3-bromo-2-(n-pentyl)-5-(1,3-dioxolan-2-yl)thiophene | 944243-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-bromo-2-(n-pentyl)-5-(1,3-dioxolan-2-yl)thiophene
• 英文别名: 4-bromo-5-n-pentyl-2-(1,3-dioxolane)thiophene；2-(4-Bromo-5-pentylthiophen-2-yl)-1,3-dioxolane；2-(4-bromo-5-pentylthiophen-2-yl)-1,3-dioxolane
• CAS: 944243-52-1
• 化学式: C₁₂H₁₇BrO₂S
• 分子量: 305.236
• InChiKey: RQAPWABEYMXKQH-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(n-pentyl)-5-(1,3-dioxolan-2-yl)thiophene 在 吡啶 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 为溶剂， 生成 1,2-bis(2-n-pentyl-5-formyl-3-thienyl)perfluorocyclopentene
  参考文献：
  名称：

  Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives

  摘要：

  Photochromic symmetrical diarylethene derivatives 1a-6a bearing different long alkyl chains at 2-position of thiophene rings have been synthesized and their structures have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their optoelectronic properties, such as photochromism in solution as well as in the crystalline phase and electrochemical performance was investigated in detail. These diarylethenes have showed good photochromic behavior both in solution and in the single crystalline phase. Introduction of the long alkyl chains at 2-position of bis(5-formyl-3-thienyl) perfluorocyclopentene increased the absorption coefficients of both open- and closed-ring isomers and induced bathochromic shifts of the maximal wavelength absorption of the closed-ring isomers. The long alkyl chains can also decrease the cyclization/cycloreversion quantum yields and the oxidation potentials. The cyclic voltammetry indicated that the band gap of these diarylethene derivatives was significantly affected by the alkyl chain length. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.049
• 作为产物：
  描述：

  5-pentylthiophene-2-carbaldehyde 在 溴 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 苯 为溶剂， 生成 3-bromo-2-(n-pentyl)-5-(1,3-dioxolan-2-yl)thiophene
  参考文献：
  名称：

  Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives

  摘要：

  Photochromic symmetrical diarylethene derivatives 1a-6a bearing different long alkyl chains at 2-position of thiophene rings have been synthesized and their structures have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their optoelectronic properties, such as photochromism in solution as well as in the crystalline phase and electrochemical performance was investigated in detail. These diarylethenes have showed good photochromic behavior both in solution and in the single crystalline phase. Introduction of the long alkyl chains at 2-position of bis(5-formyl-3-thienyl) perfluorocyclopentene increased the absorption coefficients of both open- and closed-ring isomers and induced bathochromic shifts of the maximal wavelength absorption of the closed-ring isomers. The long alkyl chains can also decrease the cyclization/cycloreversion quantum yields and the oxidation potentials. The cyclic voltammetry indicated that the band gap of these diarylethene derivatives was significantly affected by the alkyl chain length. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.049

文献信息

• Syntheses and Substituent Effects on the Properties of Unsymmetrical Photochromic Diarylethenes Bearing a Benzothiophene Unit
  作者：Shouzhi Pu、Min Li、Gang Liu、Zhanggao Le

  DOI：10.1071/ch08289

  日期：——

  Photochromic unsymmetrical diarylethenes 1a–5a that bear different electron-donating or electron-withdrawing substitutes have been synthesized, and the structures of 2a–5a determined by single-crystal X-ray diffraction analysis. Substituent effects on their optoelectronic properties, including photochromism, fluorescence, and electrochemical properties are investigated in detail. The strong electron-donating

  合成了带有不同给电子或吸电子取代基的光致变色不对称二芳基蒽1a - 5a，并通过单晶X射线衍射分析确定了2a - 5a的结构。详细研究了取代基对其光电性能的影响，包括光致变色，荧光和电化学性能。强电子给体取代基对闭环异构体的最大吸收量和摩尔系数具有有效的贡献，而吸电子取代基可将二芳烃的最大吸收量显着转移至更长的波长并增加其环化量子产率。二芳烃2，3和4在溶液中和在单结晶相表现出良好的光致变色。但是，双芳烃5在结晶相中没有显示光致变色现象。当用紫外线和可见光交替照射时，二芳烃1、2和3表现出良好的荧光转换，并且它们在光固定状态下的荧光转化率在己烷中均大于80％。另外，循环伏安图测试表明，不同的给电子和吸电子取代基对这些二芳基蒽的电化学行为具有显着影响。
• Synthesis and the optoelectronic properties of diarylethene derivatives having benzothiophene and n-alkyl thiophene units
  作者：Shouzhi Pu、Min Li、Congbin Fan、Gang Liu、Liang Shen

  DOI：10.1016/j.molstruc.2008.08.023

  日期：2009.2

  Abstract Six new unsymmetrical diarylethenes having both benzothiophene and n -alkylthiophene units have been synthesized. The structures of diarylethenes 2a – 6a were determined by single-crystal X-ray diffraction analysis. The results showed that the alkyl chain length had a significant effect on the optoelectronic properties of these diarylethenes, including photochromism, fatigue resistance, fluorescence

  摘要 合成了六种新的同时具有苯并噻吩和正烷基噻吩单元的不对称二芳基乙烯。二芳基乙烯2a-6a的结构由单晶X射线衍射分析确定。结果表明，烷基链长对这些二芳基乙烯的光电性能有显着影响，包括光致变色、抗疲劳、荧光和电化学性能。长烷基链可以增加环化/环回复量子产率，但会降低二芳基乙烯 1 – 6 的吸收最大值。长烷基链还可以导致闭环异构体 1b-6b 在溶液和 PMMA 膜中的吸收最大值发生显着的红移。所有这些二芳基乙烯衍生物在己烷中都显示出良好的荧光转换（猝灭至约 10%）。随着烷基链长度变长，二芳基乙烯1-6的发射强度和荧光量子产率逐渐降低。此外，循环伏安测试表明，烷基链长对这些二芳基乙烯的电化学行为有显着影响。