5-bromo-3,3''-dihexyl-2,2':5',2''-terthiophene | 155143-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-bromo-3,3''-dihexyl-2,2':5',2''-terthiophene
• 英文别名: 5-bromo-3-hexyl-2-[5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 155143-83-2
• 化学式: C₂₄H₃₁BrS₃
• 分子量: 495.612
• InChiKey: KXSMQGGZQIUWSY-UHFFFAOYSA-N

物化性质

• 沸点：
  544.5±50.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.21
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromo-3,3''-dihexyl-2,2':5',2''-terthiophene 在 正丁基锂 、 四丁基溴化铵 、 potassium acetate 、 palladium diacetate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Oxidation States of Unsymmetrically Substituted Quaterthiophenes with Two Terminal Ferrocenyl Groups

  摘要：

  制备出了具有两个末端二茂铁基团的不对称取代四联噻吩长π共轭体系。通过取代甲氧基和己基，引入了 π 共轭体系化学结构的各向异性。通过电化学和光谱研究，评估了二茂铁基四噻吩的氧化态以及两个末端之间的相互作用。由于四联噻吩的不对称，被两个甲氧基和一个己基充分取代的二茂铁基四联噻吩的单电子氧化发生在一个指定的二茂铁分子上。单电子氧化物延伸到四联噻吩分子中，并明显与另一个二茂铁末端分子发生作用。

  DOI：

  10.1246/bcsj.20100201
• 作为产物：
  描述：

  2-溴-3-己基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 5-bromo-3,3''-dihexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  具有19％PCE的钙钛矿型太阳能电池的面向面取向的无掺杂剂空穴传输材料的分子工程†

  摘要：

  通过明智的分子工程，系统地设计，合成和表征了新型无掺杂星形D–π–A型空穴传输材料，其编码为KR355，KR321和KR353。已经发现KR321在钙钛矿薄膜上形成了一个特定的面朝上的组织，这有利于垂直电荷载流子的传输，并且我们首次证明了这种特殊的分子堆叠功能与混合钙钛矿组合使用时可导致功率转换效率超过19％（ FAPbI 3）0.85（MAPbBr 3）0.15。使用没有任何化学添加剂或掺杂的原始空穴传输层获得的19％的效率是最高的，这证明了平面施主核，π间隔基和外围受体的分子工程学导致了高迁移率，并且该设计提供了对以下方面的有用见解用于钙钛矿太阳能电池和光电应用的下一代HTM的合成。

  DOI：

  10.1039/c7ta01718a

文献信息

• Effect of the π-linker on the performance of organic photovoltaic devices based on push–pull D–π–A molecules
  作者：Hong Chul Lim、Jang-Joo Kim、Jyongsik Jang、Jong-In Hong

  DOI：10.1039/c8nj00915e

  日期：——

  Two push–pull D–π–A molecules, 3T and DTT as donor materials, were synthesized and characterized for solution-processed bulk heterojunction (BHJ) organic photovoltaic (OPV) devices. The π-linker plays a vital role not only in electrochemical and thermal properties but also affects the thin film morphology of 3T and DTT. 3T showed the high electrochemical stability with a faster electrode reaction rate

  合成了两个推挽式D–π–A分子，即3T和DTT作为供体材料，并对其进行了固溶异质结（BHJ）有机光伏（OPV）器件的表征。π-连接基不仅在电化学和热学性质方面起着至关重要的作用，而且还影响3T和DTT的薄膜形态。3T表现出较高的电化学稳定性，电极反应速度更快。基于3T的固溶处理的OPV器件比基于DTT的器件具有更高的功率转换效率，因为它具有出色的电化学性能。
• Oxidation of Ferrocenyl End-Substituted Oligothiophenes
  作者：Masa-aki Sato、Mune-aki Sakamoto、Shin-ichiro Kashiwagi、Tomohiro Suzuki、Masao Hiroi

  DOI：10.1246/bcsj.74.1737

  日期：2001.9

  A ferrocenyl end-substituted terthiophenes derivative and a sexithiophene derivative were prepared as model compounds for a molecular wire. Electrochemical measurements and absorption spectroscopy were performed to elucidate the oxidation process and the oxidized states of those model compounds. The first oxidation of the model compounds took place in the ferrocene moieties (terminals). The resultant oxidized species in the ferrocene moieties seeped into the oligothiophene moieties (wires) and spread over two or three thiophene rings. Further oxidation of the ferrocenyl-terthiophene derivative did not occur, whereas that of the ferrocenyl-sexithiophene derivative produced an oxidized species, such as a cation radical in the sexithiophene moiety.

