5'-Bromo-5-propyl-[2,2']bithiophenyl | 867171-04-8

• 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-5-propyl-[2,2']bithiophenyl
• 英文别名: 5-Bromo-5'-propyl-2,2'-bithiophene；2-bromo-5-(5-propylthiophen-2-yl)thiophene
• CAS: 867171-04-8
• 化学式: C₁₁H₁₁BrS₂
• 分子量: 287.244
• InChiKey: WBAKUKCZSKYMKD-UHFFFAOYSA-N

物化性质

• 沸点：
  319.1±37.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5'-Bromo-5-propyl-[2,2']bithiophenyl 在 正丁基锂 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 5-Propyl-[2,2';5',2'';5'',2''']quaterthiophene
  参考文献：
  名称：

  High Carrier Mobility up to 0.1 cm²/Vs and a Wide Mesomorphic Temperature Range of Alkynyl-Substituted Terthiophene and Quaterthiophene Derivatives

  摘要：

  Smectic semiconductors with high carrier mobility were designed and synthesized. The hole mobility of 3-TTP-yne-4 and 3-QTP-yne-3 at room temperature was 0.06 cm(2)/Vs and 0.1 cm(2)/Vs, respectively. They exhibit highly ordered smectic phases around room temperature, with softness to some extent, which make it possible homogeneous film with low defect density. Intermolecular distance in the smectic phase of 3-QTP-yne-4 is almost same as that of 3-TTP-yne-4. In this material, larger pi-conjugate system results in higher carrier mobility.

  DOI：

  10.1080/15421400590954722
• 作为产物：
  描述：

  5-Propyl-[2,2']bithiophenyl 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 生成 5'-Bromo-5-propyl-[2,2']bithiophenyl
  参考文献：
  名称：

  Mesomorphic behaviors and charge carrier transport in terthiophene derivatives

  摘要：

  We synthesized dialkylterthiophene derivatives omega-substituted with cyclohexylethyl moiety, which exhibit smectic mesophases at room temperature, and investigated their charge carrier transport properties. In particular, transpentylcyclohexylethyl-propylterthiophene (3-TTP-C2CH-5) held SmB phase at room temperature. Furthermore, a 3:1 mixture of 3-TTP-C2CH-5 and (2-methylbutyl)-dodecylterthiophene (5*-TTP-12) showed the SmB phase between 101degreesC and -15degreesC, and the highly ordered smectic phase below -15degreesC. In the SmB phase of the mixture, hole and electron mobility was 10(-3) cm(2)/Vs, and independent of temperature and electric field over room temperature. However, below room temperature, the mobility depended on both temperature and electric field, as is often observed in organic amorphous solids and formarized by Gaussian disorder model, suggesting that the carrier transport in the smectic mesophase can be explained by the hopping conduction in disordered molecular sites.

  DOI：

  10.1080/15421400490434315
• 作为试剂：
  描述：

  5-Propyl-[2,2']bithiophenyl 、 N-溴代丁二酰亚胺(NBS) 、 disodium;carbonate 在 四氢呋喃 、 乙醚 、 水 、 Sodium sulfate-III 、 silica gel 、 5'-Bromo-5-propyl-[2,2']bithiophenyl 作用下， 反应 12.0h， 生成 5'-Bromo-5-propyl-[2,2']bithiophenyl
  参考文献：
  名称：

  Organic semiconductor material, organic semiconductor structure, and organic semiconductor device

  摘要：

  本发明的目的是提供一种有机半导体材料，能够在包括常温在内的广泛温度范围内表现出液晶相，并表现出高电荷载流子迁移率，以及由该有机半导体材料形成的有机半导体结构和有机半导体器件。为达到上述目的，本发明提供了一种有机半导体材料，其包括在下列化学式1中所示的四噻吩骨架，其中化学式1中的R1是C1到C20的烷基或氢，而R2是C1到C20的烷基或氢。

  公开号：

  US20060076554A1

文献信息

• Mesomorphic behaviors and charge carrier transport in terthiophene derivatives
  作者：Masahiro Funahashi、Jun-Ichi Hanna

