8'-bromo-5,5"8,8"-tetraoctyl-2,2':5',2"-terbenzo[1,2-b:3,4-b':5,6-b"]trithiophene | 1260140-93-9

• 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: 8'-bromo-5,5"8,8"-tetraoctyl-2,2':5',2"-terbenzo[1,2-b:3,4-b':5,6-b"]trithiophene
• 英文别名: 4-Bromo-9,14-bis(9,14-dioctyl-3,8,13-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,14-hexaen-4-yl)-3,8,13-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,14-hexaene
• CAS: 1260140-93-9
• 化学式: C₆₈H₇₇BrS₉
• 分子量: 1262.86
• InChiKey: RICOSYLDZQXKCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  31.1
• 重原子数：
  78
• 可旋转键数：
  30
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  254
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8'-bromo-5,5"8,8"-tetraoctyl-2,2':5',2"-terbenzo[1,2-b:3,4-b':5,6-b"]trithiophene 、 trimethyl(5,5",8,8"-tetraoctyl[2,2':5',2"-terbenzo[1,2-b:3,4-b':5,6-b"]trithiophen]-8'-yl)stannane 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以67%的产率得到2,2'-bis{5,8-bis(5",8"-dioctylbenzo[1,2-b:3,4-b':5,6-b"]trithiophen-2"-yl)}benzo[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：

  苯并[1,2-b:3,4-b':5,6-b'']三噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 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

文献信息

• 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.