1,3-bis-(5-bromothiophen-2-yl)benzo[c]thiophene | 224453-00-3

• 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: 1,3-bis-(5-bromothiophen-2-yl)benzo[c]thiophene
• 英文别名: 1,3-bis(5-bromothiophen-2-yl)benzo[c]thiophene；1,3-Bis(5-bromo-2-thienyl)benzo[c]thiophene；1,3-Bis(5-bromothiophen-2-yl)-2-benzothiophene
• CAS: 224453-00-3
• 化学式: C₁₆H₈Br₂S₃
• 分子量: 456.246
• InChiKey: BXNDUBUHEDYEFV-UHFFFAOYSA-N

物化性质

• 沸点：
  503.1±45.0 °C(Predicted)
• 密度：
  1.789±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,3-bis-(5-bromothiophen-2-yl)benzo[c]thiophene 在 哌啶 、 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.5h， 生成 1,3-bis(5-ethynyl-2-thienyl)benzo[c]thiophene
  参考文献：
  名称：

  Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives

  摘要：

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.

  DOI：

  10.3987/com-14-13145
• 作为产物：
  描述：

  甲酮,1,2-亚苯基二[2-噻嗯基- 在 劳森试剂 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 生成 1,3-bis-(5-bromothiophen-2-yl)benzo[c]thiophene
  参考文献：
  名称：

  新型1,3-双（5-二芳基氨基噻吩-2-基）异亚硫醚的合成。

  摘要：

  我们报告了新型的1,3-双（5-二芳基氨基噻吩-2-基）异噻吩环的合成，电化学和光学性质，这是通过钯与二芳基胺的1,3-双（5-溴噻吩-2-基）异噻吩环的钯催化胺化反应而获得的。

  DOI：

  10.1039/b202943j

文献信息

• Bis[bis-(4-alkoxyphenyl)amino] Derivatives of Dithienylethene, Bithiophene, Dithienothiophene and Dithienopyrrole: Palladium-Catalysed Synthesis and Highly Delocalised Radical Cations
  作者：Susan A. Odom、Kelly Lancaster、Luca Beverina、Kelly M. Lefler、Natalie J. Thompson、Veaceslav Coropceanu、Jean-Luc Brédas、Seth R. Marder、Stephen Barlow

  DOI：10.1002/chem.200700668

  日期：2007.11.26

  2'-bithiophene (2), 2,6-bis[bis(4-butoxyphenyl)amino]dithieno[3,2-b:2',3'-d]thiophene (3), N-(4-tert-butylphenyl)-2,6-bis[bis(4-methoxyphenyl)amino]dithieno[3,2-b:2',3'-d]p yrrole (4 a) and N-tert-butyl-2,6-bis[bis(4-methoxyphenyl)amino]dithieno[3,2-b:2',3'-d]pyrrole (4 b)--have been synthesised. The syntheses make use of the palladium(0)-catalysed coupling of brominated thiophene species with diarylamines

  具有基于噻吩的桥的五种二胺-（E）-1,2-双5- [双（4-丁氧基苯基）氨基] -2-噻吩基}乙烯（1），5,5'-双[双（4） -甲氧基苯基）氨基] -2,2'-联噻吩（2），2,6-双[双（4-丁氧基苯基）氨基]二噻吩并[3,2-b：2'，3'-d]噻吩（3） ，N-（4-叔丁基苯基）-2,6-双[双（4-甲氧基苯基）氨基]二硫代[3,2-b：2'，3'-d] p吡咯（4 a）和N-已经合成了叔丁基-2,6-双[双（双（4-甲氧基苯基）氨基]二硫代[3,2-b：2'，3'-d]吡咯（4 b）。该合成利用了钯（0）催化的溴化噻吩物质与二芳基胺的偶联，在某些情况下通过微波辐射加速了偶联。所有分子都容易进行氧化，相对于二茂铁/二茂铁，4b在-0.4 V时最容易被氧化，通过向中性物质中加入三（4-溴苯基）六氯锑酸铵生成相应的自由基阳离子的溶液。自由基阳离子的近红外光谱显示出对称离域物质（即
• Synthesis, characterization, and electrogenerated chemiluminescence of phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes
  作者：Ullrich Mitschke、Peter Bäuerle

