2-bromo-5-iodo-3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxymethyl)thiophene | 1315503-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-bromo-5-iodo-3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxymethyl)thiophene
• 英文别名: 2-Bromo-5-iodo-3-(2-(2-(2-methoxy-ethoxy)ethoxy)ethoxy)methylthiophen；2-bromo-5-iodo-3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl]thiophene
• CAS: 1315503-15-1
• 化学式: C₁₂H₁₈BrIO₄S
• 分子量: 465.147
• InChiKey: WSEXKAYVDNVFDD-UHFFFAOYSA-N

物化性质

• 沸点：
  433.3±45.0 °C(Predicted)
• 密度：
  1.694±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 碘苯二乙酸 、 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-bromo-5-iodo-3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxymethyl)thiophene
  参考文献：
  名称：

  Synthesis and characterization of block copolythiophene with hexyl and triethylene glycol side chains

  摘要：

  A well-defined diblock copolythiophene, poly(3-hexylthiophene)-b-poly(3-(2-(2-(2-methoxyethoxy) ethoxy)ethoxy)methylthiophene) (P3HT-b-P3TEGT) was successfully synthesized by a Grignard metathesis (GRIM) polymerization. The structure of the block copolymer was confirmed by size exclusion chromatography (SEC), H-1 NMR spectroscopy, differential scanning calorimetry (DSC), ultraviolet-visible (UV-vis) spectroscopy and fluorescence spectroscopy. The self-assembled structure of the block copolythiophene was investigated by atomic force microscopy (AFM), transmission electron microscopy (TEM), small-angle X-ray scattering (SAXS), and synchrotron grazing incidence X-ray scattering (GIXS). These analyses found that the block components in films form vertically oriented lamellar structure via phase separation. Furthermore, both the phases were found to consist of molecular multi-layers respectively, in which the layers stack in the out-of-plane of the film. The P3HT phase exhibited crystalline, which is originated from the pi-pi stacked thiophene backbones. In contrast, the poly(3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methylthiophene) (P3TEGT) phase revealed amorphous. Overall, the amphiphilic nature of P3HT-b-P3TEGT successfully demonstrated to lead to well-defined self-assembly structure in films. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.06.037

文献信息

• Excited-State Dynamics of Water-Soluble Polythiophene Derivatives: Temperature and Side-Chain Length Effects
  作者：Ying-Zhong Ma、Robert W. Shaw、Xiang Yu、Hugh M. O’Neill、Kunlun Hong

  DOI：10.1021/jp304526h

  日期：2012.12.13

  We report synthesis and detailed spectroscopic study of three water-soluble polythiophene derivatives with distinct homologous oligo(ethylene oxide) side-chain lengths and lower critical solution temperatures (LCSTs). The linear absorption spectra exhibit reversible shifts and broadening with the variation of their aqueous solution temperature, whereas the corresponding steady-state fluorescence emission spectra were found to show negligible shifts and only minor changes in their line shape. Measurements of picosecond time-resolved fluorescence at chosen emission wavelengths reveal a strong dependence of the isotropic decays on both side-chain length and aqueous solution temperature. With lengthening of the side chain, the isotropic decays become not only remarkably slow but also increasingly complex. Except for the polymer with the shortest side chain, significant acceleration of the isotropic decays was found when the solution temperature was raised to the corresponding LCSTs and beyond, which further causes formation of large aggregates as evident by the physical appearance change from clear solutions to turbid suspensions. Direct evidence for a temperature-induced change of polymer chain conformation was obtained through measurements of time-resolved fluorescence anisotropies, which are characterized by a substantial increase of the initial values from similar to 0.2 to 0.4 and the appearance of a pronounced fast decay component with an estimated lifetime of 36 ps. The high initial anisotropy of similar to 0.4 observed for the two polymers with longer side-chains above their LCSTs suggests that the polymer chains are highly ordered in the aggregates. The observed effects of side-chain length and solution temperature are discussed by considering the conformational relaxation of the polymer backbones and occurrence of interchain energy transfer.