  DOI：10.1080/15421400490434315

  日期：2004.1

  We synthesized dialkylterthiophene derivatives omega-substituted with cyclohexylethyl moiety, which exhibit smectic mesophases at room temperature, and investigated their charge carrier transport properties. In particular, transpentylcyclohexylethyl-propylterthiophene (3-TTP-C2CH-5) held SmB phase at room temperature. Furthermore, a 3:1 mixture of 3-TTP-C2CH-5 and (2-methylbutyl)-dodecylterthiophene (5*-TTP-12) showed the SmB phase between 101degreesC and -15degreesC, and the highly ordered smectic phase below -15degreesC. In the SmB phase of the mixture, hole and electron mobility was 10(-3) cm(2)/Vs, and independent of temperature and electric field over room temperature. However, below room temperature, the mobility depended on both temperature and electric field, as is often observed in organic amorphous solids and formarized by Gaussian disorder model, suggesting that the carrier transport in the smectic mesophase can be explained by the hopping conduction in disordered molecular sites.
• US7405003B2
  申请人：——

  公开号：US7405003B2

  公开（公告）日：2008-07-29
• High Carrier Mobility up to 0.1 cm²/Vs and a Wide Mesomorphic Temperature Range of Alkynyl-Substituted Terthiophene and Quaterthiophene Derivatives
  作者：Masahiro Funahashi、Jun-ichi Hanna

  DOI：10.1080/15421400590954722

  日期：2005.6

  Smectic semiconductors with high carrier mobility were designed and synthesized. The hole mobility of 3-TTP-yne-4 and 3-QTP-yne-3 at room temperature was 0.06 cm(2)/Vs and 0.1 cm(2)/Vs, respectively. They exhibit highly ordered smectic phases around room temperature, with softness to some extent, which make it possible homogeneous film with low defect density. Intermolecular distance in the smectic phase of 3-QTP-yne-4 is almost same as that of 3-TTP-yne-4. In this material, larger pi-conjugate system results in higher carrier mobility.
• Organic Semiconductors with Helical Structure Based on Oligothiophene derivatives Exhibiting Chiral Nematic Phase
  作者：Masahiro Funahashi、Nobuyuki Tamaoki

  DOI：10.1080/15421400701735723

  日期：2007.12.13

  We have synthesized 2-[5-(4-[(S)-2-methylbutoxy]phenyl)-3-methyl]-2'''-propyl-2: 5'-2'-5 ''-2 ''-5"'-quaterthiophene (10), a liquid crystalline semiconductor that exhibits a chiral nematic phase, and used the time-of-flight technique to determine its carrier mobility behavior. In the chiral nematic phase, the positive carrier mobility was 2 x 10(-4)cm(2)/Vs at 120 degrees C and the negative carrier mobility was 1 x 10-4 cm(2)/Vs, both of which we attribute to electronic processes. For the negative carrier, in addition to the fast electronic process, we also observed a slow carrier transport, having mobility on the order of 10(-5)cm(2)/Vs, which we attribute to ionic conduction. Chiral dimers containing binaphthyl group exhibited stable glassy cholesteric phase and cholesteric thin films with selective reflection band in visible light area could be fabricated. They emitted circularly polarized light with dichroic parameter of 1.3 when UV light was illuminated.
• Organic semiconductor material, organic semiconductor structure, and organic semiconductor device
  申请人：Maeda Hiroki

  公开号：US20060076554A1

  公开（公告）日：2006-04-13

  The object is to provide an organic semiconductor material, enabling to exhibit liquid crystal phase at wide temperature range including at least ordinary temperature and to exhibit high charge carrier mobility, and an organic semiconductor structure and organic semiconductor device formed from the organic semiconductor material. To achieve the object, the present invention provides an organic semiconductor material comprising a quaterthiophene skeleton shown in a following chemical formula 1, wherein R1 in the chemical formula 1 is an alkyl group of C1 to C20 or a hydrogen, and R2 is an alkyl group of C1 to C20 or a hydrogen.

  本发明的目的是提供一种有机半导体材料，能够在包括常温在内的广泛温度范围内表现出液晶相，并表现出高电荷载流子迁移率，以及由该有机半导体材料形成的有机半导体结构和有机半导体器件。为达到上述目的，本发明提供了一种有机半导体材料，其包括在下列化学式1中所示的四噻吩骨架，其中化学式1中的R1是C1到C20的烷基或氢，而R2是C1到C20的烷基或氢。