2-(2-ethylhexylthio)thiophene | 1330786-48-5

• 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-(2-ethylhexylthio)thiophene
• 英文别名: 2-(2-Ethylhexylsulfanyl)thiophene
• CAS: 1330786-48-5
• 化学式: C₁₂H₂₀S₂
• 分子量: 228.423
• InChiKey: SFZKZYTWICUMKY-UHFFFAOYSA-N

物化性质

• 沸点：
  310.2±15.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-(2-ethylhexylthio)thiophene 在 正丁基锂 、 四溴化碳 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 2,6-dibromo-4,8-bis(5-((2-ethylhexyl)thio)thiophen-2-yl)benzo[1,2-b:4,5-b']-dithiophene
  参考文献：
  名称：

  Enhanced Photovoltaic Performance of Asymmetrical Benzo Dithiophene Homopolymer Donor Materials in Nonfullerene Acceptor-Based Organic Photovoltaics

  摘要：

  Although much promising synthetic progress in conjugated polymer-based organic solar cells (OSCs) has resulted in significant improvement in power conversion efficiencies (PCEs) of from over 15 to >19.0% in the last five years, the sophisticated and complex reactions from at least two families’ monomers with remarkably different electron push–pull effects could still pose an unavoidable material burden for the commercialization of OSCs in the coming future. Therefore, the method of preparing a homopolymer from a sole monomer would significantly reduce the synthetic steps and costs in order to pave the way for the large-scale production of OSC materials. Therefore, alkylthio-thiophenyl-substituted benzo[1,2-b;4,5-b′]dithiophene (BDTTS) as the sole and key structural moiety with dihalogen and distannyl functional groups was designed and synthesized, respectively, in this study, for facile monomer syntheses and polymerizations to achieve three wide-bandgap homopolymer donors of BDTTS-alt-BDTT-Cl (P13), BDTTS-alt-BDTT (P15), and BDTTS (P14), respectively. The structural symmetry dependency on their physical, electrochemical, and optical properties, thin-film morphologies, and photovoltaic (PV) performance was investigated in detail. As a result, OSCs based on the asymmetric polymer P15, paired with BTP-eC9 as the electron acceptor, presented the best PV performance, with a PCE of 11.5%, a fill factor (FF) of 65.87%, and a short-circuit current (JSC) of 22.04 mA·cm−2, respectively. This PCE value is among the highest ones reported for BDT-type homopolymer donor-based OPVs, providing us with knowledge for obtaining promising PV performance from devices made of P15-like materials.

  DOI：

  10.3390/molecules29061332
• 作为产物：
  描述：

  噻吩 、 溴代异辛烷 在 正丁基锂 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(2-ethylhexylthio)thiophene
  参考文献：
  名称：

  基于烷硫基噻吩或烷硫基硒基-BDT供体单元和DPP受体单元的DA共聚物的合成和光电性能

  摘要：

  两种新型2D共轭DA共聚物PBDTT-S-DPP和PBDTSe-S-DPP，基于苯并二噻吩（BDT）供体单元，具有烷硫基噻吩或烷硫基硒醚共轭侧链和2,5-双（2-丁基辛基）-3,6-二（噻吩-2-基）吡咯并[3,4-合成了c]吡咯-1,4（2H，5H）-二酮）（DPP）受体单元，用作聚合物太阳能电池（PSC）中的施主材料。通过吸收光谱，循环伏安，热重分析，密度泛函理论的理论计算，X射线衍射和光伏测量对这两种聚合物进行了表征。结果表明，BDT单元上的烷硫基噻吩/硒基侧基和DPP受体单元上的分子内氢键相互作用在影响聚合物的吸收，HOMO能级，分子平面性和结晶度方面起着重要作用。基于以下内容的PSCPBDTT-S-DPP或PBDTSe-S-DPP作为施主，PC 71 BM作为受主，其功率转换效率（PCE）为5.62％和5.01％，相对较高的V oc分别为0.79 V和0.76V。

  DOI：

  10.1016/j.orgel.2016.02.040

文献信息

• Molecular Design and Application of a Photovoltaic Polymer with Improved Optical Properties and Molecular Energy Levels
  作者：Huifeng Yao、Hao Zhang、Long Ye、Wenchao Zhao、Shaoqing Zhang、Jianhui Hou

  DOI：10.1021/acs.macromol.5b00649

  日期：2015.6.9

  (E)-5-(2-(5-(Alkylthio)thiophen-2-yl)vinyl)thiophene-2-yl functional groups were introduced onto 4- and 8-positions of BDT units, and this building block was used to construct a new derivative polymer of PTB7, named as PBT-TVT. Benefiting from the prolonged conjugation of the conjugated side groups on BDT units, the optical absorption property of PBT-TVT can be improved greatly compared to that of PTB7, so an inspiring result of 7.67% was obtained by using PBT-TVT as the donor and PC61BM as the acceptor in polymer solar cells (PSCs), which is much higher than that of the PTB7:PC61BM-based device and also one of the highest results for PSCs with PC61BM. In electrochemical cyclic voltammetry (CV) measurements, PBT-TVT showed a deeper HOMO level than PTB7 so the device based on the former exhibits higher open circuit voltage than the latter. Moreover, in comparison with PTB7, the new polymer PBT-TVT exhibited stronger interchain pi-pi interaction and thus higher hole mobility. Overall, the results in this work indicated that PBT-TVT is a promising donor polymer, and the strategy used in this work will be beneficial for molecular design of polymer photovoltaic materials for large-scale production of PSCs.

