2,6-二溴-4,8-​​双-（2-乙基己氧基）苯并[1,2-b;4,5-b']二噻吩 | 215591-73-4

• 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
• 中文名称: 2,6-二溴-4,8-​​双-（2-乙基己氧基）苯并[1,2-b;4,5-b']二噻吩
• 中文别名: 5,5''-二溴-3,3''-二己基-2,2':5',2''-三联噻吩；4,5-B']二噻吩
• 英文名称: 5,5''-dibromo-3,3''-dihexyl-2,2':5',2''-terthiophene
• 英文别名: 5-bromo-2-[5-(5-bromo-3-hexylthiophen-2-yl)thiophen-2-yl]-3-hexylthiophene
• CAS: 215591-73-4
• 化学式: C₂₄H₃₀Br₂S₃
• 分子量: 574.508
• InChiKey: BDRBPSFUGHNLCG-UHFFFAOYSA-N

物化性质

• 沸点：
  568.8±50.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,6-二溴-4,8-​​双-（2-乙基己氧基）苯并[1,2-b;4,5-b']二噻吩 以2%的产率得到
  参考文献：
  名称：

  Sato Masa-aki, Hiroi Masao, Chem. Lett, (1994) N 6, S 985-988

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3''-二己基-2,2'：5'，2''-对噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以92%的产率得到2,6-二溴-4,8-​​双-（2-乙基己氧基）苯并[1,2-b;4,5-b']二噻吩
  参考文献：
  名称：

  可溶性低带隙低聚噻吩-[all] -S，S-二氧化物基共轭低聚物和聚合物的合成与表征

  摘要：

  可溶性oligothiophene-的一个新家族的合成和表征小号，小号-dioxides以及它们作为积木形成polythiophene-使用小号，小号通过微波辅助Stille偶联聚合描述-dioxides。将砜基团并入聚噻吩主链中会导致聚合物带隙变窄，同时聚噻吩S，S和相对于聚噻吩，二氧化物的含量更低，这种趋势对于最低的未占据分子轨道要比最高的占据分子轨道强得多，从而导致更大的电子接受能力。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年

  DOI：

  10.1002/pola.24641

文献信息

• 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。
• Preparation of Long Alkyl-substituted Oligothiophenes
  作者：Masa-aki Sato、Masao Hiroi

  DOI：10.1246/cl.1994.985

  日期：1994.6

  New hexyl-substituted oligothiophenes (sexi-, novi-, duodeci-, and quindeci-thiophenes) were prepared by a Ni(O)-catalyzed coupling reaction of a 5,5″-dibromo-3,3″-dihexyl-2,2′:5′,2″-terthiophene. The structures were determined by 1H NMR spectra, GPC data, and elemental analyses. Their π–π* transitions were compared with those of poly(alkylthiophenes).

  通过 Ni(O) 催化的 5,5″-二溴-3,3″-二己基-2,2′:5′,2″-四噻吩的偶联反应，制备了新的己基取代的低聚噻吩（semi-、novi-、duodeci 和 quindeci-噻吩）。这些化合物的结构是通过 1H NMR 光谱、GPC 数据和元素分析确定的。将它们的 π-π* 转变与聚（烷基噻吩）的π-π* 转变进行了比较。
• Self-assembled nanostructures of a series of linear oligothiophene derivatives adsorbed on surfaces
  作者：Xuan Peng、Ting Meng、Lilei Wang、Linxiu Cheng、Wenchao Zhai、Ke Deng、Chang-Qi Ma、Qingdao Zeng

  DOI：10.1016/j.cclet.2022.05.082

  日期：2023.2

  have shown that the molecular structures of oligothiophene derivatives including molecular skeleton and alkyl chains have a significant effect on their self-assemblies on the surface. In this work, a series of linear oligothiophene derivatives (DCV-nT-Hex, n = 3∼11) modified with terminal dicyanovinyls and alkyl chains were adopted to further investigate the different assembly behaviors at liquid-solid

  许多先前的研究表明，包括分子骨架和烷基链在内的低聚噻吩衍生物的分子结构对其在表面的自组装具有显着影响。在这项工作中，采用了一系列用末端二氰基乙烯基和烷基链修饰的线性低聚噻吩衍生物（DCV- n T-Hex，n  = 3∼11），通过扫描隧道显微镜进一步研究了液-固界面的不同组装行为（ ST）。有趣的是，通过氢键和范德瓦尔斯相互作用，DCV-3T-Hex 形成锯齿形和花状结构，而 DCV- n T-Hex ( n = 4∼11)形成层状结构。密度泛函理论 (DFT) 计算表明，对于 DCV- n T-Hex 的最有利配置，烷基链的不同分布影响分子间相互作用，并最终导致不同的组装结构。与 DCV- n T-Hex 的其他结构 ( n  = 4∼11)相比，DCV-3T-Hex 的锯齿形和花形结构具有优先的热力学稳定性。此外，偶数 ( n = 4, 6, 8, 10) 的 DCV- n T-Hex
• 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.
• Sato Masa-aki, Hiroi Masao, Synth. Metals, 71 (1995) N 1-3, S 2085-2086
  作者：Sato Masa-aki, Hiroi Masao

  DOI：——

  日期：——