2-hexylsulfanylthiophene | 6911-41-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-hexylsulfanylthiophene
• 英文别名: 2-(hexylthio)thiophene；2-(hexylsulphanyl)thiophene；2-hexylmercapto-thiophene；2-Hexylmercapto-thiophen
• CAS: 6911-41-7
• 化学式: C₁₀H₁₆S₂
• 分子量: 200.369
• InChiKey: JQTDBXKCLAEDHG-UHFFFAOYSA-N

物化性质

• 沸点：
  130 °C(Press: 9 Torr)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hexylsulfanylthiophene 在 三氯氧磷 作用下， 生成 5-hexylmercapto-thiophene-2-carbaldehyde thiosemicarbazone
  参考文献：
  名称：

  Profft, Monatsberichte der Deutschen Akademie der Wissenschaften zu Berlin, 1959, vol. 1, p. 180,181

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩基锂 、 二己硫 以 四氢呋喃 为溶剂， 生成 2-hexylsulfanylthiophene
  参考文献：
  名称：

  Direct Preparation of 3-Thienyl Organometallic Reagents:  3-Thienylzinc and 3-Thienylmagnesium Iodides and 3-Thienylmanganese Bromides and Their Coupling Reactions

  摘要：

  3-Thienylzinc and 3-thienylmagnesium iodides can be generated from the direct oxidative addition of Rieke zinc and magnesium to 3-iodothiophene, respectively. The direct preparation of 3-thienylmanganese bromides from the reaction of Rieke manganese with 3-bromothiophene and 3,4-dibromothiophene is also performed. These 3-thienyl organometallic reagents have been found to be regiostable intermediates and undergo coupling reactions with a variety of versatile electrophiles such as acid chlorides, aryl iodides, aldehydes, and disulfide.

  DOI：

  10.1021/jo970778b

文献信息

• Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling
  作者：Md Muktadir Talukder、Justin T. Miller、John Michael O. Cue、Chinthaka M. Udamulle、Abhi Bhadran、Michael C. Biewer、Mihaela C. Stefan

  DOI：10.1021/acs.organomet.0c00732

  日期：2021.1.11

  significantly reduced by air and moisture sensitivity, as well as harsh reaction conditions. Herein, we report four highly air- and moisture-stable well-defined mononuclear and bridged dinuclear α-diimine Ni(II) and Pd(II) complexes for C–S cross-coupling. Various ligand frameworks, including acenaphthene- and iminopyridine-based ligands, were employed, and the resulting steric properties of the catalysts were

  空气和水分的敏感性以及苛刻的反应条件大大降低了过渡金属催化体系在CS交叉偶联反应中的作用。在此，我们报告了用于C–S交叉偶联的四种高度空气和水分稳定的定义明确的单核和桥接双核α-二亚胺Ni（II）和Pd（II）配合物。使用了各种配体构架，包括基于ph和亚氨基吡啶的配体，并评估了催化剂的最终空间性质，并将其与反应结果相关联。在有氧条件和低温下，与以前报道的催化剂相比，Ni和Pd体系均表现出更宽的底物范围和官能团耐受性。由含有烷基，苄基和杂芳基的硫醇合成了40多种化合物。也，从硫醇和卤化物源掺入药学上有活性的杂芳基部分。值得注意的是，通过在广泛的底物范围内提供几乎定量的产率，桥接的双核五坐标Ni络合物的性能优于其余三个单四坐标或六坐标Ni的络合物。
• Three-dimensional tetra(oligothienyl)silanes as donor material for organic solar cells
  作者：Sophie Roquet、R?mi de Bettignies、Philippe Leriche、Antonio Cravino、Jean Roncali

  DOI：10.1039/b604261a

  日期：——

  Tetrahedral conjugated systems involving four conjugated oligothiophene chains fixed onto a central silicon node (1, 2) have been synthesized and used as donor materials in hetero-junction solar cells. Bilayer solar cells have been realized by thermal evaporation of compounds 1 and 2 as donors and N,N′-bis-tridecylperylenedicarboxyimide as an acceptor. Comparison of the performances of these devices to those of a reference system based on dihexylterthienyl (H3T) shows that despite comparable effective conjugation lengths, the 3D compounds 1 and 2 lead to a power conversion efficiency four–five times higher, suggesting better absorption of the incident light and better hole transport properties. Whereas fabrication of bulk hetero-junction with H3T was prevented by the lack of film forming properties, a prototype bulk hetero-junction based on compound 2 as the donor and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as the acceptor has been realized. A short-circuit current density of 1.13 mA cm−2 and a power conversion efficiency of 0.30% has been measured under AM 1.5 simulated solar irradiation at 80 mW cm−2.

