bis(2-iodothien-3-yl)methane | 1352312-45-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: bis(2-iodothien-3-yl)methane
• CAS: 1352312-45-8
• 化学式: C₉H₆I₂S₂
• 分子量: 432.088
• InChiKey: SKOBFUTUGQYRQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  bis(2-iodothien-3-yl)methane 在 正丁基锂 、 噻吩-2-甲酸亚铜(I) 、 potassium iodide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 2,6-二硼酸频哪醇酯-4,4-二(2-乙基己基)-二噻吩并环戊二烯
  参考文献：
  名称：

  Atomistic Band Gap Engineering in Donor–Acceptor Polymers

  摘要：

  We have synthesized a series of cyclopentadithiophene-benzochalcogenodiazole donor-acceptor (D-A) copolymers, wherein a single atom in the benzochalcogenodiazole unit is varied from sulfur to selenium to tellurium, which allows us to explicitly study sulfur to selenium to tellurium substitution in D-A copolymers for the first time. The synthesis of S- and Se-containing polymers is straightforward; however, Te-containing polymers must be prepared by postpolymerization single atom substitution. All of the polymers have the representative dual-band optical absorption profile, consisting of both a low- and high-energy optical transition. Optical spectroscopy reveals that heavy atom substitution leads to a red-shift in the low-energy transition, while the high-energy band remains relatively constant in energy. The red-shift in the low-energy transition leads to optical band gap values of 1.59, 1.46, and 1.06 eV for the S-, Se-, and Te-containing polymers, respectively. Additionally, the strength of the low-energy band decreases, while the high-energy band remains constant. These trends cannot be explained by the present D and A theory where optical properties are governed exclusively by the strength of D and A units. A series of optical spectroscopy experiments, solvatochromism studies, density functional theory (DFT) calculations, and time-dependent DFT calculations are used to understand these trends. The red-shift in low-energy absorption is likely due to both a decrease in ionization potential and an increase in bond length and decrease in acceptor aromaticity. The loss of intensity of the low-energy band is likely the result of a loss of electronegativity and the acceptor unit's ability to separate charge. Overall, in addition to the established theory that difference in electron density of the D and A units controls the band gap, single atom substitution at key positions can be used to control the band gap of D-A copolymers.

  DOI：

  10.1021/ja208917m
• 作为产物：
  描述：

  di(3-thienyl)methane 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到bis(2-iodothien-3-yl)methane
  参考文献：
  名称：

  Atomistic Band Gap Engineering in Donor–Acceptor Polymers

  摘要：

  We have synthesized a series of cyclopentadithiophene-benzochalcogenodiazole donor-acceptor (D-A) copolymers, wherein a single atom in the benzochalcogenodiazole unit is varied from sulfur to selenium to tellurium, which allows us to explicitly study sulfur to selenium to tellurium substitution in D-A copolymers for the first time. The synthesis of S- and Se-containing polymers is straightforward; however, Te-containing polymers must be prepared by postpolymerization single atom substitution. All of the polymers have the representative dual-band optical absorption profile, consisting of both a low- and high-energy optical transition. Optical spectroscopy reveals that heavy atom substitution leads to a red-shift in the low-energy transition, while the high-energy band remains relatively constant in energy. The red-shift in the low-energy transition leads to optical band gap values of 1.59, 1.46, and 1.06 eV for the S-, Se-, and Te-containing polymers, respectively. Additionally, the strength of the low-energy band decreases, while the high-energy band remains constant. These trends cannot be explained by the present D and A theory where optical properties are governed exclusively by the strength of D and A units. A series of optical spectroscopy experiments, solvatochromism studies, density functional theory (DFT) calculations, and time-dependent DFT calculations are used to understand these trends. The red-shift in low-energy absorption is likely due to both a decrease in ionization potential and an increase in bond length and decrease in acceptor aromaticity. The loss of intensity of the low-energy band is likely the result of a loss of electronegativity and the acceptor unit's ability to separate charge. Overall, in addition to the established theory that difference in electron density of the D and A units controls the band gap, single atom substitution at key positions can be used to control the band gap of D-A copolymers.

  DOI：

  10.1021/ja208917m