2,5-dibromo-3,4-didodecylthiophene | 174509-52-5

• 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: 2,5-dibromo-3,4-didodecylthiophene
• CAS: 174509-52-5
• 化学式: C₂₈H₅₀Br₂S
• 分子量: 578.579
• InChiKey: PTICDQBEEXSPMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  31
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  2,5-dibromo-3,4-didodecylthiophene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到2,5-dibromo-3,4-didodecylthiophene-1,1-dioxide
  参考文献：
  名称：

  3,4-Ethylenedioxy-substituted bithiophene-alt-thiophene-S,S-dioxide regular copolymers. Synthesis and conductive, magnetic and luminescence properties.

  摘要：

  通过阳极偶联不同的3,4-乙二氧基取代的2,5-双(2-噻吩基)噻吩-S,S-二氧化物制备了聚共轭常规联噻吩-替代噻吩-S,S-二氧化物共聚物。通过循环伏安法、FTIR反射吸收和紫外可见光谱、MALDI-TOF质谱、电化学石英晶体微天平、原位ESR和原位电导率技术、光致发光和电致发光测量对聚合物进行了表征。聚合物链中由亚乙基二氧基和S,S-二氧化物部分控制的富电子和贫电子噻吩环的规则交替产生了有限的电导率窗口。噻吩-S,S-二氧化物环的β-位置的烷基保护产生低缺陷且可溶的低聚物，并在单层有机发光器件（OLED）中进行了研究。光致发光量子效率约为在亮度为 100 cd m−2 时获得了 1% 和 0.01% 光子/电子的外部电致发光量子效率。

  DOI：

  10.1039/b206669f
• 作为产物：
  描述：

  3,4-didodecylthiophene 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以78%的产率得到2,5-dibromo-3,4-didodecylthiophene
  参考文献：
  名称：

  3,4-Disubstituted Polyalkylthiophenes for High-Performance Thin-Film Transistors and Photovoltaics

  摘要：

  We demonstrate that poly(3,4-dialkylterthiophenes) (P34ATs) have comparable transistor mobilities (0.17 cm(2) V-1 s(-1)) and greater environmental stability (less degradation of on/off ratio) than regioregular poly(3-alkylthiophenes) (P3ATs). Unlike poly(3-hexylthiophene) (P3HT), P34ATs do not show a strong and distinct pi-pi stacking in X-ray diffraction. This suggests that a strong pi-pi stacking is not always necessary for high charge-carrier mobility and that other potential polymer packing motifs in addition to the edge-on structure (pi-pi stacking direction parallel to the substrate) can lead to a high carrier mobility. The high charge-carrier mobilities of the hexyl and octyl-substituted P34AT produce power conversion efficiencies of 4.2% in polymer:fullerene bulk heterojunction photovoltaic devices. An enhanced open-circuit voltage (0.716-0.771 eV) in P34AT solar cells relative to P3HT due to increased ionization potentials was observed.

  DOI：

  10.1021/ja207429s

文献信息

• SEMICONDUCTOR MATERIALS PREPARED FROM DITHIENYLVINYLENE COPOLYMERS
  申请人：Mishra Ashok Kumar

  公开号：US20120217482A1

  公开（公告）日：2012-08-30

  Disclosed are new semiconductor materials prepared from dithienylvinylene copolymers with aromatic or heteroaromatic π-conjugated systems. Such copolymers, with little or no post-deposition heat treatment, can exhibit high charge carrier mobility and/or good current modulation characteristics. In addition, the polymers of the present teachings can possess certain processing advantages such as improved solution-processability and low annealing temperature.

  本发明揭示了由含芳香或杂芳香π-共轭系统的二噻吩乙烯共聚物制备的新型半导体材料。这种共聚物在很少或没有沉积后热处理的情况下，可以表现出高载流子迁移率和/或良好的电流调制特性。此外，本发明所述的聚合物还具有某些加工优点，如改善的溶液加工性和低退火温度。
• Synthesis and Characterization of Pentathiophene Based Copolymer for Organic Thin Film Transistor
  作者：Jonggwang Park、Jin-Uk Ju、Ran Kim、Jaeyoung Hwang、Jong-Man Park、Yun-Hi Kim

  DOI：10.1166/jnn.2014.8804

  日期：2014.8.1

  The new dialkylated pentathiophene based copolymer was synthesized by Suzuki coupling reaction. The PD5TADF is synthesized and used as an active material for organic thin film transistor (OTFTs). The copolymer has good solubility in common organic solvent such as toluene, tetrahydrofuran (THF), chloroform, chlorobenzene and dichlorobenzene. The number average molecular weight (Mn ) was measured to be 148,000. The TGA curve shows that the polymers exhibit good thermal stability with a weight loss of less than 5% upon heating to 419 °C with glass temperature at 184.9 °C. The ultraviolet (UV) maximum of the polymer was found at 494 nm in solution and 498 nm in the film. A thin-film transistor with PD5TADF was found to exhibit typical p-channel FET characteristics with a hole mobility of 2.6×10−4 cm2/Vs and an on/off ratio of 3.04×104 with a threshold voltage of −4.5 V.

