trimethyl-(thieno[3,4-b]thiophen-2-yl)silane | 198489-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: trimethyl-(thieno[3,4-b]thiophen-2-yl)silane
• 英文别名: 2-(trimethylsilyl)thieno[3,4-b]thiophene；TT-TMS；Trimethyl(thieno[2,3-c]thiophen-2-yl)silane
• CAS: 198489-56-4
• 化学式: C₉H₁₂S₂Si
• 分子量: 212.412
• InChiKey: QUDLRCGOBNKMAC-UHFFFAOYSA-N

物化性质

• 沸点：
  285.9±20.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trimethyl-(thieno[3,4-b]thiophen-2-yl)silane 在 水 作用下， 反应 1.0h， 生成 噻吩并[3,4-b]噻吩
  参考文献：
  名称：

  Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

  摘要：

  A series of new low-band-gap thieno- or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br(2), 5Br(2), and 6Br(2)) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (similar to 0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

  DOI：

  10.1021/cm102395v
• 作为产物：
  描述：

  三甲基乙炔基硅 在 copper(l) iodide 、 正丁基锂 、 二乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 10.5h， 生成 trimethyl-(thieno[3,4-b]thiophen-2-yl)silane
  参考文献：
  名称：

  Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

  摘要：

  A series of new low-band-gap thieno- or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br(2), 5Br(2), and 6Br(2)) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (similar to 0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

  DOI：

  10.1021/cm102395v

文献信息

• Diisobutylaluminum Hydride Promoted Selectivity-Switchable Synthesis of Benzothiophene Oxides and Benzothiophenes via an Al–Li-Dimetalated Intermediate
  作者：Seiya Uchida、Hidenori Kinoshita、Katsukiyo Miura

  DOI：10.1021/acs.orglett.0c00884

  日期：2020.4.17

  We developed an efficient and direct method for synthesis of benzothiophene oxides from 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzenes and thionyl chloride as an easily accessible source of the sulfinyl group. Benzothiophenes were also synthesized selectively by simply increasing the amount of thionyl chloride. These methods achieved efficient syntheses of various benzothiophene oxides and benzothiophenes

  我们开发了一种有效而直接的方法，可以从1-溴-2- [2-（2-（三甲基甲硅烷基）乙炔基]苯和亚硫酰氯作为亚硫酰基的容易获得的来源来合成苯并噻吩氧化物。通过简单地增加亚硫酰氯的量也可以选择性地合成苯并噻吩。这些方法实现了各种苯并噻吩氧化物和苯并噻吩的有效合成。还证明了获得的苯并噻吩氧化物的进一步改性。
• 醌式近红外荧光化合物及其制备方法和应用
  申请人：中国科学院化学研究所

  公开号：CN104961746B

  公开（公告）日：2017-09-29

  本发明公开了一种基于醌式二噻吩结构的荧光化合物及其制备方法，该类分子具有波长可调的强近红外荧光性质，在生物成像和有机近红外发光二极管等方面具有广泛的应用前景。其结构通式如下：
• Developing Quinoidal Fluorophores with Unusually Strong Red/Near-Infrared Emission
  作者：Longbin Ren、Feng Liu、Xingxing Shen、Cheng Zhang、Yuanping Yi、Xiaozhang Zhu

  DOI：10.1021/jacs.5b03899

  日期：2015.9.9

  Despite the dominant position of aromatic fluorophores, we report herein the design and synthesis of quinoidal fluorophores based on rarely emissive quinoidal bithiophene. Quinoidal bitheno[3,4-b]thiophene, QBTT-C6, consisting of cruciform-fused (E)-1,2-bis(5-hexylthiophen-2-yl)ethene and quinoidal bithiophene, shows a fluorescence quantum yield of 8.5%, 25-fold higher than that of the parent quinoidal

  尽管芳香族荧光团占主导地位，但我们在此报告了基于很少发光的醌型联噻吩的醌型荧光团的设计和合成。醌式联苯[3,4-b]噻吩，QBTT-C6，由十字形稠合的 (E)-1,2-双(5-己基噻吩-2-基)乙烯和醌式联噻吩组成，其荧光量子产率为 8.5 %，比母体醌型 QBT 发色团高 25 倍，但其最大发射波长相似。QBTT-Ar 具有分子内电荷转移的特点，可以进一步将最大发射转移到近红外区域。通过将芳基上的取代基从吸电子三氟甲基调整为给电子甲氧基，可以可编程地增强分子内电荷转移。不料，观察到分子内电荷转移与荧光量子产率之间存在正相关关系；因此，QBTT-FL 为醌型低聚噻吩提供了高达 53.1% 的前所未有的高荧光量子产率。通过详细的光物理和理论研究，我们证明了 QBTT-Ar 中的非辐射系统间交叉（S1 → T2）受到显着限制，这可归因于小活化能的更快反向系统间交叉（T2 → S1）特性。这项
• Syntheses of Novel Group 15 and 16 Thieno[2,3-b]-, Thieno[3,4-b]-, and Thieno[3,2-b]-heteroles
  作者：Takashi Tsuchiya、Shuji Yasuike、Jyoji Kurita

  DOI：10.3987/com-97-7911

  日期：——