5-hexyl-2-iodothiophene | 710338-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-hexyl-2-iodothiophene
• 英文别名: 2-hexyl-5-iodothiophene；2-n-hexyl-5-iodothiophene
• CAS: 710338-91-3
• 化学式: C₁₀H₁₅IS
• 分子量: 294.2
• InChiKey: MRUNHRNYCUPSOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-hexyl-2-iodothiophene 在 indium 、 palladium 10% on activated carbon 、 四丁基溴化铵 、 lithium chloride 作用下， 以 水 为溶剂， 反应 24.0h， 以77%的产率得到5,5′-二己基-2,2′-联噻吩
  参考文献：
  名称：

  通过（杂）芳基碘化物的水上和空中均偶联， 方便地合成有机电子导向的结构单元†

  摘要：

  我们在此报告了一种操作简单的均偶联反应，其目标是方便合成有机电子重要的结构单元。各种合成上有用的联噻吩衍生物和官能化联苯可通过水上和空气中协议使用Pd / C作为催化剂有效地制备。我们发现，在（杂）芳基碘化物的情况下，由于Pd（OAc）2的存在，与使用Pd（OAc）2相比，Pd / C的同质耦合转化率更高且更清洁。引发更多的副反应，包括脱卤和低聚。在最佳条件下，对酯，酮，醛，腈，硝基，氯和溴等官能团的耐受性良好。我们希望本方法学将为绿色化学与基于噻吩的有机材料的桥接做出宝贵的合成贡献。

  DOI：

  10.1039/c5ra13517f

文献信息

• 2D Side‐Chain Engineered Asymmetric Acceptors Enabling Over 14% Efficiency and 75% Fill Factor Stable Organic Solar Cells
  作者：Jinru Cao、Hongtao Wang、Shenya Qu、Jiangsheng Yu、Linqiang Yang、Zhuohan Zhang、Fuqiang Du、Weihua Tang

  DOI：10.1002/adfm.202006141

  日期：2020.12

  conversion efficiency (PCE) of 14.02% with a fill factor (FF) of 75.06%, outperforming PBDB‐T devices with IPT2F‐Th (12.52%, 71.20%), IPT2F‐Ph (13.13%, 72.11%), and octylated IPT‐2F (13.70%, 71.50%). The PCE over 14% and FF over 75% are among the highest values for 2D FREAs OSCs reported to date. More importantly, outstanding thermal stability and light soaking stability are observed with PCE over 12% maintained

  有源层的电荷传输和形态是有机太阳能电池（OSC）中器件性能和稳定性的关键考虑因素。可以通过精心设计的稠环电子受体（FREA）的分子设计，尤其是共轭延伸和侧链工程来微调这些性质。在这项工作中，N在高效的不对称FREA设计中探索了功能化的共轭。来自主链的N共轭侧链的扭曲使三个FREA具有相似的能级和光吸收（约850 nm边缘）。它们与PBDB-T的混合物显示出高的载流子迁移率和有序的相分离。令人兴奋的是，基于IPT2F‐TT的OSC的主电源转换效率（PCE）为14.02％，填充因子（FF）为75.06％，优于IPT2F‐Th（12.52％，71.20％），IPT2F‐Ph的PBDB‐T设备（13.13％，72.11％）和辛基IPT-2F（13.70％，71.50％）。迄今为止，报告的2D FREA OSC的PCE超过14％，FF超过75％。更重要的是，在热老化或光老化100小时后，PCE保持超
• Synthesis and photophysical properties of 2,5,8,11-tetrakis(5-hexylthiophen-2-yl)tetrathieno[2,3-<i>a</i>:3′,2′-<i>c</i>:2′′,3′′-<i>f</i>:3′′′,2′′′-<i>h</i>]naphthalene
  作者：Libin Gao

  DOI：10.1107/s0108270113010895

  日期：2013.6.15

  The title compound, C₅₈H₆₄S₈, has been prepared by Pd-catalysed direct C—H arylation of tetrathienonaphthalene (TTN) with 5-hexyl-2-iodothiophene and recrystallized by slow evaporation from dichloromethane. The crystal structure shows a completely planar geometry of the TTN core, crystallizing in the monoclinic space groupP2₁/c. The structure consists of slipped π-stacks and the interfacial distance between the mean planes of the TTN cores is 3.456 (5) Å, which is slightly larger than that of the comparable derivative of tetrathienoanthracene (TTA) with 2-hexylthiophene groups. The packing in the two structures is greatly influenced by both the aromatic core of the structure and the alkyl side chains.

  标题化合物 C58H64S8 是通过钯催化四噻吩萘（TTN）与 5-己基-2-碘噻吩的直接 C-H 芳基化反应制备而成，并通过从二氯甲烷中缓慢蒸发而重结晶。晶体结构显示出 TTN 核心的完全平面几何形状，在单斜空间群 P21/c 中结晶。该结构由下滑的 π 叠层组成，TTN 核心平均平面之间的界面距离为 3.456 (5) Å，比带有 2-hexylthiophene 基团的四噻吩蒽（TTA）同类衍生物的界面距离略大。这两种结构的堆积受结构的芳香核心和烷基侧链的影响很大。
• Improved stability of organic field-effect transistor performance in oligothiophenes including β-isomers
  作者：Minoru Ashizawa、Takuro Niimura、Yan Yu、Kazuma Tsuboi、Hidetoshi Matsumoto、Ryo Yamada、Susumu Kawauchi、Akihiko Tanioka、Takehiko Mori

  DOI：10.1016/j.tet.2012.02.004

  日期：2012.4

  Dialkyl quarter-and quinquethiophenes end-capped with beta-connected thiophenes are prepared, and the field-effect transistor (FET) properties are investigated. Molecular orbital calculation as well as the redox and optical measurements indicate that the beta-isomers have low-lying HOMO levels and large energy gaps compared with the alpha-isomers. Molecular packing of the dihexylquaterthiophene with beta-isomers consists of a typical herringbone motif analogous to the alpha-isomers. In the single crystal, the alkyl chains are extending in the tilted directions from the core molecular plane, but straightly extending in the thin films, resulting in even more perpendicular molecular arrangement to the substrate than the alpha-isomers. These beta-isomers show p-type FET performance comparable to the corresponding alpha-isomers, whereas all new oligothiophenes show air stability better than the corresponding alpha-isomers. In particular, dihexylquinquethiophene with beta-isomers has shown significantly improved air stability maintained over 270 days. This stabilization effect is ascribed to the low-lying HOMO level and the dense packing realized by perpendicular molecular arrangement. (C) 2012 Elsevier Ltd. All rights reserved.
• NEAR-INFRARED TERNARY TANDEM SOLAR CELLS
  申请人：The Regents of the University of Michigan

  公开号：US20210320270A1

  公开（公告）日：2021-10-14

  A photovoltaic cell comprises an anode, a cathode, a first subcell positioned between the anode and the cathode, the first subcell comprising a first donor material and a first acceptor material, and a second subcell positioned between the first subcell and the cathode, the second subcell comprising a second donor material and a second acceptor material. A method of fabricating a photovoltaic cell is also described.