  新的二烷基化五苯并呋喃共聚物通过铃木偶联反应合成。PD5TADF合成后用作有机薄膜晶体管（OTFT）的活性材料。该共聚物在常见的有机溶剂中具有良好的溶解性，如甲苯、四氢呋喃（THF）、氯仿、氯苯和二氯苯。数均分子量（Mn）测得为148,000。TGA曲线显示，聚合物具有良好的热稳定性，在玻璃温度为184.9°C时，加热至419°C时重量损失小于5%。聚合物的紫外（UV）最大值在溶液中为494 nm，在薄膜中为498 nm。用PD5TADF制成的薄膜晶体管表现出典型的p沟道FET特性，空穴迁移率为2.6×10−4 cm2/Vs，导通/关断比为3.04×104，阈值电压为−4.5 V。
• Semiconductor materials prepared from dithienylvinylene copolymers
  申请人：BASF SE

  公开号：EP2626375A1

  公开（公告）日：2013-08-14

  Disclosed are new semiconductor materials prepared from dithienylvinylene copolymers with aromatic or heteroaromatic π-conjugated systems. Such copolymers, with little or no post-deposition heat treatment, can exhibit high charge carrier mobility and/or good current modulation characteristics. In addition, the polymers of the present teachings can possess certain processing advantages such as improved solution-processability and low annealing temperature.

  所公开的是由具有芳香族或杂芳族 π 共轭体系的二噻吩乙烯共聚物制备的新型半导体材料。这种共聚物几乎不需要沉积后热处理，就能表现出高电荷载流子迁移率和/或良好的电流调制特性。此外，本发明的聚合物还具有某些加工优势，如改善的溶液加工性和较低的退火温度。
• Molecular compositions, materials, and methods for efficient multiple exciton generation
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US10636974B2

  公开（公告）日：2020-04-28

  Embodiments of the present invention provides compounds, compositions, and methods for their preparation that provide efficient intramolecular fission, such that local order and strong nearest neighbor coupling is no longer a design constraint. Inventive materials include organic oligomers and polymers designed to exhibit strong intrachain donor-acceptor interactions and provide intramolecular singlet fission, whereby triplet populations can be generated in very high yields of, e.g., 170% or more. The inventive disclosure is directed to polymers of the general formula: [SA-SD]n with a strong electron acceptor (SA), a strong electron donor (SD), and n a positive integer equal to or greater than two; methods for their preparation and monomers used therein, blends, mixtures and formulations containing them; the use of the polymers, blends, mixtures and formulations as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.

  本发明的实施方案提供了可提供高效分子内裂变的化合物、组合物及其制备方法，从而使局部有序和强近邻耦合不再是设计上的限制因素。本发明的材料包括有机低聚物和聚合物，其设计旨在表现出强链内供体-受体相互作用，并提供分子内单子裂变，从而以极高的产率（例如 170% 或更高）产生三重子群。本发明公开了通式聚合物：[SA-SD]n，其中有一个强电子受体（SA），一个强电子供体（SD），n 为等于或大于二的正整数；其制备方法和其中使用的单体，含有它们的共混物、混合物和制剂；这些聚合物、共混物、混合物和制剂在有机电子（OE）器件中作为半导体的用途，特别是在有机光伏（OPV）器件中的用途，以及包含这些聚合物、共混物、混合物或制剂的 OE 和 OPV 器件。
• 3,4-Disubstituted Polyalkylthiophenes for High-Performance Thin-Film Transistors and Photovoltaics
  作者：Sangwon Ko、Eric Verploegen、Sanghyun Hong、Rajib Mondal、Eric T. Hoke、Michael F. Toney、Michael D. McGehee、Zhenan Bao

  DOI：10.1021/ja207429s

  日期：2011.10.26

  We demonstrate that poly(3,4-dialkylterthiophenes) (P34ATs) have comparable transistor mobilities (0.17 cm(2) V-1 s(-1)) and greater environmental stability (less degradation of on/off ratio) than regioregular poly(3-alkylthiophenes) (P3ATs). Unlike poly(3-hexylthiophene) (P3HT), P34ATs do not show a strong and distinct pi-pi stacking in X-ray diffraction. This suggests that a strong pi-pi stacking is not always necessary for high charge-carrier mobility and that other potential polymer packing motifs in addition to the edge-on structure (pi-pi stacking direction parallel to the substrate) can lead to a high carrier mobility. The high charge-carrier mobilities of the hexyl and octyl-substituted P34AT produce power conversion efficiencies of 4.2% in polymer:fullerene bulk heterojunction photovoltaic devices. An enhanced open-circuit voltage (0.716-0.771 eV) in P34AT solar cells relative to P3HT due to increased ionization potentials was observed.