  制备了一种二茂铁端取代的噻吩衍生物和一种噻吩衍生物，作为分子金属丝的模型化合物。为阐明这些模型化合物的氧化过程和氧化态，进行了电化学测量和吸收光谱分析。模型化合物的第一次氧化发生在二茂铁分子（终端）中。二茂铁分子中的氧化物渗入低聚噻吩分子（线），并扩散到两个或三个噻吩环上。二茂铁基-三噻吩衍生物不会发生进一步氧化，而二茂铁基-四噻吩衍生物则会产生氧化物，例如噻吩分子中的阳离子自由基。
• Symmetrical alkyl-substituted oligothiophenes as ligands: complexation of the [(η-C5H5)Ru]+ moiety by hexyl-substituted ter-, quater- and quinque-thiophenes
  作者：Christopher L. Jones、Simon J. Higgins

  DOI：10.1039/a809623f

  日期：——

  The soluble, symmetrical oligothiophenes 3,3 "-dihexyl-2,2':5',2 "-terthiophene 7 and 4',3'''-dihexyl-2,2':5',2 ":5",2"':5''', 2""-quinquethiophene 9 and the unsymmetrical oligothiophenes 3'-hexyl-2,2':5',2 "-terthiophene 6 and 3,3 "-dihexyl-2,2':5',2 ":5",2'''-quaterthiophene 11 have been prepared by Kumada-type coupling reactions, using 2-bromothiophene, 2,5-dibromothiophene, 2-bromo-3-hexylthiophene and 2,5-dibromo-3-hexylthiophene as building blocks. Their behaviour as ligands towards the cyclopentadienylruthenium (II) moiety has been examined, by carrying out ligand exchange reactions between [(eta-C5H5)Ru(CH3CN)(3)]PF6 and an excess of the oligothiophene in CH2Cl2, and characterising the product(s) by FAB mass spectrometry and H-1 and C-13H-1} NMR spectroscopy. Upon complexation of a thiophene ring (eta(5)), the thienyl proton resonances of that ring shift upfield, as do the C-13 resonances. With terthiophene 7, in which the outer thiophene rings bear alkyl groups, the product is [(eta-C5H5)Ru(eta-7)]PF6 13, a single regioisomer in which exclusively an outer thiophene ring is complexed by the cyclopentadienylruthenium (II) moiety. With terthiophene 6, however, in which the inner thiophene ring bears an alkyl substituent, a mixture of all three possible regioisomers of [(eta-C5H5)Ru(eta-6)]PF6 12 is obtained. Similarly, with the symmetrical quinquethiophene 9, two regioisomers of the complex [(eta-C5H5)Ru(eta-9)]PF6 14 are obtained, one in which an outer thiophene ring is complexed, and one in which an inner alkylthiophene ring is complexed. With the unsymmetrical quaterthiophene 11, which includes all four types of thiophene ring (inner and outer alkylthiophene, inner and outer unsubstituted thiophene), 93% of the product [(eta-C5H5)Ru(eta-11)]PF6 15 is the regioisomer in which the outer alkylthiophene ring is complexed. These results show that there are two factors controlling the site of complexation, a tendency for the outermost ring to complex and a tendency for an alkylthiophene ring to complex. Where these conflict, a mixture of regioisomers is obtained. The electrochemistry of both the free oligothiophenes and of their Ru(ll) complexes has been compared. On complexation, there is a substantial positive shift in the oxidation potential of the oligothiophene, and a new, irreversible reduction is observed at ca.-1 V. Although polythiophene films could be deposited by electrooxidation of the free oligothiophenes in acetonitrile, electroactive polymer films could not be deposited by electrooxidation of the complexes in dichloromethane.