2,5-dioctylbenzo[1,2-b:3,4-b':5,6-b"]trithiophene | 1227939-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,5-dioctylbenzo[1,2-b:3,4-b':5,6-b"]trithiophene
• 英文别名: 4,9-Dioctyl-3,8,13-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1(12),2(6),4,7(11),9,14-hexaene
• CAS: 1227939-54-9
• 化学式: C₂₈H₃₈S₃
• 分子量: 470.808
• InChiKey: SAOKSPAHPNDLFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dioctylbenzo[1,2-b:3,4-b':5,6-b"]trithiophene 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 8'-bromo-5,5"8,8"-tetraoctyl-2,2':5',2"-terbenzo[1,2-b:3,4-b':5,6-b"]trithiophene
  参考文献：
  名称：

  Synthesis and Characterization of Benzo[1,2-b:3,4-b′:5,6-b′′]trithiophene (BTT) Oligomers

  摘要：

  Two dimers (2, and 3), dendritic tetramer (4), hexamer (5), and decamer (6) of benzo[1,2-b:3,4-b':5,6-b '']trithiophene (BTT), a potential pi-core unit with C-3h symmetry, were synthesized, characterized, and evaluated for possible use as organic semiconductors. Single crystal X-ray analyses of the dimers (2 and 3) revealed that they have planar molecular structures with dihedral angles of almost 180 degrees between two BTT units. In accordance with the rigid and planar molecular structure, the unsubstituted dimer (2) is poorly soluble, whereas the octyl-substituted dimer (3) has improved solubility. Although the solubility of the dendritic tetramer (4) is decreased, further extended systems, i.e., the dendritic hexamer (5) and decamer (6), have solubilities better than that of 4. With increasing numbers of BTT units in the molecule, the experimentally determined energy levels of HOMO shift upward slightly and the HOMO-LUMO energy gaps become smaller, but the extent of HOMO destabilization and reduction of the HOMO-LUMO gap are not significant. Taking into account the energy levels of the frontier orbitals, 3-6 could be useful as p-channel organic semiconductors rather than n-channel. In fact, the spin-coated thin film of 3 with edge-on molecular orientation acted as an active channel of field-effect transistors that showed hole mobilities as high as 0.14 cm(2) V-1 s(-1), indicating that the BTT core is a useful pi-conjugated system for application to organic semiconductors, although 4-6 gave FET characteristics rather inferior to those of 3, owing to their amorphous nature in the thin film state.

  DOI：

  10.1021/jo2005044
• 作为产物：
  描述：

  1,3,5-三氯苯 在 copper(l) iodide 、 四(三苯基膦)钯 正丁基锂 、 sodiumsulfide nonahydrate 、 硫酸 、 碘 、 二异丙胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 为溶剂， 反应 187.0h， 生成 2,5-dioctylbenzo[1,2-b:3,4-b':5,6-b"]trithiophene 、 2,5,8-trioctylbenzo[1,2-b:3,4-b':5,6-b"]trithiophene 、 4-Octyl-3,8,13-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,14-hexaene
  参考文献：
  名称：

  NOVEL HETEROCYCLIC COMPOUND AND USE THEREOF

  摘要：

  公开号：

  EP2361915B1

文献信息

• Novel Heterocyclic Compound And Use Thereof
  申请人：Kuwabara Hirokazu

  公开号：US20110204295A1

  公开（公告）日：2011-08-25

  Disclosed are a heterocyclic compound characterized by being represented by formula (1), and a composition of the compound. Also disclosed is an organic electronic device using the compound. (In formula (1), X 1 , X 2 and X 3 each independently represents a sulfur atom or a selenium atom; and R 1 -R 6 each independently represents an aromatic hydrocarbon group, an aliphatic hydrocarbon group, a halogen atom, a hydroxyl group, an alkoxyl group, a mercapto group, an alkylthio group, a boronic acid group, a nitro group, a substituted amino group, an amide group, an acyl group, a carboxyl group, an acyloxy group, a cyano group, a sulfo group, a sulfamoyl group, an alkylsulfamoyl group, a carbamoyl group, an alkylcarbamoyl group or a hydrogen atom, provided that all the R 1 -R 6 are not hydrogen atoms at the same time.) The compound represented by formula (1) is suitable for use in an organic electronic device such as an organic EL element, an organic transistor element and a liquid crystal element.

  本发明涉及一种由公式（1）表示的杂环化合物，以及该化合物的组合物。还公开了使用该化合物的有机电子器件。（在公式（1）中，X1、X2和X3分别独立地表示硫原子或硒原子；R1-R6分别独立地表示芳香族碳氢基团、脂肪族碳氢基团、卤素原子、羟基、烷氧基、巯基、烷硫基、硼酸基、硝基、取代氨基、酰胺基、酰基、羧基、酰氧基、氰基、磺酰基、磺酰胺基、烷基磺酰胺基、氨基甲酰基、烷基氨甲酰基或氢原子，前提是所有R1-R6不同时为氢原子。）公式（1）表示的化合物适用于有机电子器件，如有机EL元件、有机晶体管元件和液晶元件。
• US8313671B2
  申请人：——

  公开号：US8313671B2

  公开（公告）日：2012-11-20
• NOVEL HETEROCYCLIC COMPOUND AND USE THEREOF
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP2361915B1

  公开（公告）日：2015-01-28
• Synthesis and Characterization of Benzo[1,2-<i>b</i>:3,4-<i>b′</i>:5,6-<i>b′′</i>]trithiophene (BTT) Oligomers
  作者：Tomoya Kashiki、Masahiro Kohara、Itaru Osaka、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1021/jo2005044

  日期：2011.5.20

  Two dimers (2, and 3), dendritic tetramer (4), hexamer (5), and decamer (6) of benzo[1,2-b:3,4-b':5,6-b '']trithiophene (BTT), a potential pi-core unit with C-3h symmetry, were synthesized, characterized, and evaluated for possible use as organic semiconductors. Single crystal X-ray analyses of the dimers (2 and 3) revealed that they have planar molecular structures with dihedral angles of almost 180 degrees between two BTT units. In accordance with the rigid and planar molecular structure, the unsubstituted dimer (2) is poorly soluble, whereas the octyl-substituted dimer (3) has improved solubility. Although the solubility of the dendritic tetramer (4) is decreased, further extended systems, i.e., the dendritic hexamer (5) and decamer (6), have solubilities better than that of 4. With increasing numbers of BTT units in the molecule, the experimentally determined energy levels of HOMO shift upward slightly and the HOMO-LUMO energy gaps become smaller, but the extent of HOMO destabilization and reduction of the HOMO-LUMO gap are not significant. Taking into account the energy levels of the frontier orbitals, 3-6 could be useful as p-channel organic semiconductors rather than n-channel. In fact, the spin-coated thin film of 3 with edge-on molecular orientation acted as an active channel of field-effect transistors that showed hole mobilities as high as 0.14 cm(2) V-1 s(-1), indicating that the BTT core is a useful pi-conjugated system for application to organic semiconductors, although 4-6 gave FET characteristics rather inferior to those of 3, owing to their amorphous nature in the thin film state.