methyl-1,3-benzothiazol-3-ium-3-yl)acetate;hydrobromide
• CAS: 3121-52-6
• 化学式: Br*C₁₀H₁₀NO₂S
• 分子量: 288.165
• InChiKey: NOFDPRUYWCIJRV-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(2-甲基-1,3-苯并噻唑-3-鎓-3-基)乙酸溴化物 在 重水 作用下， 以 氘代二甲亚砜 为溶剂， 生成 (2-Hydroxy-2-methyl-benzothiazol-3-yl)-acetic acid
  参考文献：
  名称：

  NMR spectroscopy study of 2-methylbenzoxazolium salts hydroxylation in DMSO-d6 solution

  摘要：

  2-Methylbenzoxazolium salts showed an unexpected transformation at room temperature, promoted by residual water present in dimethyl sulfoxide. This transformation was followed up inside of an NMR sample tube using DMSO-d(6) as solvent, in a series of representative quaternary ammonium salts with carboxymethyl, ethyl, pentyl and decyl N-alkyl chains, resulting in an exclusive product. The corresponding benzothiazolium and benzoselenazolium salts presented a si similar behavior after heating at a temperature of 50 degrees C with the addition of one drop of D2O for the first of these two salts. This reaction could play a very important role in explaining certain secondary reactions occurring in the preparation of compounds where these salts are precursors, classically in cyanine dye synthesis. Four new benzoxazolols were characterized by NMR spectroscopy and HR FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.091
• 作为产物：
  描述：

  2-氨基苯硫醇 以 甲苯 为溶剂， 生成 2-(2-甲基-1,3-苯并噻唑-3-鎓-3-基)乙酸溴化物
  参考文献：
  名称：

  Synthesis of novel colorants for DSSC to study effect of alkyl chain length alteration of auxiliary donor on light to current conversion efficiency

  摘要：

  Five (MA1-MA5) hemicyanine based sensitizer having N, N-diethyl aniline as a primary donor and hydroxy or alkoxy as an auxiliary donor have been synthesized to establish a correlation between amphiphilic nature of the sensitizer and charge recombination. A strong electron withdrawing 3-(carboxymethyl)-2-methylbenzo[d]thiazol-3-ium bromide has been explored as an acceptor. All the dyes were characterized by H-1-NMR, C-13-NMR and CHN analysis. The photophysical properties of these dyes were recorded in seven different solvents which do not show any significant impact on absorption and emission maxima while molar absorptivity coefficient decreases with increase in alkyl chain length. These dyes show very poor emission in all the solvents. Nano crystalline mesoporous TiO2 based dye-sensitized solar cells were fabricated using MA1 to MA5 sensitizers to evaluate their photovoltaic performance. MA5 having six carbon alkyl chain shows maximum efficiency of 4.97% while MA1 without any alkyl chain shows the lowest efficiency of 3.40%. As the length of alkyl chain increase efficiency increase due to increment in short circuit current (J(sc)) and retardation in the recombination process. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) were explored to obtain vertical excitation, HOMO-LUMO energy and electron density distribution.

  DOI：

  10.1016/j.jphotochem.2019.03.043

文献信息

• Efficient electron injection due to a special adsorbing group’s combination of carboxyl and hydroxyl: dye-sensitized solar cells based on new hemicyanine dyes
  作者：You-Sheng Chen、Chao Li、Zhang-Hua Zeng、Wei-Bo Wang、Xue-Song Wang、Bao-Wen Zhang

  DOI：10.1039/b418906j

  日期：——

  A series of new benzothiazolium hemicyanine dyes (HC-1, HC-2, HC-3, HC-4, and HC-5 in Scheme 1) were designed and synthesized for sensitization of nanocrystalline TiO2 electrodes by introducing carboxyl, hydroxyl, or sulfonate anchoring groups onto the dyes' skeletons. A naphthothiazolium hemicyanine with both sulfonate and hydroxyl (HC-6) was also prepared for comparison. The photophysical and photoelectrochemical studies revealed that three kinds of efficiencies, i.e. the fluorescence quenching efficiencies of the dyes by colloidal TiO2, the monochromatic incident photon-to-current conversion efficiencies (IPCEs) for the dye-sensitized TiO2 electrodes, and the overall photoelectric conversion efficiencies (η) for the dye-sensitized solar cells (DSSCs) based on these hemicyanines, all depended strongly on the anchoring group types and decreased in the order: carboxyl + hydroxyl > carboxyl > sulfonate + hydroxyl, indicating the importance of the dyes' adsorbing groups for their sensitization effects in DSSCs. The combination of carboxyl and hydroxyl as anchoring groups led to highly efficient IPCEs over a wide spectrum region with the maximum IPCE of 73.6% and a η of 5.2% under AM1.5 Global simulated light (80 mW cm−2) for the HC-1 based DSSC, which may result from the complex formation between HC-1 and TiO2 and the cathodic shift of the excited state oxidation potential.

