4-(2-bromo-5-iodothiophen-3-yl)-1-hexyl-1H-1,2,3-triazole | 1245737-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-(2-bromo-5-iodothiophen-3-yl)-1-hexyl-1H-1,2,3-triazole
• 英文别名: 4-(2-Bromo-5-iodothiophen-3-yl)-1-hexyltriazole
• CAS: 1245737-51-2
• 化学式: C₁₂H₁₅BrIN₃S
• 分子量: 440.146
• InChiKey: KMHBTBJXOWOJLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-bromo-5-iodothiophen-3-yl)-1-hexyl-1H-1,2,3-triazole 在 叔丁基氯化镁 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 、 4-(2-bromothiophen-3-yl)-1-hexyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Impact of Pendant 1,2,3-Triazole on the Synthesis and Properties of Thiophene-Based Polymers

  摘要：

  pi-Conjugated moieties are often attached to conjugated polymers to systematically alter their electronic properties. Herein, we report the synthesis and properties of a thiophene polymer hearing a triazole moiety in the third position. Through NMR-based quenching studies, we show that the placement of the triazole moiety alters reaction pathway of the Ni(0)-mediated Grignard metathesis polymerization possibly through chelation. When compared with a triazole on the main chain, the pendant triazole moiety acts as in electron donor and lowers the band gap of the polymer. The triazole moiety also does not hinder the packing of the conjugated backbone. We also show that the fluorescence of this polymer is quenched with PCBM. indicating its potential as a candidate or organic photovoltaic devices.

  DOI：

  10.1021/ma101657e
• 作为产物：
  描述：

  [(2,5-dibromothiophen-3-yl)ethynyl](trimethyl)silane 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 三氟甲磺酸 、 叔丁基氯化镁 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 4-(2-bromo-5-iodothiophen-3-yl)-1-hexyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Impact of Pendant 1,2,3-Triazole on the Synthesis and Properties of Thiophene-Based Polymers

  摘要：

  pi-Conjugated moieties are often attached to conjugated polymers to systematically alter their electronic properties. Herein, we report the synthesis and properties of a thiophene polymer hearing a triazole moiety in the third position. Through NMR-based quenching studies, we show that the placement of the triazole moiety alters reaction pathway of the Ni(0)-mediated Grignard metathesis polymerization possibly through chelation. When compared with a triazole on the main chain, the pendant triazole moiety acts as in electron donor and lowers the band gap of the polymer. The triazole moiety also does not hinder the packing of the conjugated backbone. We also show that the fluorescence of this polymer is quenched with PCBM. indicating its potential as a candidate or organic photovoltaic devices.

  DOI：

  10.1021/ma101657e

文献信息

• Enhancing sensing of nitroaromatic vapours by thiophene-based polymer films
  作者：G. Nagarjuna、Abhishek Kumar、Akshay Kokil、Kedar G. Jadhav、Serkan Yurt、Jayant Kumar、D. Venkataraman

  DOI：10.1039/c1jm12949j

  日期：——

  Optical sensing, via fluorescence quenching, of nitroaromatic vapours using polythiophenes has received limited attention due to their rather low sensory response. We hypothesized that a dipolar 1,2,3-triazole moiety can enhance the interaction of DNT and TNT with the polymer in thin films and bulky side chains can decrease the chain packing in thin films resulting in enhanced analyte diffusion. Herein we show that thin films of thiophene-based polymers containing 1,2,3-triazole with appropriate alkyl side chains show enhanced fluorescence quenching in the presence of nitroaromatic vapours.

  通过荧光猝灭对含有聚噻吩的硝基芳烃蒸气进行光学传感的研究受到的关注有限，因为其感应响应相对较低。我们假设，极性1,2,3-三唑部分能够增强DNT和TNT与聚合物在薄膜中的相互作用，而笨重的侧链可以降低薄膜中的链堆积，从而增强分析物扩散。本研究表明，含有适当烷基侧链的1,2,3-三唑的噻吩基聚合物薄膜在存在硝基芳烃蒸气时显示出增强的荧光猝灭现象。