  DOI：10.1039/b006553f

  日期：——

  To overcome the insolubility of higher oligothiophenes and simultaneously to enhance their processability with respect to an application in molecularly doped organic light-emitting devices (OLEDs) we synthesized phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes 1–5. Significantly improved solubilities in polar solvents of up to three orders of magnitude were found and their optical and electrochemical properties were investigated in solution. Reflecting small conformational changes and the almost complete electronic separation of the substituents, phenyl substitution and the introduction of a spiro core by bridging the central bithienyl unit only slightly affected optical and redox properties in comparison to the unmodified oligothiophenes (6–8). In contrast, the presence of an isothianaphthene (benzo[c]thiophene) unit in the oligomeric chain led to a distinct approximation of the frontier orbitals and consequently to a red-shift of both absorption and fluorescence. Finally, we demonstrated the applicability of some oligomers as dopants for OLEDs by electrogenerated chemiluminescence (ECL).

  为了克服高阶寡聚噻吩的不溶性并同时提高它们在分子掺杂有机发光二极管(OLEDs)应用中的可加工性,我们合成了苯基取代的、苯基稠合的和螺芴基桥连的寡聚噻吩1-5。研究发现这些化合物在极性溶剂中的溶解度显著提高了最多三个数量级,并对它们在溶液中的光学和电化学性质进行了研究。与未修饰的寡聚噻吩(6-8)相比,苯基取代和通过桥连中心联噻吩基团引入螺环核心仅略微影响了光学和氧化还原性质,这反映了构象的微小变化和取代基之间几乎完全的电子分离。相比之下,寡聚物链中异噻萘(苯并[c]噻吩)单元的存在导致前沿轨道的明显趋近,因此吸收和荧光都发生红移。最后,我们通过电化学发光(ECL)证明了某些寡聚物作为OLED掺杂剂的适用性。
• Synthetic Approach to and Characterization of a Fullerene-DTBT-Fullerene Triad
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.1055/s-0032-1316902

  日期：——

  The synthesis of a new fullerene-dithienylbenzo[c]thiophene (DTBT)-fullerene triad is reported. The synthetic approach involves the synthesis of a DTBT unit, a Sonogashira reaction to introduce two acetylenic groups, and the coupling with fullerene. The product showed an absorption at lambda = 485 nm and a fluorescence band at lambda = 575 nm.
• Synthesis of novel 1,3-bis(5-diarylaminothiophen-2-yl)isothianaphthenes
  作者：Roman Kisselev、Mukundan Thelakkat

  DOI：10.1039/b202943j

  日期：2002.7.1

  We report the synthesis, electrochemical and optical properties of novel 1,3-bis(5-diarylaminothiophen-2-yl)isothianaphthenes obtained by palladium-catalysed amination of 1,3-bis(5-bromothiophen-2-yl)isothianaphthene with diarylamines.

  我们报告了新型的1,3-双（5-二芳基氨基噻吩-2-基）异噻吩环的合成，电化学和光学性质，这是通过钯与二芳基胺的1,3-双（5-溴噻吩-2-基）异噻吩环的钯催化胺化反应而获得的。
• Synthesis and Photophysical Properties of Some Dithienylbenzo[c]thiophene Derivatives
  作者：Maurizio D'Auria、Ambra Guarnaccio、Rocco Racioppi、Antonio Santagata、Roberto Teghil

  DOI：10.3987/com-14-13145

  日期：——

  The synthesis of a new fullerene - dithienylbenzo[c]thiophene (DTBT) - fullerene triad has been reported. The synthetic scheme provides the synthesis of DTBT unit, a Sonogashira reaction to introduce two acetylenic groups and the coupling with fullerene. The product showed an absorption at 485 rim and a fluorescence band at 575 nm. Treatment of 5-(3-(5-ethynyl-2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde with LHDMS gave a dimeric product that showed an absorption at 475 nm and a fluorescence band at 595 nm. Furthermore, 5-(3-(2-thienyl)benzo[c]-1-thienyl)thiophene-2-carbaldehyde was treated with hydrazine to give the corresponding adduct that showed an absorption at 480 nm and a fluorescence band at 605 rim.