  (E)-5-((5-甲基硫代苯乙烯-2-基)丁二烯-2-yl) thiophene-2-yl基团被引入到 BDT 单元的 4- 和 8- 位，作为构建块构建了新的 PTD 型聚合物共聚物 PBT-TVT。借助 BDT 单元上的共轭基团及侧链共轭基团的伸长共轭作用，PBT-TVT 所具有的光学吸收性能较之 PTB7 型，极大地得到了提升。在聚能太阳能电池（PSCs）的实验中，以 PBT-TVT 作为供体，采用 PC61BM 作为接受体，获得了 7.67% 的光电转化效率，较基于 PTB7-PC61BM 型装置明显高于前者，且数值并列目前基于 PC61BM 的聚能太阳能电池中最高之一。再者，在电化学循环伏安特性（CV）测量中，PBT-TVT 的 HOMO 能级较 PTB7 更为深入，因而基于 PBT-TVT 的聚能太阳能电池工作装置的开路电压明显更高；同时，相比 PTB7，PBT-TVT 新聚合物显示出较强的空间链间共轭作用及由此产生的高质子迁移率。综上所述，本研究中所取得的结果表明，PBT-TVT 是有望作为供体聚合物的一种，且本研究采用的方法对于后续分子设计聚能光伏材料生产大尺寸聚能太阳能电池具有很好的指导意义。
• Enhanced open-circuit voltage in methoxyl substituted benzodithiophene-based polymer solar cells
  作者：Xiaonan Xue、Tao Liu、Xiangyi Meng、Xiaobo Sun、Lijun Huo、Wei Ma、Yanming Sun

  DOI：10.1007/s11426-016-0349-7

  日期：2017.2

  The open-circuit voltage (V oc) is one of the important parameters that influence the power conversion efficiency (PCE) of polymer solar cells. Its value is mainly determined by the energy level offset between the highest occupied molecular orbital (HOMO) of the donor and the lowest unoccupied molecular orbital (LUMO) of the acceptor. Therefore, decreasing the HOMO value of the polymer could lead to

  开路电压（V oc）是影响聚合物太阳能电池的功率转换效率（PCE）的重要参数之一。它的值主要由供体的最高占据分子轨道（HOMO）和受体的最低未占据分子轨道（LUMO）之间的能级偏移决定。因此，降低聚合物的HOMO值可导致高V oc，从而提高电池效率。在这里，我们报告了一种通过使用甲氧基取代的苯并二噻吩（BDT）单元降低聚合物HOMO能级的简便方法。具有甲氧基官能团的聚合物（POBDT（S）-T1）的HOMO值为–5.65 eV，比没有甲氧基单元（PBDT（S）-T1）的聚合物的HOMO值（–5.52 eV）还要深。结果，基于POBDT（S）-T1的太阳能电池显示出0.98V的高V oc和9.2％的PCE。相反，基于PBDT（S）-T1的设备显示的相对较低的V oc为0.89 V，中等的PCE为7.4％。结果表明，甲氧基基团参与共轭共聚物可以有效地降低其HOMO能级。
• Sulfonyl: a new application of electron-withdrawing substituent in highly efficient photovoltaic polymer
  作者：Ye Huang、Lijun Huo、Shaoqing Zhang、Xia Guo、Charles C. Han、Yongfang Li、Jianhui Hou

  DOI：10.1039/c1cc12575c

  日期：——

  A strong electron-withdrawing group, sulfonyl, was firstly introduced to a semiconducting polymer, PBDTTT-S. The PCE of the PBDTTT-S device reached 6.22% with a high open-circuit voltage of 0.76 V. The sulfonyl group is thus a promising candidate as a strong electron-withdrawing group applied to high-efficiency PSCs.

  我们首次在半导体聚合物 PBDTTT-S 中引入了强吸电子基团磺酰基。PBDTTT-S 器件的 PCE 达到 6.22%，开路电压高达 0.76 V。
• 一种含硫的取代基取代的二噻吩衍生物及其共轭聚合物的制备方法及应用
  申请人：兰州交通大学

  公开号：CN105367584A

  公开（公告）日：2016-03-02

  本发明公开了一种含硫的取代基取代的二噻吩并[2,3-d:2′,3′-d′]苯并[1,2-b:3,4-b′]二噻吩衍生物及其共轭聚合物以及其制备方法和应用。该含硫的取代基取代的二噻吩并[2,3-d:2′,3′-d′]苯并[1,2-b:3,4-b′]二噻吩衍生物的化学结构如结构式Ⅰ所示；基于该衍生物的共轭聚合物的化学结构如结构式Ⅱ所示。本发明公开的衍生物以及其共轭聚合物具有良好的光电活性，可用于设计高效的薄膜场效应晶体管(TFT)及聚合物光伏器件，具有良好的市场应用前景。
• Synergistic effect of side-chain and backbone engineering in thieno[2,3-<i>f</i>]benzofuran-based conjugated polymers for high performance non-fullerene organic solar cells
  作者：Keke Dou、Xunchang Wang、Zurong Du、Huanxiang Jiang、Feng Li、Mingliang Sun、Renqiang Yang

  DOI：10.1039/c8ta07544a

  日期：——

  A series of copolymers containing thieno[2,3-f]benzofuran unit with different alkyl side chains are synthesized. The best photovoltaic performance with power conversion efficiency over 11% have been realized.

  一系列含有不同烷基侧链的噻吩[2,3-f]苯并呋喃单元的共聚物被合成。实现了功率转换效率超过11%的最佳光伏性能。