  四面体共轭体系包括固定在中央硅节点上的四条共轭低聚噻吩链（1、2），已被合成并用作异质结太阳能电池的供体材料。以化合物 1 和 2 作为给体，以 N,N′-双十三烷基过二羧酰亚胺作为受体，通过热蒸发实现了双层太阳能电池。将这些器件的性能与基于二己基三噻吩（H3T）的参考系统的性能进行比较后发现，尽管有效共轭长度相当，但三维化合物 1 和 2 的功率转换效率要高出四至五倍，这表明它们对入射光的吸收更好，空穴传输性能也更好。由于 H3T 缺乏成膜特性，因此无法制作体异质结，而以化合物 2 为供体、[6,6]-苯基-C61-丁酸甲酯（PCBM）为受体的体异质结原型已经实现。在 80 mW cm-2 的 AM 1.5 模拟太阳辐照条件下，测得短路电流密度为 1.13 mA cm-2，功率转换效率为 0.30%。
• High-Efficiency Cycloruthenated Sensitizers for Dye-Sensitized Solar Cells
  作者：The-Duy Nguyen、Yen-Po Lan、Chun-Guey Wu

  DOI：10.1021/acs.inorgchem.7b02862

  日期：2018.2.5

  thiocyanate-free ruthenium sensitizers (DUY24–DUY27) containing 2-thienylpyridine moiety as cyclometalating core were synthesized for dye-sensitized solar cell (DSC) application. To the best of our knowledge, DUY24–DUY27 are four best-efficiency sensitizers having 42%–65% higher efficiencies compared to those of the published sensitizers comprising the same type of the cyclometalating ancillary ligands. The significant

  合成了四种含有2-噻吩基吡啶部分作为环金属化核的无硫氰酸盐的钌敏化剂（DUY24-DUY27），用于染料敏化太阳能电池（DSC）。据我们所知，DUY24–DUY27是四种最佳增效剂，其效率比已发布的包含相同类型环化金属辅助配体的增效剂高42％–65％。DUY24–DUY27的显着特征是它们的β-最低空位自旋轨道（β-LUSO）显着分布在环金属配体上，特别是在软硫原子上，这增强了氧化染料与碘离子之间的相互作用，从而实现了有效的染料再生。基于DUY24–DUY27的DSC的光伏性能支持染料再生（因此短路光电流密度（不仅可以降低染料分子的最高占据分子轨道能级，而且可以将β-LUSO适当地分布在软原子上，从而改善细胞的J SC）。该研究为设计用于DSC的高效钌基染料提供了重要的新指南。
• Photoelectric conversion element, dye-sensitized solar cell, metal complex dye, dye composition, and oxide semiconductor electrode
  申请人：FUJIFILM Corporation

  公开号：US11094474B2

  公开（公告）日：2021-08-17

  A photoelectric conversion element includes a conductive support, a photoconductor layer including an electrolyte, a charge transfer layer including an electrolyte, and a counter electrode, in which the photoconductor layer has semiconductor fine particles carrying a metal complex dye represented by a specific formula.

  一种光电转换元件包括导电支架、包括电解质的光电导体层、包括电解质的电荷转移层和对电极，其中光电导体层具有携带以特定公式表示的金属络合染料的半导体微粒。
• Preparation of 3-Thienylzinc and -magnesium Halide via Oxidative Addition of Active Zinc and Magnesium to 3-Iodothiophene
  作者：Xiaoming Wu、Reuben D. Rieke

  DOI：10.1021/jo00126a004

  日期：1995.10