  设计并合成了一系列新型苯并噻唑鎓半菁染料（Scheme 1中的HC-1、HC-2、HC-3、HC-4和HC-5），通过在染料骨架上引入羧基、羟基或磺酸盐锚定基团，用于纳米晶TiO2电极的敏化。同时，为了比较，还制备了一种带有磺酸盐和羟基的萘并噻唑鎓半菁染料（HC-6）。光物理和光电化学研究揭示了三种效率，即染料的荧光猝灭效率、染料敏化TiO2电极的单色光入射光子-电流转换效率（IPCEs）以及基于这些半菁染料的染料敏化太阳能电池（DSSCs）的整体光电转换效率（η），都强烈依赖于锚定基团的类型，并且按照以下顺序递减：羧基 + 羟基 > 羧基 > 磺酸盐 + 羟基，这表明染料的吸附基团对于其在DSSCs中的敏化效果至关重要。羧基和羟基作为锚定基团的组合，在广泛的光谱区域内实现了高效的IPCE，HC-1基DSSC在AM1.5全球模拟光（80 mW cm−2）下，最大IPCE达到73.6%，η为5.2%，这可能源于HC-1与TiO2之间形成的复合物以及激发态氧化电位的阴极偏移。
• A new ratiometric and colorimetric chemosensor for cyanide anion based on Coumarin–hemicyanine hybrid
  作者：Zhenghao Yang、Zhipeng Liu、Yuncong Chen、Xiaoqing Wang、Weijiang He、Yi Lu

  DOI：10.1039/c2ob25516b

  日期：——

  as a new ratiometric and colorimetric sensor for cyanide with a sensing mechanism via nucleophilic addition of cyanide anion to the benzothiolium group. Cou-BT shows high sensitivity and selectivity for cyanide detection over other common anion species in aqueous acetonitrile solution. The calculated pseudo-first-order rate constant for cyanide anion addition was (2.13 ± 0.08) × 10−2 s−1 at 298 K, and

  杂种 香豆素-半花菁染料Cou-BT是作为氰化物的一种新的比例和比色传感器而开发的，该传感器具有通过将氰化物阴离子亲核加成到苯并硫鎓基团中的感测机制。与乙腈水溶液中的其他常见阴离子种类相比，Cou-BT对氰化物的检测具有很高的灵敏度和选择性。计算出的添加氰化物阴离子的拟一级反应速率常数在298 K下为（2.13±0.08）×10 -2 s -1，并且检测极限估计为0.64μM。DFT和TDDFT计算结果表明，Cou-BT的比例和比色传感行为 它与氰化物反应时，是由于π共轭的中断和ICT的进展受阻。
• Optical Mercury Sensing Using a Benzothiazolium Hemicyanine Dye
  作者：Sergio Tatay、Pablo Gaviña、Eugenio Coronado、Emilio Palomares

  DOI：10.1021/ol0615580

  日期：2006.8.1

  hemicyanine dye toward mercury(II) in aqueous solutions are described. Mercury ions coordinate to the dye forming a 1:1 complex. This interaction induces a color change in the dye at micromolar concentrations of mercury. Furthermore, the color change and quenching of the dye emission are selective for mercury when compared with other ions such as lead(II), cadmium(II), zinc(II), or iron(II).

  [结构：见正文]描述了苯并噻唑鎓半菁染料对水溶液中汞（II）的选择性和敏感性。汞离子与染料配位，形成1：1的络合物。在汞的微摩尔浓度下，这种相互作用导致染料发生颜色变化。此外，与其他离子（例如铅（II），镉（II），锌（II）或铁（II））相比，汞对颜色的变化和染料发射的猝灭具有选择性。
• Westphal Reaction in Solid-Phase
  作者：Francisca Delgado、M. Lourdes Linares、Ramón Alajarín、Juan J. Vaquero、Julio Alvarez-Builla

  DOI：10.1021/ol035417z

  日期：2003.10.1

  [GRAPHIC]A library of cycloimonium salts has been prepared through Westphal reaction in solid-phase. By reaction of solid-support-bound azolium or azinium acetates 2, 1,2-diketones 4, and base, cycloimonium salts 5 were synthesized in good to high yield and purities.
• Photographic emulsion
  申请人：EASTMAN KODAK CO

  公开号：US02231658A1

  公开（公告）日：1941-02-11