2-(5-ethynylthiophen-2-yl)benzothiazole | 1225449-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(5-ethynylthiophen-2-yl)benzothiazole
• 英文别名: 2-(5-ethynylthiophen-2-yl)-1,3-benzothiazole
• CAS: 1225449-60-4
• 化学式: C₁₃H₇NS₂
• 分子量: 241.337
• InChiKey: CYZPHWVTLXEUGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-ethynylthiophen-2-yl)benzothiazole 、 2,7-二溴-9,9-二癸基芴 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以65%的产率得到2,2'-(5,5'-(9,9-didecyl-9H-fluorene-2,7-diyl)bis-(ethyne-2,1-diyl)bis(thiophene-5,2-diyl))dibenzothiazole
  参考文献：
  名称：

  Two-Photon Fluorescence Lysosomal Bioimaging with a Micelle-Encapsulated Fluorescent Probe

  摘要：

  我们报告了一种新型、高效、溶酶体选择性系统的双光子荧光显微镜（2PFM）成像和体外细胞存活率，该系统基于封装在 Pluronic® F-127 胶束中的双光子吸收（2PA）荧光探针（I）。染料 I 的制备是通过微波辅助合成完成的，从而提高了产量并缩短了反应时间。光物理特性分析表明，该探针具有显著的 2PA 效率。

  DOI：

  10.1007/s10895-010-0801-3
• 作为产物：
  描述：

  2-(5-bromothiophen-2-yl)benzo[d]thiazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 8.03h， 生成 2-(5-ethynylthiophen-2-yl)benzothiazole
  参考文献：
  名称：

  Two-Photon Fluorescence Lysosomal Bioimaging with a Micelle-Encapsulated Fluorescent Probe

  摘要：

  我们报告了一种新型、高效、溶酶体选择性系统的双光子荧光显微镜（2PFM）成像和体外细胞存活率，该系统基于封装在 Pluronic® F-127 胶束中的双光子吸收（2PA）荧光探针（I）。染料 I 的制备是通过微波辅助合成完成的，从而提高了产量并缩短了反应时间。光物理特性分析表明，该探针具有显著的 2PA 效率。

  DOI：

  10.1007/s10895-010-0801-3

文献信息

• A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging
  作者：Carolina D. Andrade、Ciceron O. Yanez、Luis Rodriguez、Kevin D. Belfield

  DOI：10.1021/jo1005075

  日期：2010.6.18

  The synthesis, structural, and photophysical characterization of a series of new fluorescent donor acceptor and acceptor-acceptor molecules, based on the fluorenyl ring system, with two-photon absorbing properties is described. These new compounds exhibited large Stokes shifts, high fluorescence quantum yields, and significantly, high two-photon absorption cross sections, making them well suited for two-photon fluorescence microscopy imaging. Confocal and two-photon fluorescence microscopy imaging of COS-7 and HCT 116 cells incubated with probe I showed endosomal selectivity, demonstrating the potential of this class of fluorescent probes in multiphoton fluorescence microscopy.
• New Two-Photon-Absorbing Probe with Efficient Superfluorescent Properties
  作者：Kevin D. Belfield、Carolina D. Andrade、Ciceron O. Yanez、Mykhailo V. Bondar、Florencio E. Hernandez、Olga V. Przhonska

  DOI：10.1021/jp107343k

  日期：2010.11.11

  The synthesis, linear photophysical, and photochemical parameters, two-photon absorption (2PA), and superfluorescence properties of 2,2'-(5,5'-(9,9-didecyl-9H-fluorene-2,7-diyl)bis(ethyne-2,1-diyl)bis(thiophene-5,2-diy1))dibenzo[d]thiazole (1) were investigated, suggesting its potential as an efficient fluorescent probe for bioimaging applications. The steady-state absorption, fluorescence, and excitation anisotropy spectra of 1 were measured in several organic solvents and aqueous media. Probe 1 exhibited high fluorescence quantum yield (similar to 0.7-0.8) and photochemical stability (photobleaching quantum yield similar to(3-7) x 10(-6)). The 2PA spectra were determined over a broad spectral range (640-920 nm) using a standard two-photon induced fluorescence method under femtosecond excitation. A well-defined two-photon allowed absorption band at 680-720 nm with corresponding 2PA cross sections delta(2PA) approximate to 800-900 GM was observed. The use of probe 1 in bioimaging was shown via one- and two-photon fluorescence imaging of HCT-116 cells. An amplification of the stimulated emission of 1 was demonstrated in organic solvents and thin polystyrene films, which potentially can be used for the development of new fluorescent labels with increased spectral brightness.
• Two-Photon Fluorescence Lysosomal Bioimaging with a Micelle-Encapsulated Fluorescent Probe
  作者：Carolina D. Andrade、Ciceron O. Yanez、Maher A. Qaddoura、Xuhua Wang、Curtesa L. Arnett、Sabrina A. Coombs、Jin Yu、Rania Bassiouni、Mykhailo V. Bondar、Kevin D. Belfield

  DOI：10.1007/s10895-010-0801-3

  日期：2011.5

  We report two-photon fluorescence microscopy (2PFM) imaging and in vitro cell viability of a new, efficient, lysosome-selective system based on a two-photon absorbing (2PA) fluorescent probe (I) encapsulated in Pluronic® F-127 micelles. Preparation of dye I was accomplished via microwave-assisted synthesis, resulting in improved yields and reduced reaction times. Photophysical characterization revealed notable 2PA efficiency of this probe.

  我们报告了一种新型、高效、溶酶体选择性系统的双光子荧光显微镜（2PFM）成像和体外细胞存活率，该系统基于封装在 Pluronic® F-127 胶束中的双光子吸收（2PA）荧光探针（I）。染料 I 的制备是通过微波辅助合成完成的，从而提高了产量并缩短了反应时间。光物理特性分析表明，该探针具有显著的 2PA 效率。